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Print ISBN: 978-0-99908-142-6

eBook ISBN: 978-0-99908-143-3

Chapters

Bio

Dedication

Foreword

1. Why Work Remote

2. How Remote Work Provides Companies a
Competitive Advantage

3. Misconceptions About Remote Work

4. What You Need for Effective Remote Work

5. Mitigating the Downsides of Remote Work

6. How To Convince Your Boss To Let
You Work Remotely

7. Creating Good Habits for Remote Work 158

8. How To Get Your Organization Ready
for Remote Work

9. The Ultimate List of Remote Work Resources

Bio

Will Gant is an author, software developer and consultant with over 20 years of software development experience. He has worked remotely in a variety of roles, including management, in both local and distributed teams. Additionally, on more than one occasion, he has spearheaded the efforts to implement remote work processes in a fully onsite team.

Dedication

I would like to dedicate this book to my parents, who both taught me to look for opportunities for a better life and to put in the work to make them happen. Your parents have a lot of input in making you who you are, where you are. I’ve been blessed with having two who prioritized making me ready for the world, in terms of attitude, in terms of work ethic, and in terms of going through the pain of learning to achieve growth.

Foreword

I remember when I first started out my programming career that one of my biggest goals was to be able to someday get a job that allowed me to work remotely.

I had dreams of working whatever hours I wanted, rolling out of bed in the morning and going across the hall to my office and being able to work all night instead of during the day—if I wished.

Eventually I did get that remote work job and the first remote work job I got, I pretty much failed at. I spent most of my day procrastinating and playing online games instead of actually working and then I would scramble at the end of the week to get everything done.

My biggest problem was that I was not prepared, I didn’t know what to expect—and most importantly—I didn’t know how to succeed.

That’s why when Will suggested this book I was excited. I knew that if I had many misconceptions about remote work that caused me to initially fail, that many other people did as well and that someone needed to finally write the authoritative guide on the subject.

I’m happy to say that Will has done just that. You’ll find everything you need to know about remote work in this book, starting with what the benefits (and cons are), how to actually get, or make, a remote working job, how to handle working remote, and much, much more. Pretty much every question you have about working remotely will be answered in this book and hopefully you’ll be able to avoid the same mistakes that I did.

I also happen to know Will personally and I know that he knows what he’s talking about when it comes to remote work. Will has successfully worked many remote jobs, dealt with just about every issue that can come up, working from home, and has lived to tell the tale.

So, I know that you are in good hands when Will tells you how to successfully work remotely, whether you are starting your first remote job, looking for one, or trying to convince your boss that letting you work remote will be the best thing for you and the company.

John Sonmez,

Founder of Simple Programmer

March 10th, 2020

San Diego, CA

Chapter 1

Why Work Remote

If you are reading this, you probably have at least some desire to work remotely. While we all have our individual reasons, people either tend to love the idea or hate it.

For those who love working remotely, it may mesh well with longer-term goals in life. For others, it helps improve their quality of life by saving them money, time, and stress. And yet for others, it actually makes it possible for them to have a career at all.

However, remote work also has its detractors. For some of those people, especially those who tend to be more social, remote work sounds like a terrible level of isolation. For those who lack discipline or are concerned about how management will perceive remote workers, working remotely sounds like a recipe for job loss.

Many managers have difficulty evaluating how hard someone is working without seeing them at work, and it can be difficult to prove to them that you are working if you aren’t in the office.

At the very least, if you decide to work remotely, you can almost certainly count on dealing with one or more people who are strongly against the idea.

Since the perceptions of remote work vary widely across the population and are polarizing in some circles, it’s a good idea to be aware of the advantages that remote work brings to the table for those engaged in the practice.

Not only will these advantages help you convince others of the value of your own remote work, but sometimes those who are against the idea will see the value of the arrangement for themselves. They may even eventually realize that a company’s insistence on employees being in the office is hamstringing the company and wasting time and money while making the lives of their employees measurably worse.

The people who offer strong opinions on your remote work are not limited to those who work with you. In fact, some of the loudest voices you’ll hear will be from friends, family, and even random strangers in the grocery store. In general, the average person doesn’t really understand remote work and is often hostile to the idea.

However, the disagreement of others is not a good basis for evaluating whether something is a good idea for you personally. We’re going to discuss some of the benefits that you can expect from working remotely.

Realizing these benefits will make it a lot easier to ignore the people who are against the idea of remote work when you can’t convince them, and it’s also a lot easier to bring them around if you are confident in the benefits yourself.

Remote work necessitates a number of changes in the way that companies (and the individuals within them) operate. This radical restructuring changes the way that work is conducted and evaluated and drastically alters your relationship to work.

These changes also present new challenges and opportunities. In this first chapter, we’ll discuss some of the opportunities while leaving the challenges for later.

The Cost of Your Commute

The most obvious thing that changes when you work remotely is that you won’t have to travel to the office every day. While most people acknowledge that their commute is usually an annoying waste of time, most of us don’t really know how harmful our commute actually is.

From personal experience, I can tell you that once you find out how expensive your commute really is, you’ll also be far more motivated to rid yourself of it. Knowing what your commute costs will also help you in negotiations for remote work.

The first and most obvious cost imposed by commuting by car are the costs of gas and vehicle wear and tear. As of 2018, the average American commute is 16 miles each way and usually constitutes a little less than an hour of driving each day.

As of 2015, the average American spends $2,600 each year commuting to work. In some cities, the numbers are far worse, with many commutes being double the average or even more. Even for non-Americans, commutes can be very costly, especially if you are driving yourself to the office. Fuel and vehicle maintenance will always have a cost no matter where you live.

In addition to the obvious costs associated with a vehicle, there are many other costs that you probably haven’t considered. Vehicle insurance costs often increase based on mileage, as do the risks of an accident.

Additionally, you may have to pay for parking and other fees. These add up over time and don’t tend to make it into statistics, even though they do hit your bank account.

While using public transportation is often cheaper than commuting by car, it comes with its own issues. First among them is that it still costs money and may also take longer than a trip by car. Additionally, public transport in many places is severely lacking and fairly unpleasant. If it works, it can save you some money but not nearly enough to make commuting a good idea.

There are a few other monetary costs imposed by commuting that are easy to miss. When you have to physically go to an office, that usually means that you either have to pack your lunch or go buy something on lunch break. Either of these choices can impose extra costs in terms of either time or money that you wouldn’t have had at home, with the latter often being substantially more expensive.

However, many workplaces don’t have a suitable place to eat a bagged lunch or may have environmental problems that make it impossible to eat at your desk. This can be anything, from co-workers who interrupt you continually whether you are eating or not to simply not having enough desk space for lunch.

This gets even more expensive and unpleasant if you have dietary issues or are trying to lose weight.

For instance, I live outside of Nashville, Tennessee, and have regularly worked in one of the nearby communities that has a heavy tech presence. If you want to get something for lunch that is reasonably healthy, you are usually looking at $15-20 in cost. That cost is insane and adds up quickly over time, especially if there is no good way to bring your lunch and eat at your desk. In fact, if you have a month with 22 working days, lunch can add up to as much as $440.

Additionally, when commuting to an office, you may also have to spend more money on clothing to meet business dress codes and more money on health care from being in a building full of people who get sick, and you are often forced to use at least some of your vacation days for things like waiting on home repairs, inclement weather, or staying home with a sick child.

There is a real cost to these vacation days, although you probably don’t see it in your paycheck. Really, you’re only going to notice their absence if you run out of allotted days off and have to take unpaid leave. Essentially, you are forced to waste your days off simply so that the rest of your life can function, even though you’re otherwise perfectly capable of working those days.

The Costs You Aren’t Considering

No matter how well you minimize the monetary cost of commuting, the practice also comes with another substantial and ugly cost. And that cost is best expressed as a combination of time, attention, and misallocated money.

That’s right, if you are spending money, time, and attention on a commute, you aren’t spending it in a way that is most advantageous to you. Instead, you can consider any commuting-related expense as essentially being forced to subsidize your employer’s unwillingness to let you work remotely.

The costs of this are far in excess of what you might imagine. While in the previous section, we noted some sources that suggested that the average American spends $2,600 a year to commute, that’s far from the total cost. When talking through the financial costs, let’s do some math. To make this simple, we’re going to make some assumptions:

- We’ll assume that you are paid $50,000 a year. I hope it’s more than that, but if it isn’t, this round number will underscore just how expensive driving to an office actually is.

- We’ll assume you have two weeks of paid time off a year and only work 40 hours a week. That comes up to roughly 2,000 hours in a working year (again, roughly).

- This means that your hourly rate is $50,000/2000 hours or $25 an hour. In this example, we’re leaving off retirement benefits and health insurance as well as any other incidental expenses covered by work. This also completely ignores taxes.

- This also means that you’d be working 250 days a year, with the income for each day being $200.

- We’re also assuming that you have a half-hour commute each way. While this is slightly more than the average of 26 minutes, you should also bear in mind that you are probably leaving a little early so that traffic doesn’t make you late.

- We’re also going to assume that you have a one-hour lunch break. While you aren’t paid for the lunch break, it’s unlikely that you are allowed to simply skip lunch and go home early. It’s also unlikely that you are able to work on your own stuff on work computers. Effectively then, this becomes an hour every day that is under someone else’s control, for which you don’t get paid.

- We’ll assume that if you do eat lunch, that you can do so for $10. While on the low end for lunch prices in most places developers tend to hang out, we’ll use this price primarily to show you that even trying to eat cheaply will not help very much. We’ll also assume that if you bring your own lunch from home that it costs you approximately $5 (this is quite possibly on the high end, depending on what you eat).

- We’ll assume that breakfast costs you $5. I can’t eat breakfast for this amount, but it makes the math easy.

- We’re assuming that you are getting eight hours of sleep a night. So, given the above, let’s talk about the real cost using some relatively simple math.

- You think you are getting paid $200 for eight hours of work ($25/hour). However, including the time taken for lunch and the commute, you actually are burning up at least 10 hours a day, so you are really only getting about $20 an hour.

- It’s probably worse than that, however, as you also can’t plan to do anything very close to the time you arrive at work or arrive home because all it takes is a small traffic jam for you to be late.

In effect, an eight-hour day at a job will use up at least 10 hours of your day and possibly much more.

If you consider the extra time that is lost to traffic or to handling the logistics of traveling (filling up your gas tank, car maintenance, time lost to traffic accidents, and time spent going to and from your parking location), it could very easily approach 12 hours a day of lost time, especially if part of your commute is prone to traffic jams.

Even if all of the above doesn’t add up to 12 hours a day lost to an “eight-hour” job, commuting also limits the times when you are able to run errands.

Since most everyone else is on a similar schedule, this can mean that an evening stop at the grocery store, post office, or bank takes longer simply due to the number of people there at the same time. In many cases, this is the difference between being the only person in the line and being the 10th.

Given that, a 12-hour estimate is probably on the low end and is quite possibly optimistic. Since you’ve already lost 12 hours of your day to work and your commute, and assuming that you sleep for eight hours a night, this means that you only truly control four hours of your day in any measurable sense.

And you are expected to get dressed for work, bathe (hopefully), eat, and handle family life and intimate relationships during that time.

If you look through the previous explanation and realize all the numbers I put in are optimistic, you realize that the commute is potentially taking a three- to four-hour block of your day away from you, every single day.

Considering your low initial hourly rate of $25, that is an expense of $75-$100 a day for the commute (and you get the privilege of all the added financial expense of the commute that we mentioned in the previous section). Over the course of a work year, that’s $18,750-$25,000 worth of time. In other words, 3/8ths to 1/2 of your current salary. And you get to pay for the privilege …

While you are probably already convinced that a commute is absolutely horrible under these circumstances, let’s take this a little further. You have four hours that are roughly “under your control” during a workday, but these hours are probably split between the morning and evening.

If you have children that are attending school, you probably spend time and money getting them to and from school. This tends to mean additional driving and child care expenses, which can be substantial for younger children, especially if they are too young to be in public school.

The schedule at many child care facilities is also pretty bad for working parents. It’s common for such locations to open at 7 am and close at 6 pm, for instance.

This means that if there is any distance between your house and day care, one spouse will have to drop off the child while the other picks them up because there is simply no way to get an eight-hour workday with a commute and a lunch break in between the time the facility opens and closes.

So, you have four hours, but you don’t really have four hours. It’s probably three and a half hours at best. However, you also have another problem. If you are commuting to a desk job, this means that you are sitting most of the day, including the time you are in the car.

Combine that with the kind of lunch you can get for 10 bucks, and you have a recipe for serious health problems over time. To mitigate that, you are going to need to work out regularly. Many people will find a gym close to their house simply so that they can shower at home.

This means that your gym time is limited just like everyone else’s, which means that your workouts take longer too. It’s anecdotal, I know, but every single time I’ve had to wait on a gym bro to quit curling the bar inside a squat rack, it’s been in the evenings. Commuting forces you to lose even more time if you want to remain healthy.

Basically, it’s possible for your commute to completely destroy most of your free time during a workweek either because of the time required for travel or the time that gets wasted because of your (and everyone else’s) commute.

This insidious waste of large swaths of your time is probably not something that you have really considered unless you’ve thought a lot about what your commute is really costing you, but it costs you nonetheless.

Given that your free time is so limited during the week, you’ll also find yourself spending an excessive amount of your time on the weekend either catching up on sleep, running errands, or exercising. This makes weekends far less relaxing, limits what you can do with them, and makes them more difficult to enjoy.

The Real Issue: Opportunity Cost

While you are paying a hidden, insidious cost for the time and money wasted on driving to and from an office, commuting to work can also limit your future success in various ways.

A few decades ago, the expectation of many workers was that they would start working for a company soon after college and then retire with a pension 40 years later. If you read that previous sentence, you probably rolled your eyes nearly as much as I did when I wrote it.

The reality now is that not only are employees less likely to stay at a company for decades but that the companies themselves are less likely to keep an employee around for a very long time. You’re on your own as far as your longer-term career plans, retirement savings, and any personal goals that you want to achieve.

Since you can’t (and arguably shouldn’t) depend on an employer to provide for your longer-term career, you need to carefully consider how commuting to work impacts this.

Given approximately half a dozen hours a week of wasted time in a commute, one would be wise to consider what else they could be doing with just the drive time and money spent on commuting. Here are some examples:

- Many training videos on programming or other IT topics are less than five hours in length. A single week’s worth of commutes could give you a running start at learning a new programming language and shifting your career toward something more fun, lucrative, and fulfilling than whatever you are doing now while helping to protect you from downsizing.

- If you work out for half an hour a day, every day, your commute is using more time than a workout and a long shower afterward.

- The time for a commute is more than the time required for making many home-cooked meals, which are often healthier and usually cheaper than what you can get at a restaurant.

- Five hours a week is more than enough time to launch a blog, write a book, or even build a small e-commerce website. If you aren’t planning on doing your day job forever, a commute is literally costing you a future option that could change your life. For perspective, I have a podcast and spend five to seven hours a week on it.

- While five hours a week isn’t really enough to reach fluency in a foreign language in a short period of time, it still makes a sizable dent in the amount of time that such a goal might take. For example, I was able to reach an intermediate level in spoken Russian while practicing only during my commutes. Had I spent that time practicing at home, I would have progressed even more rapidly.

- $2,600 a year is enough for a pretty nice vacation, drinks included, in many places.

- If you don’t have to drive to the office on a regular basis, you might be able to move to a lower-cost, more relaxed place to live. Housing costs are a substantial portion of almost everyone’s living expenses, so being able to lower them is extremely valuable.

- If you work an extra five hours a week in a more relaxed environment, you can easily outperform co-workers who aren’t able to work remotely. Managed correctly, this can make a huge impact on your career.

While commuting is not optimal, simply because of the time and money that it requires, the best real argument against the practice is the enormous opportunity cost that it represents.

What happens if you write a bestselling novel in the time that you weren’t commuting? What if you learn a foreign language and eventually move to Europe like you always wanted to? What if you build a successful side business that lets you escape from the rat race forever? What if having the time to work out means you live an extra 20 years and get to see your grandchildren get married?

The upside of avoiding a commute is hard to calculate, and very personal, but it’s almost certain that you have one. When you can avoid having a substantial portion of your day wasted staring at someone else’s brake lights, all kinds of possibilities open up, including many that you couldn’t conceive of when you first started considering the idea.

Realistically, if you never do anything in the list above while working remotely and instead spend all the spare time created sitting on the couch with your spouse watching TV, it’s probably still a better, more peaceful life than one spent in rush hour traffic. At the very least, you have the option of doing something other than watching TV.

The real point of understanding the horrible human cost of commuting is not to make you bitter about it or annoyed that you have to drive to work. The real point of such an exercise is to let you see the opportunities that are available to you.

Once you realize what the commute costs, you’ll be far more willing to go to the effort to be rid of it. Your commute costs you every single day. If you want a quick plan to do this, I suggest downloading the bonus material for this book (https://simpleprogrammer.com/remoteworkbonus).

Upsides of Remote Work

We discussed the opportunity costs of commuting in the previous section, but to really grasp how valuable remote work can be, we also need to discuss the opportunities that it provides.

Making one’s life better isn’t just about avoiding things that make life worse but about embracing things that improve life. In this section, we’ll discuss some of these.

It’s important to note that you really don’t need very many of these opportunities to go well for remote work to represent a substantial advantage to both your finances and your quality of life. However, you should consider them, since even slight improvements over time can really improve your life.

Unexpected Savings

By now, you realize how expensive commuting actually is, but working remotely also creates a number of cost savings that are often surprising. One of the biggest of these is child care expenses.

If you have one or more children who are old enough so they don’t need to be constantly monitored, then working remotely will easily allow you to save hundreds of dollars a month. When children are old enough so they can entertain themselves, there is little reason to pay someone else to do so.

The average school day for children is significantly shorter than the average workday for adults. Children also tend to be sent to school somewhere close to where they live, while adults may have to commute across or into a city in order to work.

This means that parents tend to have to pay for child care both before and after the school day simply because it’s a really bad idea for younger children to be home by themselves. To add insult to injury, most of the child care that is available before and after school also requires that you drop off or pick up the children, if not both.

If you work remotely, however, your children may be able to ride a bus to and from school, saving both the cost of day care and the “mini commute” required to take them there. While the above doesn’t help much if you have very young children who need constant attention, at some point, it will represent huge savings in both time and money.

Additionally, working remotely can save you a lot of money on food, as it is easier to simply warm up something out of the refrigerator than it is to go out to eat somewhere nearby.

When going to an office, eating at your desk is a lot more effort, since it means that you have to both pack a lunch and ensure that your co-workers actually let you eat without interrupting you.

In many offices where I’ve worked, the majority of the staff end up going out to lunch every single day, both for a change of scenery and so that they can eat lunch without being interrupted by phone calls, co-workers stopping by for “a quick question,” and the background noise of the office.

If your home is a relatively peaceful place that you enjoy, you’ll be less incentivized to go out to eat in the first place. Considering that it can be difficult to get something filling and reasonably healthy for lunch for less than $15, it doesn’t take very long for remote work to save you a lot of money.

You’ll find that even as remote work saves you a lot of time, one of the unexpected side effects is that it saves you money in surprising ways. Most things are cheaper when you have control over your own life, and remote work helps you achieve that.

Respect and Better Evaluations

It’s been said that the modern workplace is often a bit of a dystopia. You are forced to drive to the office, dress in fairly uncomfortable clothes, and sit at a desk for eight hours or more, usually in a room with a bunch of other people, while you all pretend to work.

It’s also completely obvious to anyone who has done it that most people don’t work for at least a third of the day, with many truly focused and working for less than half of the day.

When management is lazy, such a system tends to mean that those who “work” the longest days are seen as being the best employees even if they provide little or no actual value (some are a net negative, including a sizable percentage of the managers in such a system). It’s a system that favors schmoozing with the boss and pretending to work over actually doing valuable work.

The downstream effects of such a terribly organized system are countless. Human beings will adapt to most systems of evaluation, no matter how pathological they are, in an effort to better their situation.

If the environment is pathological enough, then the behavior of people in that environment will be pathological too, on average, with those who are less pathological being left behind and the worst specimens rising to the top of the hierarchy.

You may well see this in your own office environment if you look around. Just look at the list below, and think about how many times you’ve noticed these behaviors in the last few weeks of work.

- A worker whose job is mostly oriented around typing who seems to spend most of their time using the mouse will suddenly click something and start typing every single time a member of management comes into their view.

- The entire office is working together in an open space for the sake of “collaboration,” and everyone is wearing noise-canceling headphones because they don’t want to hear Billy’s loud phone conversation about sports, his upcoming and very personal surgery, or his arguments with his teenage daughter about using the car.

- A girl works in the office, and everyone knows that she has irritable bowel syndrome because everyone noticed how frequently she’s in the bathroom instead of sitting at her desk working (because they weren’t working either).

- Two people in the office are constantly gossiping about each other because of some slight that happened a year ago. The people who sit near them have taken sides in the conflict.

- One guy is getting divorced and periodically sobs uncontrollably at his desk while the people near him spend the day squinting at their screens and trying to avoid the distraction. Everyone is uncomfortable, but no one talks to him because they don’t want to be seen “not working.”

- One unattached coworker without children, pets, or hobbies sits at her desk for 12 hours a day. Nobody can really see anything that she gets done, but management heaps praise on her for her work ethic.

- A hard-working guy with two children at home who does excellent work is written up for leaving 15 minutes early so he can go to his daughter’s piano recital, even though he worked all weekend. He knows this will come up in his next evaluation when it is decided whether his raise will exceed inflation.

None of the items listed previously (or the half dozen others you thought of while reading the list) is a natural behavior of happy, well-adjusted people who are working in a system that incentivizes the production of value.

Instead, these are the perfectly predictable behaviors of people forced to work in a system where the appearance of creating value is measured rather than the actual creation of value. The resulting environment ends up looking more like something from a Dilbert cartoon rather than a place where any of us want to work.

When working remotely under normal circumstances, a lot of these problems go away. It’s much harder to determine whether someone is sitting at their desk for the full eight hours a day when they are sitting at a desk in their own home.

Instead, if you want to manage remote workers effectively, you have to measure productivity by other means. Usually, rather than the typical “butts in seats” measurement, you have to look at what someone actually produces.

While the misalignment of office incentive structures could be the subject of a book or two on its own, it’s pretty easy to determine whether you are being evaluated based upon reasonable standards or not. Consider the following:

- When you take a break at work, do you feel the need to conceal this fact from management?

- Let’s say that you suddenly became twice as fast at completing your work. Would you be paid twice as much and be required to work only half as much or would you simply get twice as much work for the same amount of money?

- Do you find yourself furtively reading the news, texting, or playing games on your phone while trying to look busy?

- Does management claim to value collaboration but value individual contributors over the group? In other words, if you help junior members of the team become more effective, are you doing so as part of your job or are you actively hurting yourself because it won’t matter at review time?

- Do you find yourself completing all your work for a day and then staring at the wall for the rest of the day because you can’t leave early?

- Do you find yourself hesitating to do things more efficiently because it just means that you’ll be assigned more work?

- Do you find yourself sandbagging on project estimates because you know that you’ll be eating the cost of any underestimation but that overestimating means that you actually get to take a break?

- Do you find yourself resenting co-workers who take a lot of breaks or handle personal business while on the clock?

If any of the things in the previous list hit a little too close to home, it’s a good sign that your work environment values “butts in seats” and the appearance of productivity over actually getting work done.

While remote work can’t entirely fix this, it does make it much more difficult for management to value the appearance of productivity over actual productivity. “Butts in seats” is one of the worst ways to measure the productivity of a team, especially for teams of creative people working on problems that tend to change over time.

When a team is remote, a “lazy” manager is more likely to choose to measure the team based upon productivity than upon whether they are currently pretending to work. This actually incentivizes the team to be more productive rather than simply trying to look busy. The value of this paradigm shift cannot be understated.

The points above are not intended to be taken as complaints. Rather, they are good things because that means that it will be far easier to show that working remotely provides far more value than watching the clock and pretending to work in an office.

Medical Issues

The modern office is not always the most comfortable place to work. In fact, the odds are good that you really don’t like the office either. However, for many people, the modern office is more than uncomfortable and can exacerbate underlying medical conditions.

While there are laws that are supposed to protect people with medical issues in an office environment, those laws do a poor job of protecting employees in transit or at lunch and do nothing about the kind of embarrassing issues that certain medical conditions may cause.

While you may be young and have no serious medical problems, these things tend to creep up on you. When I was in my 20s, I was seldom sick and thought I was indestructible (and did stupid things in accordance with that belief of which I’m often reminded now that I’m older).

Two hernia surgeries, a throat surgery, and a couple of “interesting” food sensitivities later, I can tell you that even with some accommodations, the office environment is not a suitable one when you have certain medical conditions. Good friends of mine have more severe and long-lasting medical issues, and it’s even worse for them.

Being in an office for the entire day can be difficult if you have certain medical conditions. If you are pregnant or if you have issues like irritable bowel syndrome or cancer, you may not want to be in the office simply because you don’t want your health to be the subject of conversation.

There is no real privacy in most office environments, and people tend to butt into your business far more than is reasonable. For instance, with both of my hernia surgeries, I had co-workers who insisted that it was either combative martial arts or weightlifting that caused the problem.

I had to argue with people at work about what caused my hernias, when I was actually there and awake when both happened. Both were from coughing, but the office “experts” were so socially inept that they had to continue weighing in and arguing with me.

While this is a human-resources issue in some cases, it often doesn’t quite rise to that level while still being embarrassing and distracting enough to be annoying.

When working remotely at your own house, you often have better opportunities to mitigate medical issues with minimal disruption to the rest of the staff. You don’t have to remember to bring your medicine with you to work, and you don’t have to ask a bunch of questions about any food that is being offered to avoid getting sick.

Further, if your medical issues are of a personal nature and uncomfortable, you are free to set up your work environment to make them less of a problem, without a bunch of busybodies asking questions.

Even beyond the office busybodies, certain medical conditions make travel more difficult. For instance, if you have problems with your eyesight, you might be able to work well with some assistive technology, but you may be unable to drive to work.

If you can’t drive, someone has to bring you, which means that you are now subject to someone else’s schedule even if it is that of a city bus. Additionally, this may also restrict where you can live, as public transportation is very spotty in many parts of the country.

It would be understandable to have to come in to the office if it were really required for the operation of the company, but it’s absolutely ridiculous when it actually makes the company less efficient. In a surprising number of cases, the “required” time in the office is doing nothing for the company but is stressing out the employees and burning cash.

Remote work has the possibility of giving autonomy and dignity back to people with severe medical problems. While you may not currently have any serious medical issues, remote work can seriously improve your quality of life if you do.

Family Issues

In addition to your own medical issues, conditions within your family can make remote work an attractive possibility. At some point in our lives, most of us will find ourselves caring for sick children, spouses, parents, or siblings. While some severe illnesses run their course in a matter of days or weeks, many others last for a lifetime.

If you’ve ever had the experience of caring for a sick relative who is dealing with a chronic illness, you know that it adds an element of unpredictability to your life. It’s also pretty unlikely that your chronically ill relative is going to be sitting in a corporate office with you, which means that your commute makes it much more difficult to take care of them while keeping your job.

Taking care of a family member can result in regularly having to leave the office, drive home, and then take the relative to a doctor on short notice. It may also require you to pay someone else to be there to take care of your loved ones, which tends to be expensive and can reduce their quality of life. While many people are comfortable accepting a little help from a relative who lives in the house with them, the situation takes on an entirely different tone when outside professionals have to be hired.

Besides chronic medical conditions, many people have children or spouses with other problems that require regular attention. Some of those problems are things that you’d rather keep to yourself.

Imagine that your son is a recovering drug addict or your daughter has an eating disorder. Or imagine that you are having to take care of your grandchildren after their parents died in a car accident (or they went to jail).

While these situations may have a medical component, they also have behavioral components. These are situations that can happen to the best of people, and they are things that require significant amounts of your time and attention to deal with.

Additionally, they are the sort of situations that can bring out some of the cattiest and most spiteful behavior from co-workers who will judge you for taking care of your family, especially if they see you leave work early.

As discussed previously, the modern office environment has a warped set of standards for what constitutes good work, and that set of standards tends to result in people having an excessive amount of interest in their co-workers’ personal business. This is especially true if people feel that their own time at work is wasted and end up resenting you for not having your time wasted.

Working from home will not fix chronic problems within your family, but it will give you more time and attention to be able to do what needs to be done to help the situation. It will also help keep your judgmental co-workers out of your business.

While you should be keeping good boundaries with people at work anyway, when you have a chronically ill or troubled relative, that can sometimes be difficult to manage. Sick or troubled family can often create a serious emotional rollercoaster that will be exacerbated by a long commute or judgmental co-workers.

Working remotely can reduce some of the nasty time constraints that you will encounter if someone in your family gets very sick.

Financial Issues

If you have severe financial issues, working remotely can help save you from bankruptcy. While there is a popular stigma that major financial problems are due to bad decisions, that isn’t entirely true of all of them (nor is it relevant when you are trying to make good decisions to correct the problem).

Lots of people have massive student loan debts or lost everything to medical costs, a divorce, or a business going under. If you are trying to recover from crippling debt, the $2,600 a year that the average American spends on commuting looks like an easy way to get rid of some of the debt.

It also reduces the risk of a car breakdown driving you deeper into the hole, since you won’t be traveling as much.

When comparing a remote job to an on-site job with the same pay rate, the remote job constitutes a significant raise, especially when you consider the opportunity cost represented by an on-site job.

Working remotely and carefully managing your other expenses could easily save you closer to 10 thousand dollars a year, especially taking into account expenses like child care. It can also enable you to take on additional jobs that can help you pay down your debt.

Additionally, remote work can make it possible to move to places where the cost of living is lower. The impact of this can be profound. If your job allows you to move to a small town rather than a large city, you can often buy similar housing for less than half of what it would cost in a city.

Additionally, many other costs are far lower the further you get away from major population centers. While such places can be boring, depending on how you entertain yourself, they can be a viable option for saving money and getting rid of debt. However, this is much harder to accomplish when you are forced to go into an office every day.

Better Use of “Waste” Time

The final benefit of working remotely is what it lets you do with dead spaces in your schedule. When regularly going into an office, you’ll find that there are certain times of the day when you really can’t do anything useful, but you are expected to pretend to be working anyway.

For instance, if you have a 9 o’clock meeting that usually lasts 15 minutes and a 10 o’clock meeting, there is often little point in trying to get anything done between 9:15 and 9:59, since by the time you get into a flow state, you will be interrupted by the second meeting. Due to the incentive structure in a typical office, you may well find yourself stuck at your desk, pretending to be busy for 45 minutes.

While there are ways to use the time effectively, many office schedules seem designed to eliminate the kind of periods of quiet focus that are required to complete difficult work.

However, if you are working remotely from your house, those 45 minutes can prove extremely valuable. It’s a great time to put food in the refrigerator to thaw for dinner, put in a load of laundry, or even just get up and stretch without everyone looking at you like a total slacker.

Because remote workers tend to be judged based upon their productivity (rather than their presence and ability to pretend to work), you can actually complete small tasks that help you.

While I’m not advocating doing a lot of personal stuff during work time, there is some value in doing a few small tasks during time that would otherwise be completely wasted during the workday.

Additionally, because your meetings are conducted remotely, you can also recover at least some of the time wasted in useless meetings by muting your microphone and continuing to work. If your employer regularly requires you to attend meetings that are a complete waste of time, this can be a great time to be productive.

It’s unpleasant to have your time wasted at work, especially if you are required to work more to finish your assigned tasks. It feels like you are subsidizing your employer’s bad practices with your personal time because you are. Working remotely provides options that can help you use your time more wisely.

The Benefits of Remote Are Worth It

There are a lot of possible advantages that working remotely can confer. While many people grasp that the practice is advantageous, it’s often hard to truly quantify just how advantageous it is.

Not only does it give you more free time and save you money, but it changes the way your work is evaluated in rather profound ways. It can also help you deal with difficult situations in life, including medical, financial, and family issues.

Finally, it can keep your job from wasting valuable time during the day. Remote work is about far more than just working at home. It’s about making a life that works for you rather than against you.

Chapter 2

How Remote Work Provides Companies a Competitive Advantage

While working remotely is an excellent deal for developers and other IT professionals, you should never, ever try to sell the idea of it by touting how beneficial it is to you. That’s a recipe for disaster, and it almost never works.

I worked with a guy once who tried to convince management to let him work from home because it would reduce his child care costs and commute time. Not only did he fail to sell management on the idea, but he also irritated them to the point that they never allowed him to work from home.

When I suggested that the same company should allow me to work from home so that I could be more productive without distractions, I was allowed to do so the next day.

It is very difficult to sell an idea to others based on how it will help you, but it is much easier to do so when you talk about how it will help them.

If you want to convince management that working remotely is a good idea, you need to understand what it can do for a company on a day-to-day practical level as well as at a strategic level. Allowing employees to work remotely offers tremendous value and flexibility for companies.

In other words, if you can demonstrate that it helps the other party, they are more likely to work with you. The characteristics of a remote-first (or even remote-only) workspace can really correct a lot of issues in a workplace.

These issues are roughly subdivided into three categories of problems. In this second chapter, we’ll discuss these problems and how they can be mitigated using remote work. Try to consider whether your own company could benefit from remote work based on the impact of these issues.

Of course, some things might not apply to your current work environment. You must determine which are relevant and which are not so you can address those concerns with management when trying to convince them to let you work remotely.

The Three Issues Remote Work Can
Help With

The first category of problems that remote work can help solve is the issue of obtaining and keeping more skilled employees.

If you ask a hiring manager at most companies these days, it’s becoming harder to recruit new employees and to keep existing ones. Furthermore, because of the relative scarcity of certain types of IT professionals (software developers and security professionals especially), companies are simply forced to pay more for the same talent.

When your only leverage on the market is price, the only way to beat the competition is a bidding war. That’s expensive, and it’s a race toward drastically overpaying for help.

The second category of problems that remote work helps with is the category of organizational flexibility and resilience. While having a single location helps with the type of “collaboration” we lovingly outlined previously, it does introduce some downsides.

For one, requiring everybody to be in the office means that work doesn’t happen when people can’t get there. Traffic, inclement weather, and personal issues can mean that a company can’t effectively respond to problems when people aren’t in the office. Depending on where the company is located, this represents a profound risk to business continuity.

Finally, remote work can also significantly help with costs. Office space is not cheap. Not only do companies have to rent the space they use, but their employees also have to live close enough for a daily commute.

The latter means that the employees also have to be paid enough to live near expensive office space. This is a hidden cost that is often ignored.

Let’s now take a closer look at each of these issues.

As we saw previously, some of them might be relevant to your own situation, while others aren’t. Identifying them and focusing your efforts on what is relevant will greatly enhance your chances to come to an agreement with management, and to do so in a way that benefits the company.

In effect, you need to figure out which issues give you the most leverage in the discussion and go from there.

Recruitment and Retention

It’s very expensive to lose employees. While exact figures are hard to come by, replacing a software developer or other IT professional can easily cost well into the five figure range—just counting the money and time required to find, interview, and onboard a new developer.

When you consider the opportunity cost of turnover, it’s even worse. It’s also quite common for IT professionals to change jobs on a fairly frequent basis, so anything that reduces the frequency of such changes constitutes a significant business advantage.

According to the 2017 State of Remote Work report, companies that allow remote work experience 25% less turnover.

Remote work is more than simply another way to get things done—it’s also an effective recruitment and retention tool that allows employers to compete on more than salary and benefits.

The same report indicates that fully remote companies (companies with no corporate headquarters) were able to fill positions 33% faster than other companies.

Additionally, the 2017 report showed that managers see equal performance between their remote and on-site employees. While “merely” equal performance doesn’t sound particularly compelling, bear in mind that the on-site employees are often sitting in expensive real estate that costs the company money on an ongoing basis.

It’s costing more money for the same work.

In many cases, remote employees represent a significant cost savings for the same amount of work. This savings often means you can hire more people.

While discussions of employee retention often center around employees voluntarily leaving a job for a better one, that’s not always the case. Sometimes employees have to leave due to their own medical issues or those of their close family. In these cases, the opportunity to work remotely may mean that they can keep their current job rather than having to quit due to circumstances beyond their control.

Larger Hiring Pool

In addition to the greater ease of recruiting and retaining employees, remote work also greatly increases the size of the labor pool available at a given price to the companies that allow it.

For instance, consider the typical software company in many major cities. They’ll usually have an office headquarters in a reasonably expensive area (so that the employees don’t get mugged at night while leaving the office).

Any employees they manage to hire have to live close enough to be able to commute to the office, and their pay has to be high enough to afford doing so. While there are clearly a lot of people who will meet these criteria in almost any major city, the number of people who could afford to take a similar salary to work remotely is considerably higher.

Because employee recruitment and retention is such an expensive and time-consuming part of running a business, anything that either lowers the costs of hiring or increases the number of potential employees constitutes a significant business advantage. This is especially helpful in areas where salaries are high, the local population is not particularly tech-savvy, or where terrible commutes and gridlock make travel difficult.

Organizational Resiliency

Most inhabited parts of this planet have at least some extreme weather, geological, or social events that can disrupt work. While one can anticipate many of these issues (hurricanes, for instance), many other issues tend to give little or no warning of their impending interference in your business.

Tornadoes, earthquakes, forest fires, heavy rain and snow, and even social unrest can often seem to come out of nowhere. If they happen during a workday, these events can often mean that people are unable to reach the office, have to leave early, or even get stuck in transit.

For example, I currently live in Nashville, Tennessee. While we haven’t had any significant earthquakes in living memory and are insulated from coastal hurricanes, we are extremely unprepared for the sort of winter weather that happens farther north.

It’s routine for schools to be closed here when less than half an inch of snow has fallen, while 2 inches of snow can render many of the roads impassable due to people having no practice driving in snow.

When you combine this with our hilly terrain and the tendency of “snow” to really be “ice,” a small winter storm can paralyze parts of the city. However, such events usually are not bad enough to mean that the electricity isn’t working. Employees who are able to work from home are generally able to do so with very little disruption.

Additionally, we periodically have problems with flooding. In some cases, the flooding is fairly extensive (2010 was an especially bad year, with much of downtown being flooded and the power being out for days in many areas). In this case, many remote employees were not able to work from home but were able to work from the homes of relatives or from coffee shops.

In some cases, like that of one of my clients, the remote employees were able to keep critical systems running until the floodwaters receded. Remote work can help build a degree of redundancy into an organization, simply because it changes the way people interact with critical systems.

In my client’s case, remote workers were the reason they had moved many things (including source control) into the cloud. That move to the cloud meant that when the floodwaters entered the server room, most of the critical infrastructure wasn’t there.

If your team is distributed, it will change the way your organizational resources are managed. One unexpected effect of these changes tends to be that organizations are more resilient to disasters and other problems with local conditions.

Additionally, if your team is distributed over a wider geographic area, some local disruptions may not bother some remote team members at all.

Lower Office Space Costs

Popular cubicle sizes are 9 feet by 12 feet for managers, 8 feet by 10 feet for senior staff, 8 feet by 8 feet for general staff, and 6 feet by 6 feet for support personnel.

Respectively, that’s 108 square feet for managers, 80 square feet for senior staff, 64 square feet for general staff, and 36 square feet for support personnel. While this highlights the disparity in space given to people in general, it also makes it pretty easy to calculate how much it costs to house employees on-site.

For instance, in one of the heavy tech-centric areas near where I live (Brentwood, near Nashville), commercial office space costs around $27 a year, per a square foot. Given this, we can calculate how much each type of worker costs just in terms of the space required for their seating and work area. We can consider the following figures, just for cubicle space:

- Manager cubicle: 9’ x 12’ or 108 square feet. At local prices, that’s $2,916 a year, just for the cubicle.

- Senior staff: 8’ x 10’ or 80 square feet. That’s $2,160 yearly at local prices.

- General staff: At 8’ x 8’, that’s 64 square feet, or $1,728 yearly.

- Support personnel: For the 36 square feet they get, that’s $972 yearly.

In addition to the rather alarming prices for the square footage taken up by cubicles, workers will also require a number of other things to go about their jobs. These include things like bathrooms, meeting rooms, hallways, common area spaces such as kitchens and dining areas, and parking.

Depending on where your offices are located, it only takes reducing your office footprint by a few cubicles to easily cover the salary for another support or development person. If you manage to reduce your footprint by half, it can make a truly huge impact on your company’s bottom line.

The cost of office space is something that is seldom taken into account to the degree that it should be. Not only is it expensive to keep employees on-site to work, but office space is seldom rented on a month-to-month basis.

Rather, office space tends to be leased over a longer period of time on a contractual basis. If your company’s market situation changes drastically, these long term leasing contracts can create a lot of headaches.

Picture, if you will, a company whose product suddenly starts selling like hotcakes. Rather than just needing to incrementally add personnel, the company needs to double in size over a period of less than a year.

If you are lucky, you have additional office space nearby you can rent. If you are unlucky, you may be forced into a more expensive office space, forced to break your lease, or stuck with having a company split between two locations. Often, it’s some combination of the three.

The reverse is also true. I worked for one company that had huge, posh offices that was suddenly faced with drastic market changes. They had to let go of nearly half the staff but were stuck with their lease for another few years. The office space rental was one of the major factors in the company continuing to lose market share.

The end result was the liquidation of assets at pennies on the dollar and the termination of the remainder of the staff. The inflexibility of office space leases can be an existential threat to a company, and it usually isn’t recognized as such until it is too late.

Wage Arbitrage

In addition to the costs of office space and benefits to the hiring process, remote work makes it easier to hire developers at a lower cost. Developers near your office may well be willing to work for a lower price, simply to be able to avoid the commute.

This is especially true if you are in a major city with significant traffic issues or are located far from inexpensive housing. The reduced cost to employees may well offset the lower salaries.

Depending on your location, you may also find that salaries for many employees are far cheaper in other cities or even outside of your own country.

To give an example, the average senior C#/ASP.NET developer in Nashville can expect to make around $104K a year, while a similar senior developer just down the road in Memphis might only make $96K a year (numbers retrieved from Indeed.com).

While an eight thousand dollar difference in price may not seem like much, when combined with the cost savings in office rent and the larger hiring pool, the difference can be substantial. Additionally, these numbers are numbers for major cities—once you get into smaller towns, the pay rates are often significantly lower.

I’ve seen senior developers at my own level earn 25% less than I do while doing very similar work in a much smaller town. Even at the lower salary, they still have a better quality of life than I do in a large city.

However, when a company needs to accommodate remote workers, the very same accommodations that allow employees to work from home can also enable employees to work from nearly anywhere. This can significantly lower salary costs, especially when your processes are flexible enough to allow for work in distant countries with much lower living expenses.

While it is harder to coordinate teams over large distances and multiple time zones, the cost savings can often be worth it, especially if the remote workers bring skills or knowledge to the team that you wouldn’t otherwise have. Managed properly, a remote work environment can allow you to build a team that would be impossible to create in your current location.

Allowing remote work also allows people with difficult life situations to still be gainfully employed by your company. Whether a person is facing a serious disability that limits their ability to drive, has a sick child, or is otherwise in a life situation that keeps them from working in most jobs, remote work can be a true blessing for many.

While you probably shouldn’t underpay someone simply because of their life situation, you may find that you get better results for your money even if you pay them a competitive rate. When you give someone an opportunity that others do not, it often creates the kind of loyalty that you have to experience to believe.

I’ve seen absolutely phenomenal work done by people who had a life situation that precluded most jobs. If you want a good way to hire extremely loyal employees, look no further than the people who are in difficult situations. There is a huge difference between hiring someone for whom you are “just another employer” instead of the person that gave them a chance when no one else would.

At a societal level, remote work offers the opportunity to lift many people out of poverty and misery. This can include people on the other side of the planet, and it can include people down the street. While many companies brag about their ability to make the world a better place, allowing your employees to work from home is a way to actually accomplish that.

What Remote Work Really Is

At the end of the day, none of us really care all that much about how much we are paid. We care about what that pay can do for us and what kind of life we can create for ourselves with that money. If a million dollars could only buy a candy bar, almost nobody would buy a lottery ticket. The number in our salary isn’t what matters—it’s the options that number allows us to create.

Everyone’s vision of the perfect version of their own life is different, but almost every vision takes time, attention, and money to accomplish. When a company creates an opportunity for someone to build a better version of their own life, employees notice.

Rather than just being “technology company #2348 who has yet another web development job,” as a remote company you are offering a better, more flexible life for your employees. In the eyes of a potential employee, this changes your company from just another job option to an incredible opportunity that gives them back hours a day.

Furthermore, once they become employees, this benefit will—unless you really screw up—make them happier, healthier, and prouder of where they work. While you can’t really quantify goodwill from your employees (and their families), it can have an incredible effect on team morale.

Remote work changes the way employees and potential employees evaluate companies. While it’s great to work in a “cool” industry and have top of the line pay scales, most companies are in “boring” industries and have pay scales that are closer to average.

If you don’t want to be constantly competing on price for your development team, remote work is one excellent way to outshine the competition. As the practice becomes more accepted and common, your competition will be doing it, too. You are far better off making your competition react to you than you are being forced to react to them.

Remote Work … Works for Companies, Too

There are a number of valid business reasons to allow your employees to work remotely. In addition to the tremendous benefits to recruitment and retention, remote work allows organizations to be more resilient.

Remote work can also lower office space costs, reduce the amount a company spends on wages, and make it easier to compete with other companies without simply throwing money at the problem. Remote work changes employment from “just a job” to a way of creating a better life for your employees.

While allowing employees to work remotely is not the best choice for all companies, it can be a huge game-changer when it works for yours. The benefits of allowing it can be worth more than is initially obvious.

Chapter 3

Misconceptions About Remote Work

Have you ever discussed remote work with someone who has never worked remotely? How did it go? If they were like most people, it probably didn’t go all that well. It can be difficult for people to understand how someone could work from home, be productive, and end up being a normal human being at the end of the day.

Whether they are concerned about the quality of life that a remote worker can expect, assert that career growth is impossible while working remotely, or even comment on needing to have everyone on-site for “communication,” you’ll hear from plenty of cynics, you being an advocate for remote work.

While there are legitimate concerns about how businesses operate with remote workers, most of the issues people bring up are simple misconceptions.

You’ll also find that in addition to misunderstandings about remote work, there are many misconceptions about the people who work remotely. At some point during your career, you’ll have to face these if you want to be able to work remotely. While the mistaken assumptions of the general public are not your problem, your employer is a member of the general public. Any misconception that is widespread in the population is likely to be shared by them.

Rather than racking your brain or doing an internet search to help you address a misconception, all the answers are here so that you can refer to them when you encounter a skeptic.

There is another reason we are discussing these misconceptions now. As you move forward with your plan to build your remote working environment and convince your boss to let you use it, you should be aware of these objections so that you can design your workspace and systems to make as many of these objections invalid as you possibly can.

Quality of Life

When discussing the practice of working remotely, one of the most common strategies that people use to derail the conversation is talking about how remote work “harms” the remote worker.

While there are legitimate issues that can make remote work a risk to a person’s sanity and health, most of those are far more easily mitigated than similar risks in an office environment.

It’s common for people who dislike the idea of remote work to try and paint home offices as awful dystopias when the modern open office plan couldn’t even have been imagined by Dante when he wrote the Inferno. The modern office is only the preferred dystopia because it is a well-known dystopia, not because it isn’t a dystopia.

The arguments against remote work that discuss quality of life are fairly predictable and easily countered. In fact, these are so predictable that you’re likely to encounter most of them within the first six months of working remotely. I know I did, as did a number of my friends.

Such assertions also come up in internet forums as well, especially when managers are trying to understand why their employees might want to work from home.

Remote Workers Are Isolated and Lonely

One of the most commonly stated myths about remote workers is that they are isolated and lonely. Out of all the criticisms of remote work, this is the one that I’ve experienced the most. Essentially, the claim is that because remote employees don’t interact with their co-workers face to face, they don’t interact with anyone at all.

There are multiple, deeply false premises in this myth. The first is that people cannot interact effectively without being face to face. While remote employees are not constantly in the office with their co-workers, that doesn’t mean that they aren’t interacting.

In fact, remote interactions are often better because they are intentional. Rather than a random co-worker interrupting you to talk about last week’s game while you are facing an impending deadline, an interaction with another remote employee needs to be decided upon in advance and generally agreed upon by both parties. In contrast to disruptive office chatter and gossip, remote interactions tend to be more considerate and positive than in-office interactions.

There is another false premise within the notion that remote workers are lonely. When making the assertion that people are lonely because of the lack of office interactions, people tend to forget that the office environment is not the entirety of someone’s interpersonal interactions.

Generally, people have families, friends, and neighbors whom they interact with outside of work. Working remotely actually gives you time to interact with those people both during the workweek and possibly even during the workday.

Rather than driving halfway across the city to work at a desk and spending much of your “free” time staring at other people’s brake lights, working in a remote position allows you to interact more with the people you care most about.

The final false premise within this notion is that being alone is synonymous with loneliness. While many people can’t stand being in a quiet room by themselves, there are a large number of people who actually prefer to be alone. For those who prefer quiet and solitude, the typical open office environment is as uncomfortable as solitude is for the extrovert.

Remote Workers Are Overworked

Another common misconception is that remote workers have an excessive amount of work. Because the effectiveness of remote workers can only really be determined by their work product (instead of their presence), one might be forgiven for believing that a remote worker needs to complete substantially more work to meet management’s expectations.

This criticism has some reasonable elements. In organizations without formal evaluation processes, a dynamic can develop where remote employees are overworked in an effort to prove that they are effective.

However, in these organizations, the same dynamic also applies to the more efficient workers in the office. If an employee gets more done than other employees in the same number of hours, the lack of a formal process of evaluation will ensure that their efficiency is neither recognized nor rewarded. In this case, it’s the lack of formal processes in the office that are the problem.

One of the best things about remote-friendly companies is that they must have a more reasonable way of evaluating their employees simply to operate well. If the company is not operating well, it’s unlikely to be any better for those who go into the office.

Remote Workers Have Poor Work/Life Balance and Are Connected 24/7

Another common assertion that is made regarding remote workers is that they have no work/life balance, are available 24/7, and are constantly having their family time interrupted by work-related concerns.

As someone who has worked remotely quite a bit, I’ve rarely experienced this, and only when a tight deadline is approaching. It is short-term, directly related to a small, temporary problem and is usually followed by extended periods of time in which work/life balance is respected.

Like working in an office environment, working from home for most organizations will occasionally require you to work a few extra hours in response to an aggressive deadline or an outage or as a result of major changes in the team.

Similarly, just like being in an office, if you are frequently having to work long hours, that’s usually a sign that the company is doing something wrong rather than a characteristic of working remotely.

In fact, in a remote environment, excessive work hours are an even more sure sign of a pathological working environment than they are in an office, since the employees have more flexible working conditions and work hours. For instance, in an office, you might end up working a little extra because at least part of the day is not an effective work time for you or because of noise and other interruptions. However, if you are able to choose when you work, can carefully mitigate most interruptions, and work in an optimal environment, it’s a really bad sign if you still end overloaded.

Remote Workers Can Work Even When They Are Sick

Another common misconception is that remote workers can or should work while they are too sick to go in to the office. While most of us who work remotely have done so (especially when we were younger and thought ourselves indestructible), this is only occasionally true.

For the most part, if an employee is too sick to go into the office, they are probably too sick to work effectively from home. This doesn’t mean that you can’t try to work when you are sick, but it does mean that you shouldn’t be expected to do so.

Remote employees do have a few advantages when it comes to working while sick. In some cases, a medical situation may mean that you can’t reasonably drive into an office but you are still capable of working.

For instance, after hernia surgery, I was capable of working sitting up in bed within a couple of days but couldn’t drive for nearly a week. Being able to work remotely meant that had my absence been unplanned, it still wouldn’t have been an emergency for the team. As it was, I ended up working from bed because I was bored and moving hurt too much.

Even when working remotely, employment laws still apply. This means that employers generally will not force you to work while you are too sick to do so. However, you’ll have the option to do so if you feel that you need to. This can also help save your sick days for when they are really needed rather than wasting them simply because you have a light fever.

Home Offices Are Not Healthy, Ergonomic, or Appropriate for Work

When discussing remote work, another concern that is frequently brought up is that home offices are often considered to be poor working spaces.

Whether it’s about being crammed into a crowded closet to work, tables and chairs that are not ergonomic, or even that the environment at home is less healthy than in the office, you’ll hear this one a lot. And they have cause for concern, to an extent—repetitive motion injuries, back and neck injuries from bad furniture, and eyestrain from bad lighting and cheap monitors are certainly a risk.

However, this risk is easily countered. When someone works from home, all a company needs to do is make sure that they have, at a minimum, appropriate space and furniture to do their jobs.

It’s not much harder than making sure that people have decent working environments at the office. If a company is truly that concerned, it’s also reasonable that they supply at least some of the equipment that will be in use.

Additionally, because there is no stigma when a remote employee stands up and walks around in their own house, the risk of repetitive strain injuries can be lower than you might find in an office environment where everyone is expected to stay at their desks and look busy.

Remote Workers Become Socially Awkward

A final quality of life issue that will come up in discussions of remote work is the notion that remote workers will become socially awkward over time from being isolated. As explained before, remote work doesn’t really imply isolation, especially not to the degree that would cause someone to lose social skills.

On the contrary, working in an office may well result in developing a degree of social awkwardness. Think about the average open office work environment of today. It’s filled with people pretending to work while trying to drown out the noise from everybody in the room.

It leads to an environment where everyone wears headphones and uses email and chat to communicate, even with the person at the next desk. People in such environments often grow to resent those around them.

Compare the actual reality of the average development office to that of the average home workspace. While neither situation is likely to result in someone sitting on a beach in a loincloth, yelling at a soccer ball on a deserted island like Tom Hanks in Cast Away, the average office environment seems more likely to produce frustration and irritation with co-workers.

Social isolation is not a function of where you work. It’s a function of how you work and your personality.

Career Growth

Another type of concern over remote work has to do with the career options of remote workers.

Like the concerns about the health and wellness of employees, concerns about the quality and longevity of employee careers are legitimate. However, these concerns often come out of an antiquated understanding of the normal career trajectory of developers and other IT professionals.

Decades ago, a recent college graduate could expect to get a job and stay in it for many years, possibly even retiring from the company. In such a scenario, it was expected that career progression was a concern of the employer as well as the employee.

However, that model of employment has been gone for years. Nobody expects to be employed by the same company for 40 years any more, but the expectations around career growth have not caught up to the reality of modern employment.

Rather than the employer being deeply interested in the career trajectories of their employees, the current model suggests that the employees are on their own. Any criticisms of remote work from the perspective of career growth must take this new paradigm into account.

Remote Work Damages Career Growth

You’ll often hear people state, without evidence, that remote work inhibits the ability of an employee to develop so that they can be promoted. Out of all the criticisms of remote work in this section, this is the only one that has some merit.

It’s not that you can’t learn what is necessary for the next stage of your career remotely but that it’s difficult to conduct all the spontaneous social interactions that may be needed to impress management enough to promote you without being in the office.

However, this is changing. With remote workers in the mix, the older methods of employee evaluation don’t work as well anymore. As time goes on, the processes for determining who should be promoted will also be forced to change.

In fact, this is already happening at many companies that are largely or fully remote. Furthermore, as the workforce becomes ever more likely to change jobs with greater frequency, the social impression you make at any one company is of decreasing value compared to the real business results you can prove.

It’s also completely possible to develop your interpersonal work relationships without being face to face all the time, though it’s certainly harder and must be done intentionally.

In other words, while there is certainly reason to be concerned about your ability to grow as a remote employee, these problems can be mitigated. In addition, being able to handle interpersonal work relationships properly is necessary to maintain the quality of your work relationships anyway.

You Can’t Train People Remotely

You’ll also hear that it is impossible to train people remotely. The idea is that everyone has to be in a room together to learn how internal systems work or that everyone has to attend work-provided training.

Essentially, when someone says this, what they are really implying is that they have no way to effectively train people remotely, nor do they have any way to record their training for future use, because either of those would go a long way toward training remote employees.

Not only are these things doable, but this assertion makes assumptions about how training and documentation that are actually bad for the company in the long term should work.

Imagine, if you will, a company that isn’t remote, that requires all new employees to go through training sitting down in a room together. This causes a number of problems for the company.

First of all, it slows down the onboarding of new employees because it is dependent on a room being available and someone being available to teach in it. Secondly, onboarding documentation is one of the most valuable types of documentation you can have if your company is growing quickly—you’ll eventually have to have onboarding resources for new employees even in a nonremote company, simply to make sure that everyone gets the same level of training.

Finally, people don’t perfectly absorb information that they are shown during onboarding, so you really should have these resources on hand for review anyway.

In essence, the inability of a company to train their employees remotely points toward other problems that will hamstring that company’s ability to grow. Like many other objections to remote work, this one is a result of bad processes that will eventually cause problems in a fully on-site company as well.

You Can’t Conduct Employee Evaluations Remotely

Another criticism of remote work that you’ll hear is that it makes annual or semiannual employee reviews more difficult. It is true that it does make it more difficult for some managers.

However, that’s offset by the number of managers who are comfortable with conducting reviews over the internet. The technology for successfully conducting reviews is inexpensive, widely available, and easy to use. Most of what happens in an in-person interview can just as easily happen over the internet using video conferencing software, and coding demonstrations can easily be done using screen-sharing technology.

For those who are currently managing teams, remote reviews are something that is going to become more common. Such reviews come with benefits for the manager, especially in regards to the flexibility of scheduling.

As it is, many managers are constantly running between meetings, sometimes in different locations. If an interview can be done remotely, it’s a lot easier to schedule without having to worry about being in the same place as the interviewee. It’s worth figuring out how to do it well.

As a manager, you need to prepare yourself for a future where remote work is more common and where managerial processes have to be conducted without the other party in the office. It’s very risky to your career to be fixated on just managing teams in a single location when the future seems increasingly unlikely to work that way.

We Can’t Accurately Measure the Performance of Remote Employees

One recurring problem with remote work is that it forces organizations to change the way they evaluate employees. Rather than the old school “butts-in-seats” style of evaluation, you have to actually evaluate employees based on the value they provide.

This can be a difficult transition, as management in many organizations is more influenced by gut feeling and face time than it would like to admit.

It is, however, a necessary transition. Much of current management practice is rooted in practices from the middle of the last century. Back then, it made sense because the amount of work completed typically correlated directly with the amount of time spent in the office.

Now, however, that is not the case, especially in knowledge-heavy disciplines involving technology. In the modern era, employees are often thinking about work outside the office.

Further, many are disengaged and thinking about something else while sitting at their desks. In short, your ability to judge employee performance as a manager is absolutely terrible if you are simply relying upon presence in the office as a measure of productivity.

Under this system, the same situation that keeps you from measuring the performance of your remote employees also makes it difficult to accurately measure the performance of your on-site employees.

Such a setup not only means that you are undervaluing your best employees, but it also tends to mean that the best employees will leave while the worst stay. If you are doing this, you are risking the health of your entire company over time. In fact, this result is so common that they call it the Dead Sea Effect.

Remote Workers Can’t Learn From Their Co-Workers

Another common misconception is that remote workers can’t learn from other workers in a collaborative sense. Frequently, when discussing this, people talk about the value of overhearing conversations in the office.

While there exist a lot of apocryphal stories about how someone overheard something and was thus able to solve a problem in the office, think back to how frequently you’ve seen that happen compared to how frequently you’ve seen a productive co-worker interrupted by random chatter in an office environment.

The assumption that remote workers are entirely isolated from their peers is in play here as well. However, as we’ve seen, that’s not the case.

Remote employees can, and should, collaborate with their co-workers as needed to get their jobs done. This collaboration also tends to be of a higher quality than similar in-office collaboration for a variety of reasons, not the least of which is that it doesn’t disrupt everyone else who happens to be around the “collaborators.”

Remote collaboration has to be done intentionally, with respect to the focused working time of the involved parties. It takes a lot more upfront effort to schedule a call than it does to simply walk over to someone’s desk. Consequently, people tend to be more considerate and more prepared before they interrupt someone else’s work.

It also tends to drive people to respond to questions using email instead of verbally, creating a much better “paper trail” of the informal decisions that were made. Not only does this help later on when trying to determine why certain decisions were made, but it also means that interruptive communication styles are only used when they are needed rather than just when they are preferred by certain people.

You’ll find in many offices that one or two people prefer interruptive communication styles and force their preference on everyone else. It’s an especially bad problem in open office environments where the productive, but easily distracted, find themselves continually interrupted by people who could have just sent an email.

Remote Workers Have No Control Over
Their Projects

A concern that workers might have about going remote is the idea that remote workers have less input in regards to project scope, project design, and distribution of workload. In reality, this is not the case, as the remote workers are still just as involved as the on-site employees.

This is a valid concern, as some companies tend to treat their remote employees as second-class citizens, telling them that they are only interested in their results, not their input.

Such practices are a really bad idea at an organizational level, especially in an agile or “agile-like” environment, where employee input is considered critical to the success of the development process as a whole. It is very rarely an intelligent decision to play favorites with employees, and this remains true even if some of them are remote. Such a setup leads to resentment and to the best people leaving while the worst learn to play politics.

If companies want to keep good employees around, the employees need to have some say in how their work gets done. This is also true for remote employees. While the latter might stick around a little longer because it may take a little longer to find a remote job, it doesn’t mean that they won’t think about finding something else if they are left out of major decisions that impact their lives.

Remote Managers Can’t Manage
On-Site Teams

Another misconception is that remote managers can’t manage on-site teams. Sometimes this comes up as a reason why a senior developer shouldn’t want to work remotely, as it may mean that they will be passed up for a promotion.

Since managers often require frequent communication with the people reporting to them, it’s not really surprising that this misconception comes up from time to time.

Management is also a bit of a culture shock, especially in your first management position and particularly when compared to the focused workday of the average information technology professional.

It’s common for a manager’s calendar to have so many meeting blocks on it that it looks like someone lost a game of Tetris. This sort of schedule requires a lot of interaction with the rest of the team, so it can be difficult to accomplish remotely in the traditional fashion.

However, remote managers don’t necessarily have to have as much direct, face-to-face interaction as their in-office counterparts. Much of on-site managerial interaction is face-to-face because that’s the easiest way to manage people in some of those environments, but it’s also one of the reasons that remote work improves employee productivity. The style of your typical on-site management makes it likely that people will be interrupted while they are trying to focus.

The aspiring remote manager should use the tools and processes of the remote team for monitoring. Instead of just walking over to someone’s desk to ask a question, they should ask the question using email or chat. Instead of stopping by to get a status update on a project, they should collect that during a brief morning “standup” meeting or with a daily reporting email.

Followed assiduously, this approach means that the manager stays out of the way of the team. This can mean that remote management actually improves on the productivity of an on-site team simply by embracing a non-interruptive workflow.

Communication and Culture

Companies are also concerned about what remote work will do to their internal methods of communication and the resulting company culture. While people will happily join a company for higher pay, better benefits, and more interesting work, a toxic or dysfunctional company culture can drive talent away.

Broken and dysfunctional company cultures are hugely expensive and can even be a threat to the long-term existence of the company. Not only do they cause good employees to leave, but they also tend to create a lot of friction for anyone who stays.

Therefore, it’s no surprise that managers and company officers are deeply concerned about what remote work might do to their internal company culture. In this section, we’ll go over some of the common concerns along with how to mitigate them effectively.

Research has shown that remote workers develop weaker relationships with their co-workers than those who are in-house. This largely occurs not because of the lack of interaction in remote environments, but because steps are not taken to help nurture good working relationships between employees.

While some of the objections do have a basis in reality, one of the main reasons for thinking through objections to remote work is to avoid having to react to them. Instead, you want to minimize discussion of objections that are reasonable and direct people toward objections that can easily be disproved with data.

Remote Work Means That You Can’t Do Team-Building Exercises

One thing I’ve heard from managers when discussing how remote work impacts their team is the notion that team-building exercises are difficult to conduct remotely.

Whether it’s a formal trip or just the team deciding to get lunch together, most managers prefer their teams to exhibit some degree of camaraderie, simply to make it easier for everyone to work together.

It’s clear that the classic model of team building is not going to work when people aren’t coming into the office. This doesn’t mean that team building can’t be done, but it does mean that you have to do it intentionally and in a way that takes remote team members into account.

There are a number of activities that you as a manager can do to formally help your team bond with one another, from quizzes to competitions.

Additionally, for the informal team bonding, you may simply want to have team members occasionally come in to the office or to another location. Your company is already saving money by allowing employees to work remotely, so you should have some funds available to fly people in if you must. Many companies have formalized this by having team retreats.

You should also be doing more to encourage informal employee interactions whether it’s by allowing people to have information conversations in a “breakroom” in your chat client or by allowing and expecting employees to chat amongst themselves during the day. So long as these conversations are not disruptive to work, they will help with team-building.

Meetings Are Harder and Less Effective With Remote Team Members

Another management concern when remote work is discussed is that meetings can be more difficult to do well when some or all of the team is working remotely. In my personal experience, this is one of the most irritating things to deal with, whether you are on-site or remote. Meetings themselves are bad enough without adding any other problems to them.

Technological issues have always been a plague on meetings with remote attendees. Whether due to software flakiness, people having trouble connecting, or even audio issues in the room, nearly every meeting seems to start with some level of frustration as the team tries to get to the point where they are actually able to communicate.

While this is absolutely a downside of remote work, there are things companies can do to mitigate this problem.

First, companies can minimize the number of meetings and their length. As anyone working in an office will tell you, very few meetings are conducted efficiently, and a lot of them are completely unnecessary in the first place. This is worth fixing even if your entire team is on-site.

Secondly, for remote meetings, you can’t just walk into a room and think everything will work on short notice. It’s great if it does, but that’s simply not the current reality with technology.

Instead, you need to set expectations that everyone will arrive a little before the start of the meeting so that there is time to get everything working without cutting into the time allocated to the meeting. Even if not everyone can arrive early, you’re still more likely to start on time if most people arrived early enough to troubleshoot their audio issues beforehand.

Another issue that crops up is that remote workers often can’t hear what is being said by people in on-site meetings due to bad acoustics in the meeting room. Generally speaking, the same bad acoustics make it harder to hear other people even if you are in the room. These bad acoustics also mean that customers and strategic partners can’t hear you either when you are calling them.

While an extended discussion of how to fix acoustics is outside of the scope of this discussion, most conference room acoustic problems can be corrected by having carpeted floors, sound-absorbing ceilings, and decorations along the walls (such as bookshelves full of books) that will keep sound waves from bouncing around the room. It’s easily fixed.

On-Site Employees Will Be Jealous of Remote Employees

Another issue that can occur is that employees who are stuck on-site will often become jealous of their remote co-workers. Working remotely is a huge perk, and it can lead to jealousy if distributed unequally.

Further, while many jobs can be conducted remotely, it’s entirely possible that not every job in a company can be done remotely in an effective manner.

For instance, companies involved in manufacturing may be able to move some work off-site, but anything requiring use of heavy equipment will have to remain on-site. Therefore, it’s possible that the people who have to come in to the office will feel jealous of those who don’t have to.

A lot of this depends on management. Frankly, jealousy still happens even if everyone is in the office. It occurs either because one group of people is treated with favoritism or is perceived as being treated that way. While having part of the staff working remotely is certainly an issue here, it is not the issue.

As a manager, you need to make sure that your employees don’t feel like you are playing favorites. Whether that is due to your in-office friendships creating jealousy or whether it is because some employees can work remotely, as a manager, you do have the responsibility of making sure that such issues are smoothed out.

Remote Workers Don’t Communicate Well With the Team

One thing I worried about as a manager of remote workers is that they might stop communicating with the team in a timely fashion. When someone is working remotely and doesn’t respond to an email, you can’t just walk over to their desk.

While this can be an issue with remote employees, it is just as common in on-site employees. Proper communication is critical regardless of where employees are located, and there is no excuse for remote employees failing to respond in a reasonable amount of time.

However, there is another issue here. It’s very common in office environments for people to wait until the last minute to send an email with the expectation that the person on the other end will drop whatever they are doing and respond. This is inappropriate and is not a problem with the recipient.

In an office environment, you’ll often see the sender of a last-minute email walking over to the recipient’s desk to ask “Did you get my email?” Preventing this sort of idiotic interaction is one of the reasons that allowing remote work is advantageous.

Allowing remote work means that those who don’t plan ahead have to deal with the consequences of their behavior rather than force the consequences on everyone else.

Allowing people to work remotely does not mean that management doesn’t need to set appropriate expectations for communication. If someone truly has to respond to emails within an hour, then that needs to be communicated to the employees. Most objections to remote work communications are the result of failed managerial communication of expectations.

Team Relationships Don’t Occur Remotely

Another common criticism of remote work is that friendships (and good working relationships in general) in remote teams don’t form as easily. This is also true. It does take real effort to build solid working relationships with other members of remote teams, especially when there is enough geographical separation that the team seldom experiences in-person interactions.

However, this criticism betrays an underlying premise that is largely false. That is, work friendships are necessary for a smoothly-running company. While it is certainly true that organically developed work friendships can significantly help a company, a lot of the benefit is due to the creation of informal processes.

If you think about good working relationships that you’ve seen between co-workers in the past, one thing that is almost always present is that both parties know how the other party works and thinks. This drives them to dynamically appropriate behavior when conducting business operations.

While I don’t intend to dismiss the value of good working relationships, at least some of their benefits can be realized by simply implementing clear processes for how systems should work and how employees should interact.

This has the added bonus of making it much easier to train new employees, as they can refer to written documentation rather than constantly asking existing employees for help (and possibly being less effective if they don’t “fit in” with the existing group).

Additionally, if your company keeps a Slack channel or other chat application open to employees, you’ll find that a surprising number of work friendships develop anyway.

Human beings are social animals and will develop friendships even across distances. It simply happens more slowly than it would with face-to-face interactions.

You Can’t Get a Hold of Remote Workers When You Need Them

Another common fear of managers when discussing remote work is that they may not be able to get in touch with remote employees when they need to do so. While one could reasonably argue that this is a feature, not a bug, that’s probably not the best way to debunk this particular concern.

Instead, it’s important to focus on why managers feel that they may need to get in touch with a remote employee on short notice. There are a number of reasons why this might be the case, especially for technology-facing positions:

- Many companies have development and other staff who are pressed into system maintenance and support roles. Because systems don’t tend to break at convenient times, management may have a legitimate concern that a remote employee will simply refuse to communicate if the system fails at a bad time.

- Many companies have poor scheduling practices in general, with management deciding on meetings with little warning. A remote team makes this harder and forces management to act in a disciplined fashion, which some managers don’t like very much.

- Some companies are early in their developmental stages and are rapidly changing their requirements in response to their customers or investors.

- Some companies are still stuck in the mindset that productivity is measured by “butts in seats,” and their concern about being able to contact their employees is based around “checking in to make sure they are working.”

- Some companies bill their clients based on the number of hours that their employees spend doing the work. If the employees are slacking off at home and out of reach, that essentially means that the clients are possibly overpaying.

While these concerns are all legitimate, much of the fear about being unable to reach remote workers is overblown. For most jobs these days, you are required to be connected to your co-workers anyway, just to get things done.

Rare indeed is the position that allows you to completely disconnect for days at a time with no human interaction. More than likely, if someone can’t be reached during an emergency, they were probably unreachable before the emergency.

The latter is a problem that should be handled before an emergency situation occurs, since it indicates that someone is not communicating effectively with the team.

Practical Matters

In addition to the usual points about how “remote work is going to ruin your life, career, and the company,” there are also some practical business concerns that come up when remote work is discussed.

While you personally may want to work remotely, your organization still has to be able to run effectively. The functioning of the organization will always be a much higher priority to your boss than your personal happiness, so you need to be able to address management’s concerns about business operations.

Not only does being able to handle concerns about business operations make it more likely that you’ll be allowed to work remotely, but it also changes the conversation from being about what you want to being about what the company needs.

Remember, you want to sell the idea of working remotely based on what it can do for the company, not based on what it can do for you. It’s far easier to negotiate with most people by negotiating based on self-interest rather than charity.

Remote Work Increases Costs

Management may be concerned that remote workers will increase costs. This can be in regards to anything from requiring additional VPN connections and the bandwidth to support them, to additional work that has to be done for regulatory compliance with remote employees. The sad fact is that there are additional costs to enable remote work in a secure fashion, especially when you consider things like VPN clients with per-seat licensing, additional security requirements, and possibly additional software licenses.

However, for fully remote employees, the additional costs are offset by the money saved by not having to have a physical office for the employees in question. If employees are only partially remote, however, this is still a problem.

In this case, instead of debating costs, it’s often better to point out that such expenditures will need to occur anyway in order for the company to be resilient to things like weather events and other natural disasters. While you may need things like VPN software licenses for remote workers, those things are also required for those same workers to be able to work remotely in the event of inclement weather.

Because business continuity is a major concern for most companies, it’s often helpful to point out that remote access to systems is going to be necessary in the event of major disruptions to business. In essence, these costs need to be paid anyway, and remote work has little to do with it.

Remote Work Constitutes a Security Risk

Many companies are rightly concerned about the potential security issues posed by remote workers. While corporate networks tend to be locked down with active threat scanning and restricted access to dodgy websites, doing the same for the home computers of employees is not so simple.

For one thing, if an employee is using their own machine for remote work, they probably don’t want corporate snooping, nor do they want to lock their machine down using the same kind of policy that their company might use.

For instance, many companies don’t want their employees using streaming video services during the workday both because of the cost of bandwidth and because of the sort of problems that this traffic poses (lots of it is porn, pirated movies or at the very least, videos unrelated to work).

Additionally, home computers may not have the most recent security patches, might be used by third parties who aren’t employed by the company, or may be infected with viruses and other malware. When these machines connect to an improperly configured corporate network, the result can be anything from the spreading of an infection, to taking down the entire system and causing data loss.

The implications for corporate security are profound and terrifying to security and compliance staff. And that’s before the company considers what happens when home computers are stolen and used maliciously elsewhere or what happens when an employee is fired.

However, much of the concern about security from home computers joining the corporate network is exactly the same set of problems that you have in an office when a less responsible employee is using a company computer. It’s also the same set of problems that occur when employees (such as executives and salespeople) take a company laptop to a trade show or a client’s office.

When such laptops return, it’s entirely possible for them to be compromised in some fashion, which means they can cause havoc on improperly secured company networks. In effect, if you have people who leave the building with a company laptop, you already have security concerns that are very similar to those you have with remote employees.

A long time ago, companies could secure their networks by simply having a firewall at the perimeter with strong policies about what could get into or come out of the network. Those days are long gone, and in most networks you are probably safer to assume that any traffic on the network is potentially hostile.

This means that network personnel have to lock down and protect company machines individually as well as securing the perimeter of the network. As a result, many of the security concerns posed by remote workers should already be handled as a result of properly securing the network. In effect, the company must lock down their critical internal infrastructure regardless of whether people work remotely or not.

If the company doesn’t want to properly secure the network, then it’s only a matter of time before they have a major breach regardless of whether they allow remote work or not. While some degree of security preparedness is required on the computers of the remote workers, the critical part of the security equation is the protection of sensitive systems and data, most of which do not need to reside on employee workstations.

Remote Work Decreases Productivity

Another common theme you hear when discussing remote employees is the concern that remote employees will be less productive than on-site employees. While this is certainly possible, especially if the employee is not using their time effectively, it’s far from universal.

The best way to counter this objection is to slowly build up a substantial amount of proof that shows that this assertion is unfounded. It’s easy for people to derail these discussions with “what if,” but it’s a lot harder to dispute data that indicates the opposite of their viewpoint.

Later on, we’ll be discussing some strategies for making sure that data is available before having this discussion, but essentially the idea is to prove that you can work remotely on a very limited basis before arguing that you should do so more often.

Additionally, one thing people fail to consider when discussing “productivity” is the actual meaning of the word in the context of the business. For far too many, “productivity” tends to mean “butts in seats” instead of something that actually drives the business forward.

You will need to agree on what “productivity” actually is and how to measure it before you can really have this discussion. A word to the wise: Most management you end up dealing with doesn’t have a very useful definition of it either.

Remote Workers Can’t Work Without an Internet Connection

You’ll also occasionally hear managers assert that remote employees can’t work without an internet connection. Depending on the tools you are using, this is possibly entirely true. However, neither can the people in the office. Internet access is almost as essential for productivity in most tech jobs as electrical power is.

So the real issue here is the stability of the home internet connection to the open internet and the stability of the office connection to the internet. If either of these fails and internet interactivity is required, then the remote workers won’t be able to get their jobs done. It’s also very true that home internet is often less reliable than office internet.

While it is reasonable to consider internet access to be a risk when people are working outside of the office, it’s important to realize that relying on stable internet connections is probably riskier than you might think.

The office internet could easily go out or the internal network could be disrupted. If so, does the business continue to function? If not, then remote work has little to do with it—you just have a bad risk profile in regards to internet access.

If, however, on-site employees can effectively work without internet access but remote employees cannot, it’s up to management to figure out why that is.

Are there resources on the internal network that are unavailable to the remote employees if the network is down? Do you rely on remote employees using a VPN and then remote desktop to connect to the machines to work? If so, then yes, you have a problem.

However, that same problem also poses a risk to continuity of business if your office becomes unusable. In other words, a company’s ability to support remote employees is indicative of their resilience in the face of natural disaster, damage to a building, and the like.

It’s important not only to handle this but to frequently test it to make sure that your backup plan still works—remote employees are a good way to test this every single day.

Remote Workers Still Have to Come in Occasionally, What Then?

Another concern crops up when remote workers have to come into the office. Whether it is for quarterly meetings, face-to-face reviews, or training, it is common for remote staff to have to come in at least on occasion. When they do come in to the office, here are some examples of the issues that need to be resolved:

- Where will they sit?

- What equipment will they be using while on-site?

- How will they be productive while they are in the office?

- How will they get to the office (and what will it cost) if they live out of range of an easy commute?

- How much disruption will the remote workers cause for the on-site employees?

These concerns are valid. It’s unusual for a position to be truly 100% remote. What is more common is some mix of remote and on-site. This can be anything from employees working remotely on occasions when they need to do so to a job that is remote except for a yearly on-site visit.

When remote employees come in, they are going to need a place to sit, equipment to use, a way to get there, and the ability to be productive.

One way to mitigate this problem is to make sure that the trips into the office are actually necessary, and are limited in scope and time. This makes it far easier to schedule appropriate resources and to limit the amount of disruption that the on-site employees experience.

Many of the disruptions caused by remote employees coming on-site are caused by a lack of preparation, unclear goals for the visit, or by not having a good idea of what tools will be available on-site. This is easily handled with good planning.

A recurring theme when discussing remote work is how it forces companies and individuals to plan ahead, have clear goals, and make better use of the resources they have available.

Remote Workers Are Difficult to Manage

Managers are often concerned about remote employees because they can be harder to manage. When you don’t see someone face-to-face every day, it can be difficult to gauge how they feel about their job, how heavy their workload really is, and what, if anything, is bothering them.

Due to the lack of informal conversations, it is easy to be surprised when an employee is not doing well. This can lead to losing good employees because of perfectly preventable problems.

In effect, this can be an issue only when management collects information simply by walking around and talking to people. While this is helpful in an office environment, there are two issues with it.

The first is that it ends up being highly subjective, with managers not collecting good metrics on employees. The second is that such a process often misses performance problems until those problems have become so severe that they can’t escape notice.

Good management practices require some ability to collect and process metrics on employees in a dispassionate manner. This is true of both on-site and remote employees. The difference is that with remote employees, managers aren’t able to use the more error-prone and subjective measures of employee performance.

You might think subjective measurements, while not accurate, don’t constitute a risk to the company, but they can actually be extremely risky. Not only do you risk losing your best people while promoting the incompetent, but there is also the risk that you can easily appear to be discriminating in some fashion.

If you don’t have objective metrics to back up your decisions, it’s going to be a lot harder to prove that you weren’t discriminating. In yet another example of a recurring theme, allowing people to work remotely forces businesses to use good practices that can protect them from problems down the road.

Every Company Needs an Office, Eventually

Another practical excuse that you hear when talking about remote work is that “every company needs an office, eventually.” While this was true at one point, it is no longer the case for an increasing number of companies.

As technology and management practices evolve, the need to have everyone together in the same building decreases. For many companies, there is no need to have a single office at all, and for the rest, the trend points toward further decentralization, lower rents, and no office.

It’s easy to miss trends like this, especially while running your own business. I’m turning 40 in October 2019, and I can remember a very well-known billionaire businessman saying that investing in the internet was not a good idea and that people would lose a lot of money messing with it.

He was right in the short term, as the market crash in the early 2000s proved. However, over the longer term, his earlier statements have proved to be incorrect. The same guy has even walked back from these statements himself and has since come to regret not buying stock in Amazon and Google years ago.

While it’s easy to pick on a single investor, realize that this is one of the most plugged-in people on the planet in regards to his ability to see broad industry trends and react to them. He still missed some very profound and long-term trends. Your manager doesn’t even have that much information and is similarly ignoring a trend line that is already making itself apparent in many places.

Jealousy and Ad Hominem

This is the final category of arguments that is brought to bear when remote work is suggested. Not only are all of these completely wrong, fear-based, and vaguely insulting, but they are also often the first to come up. You will be dealing with these objections frequently as you transition toward a more remote role.

These arguments are especially pernicious because they have little basis in fact and are designed to put you on the defensive. Think about how many arguments you’ve won while being on the defensive—probably very few. In other words, this is a tactic to shut down the discussion, and you’ll have to learn how to counter it if you want to take advantage of the kind of positive life changes that remote work can bring.

Remote Workers Spend All Day in Their Pajamas

Whenever remote work comes up, what most people say first is something regarding spending all day in your pajamas, not having to wear pants, or not even bathing.

This is a very strange assertion when you think about it, given that no one makes similar assertions about weekends or vacations. Odds are pretty good that when you started wanting to work remotely, “pantlessness” was probably not highest on your list of concerns. While you can wear more comfortable, casual clothing to work at home, this particular phrasing is unusual.

Most remote workers will, at some point, fail to change out of their pajamas or even clean up well before working. Initially, they may think “why does my appearance matter if I’m not getting on a call?”

If you are anything like me, you’ll also notice that you are somewhat less effective and easier to distract when you do that. Dressing at least somewhat appropriately for work is actually a pretty good way to draw a solid boundary between the way you conduct yourself while working and during leisure time.

You learn pretty quickly that being sloppy while working at home leads to sloppy work done at home, and most people seem to realize that being sloppy is not really sustainable.

When a person tells you that remote employees don’t have to put pants on when they work from home, you should ask them if that is what they would do if they were in that position. Their assertion may be a projection of what they probably would do in that situation, or it may be something that they just picked from the culture and haven’t really thought about.

If you need a rough estimate of how often people repeat things that are false but sound witty, listening to the average person talk about politics for 10 minutes should demonstrate that it is a common phenomenon. It’s no less common with emotionally charged topics in an office environment.

It’s very difficult to convince someone that remote work is a good idea without evidence to back you up. The misconception that remote workers are slobs is a prime example of it. Before you have a conversation that might end up with this as a discussion point, it’s a good idea to already have some data that backs you up.

Later on, we’ll discuss how to do just that. In the meantime, it’s best to avoid bringing up the subject with people who might use this style of objection to dismiss the idea.

Remote Workers Watch TV All Day

Another common misconception is that remote workers watch TV or are otherwise distracted all day. While it’s certainly possible that at least some workers do this, it isn’t particularly common for a variety of reasons.

In the first place, it’s hard to be productive at an acceptable level when watching TV at the same time. Unlike an office environment where someone can essentially goof off for hours as long as they stay in their cubicle, when you work at home, the only real indicator of your work ethic is what you get done.

This tends to put pressure on remote employees, causing them to work harder to make sure that it is obvious that they are being productive.

Additionally, it’s generally a better practice to have completely separate areas for being entertained and doing work. This not only keeps you from being distracted by entertainment while working, but it also lets you relax when you aren’t working rather than letting work seep into your personal time.

From working remotely off and on for years, I can tell you that you are far more likely to have work intrude into your personal life than the other way around when working from home.

In fact, later we’ll be discussing why a solid boundary between work and home is even more critical when you work out of the house. Overworking from home is a much more serious and likely problem than underworking from home, provided that you already have a decent work ethic and are motivated to do your job.

Remote Workers Shouldn’t Get the
Same Salary

Another common tactic used to stop discussion about working remotely is the implication that a remote worker should not be paid the same as someone who comes into the office even if they complete exactly as much work. While this sounds valid on the surface, it’s pretty easily disarmed.

When this comes up, ask the person making this statement whether the extra effort of physically coming into the office actually provides value to the company at all. Remember, by the time you are having these conversations, you should already have evidence that you can work remotely at least as effectively as you can in the office.

So if the same work is being accomplished in either location, what is the business value of forcing everyone to undergo an unpleasant, stressful commute while wasting time and gas?

You see, if the same amount of work is being accomplished while improving the lives of employees, reducing turnover, and making the company more resilient, there really needs to be a good reason to pay more not to have those things. It’s pretty simple.

What If They Are Just Playing With Their Kids Instead of Working?

Sometimes, managers worry that remote workers with kids will be spending their entire day playing with them instead of working. While there is probably some legitimate concern that people with very young children may spend an inordinate amount of time caring for them, it’s not much of a concern for older children.

If you have very small children, you probably do need to make sure that there is appropriate child care for them. You cannot deal with all the interruptions posed by very small children and manage the sort of productivity your employer will be expecting of you.

I don’t mean to downplay the large amount of value that parents can bring to the table remotely, but you will have a lot of problems if you try to work remotely for an extended period with small children and no child care. On the plus side, your children will still spend a lot less time in day care than they might otherwise simply because you don’t have a commute.

When your children are old enough to not need constant close supervision, you can probably get away with having them in the house while you work. Depending on their age, you may need to check on them frequently, but it’s very doable by the time they are 7 or 8 years old, in most cases.

However, the practicality of working remotely with children in the house is not the real issue when someone brings this concept up. The real issue is that they are concerned that you will not be efficient and productive when you are working remotely. Once again, you should already have some evidence that you can be productive remotely under normal circumstances before having a conversation that heads in this direction.

When you present proof to someone that you can work effectively from your house while your children are there, it’s not a good look for them to continue pressing the issue, as it gets very close to the sort of discussions that HR doesn’t like.

In this case, if you’ve proven that you can work well from home even with the kids there, someone continuing to press the issue can easily look like they are discriminating against you for having children.

Once you have solid proof of your work ethic, they are going to find something else to go after. One of the main reasons for thinking through objections to remote work is to avoid having to react to objections. Instead, you want to minimize the number of objections that are reasonable and direct people toward objections that can easily be disproved with data.

What If They Are Working for Someone Else and Billing Us?

A lot of companies are concerned that their remote workers may be working on their own projects or contract work for another company while they are on the clock. While there are security and intellectual property concerns in this area that we discussed earlier, this particular objection tends to be more focused around the idea that you are billing two companies at the same time for work.

This one is pretty easy to counter. If I can do two jobs at the same time and have a decent life working from home, that means that the office is destroying productivity at such a level that people are engaged in productive work less than half the time they are there.

This isn’t an argument for making everyone stay in the office. Rather, it’s an argument for sending everyone home where they can work more effectively. Unless you believe that your entire workforce will either be working halftime or working two jobs, such an exercise will quickly show what a real “day’s worth of work” actually is rather than whatever it currently is considered to be.

Even if an employee does find time to start doing work for another company, exactly the same thing can happen on the clock at the office. I’ve worked in multiple companies where people were working on their own stuff while supposedly “working” for the company. I’ve seen people spend hours talking on the phone about their side business or even trying to get co-workers and clients to spend money with them.

The real truth is that lots of people are going to have a business on the side. Whether it is consulting, selling some kind of product, or even the typical multilevel marketing scam, a pretty sizable portion of employees have a second job.

Not only are they likely to have something else, but the employer is unlikely to be able to stop it or even detect it if they are moderately careful, even if it is happening in the office. This is especially true given how many people bring fairly powerful smartphones into the office these days. Given this, a smarter reaction is to allow them to work from home and carefully monitor to make sure that they are getting their work done.

If they are, they will value their day job more highly than they would if they were made to go into the office, since a commute will waste time that they need for their second job. In effect, instead of the company assuming that they can control whether their employees are doing something on the side, they are setting things up so that the employees can successfully have a side business.

While counterintuitive, this approach means that barring their side business becoming a full time business, they need to make sure that the employer remains happy with their productivity in order to keep both their day job and their side business. This approach offers better leverage to the employer while allowing the employee to pursue the kind of life they want as well.

All of the previous arguments assume that the employer can adequately measure their employees’ performance at work. If they can’t do that, then they may well have people working for someone else on the clock even while in the office.

The Subtle Art of Countering Objections to Remote Work

It’s easy to counter objections to remote work if you know how to do it. Misconceptions about how remote workers get their jobs done are widespread and usually very poorly argued. With just a little bit of effort in advance, you will be better prepared to handle objections to remote work than the average person.

Additionally, as you become more aware of common objections to remote work, you should begin thinking of ways to counteract those objections by improving your own work environment, skills, and processes.

Remember that when someone objects to an idea, that doesn’t mean that they are unwilling to consider it. It simply means that it is going to take more work to convince them. Since working remotely is a fairly new concept, that means that a lot of upfront work on your part is going to be necessary to make a good first impression of remote work on them.

Chapter 4

What You Need for Effective Remote Work

If your boss is allowing you to work remotely, you may be able to do so with just your computer and other home equipment. However, that could be a bad idea.

When suggesting remote work for the long term, the idea is not only to be allowed to do so for a single day but to prove that remote work is an improvement over in-office work. If you want to do this effectively, the last thing you need is to have an equipment failure or other foreseeable problem occur. Not only will such an event be stressful, but if things go badly enough, you may ruin your employer’s impression of remote work.

To prepare effectively for remote work, you need to make sure that your home work environment is at least as good as, if not better than, your on-site work environment. Doing this well makes it more likely that you will be allowed to work from home in the future, while prepping badly is worse than not doing it at all. Remember that this experiment in remote work will be visible to management and may well color their perception of remote work for a long time. When I’ve suggested remote work in the past, I’ve had management relate stories that were at least 10 years old, and that’s a terribly long time to wait to overcome a bad impression if you haven’t prepared properly.

Remote work takes more than just the right equipment. You also need to make sure that you have an adequate workspace, appropriate software tools, and the ability to synchronize data between your work environment and your home environment.

That last point is especially important, as you need to be able to seamlessly transfer useful data between your home and work environments. After all, you don’t want to be unable to get the information that you need from your job site in order to do your job..

If the task of preparing your home work environment feels overwhelming, worry not! In this chapter, I’ll offer you a comprehensive list of everything you’ll need so that you get off to a good start.

How to Ensure a Resilient Internet Connection

Probably one of the most important things to get right when working remotely is your internet connection. While residential broadband has gotten better over the years, it is certainly far from perfect.

You might not notice a lot of outages during peak usage times, such as in the evening or overnight, but during the day, your internet connection may be spotty at times. There are a variety of reasons for this.

The first is that a lot of the maintenance of residential internet connections occurs during the day. This can be everything from lines being replaced to someone messing with the connection from the street while trying to troubleshoot your neighbor’s cable problems.

In short, it’s really easy to be surprised by how unstable your residential internet connection actually is.

Further, should you be in the middle of trying to focus on work when your internet connection suddenly dies, you’ll probably also be extremely disappointed in how slowly your internet provider will fix your problem.

When I first attempted to work remotely on a regular basis, I made it a few weeks before my internet connectivity was suddenly interrupted. When I contacted Comcast about the issue early on the Monday morning it happened, they informed me that they could have someone come out as early as the Thursday morning of the following week.

Had I not had other options in place, that would have meant nine missed workdays simply because they couldn’t get someone on-site to fix the problem.

Now, rather than simply accepting that I was going to have to either use up all of my vacation time or go back into the office courtesy of Comcast, I ended up getting a business tier connection to the house instead of a residential one. At that time, having business internet meant that the provider would respond to an outage within four hours.

A four-hour outage window is much easier to deal with than a nine-day outage window. For starters, depending on what kind of work you have to do, it’s entirely possible that you can get away with working for a few hours in a fully disconnected fashion.

While you may not be able to code in such a situation, if you are prepared you might be able to do something such as writing specifications. If you are extremely lucky, you may still be able to write code but be unable to interact with anything outside of the house.

From the outset, you need to have a solid plan for how you will handle a variety of internet problems. In order to keep this somewhat organized, we’ll begin at your computer and work outward across the internet until we reach your employer.

At each level, there are several that can go wrong, each of which you need to be able to deal with if you want to keep your internet connection working so that you can keep working. You should have plans for each thing that might fail and have those plans somewhere that doesn’t depend on a working internet connection. This means both having plans written down somewhere so that they can be retrieved without a working internet connection and having the ability to do something productive even without a working internet connection.

Your Network Card

Your computer’s network card is the first point of network failure that you need to learn how to deal with. Sometimes cards die, while at other times, forced operating system updates (thanks, Microsoft!) can break your network drivers in such a way that you can’t connect to the internet. This can make it far more difficult to fix a problem with your machine.

This is probably the hardest problem to prepare for out of the entire set of network problems you might experience. Frankly, there is not really a cheap way to circumvent this problem. However, there are a few things that can help. These fixes are intended to be stopgap solutions, but you may be stuck with them for a while if things go badly enough.

The obvious answer would be to have a spare network card on hand that you can quickly install if your main card fails. This doesn’t necessarily mean that you’ll have to open your computer case in the event of a problem, as there are relatively inexpensive external USB cards available that should suffice.

If you have a cheap laptop available, you might also be able to just switch machines. I’ve almost always had both a desktop and a laptop, and this approach has saved me a lot of grief.

If your system has both wireless capabilities and support for a wired network connection, you might consider keeping a long ethernet cable on hand if you normally rely on the wireless connection.

You should also make sure to periodically create a restore point on your computer so that you can recover easily if an update breaks your machine.

Your Home LAN

Working outward, the next thing that can go awry is your home network. There are a few common problems in this area that can knock you offline. For starters, if you are using ethernet, your physical wiring could become damaged in some way, while wireless networks can fail due to interference or configuration changes.

Much like your network card, it’s hard to completely prepare for a failure of your network wiring or wireless network. However, there are a few precautions that help here.

The first is to always have spare network cables on hand so that you can plug in to your network in another room (or directly at the router) in the case of failure. These cables are also useful when troubleshooting network issues, as testing with multiple cables will quickly show you whether the problem is with the cable or with a device.

Wireless issues make things nastier. I personally prefer not to use wireless connectivity when working, as I’ve had enough problems with it over the years that I try to avoid it altogether.

Wireless can be really handy though, especially if you like to occasionally work at your dining room table instead of in an office all day. The biggest problem you are going to experience with wireless networks is that they are very vulnerable to interference and weak signals.

There’s also not a lot you can do about it other than simply moving to a different location in the house where the signal is better or possibly getting a wireless extension point that amps up the signal in your office.

Beyond that, if either your wireless or wired network is causing problems, you can often switch from one to the other and be able to complete a workday before having to mess with your connection.

Alternatively, if you are working from a laptop, you might be able to go work in a coffee shop for a few hours. If you are going to do that, you’ll want to make sure that you know where the nearby coffee shops are and whether they have a good enough internet connection to use.

You don’t want to drive somewhere else, only to find that their network connection is extremely slow or that they don’t want to let you use it for a few hours.

Your Router

Your router is the next item that has irritating failure modes. A few things can happen to routers that you need to be prepared for:

The router could simply stop working. This can be due to malware, lightning strikes, or simply old age.

One or more of the LAN-facing ports on the router could stop working.

The ports facing your ISP or cable modem could fail.

A router firmware update could make connections intolerably slow.

Power surges or temperature management problems could make the router “flaky.”

Most of the problems above can be resolved by either replacing the router or by restarting it. The quickest way to recover most of the time is to simply unplug the router, wait a minute or two, and then plug it back in. This is often sufficient to get the device to work properly again.

However, in the more pathological cases, a router restart doesn’t fix the problem. In these cases, you need to be able to swap your router out for a spare, and you need to be able to do so quickly.

Unfortunately, swapping out a router is not a very fast process unless you are well-prepared. In order to make sure that a serious router issue isn’t a problem, you need to make sure you have a few things on hand.

First, you need a backup router. I recommend that this router be as similar as possible to your existing router so that you can configure it quickly. Keep this spare handy, and periodically get it out and update its configuration to match that of your existing router.

Secondly, you need to keep the configuration information for your existing router somewhere that doesn’t require an internet connection to retrieve. This should include all information on the various configuration screens of your existing router.

This can be helpful if your spare router configuration is not up to date or if you end up buying a new router in an emergency. Trust me, the worst feeling in the world is trying to remember how you previously configured your system while precious minutes tick by.

In addition, you should make sure that you have a good battery backup and surge protector on your router and other networking equipment. Multiple power surges can happen in a day, so you don’t want to be constantly messing with the router simply because your power is temporarily unreliable.

You may have a few other things to worry about as well, depending on your internet provider. First of all, you should make sure that the technical support line number for your internet service provider is on hand.

You should also make sure that you have any other identifying information available, such as your account number, password, and the attached billing phone number. If you set up a new router and things still don’t work, it may be necessary to call your ISP. Keeping this information on hand is a good way to make such an experience far less stressful.

Your Home Network Wiring
(Past the Router)

There are also a number of problems that can occur between your cable connection (or phone) and your internet service provider. This can be anything from loose wiring in your house to a storm (or a random drunk) taking out a telecom pole 3 miles away.

Situations like this are largely beyond your control, and you can’t simply stock spare equipment to deal with it. In general, you have to get onto a working network somewhere.

Thankfully, this problem can be solved over the short term using your mobile phone. If you can tether your device to the phone, you may be able to get by using the cellular network for a while.

On the other hand, if you need a lot more bandwidth (and don’t want to pay for it at cellular rates), then you may need a backup work location. This can be anything from your regular office, to a coffee shop, to the home of a trusted friend.

Whatever option you choose, you need to be able to get there fairly quickly, and you need to be certain that they aren’t subject to the same internet outages that you are.

I learned this the hard way a few years back when my home internet failed and I drove down the street to a nearby coffee shop. It turns out that the failure was upstream of both of us, so I had to drive around to try and find somewhere else to work.

When you have a major network outage that doesn’t appear to originate within your home network, you have a number of options available to you.

You could first call your internet service provider and see if they know about the outage. If you are lucky, it’s an issue that the provider can fix remotely. Sometimes, it’s simply a configuration issue, and they can remotely restart your cable modem.

Secondly, you should have a bookmark on the browser on your mobile phone that shows you a map of internet outages reported by your provider in the area. You can use this map to figure out where to go to get a working internet connection.

It’s a good idea to have three or four locations in mind where you can go to get a working internet connection. You should get their wireless access points configured in your laptop before you need them. The last thing you want to do is be stressed out from an internet outage and have to try and figure out why the wireless isn’t working in your local coffee shop.

Furthermore, you should also have low-priority work that you can do without an internet connection available on your local machine. This is handy when you are waiting at the house for a technician to show up. While this isn’t as pleasing to management as the completion of high priority tasks, it does allow you to be productive while the internet is down.

Finally, you should make sure any resources you need are available on your local machine as much as possible rather than assuming that the internet will be working when you need it.

If you follow the above, even large internet outages will be less of an issue for you. While internet outages can never be completely prevented, the disruptions they cause can be significantly minimized. If done correctly, your employer may not even notice that you had an outage.

Services at Your Provider

You may also run into a situation where your internet access is apparently working, but various services provided by your ISP are no longer working. The most likely cause of problems here is the Domain Name System (DNS).

DNS is the service that your computer and other networked devices use to figure out the IP addresses of the various machines you are connecting to when you are on the internet. When I first worked remotely, I was surprised by how frequently this was an issue with my internet service provider (Comcast).

One will usually notice that they are having DNS issues when they suddenly can’t reach a few websites. From experience, the most irritating issues occur when your ISP’s DNS servers are partially working or just very slow.

In this case, you might see that you can’t reach GitHub or Confluence, but you can reach Fox News or Pizza Hut’s website. While the Pizza Hut site is definitely very useful, you are more likely to need Git.

To prepare for this, you need to configure your personal machines to use your router as your DNS. Then, you need a list of a few alternate DNS servers to use in case those provided by your ISP are not working. I personally use the following and have found them to be reliable (because they are provided by Google):

For IPV4, use the servers 8.8.8.8 and 8.8.4.4

For IPV6, use 2001:4860:4860::8888 and 2001:4860:4860::8844

Make sure you keep backup DNS server addresses in a place where you can get them without a solid internet connection. You don’t want to waste time searching for this stuff when your DNS is not working properly.

In addition to DNS, if you are using Voice Over IP (VOIP) for your home phone service, you probably need to have a plan in place if the service fails. You can generally get away with using a cellphone, but you may need to inform your co-workers that your home VOIP phone is not working.

Cloud Services You Use

Additionally, you need to have an idea of what to do when one or more of the cloud services you use for work has an outage.

While at work, management is generally understanding of this problem, but they may or may not be as tolerant when you are working from home. Even if the various cloud services you use are failing, you need to make sure that you can still get work done.

If you assume that your internet connection is unreliable and plan accordingly, you can often respond better to outages than people in the office.

The strategies you should use to prepare for service outages vary depending on what tools you are using. While each situation is unique, a few broad rules apply that can help you be more resilient to outages than your office-bound colleagues.

For distributed source control tools such as Git, simply commit to your local repository and push up the main repository when you can. These tools are built to be resilient to unreliable and slow networks, so they shouldn’t cause much trouble for you.

The only exception to this is when you need a commit or branch that was created by someone else. In this case, you are probably stuck waiting until the service is back up. Thankfully, outages for these services are rare and usually short-lived.

For documentation tools such as Confluence, you may want to do most of the work offline in a different editor and then move the files up to the system when you are done. You’ll have to do a little extra work to clean up formatting issues, but you won’t be as vulnerable to losing work due to an outage.

As for chat, email, and other communication tools, an outage may mean that you can’t meet with your co-workers. In general, for chat and video conferencing tools, it’s best to have a couple of options available on your machine in case you really need them.

Sometimes, chat tools fail or an update doesn’t work on your machine. Sometimes, the corporate firewall makes it so that your co-workers can’t use a particular tool. It’s best to consider chat tools to be at least an order of magnitude less reliable than a phone and plan accordingly. If you are completely offline, having multiple available tools agreed on beforehand can also make it more likely that you can use an app on a cellular phone if you need to do so.

For email, you are often better off using a desktop email client. In general, outages are an excellent reason to move toward using more asynchronous methods of communication rather than interruptive ones.

In general, if you are relying on cloud-based services, you should still try to make sure that you rely on your internet connection as rarely as you can. Your co-workers in the office are probably not adequately prepared for a cloud service outage, so if you are prepared, your added resilience will make you more productive than they are.

Remote work discussions are a lot easier when you are able to show that outages don’t stop you from working.

Your Employer’s Internet Connection

If you are unlucky, your employer may require you to connect to the corporate network to do your job. Usually, this is done over a virtual private network (VPN).

While such connections are secure, they are subject to significant and frequent disruption because they are reliant on everything between your house and your office being in good working order. In addition, the VPN software itself often introduces an additional point of failure that you need to consider.

Your employer may take such measures because they are rightly concerned about security. As a result, it may be unwise to mitigate the risk of a VPN outage by making local copies of everything. Instead, about all you can do is make sure that you have the relevant contact information on hand for your network administrator along with a backup administrator.

Requiring a VPN to connect remotely virtually guarantees that at some point an outage will prevent you from being able to work effectively. There’s not a lot you can do to mitigate this other than reporting the issue when there is a problem. However, if you are effective enough while working remotely, it’s also possible that it won’t matter to your employer.

Your Office Computer

The final, and worst cause of failure, is the failure of your office computer. If you are required to connect to your office using a VPN and then required to use remote access software so that you can use your office desktop as if you were sitting right there in the office, then you have yet another point of failure.

Your office machine could go offline for a variety of reasons, varying from software issues, to hardware problems, to a breaker being tripped in the office. Further, if you are accessing the machine remotely, you will also have to spend some time figuring out where the problem is.

A failure on your office computer can leave you completely high and dry, and you have limited options to keep it from ruining your day. However, there are some things that can reduce the likelihood of an outage during working hours. A few simple things can help you considerably, making your work computer a less likely point of failure while you are remote.

While you may not be able to completely control your office machine, you should do as much as possible to make sure that it remains stable while you aren’t in the office. Here are a few things you should ask yourself:

Does my work machine have a battery backup and does it work? You would be surprised how frequently companies skimp on battery backups, causing machines to shut off when there are problems with power.

Can I control when software updates occur on my machine? If you can, try to disable updates, and only run them when you are on-site or when you don’t have a looming deadline.

Do I have the contact information for the people near my machine so that I can quickly contact them when the machine is unreachable?

Do I have the relevant information about my machine on hand? If you have to talk to someone at the office to fix a network issue with your computer, at a minimum, you’re going to want to know the machine name and IP address (if your assigned IP address is static).

If you have these things under control, your office machine is less likely to be the cause of an outage. However, if you are stuck using your office machine remotely, you’re going to have a lot more problems. Using an office machine remotely makes it more difficult to achieve a sustainable remote work environment.

Creating an Effective Workspace

You also need a decent workspace when you work from home. While you may think that you can be effective while sitting in your living room on the couch, the reality is that such environments are distracting, usually have poor ergonomics, and are not comfortable workspaces for the long term. Further, if you have pets or children running around, it’s almost impossible to be effectively involved in meetings in such a space.

I had a co-worker once who insisted that he be allowed to work from home for a couple of days but who was unwilling to set up a real office to work in. The company allowed him to work remotely, but he was also supposed to participate in a meeting with our board of directors to show them what he had been working on.

He dutifully camped out on his living room couch and began to work. We called him for our 9:00 scrum standup meeting. Not only could we hear Sesame Street and children arguing in the background, but he had to constantly mute his audio feed to yell at the kids.

Further, when he was on the call later with the board, his cat jumped up onto his keyboard while he was talking and pointed its backside at the screen. That story came up every single time any of us advocated to be allowed to work from our home offices.

You don’t want your employer to associate remote work with the back quarter of an agitated cat being shown to the people who pay for things. I can tell you from experience that this kind of association is hard to overcome.

The best thing about having a decent workspace is when you leave it. Instead of it being right in the middle of a “fun” area, it’s in an area dedicated for work. Having a dedicated area for work reduces the frequency of non working issues interrupting your day, and it also makes it easier to step away from your work when you are done for the day.

This boundary is key to both effective work time and to having a good balance between work and the rest of your life.

Unless you live alone, I would generally recommend that your workspace have a door that closes it off from the rest of your residence. The idea here is to make it very obvious and unambiguous when you are working so that other people can’t misinterpret it. This makes it a lot easier to set good boundaries with anyone living with you.

In general, you should also try to keep the workspace at least as clean and organized as your workspace at the office. This will help you maintain your effectiveness and put an end to the awkward and rushed tidying that otherwise occurs just before a video conference call.

Additionally, you need to pay attention to a few other things in your workspace to limit distractions. You should try for a workspace away from the main walking areas of your residence.

At the same time, you want to be well away from loud and distracting noises such as televisions, dishwashers, dryers, washing machines, and air conditioning units. Make sure that you can keep the space in question at a reasonable temperature during seasonal extremes as well. It can be really annoying to try and work in an office that is uncomfortable because of extreme temperature.

You should also do your best to make sure that you can control the lighting in the room. Pay special attention to windows facing east or west, as they are liable to produce a glare during the day.

Be mindful if your windows face toward the equator (in other words, south if you are in the Northern Hemisphere and north if you are in the Southern Hemisphere), as during certain times of the year, you’ll also get a lot of light and glare from that direction.

Make sure that you have curtains or blinds that close so that you can block out other visual distractions if you need to do so.

Finally, make sure that your workspace doesn’t tend to get dusty or overly damp, as such conditions can be rough on equipment and might cause health problems for you as well. Remember that you will be working in this room for almost as much time as you spend sleeping in your bedroom, and plan accordingly.

Desk and Seating

You might think that a cheap desk that you picked up at an office supply store is sufficient for remote work. Such a desk can work for a while, but you may eventually find yourself in pain due to repetitive strain injuries or simply bad posture while sitting.

Additionally, while you might be able to sit in a normal kitchen chair for a day or two, these chairs are not meant for long periods of seated work and can often become very uncomfortable after a few hours, to say nothing of longer stretches of time.

Proper computer desks and computer chairs are vitally important to a sustainable, long-term remote working arrangement. It doesn’t do you any good to get the ability to work remotely, only to find yourself in constant pain and unable to enjoy your newly improved quality of life. Your desk, seating, and the arrangement of your mouse and keyboard are key to doing this well.

For your desk, you should have one that will accommodate at least two monitors and a laptop. Even if you are using a desktop computer for your daily development work, you are still likely to need the extra space on the desk for a tablet, printed versions of specifications, or even a third monitor.

Also, it’s generally better to get a good articulating keyboard tray, as when a keyboard is placed directly on the desk it’s often too high up to avoid having shoulder problems.

For your chair, I would recommend getting either a high-quality office chair or a gaming chair. While you can get by for a little while with a cheap office chair, you’ll find that they get pretty uncomfortable over time.

From personal experience and that of lots of friends, one of the most frequent causes of pain is poor seating. Whether it is due to poor back support, inability to adjust the angle of the seat, or inability to rest your head, a bad office chair can lead to long-term pain.

While a long discussion of ergonomics would be a book of its own, there are some general guidelines that will help you make a better choice:

Lower back or lumbar support is necessary. You want to be able to adjust the back of the chair so that you can avoid sciatica over the long term and back pain over the short term.

You need to be able to adjust the height of the chair arms as well as the available space between the arms. It can be extremely uncomfortable to be crammed into a chair that feels like it is the wrong size.

Your chair needs to be able to swivel all the way around. It’s annoying to have a chair that doesn’t do this when trying to work for an extended period of time.

You should make sure that you have the right kind of wheels on the chair. These are different for carpet than they are for harder surfaces.

The back of the chair should have a breathable fabric. While those without this feature are comfortable when you try them out in the store, they rapidly get hot and gross if your office gets too warm.

You should be able to rest your feet comfortably on the floor, or you need to get a footrest (I use a footrest, personally).

The cushions should be of durable foam that isn’t going to wear out quickly. A lot of comfortable chairs wear quickly and become uncomfortable in short order.

It’s really important to get the right kind of chair for your home office. While it can be expensive, the cost is nothing compared to the costs of having consistent back, neck, and shoulder problems.

Make Sure You Have a Decent Computer

Next on the list of things that can make or break your remote working efforts is your computer. If you are lucky, you may have a sufficiently powerful computer provided by your job. However, it’s also quite likely that you won’t.

If the latter is the case, then you need to make sure that your personal computer is up to the task. It would be terrible to get to the point where you can work from home, only to have a severely underpowered home computer that makes it impossible to be productive.

When I first got paid to write code, I did so using a computer that had a 266 MHz processor and a huge computer hard drive that wouldn’t be considered a respectable USB drive for a child these days.

What today is thought of as an overly powerful computer in a few years will be simply “OK.” In 10 years, it will be considered extremely underpowered. Given that appropriate computer specifications change so rapidly, it’s almost impossible to recommend anything here that will be a good suggestion even a few years from now.

Thankfully, you can usually get a good idea of what kind of machine you should use by taking a look at what you have at work. Take careful notice of things like CPU speed, number of cores, amount of RAM, type of video card, and the type and speed of the drives in the system.

Now, before going out and buying a similar machine, also take note of how well that machine meets your needs. When determining what to buy, try and treat this machine’s specifications as the minimum for the machine you have at home. A more powerful home machine is excellent compensation for a slower internet connection and well worth the cost even if your job isn’t paying for it.

Additionally, take a good look at your monitors (there should generally be at least two). You’ll want something at least as good at home. This is also true if you are provided with a work laptop and additional monitors at work—you should try to do at least as well at home.

These suggestions may have a price tag that initially seems steep. However, realize that this is an investment that will be quickly offset by the lower costs and better quality of life that you’ll experience when working from home. If you really want to work remotely, you should do it on the best hardware that you can.

Time-Tracking Tools

In addition to a proper desk, decent computer, and usable workspace, I also highly recommend using a tool to track your time. While your employer probably has a time system of their own, it’s a good idea to get a cheap time system that allows you to track your activities during the day, including breaks.

It’s really easy when working remotely to get into the habit of working too little or too much. For the first few weeks of remote work, it can often help a lot if you track all of your time, including your time off the clock, to make sure that you are keeping a reasonable balance between home and the office.

Whether you find that you are getting burnt out or that you aren’t productive enough, having this information recorded will help you troubleshoot the problem.

File and Note Sync

If you are working remotely and have a computer at the office, you also need to have a good mechanism for moving files between one location and the other. Additionally, you need a good way to synchronize your notes between locations.

The best way to accomplish these goals varies considerably depending on what kind of security constraints your employer has, how you communicate with your team, and how frequently you change locations.

The main goal of all this is to make sure that the inputs to your work process (things like specifications, notes, and documentation) are available in a location-agnostic manner.

While this can be as simple as having a notebook that you always take with you to your desk or as complex as a tool like Evernote, you need to have some way of making sure that you can get information when you need it.

Even if you are working remotely using your office computer, there are occasions when you will need to have information available on your home desktop that would otherwise be on your work desktop.

For instance, if you are using Skype or another video conferencing tool to call into meetings, you will probably be using this software from your home machine instead of over something like remote desktop.

As a result, if you need your notes or other project artifacts while in the meeting, you’ll need to be able to reach them from your home desktop even if you do all your other work from the machine in the office.

Above all, your main goal should be to eliminate anything that might slow down your work while you are remote. This makes it easier for your remote work environment to compare favorably with that of your office.

Being Reachable by Phone

While most programmers I know really don’t want to respond to phone calls, there are times when it is necessary. Some companies will provide you with an IP desk phone that you can simply plug into a wired network.

These phones make it easy and transparent for others to call you. However, for companies with little experience with remote workers, you need to take additional steps to make sure that you are reachable by phone.

One easy option is to simply forward calls from your desktop phone at work to your personal cellphone. Since most people tend to keep their cellphones with them most of the time, this is an excellent way to make sure you are reachable.

Additionally, if you don’t have a work-provided desktop, it may be worth changing your email signature to also include your personal cellphone number. While you don’t want to be getting a lot of work calls on your personal cellphone, especially if the company is not paying for that cellphone, it may be worth doing just to be able to smoothly work from home.

Additionally, you should make sure that you are easily reachable by whichever chat programs are in use at your company. If you are easy to reach in chat, most tech-savvy people won’t call you anyway.

I personally really dislike the interruptions caused by phone calls, and I try to minimize those by being easy to reach in other ways. You might also find it useful to change your voicemail message to indicate other ways to reach you, as at least some people would prefer to avoid the phone as well.

Webcam and Headset

Finally, you need to make sure that you have a decent webcam and a headset with a good microphone. When you regularly find yourself on conference calls, you need to make sure that you sound and look as good as possible.

While you may think this is about tone of voice or your appearance, the real issue is that your image and sound should be as true to life as possible when you are in a meeting.

The idea here is twofold. First of all, if people can’t hear you or see your facial expressions, it is much easier to be misunderstood when you are discussing something in the context of a meeting.

Additionally, if people hardly notice that you are remote when on a call with you, it reduces the likelihood that someone will start pushing for you to come into the office.

For your webcam, you might be able to get by with the webcam on your laptop if you have one. If not, try for one of the inexpensive but HD-capable webcams that you can purchase in most electronics stores. You don’t need a professional-grade camera, but you do need one that has a reasonably good-looking output when in use.

Secondly, I recommend a headset for calls. Nothing is more annoying than being on a call with someone who doesn’t have a headset. Lacking a headset, your computer speakers are going to be emitting the noise of a meeting, which will promptly be picked up by your microphone.

Echoes created in this manner are extremely distracting and are liable to make your team extremely irritated with you. Similarly, if your microphone makes you sound like you are broadcasting from the inside of a tin can, people will have a hard time understanding you. You need a good headset to work from home.

When choosing a headset, most wireless gaming headsets are sufficient for your needs. You want a wireless headset so that you aren’t constantly dealing with problems using a cable.

It’s also good to have a headset that has a nice boom microphone so that your voice doesn’t suddenly become quieter or louder when you move your head. Ideally, this microphone will be designed in such a way that it doesn’t pick up an excessive amount of background noise.

Most gaming headsets seem to do a good enough job of this, but your experience may vary if you live in a particularly noisy environment.

Having good equipment on hand for videoconferencing will make it more likely that you will continue to be allowed to work remotely. Remember that conference calls and video conferences are the main way that people form their impression of your home work environment. You want that impression to be as positive as possible.

Equip Your Home Office Well for Productivity

You should spend some time and money making sure that your home office is suitable for work. If you want to convince your boss to let you work from your house, you have to show that the environment is at least as good as the office environment if not better.

Further, you have to be able to be effective in your environment to at least the same degree as you might expect in an office environment. It pays to get this stuff right before you even try to convince anyone to let you work remotely, as people are usually easier to convince when you haven’t already made a bad impression.

Additionally, if you have any kind of work ethic at all, you should want your home work environment to be productive so that you feel efficient.

Remote work will not make you feel good about yourself if you know that you could be far more effective in the office. If you set things up properly before you start, you can make sure that remote work is a positive experience for everyone involved.

Chapter 5

Mitigating the Downsides of Remote Work

Everything in life is a trade-off. While there are loads of benefits to being able to work remotely, it’s no panacea: You need to understand from the outset what you are giving up by not going into an office.

For instance, if you were previously relying on your co-workers to provide you with a semblance of a social life, working remotely may drastically change that for the worse. If you previously enjoyed being able to walk away from a bad job and start a new one quickly, you may be surprised to learn how much more difficult it is to get a fully remote job.

Further, it takes additional effort for your boss to recognize your contributions to the team, which can translate into lower pay, fewer promotions, and a higher risk of being downsized.

You may find that your active and continuing input on projects is more difficult, leading you to be treated like a second-class citizen, especially if the rest of the company goes into the office to work. This can be because it’s harder for you to be involved in the necessary meetings. You can also find that you are perceived as not being involved. Both of these things are problems that might cause you to be forced into the office if there is a change in management.

Overcoming the downsides of working remotely is not the responsibility of your boss, co-workers, spouse, or social circle. It’s great if they help, but you shouldn’t rely on them to help you overcome the downsides of your choice to work remotely. It is largely your decision, and it’s up to you to make sure that you and those around you don’t regret it.

You do have some advantages when working from home. For one, your day probably has fewer random interruptions by co-workers. For another, you aren’t wasting an hour or more commuting to and from the office. You also probably have more money available, assuming that you didn’t take a pay cut for the opportunity to work remotely.

While you almost certainly want to use the increased time, money, and ability to focus on things other than work, you should spend at least some of your spare time making sure that working remotely remains sustainable for you.

This whole process is very similar to how many of us felt when we first started living away from our parents. Previously, the environment sort of “took care of you,” whereas once you got out in the real world, you had to handle things yourself.

While transitioning to living alone offers freedom, very few people get out on their own without running into at least a few problems. For example, the freedom to sleep in can lead to the consequence of being late for work. Personal freedom requires maintenance.

It’s exactly the same with remote work: You don’t want to do the career equivalent of wearing dirty gym clothes to finals because you didn’t plan ahead. In this post, we’ll take a look at all the downsides of working remotely, and I’ll offer you some concrete tips that will help you mitigate them.

Social Isolation

One of the most serious problems in remote working environments is the possibility of being extremely socially isolated. While you might have family or roommates living with you, if you don’t take active steps to have some social interaction, you may end up feeling isolated, especially over months or years.

While there is wide variation in the amount of interaction that people require, almost everyone needs at least a little.

If you truly believe that you don’t need any other human interaction other than what you get remotely from your co-workers, that’s OK. Think instead in terms of your long term career: You need interaction just to maintain your personal network, even if you would otherwise prefer to be a hermit on a deserted island somewhere.

I used to think that I didn’t need much interpersonal interaction. However, eventually I learned that—while I don’t need much—I do need at least a little to be normal and well-adjusted.

In my case, I had been working at a job that was completely remote for a few months, and I thought things were going well. However, looking back, I was clearly exhibiting symptoms that might well be considered indications of depression. I had disrupted sleep, was constantly negative, and was overly fixated on whatever the next task was for work, even on weekends.

Additionally, I was losing weight from failing to eat, and I was requiring more and more caffeine to feel normal enough to be productive. As my coffee intake started increasing to more than six cups by lunch, one of my co-workers mentioned that he was getting a little stir-crazy in his house as well.

We ended up doing a Google Hangouts video session for a couple of hours a day. That lightweight simulation of being in an office with co-workers really helped both of us to get back to a more normal state of focus.

Those two hours a day ended up being some of the most productive development hours I’ve ever experienced, as we could collaborate and quickly solve small problems, relegating the larger problems for more focused time after we ended the call.

The impact of isolation seems to play out differently for different people. For some developers I’ve known, it seems to help them focus, but over a longer time period, they end up disconnected from their team and their team’s goals. This can lead to being clueless and out of touch if you let it go on for long enough.

I’ve known other developers who handled their sense of isolation by spending an excessive amount of time talking in meetings while others got even quieter. I’ve even worked with a few who developed substance abuse problems due to a combination of overwork and isolation, including one who died as a result.

Chronic isolation can often seem tempting, especially if you are stuck in a dysfunctional office environment with constant interruptions. However, as with most things, moderation is the key. If you really want to be able to work remotely over a longer period of time, it’s important to cultivate and maintain relationships outside of work.

While you might think that simply talking to your family is enough, it’s usually worthwhile to seek friends and activities outside of the house, as you probably only get a few kinds of interaction from family.

Since you probably need at least some human interaction to be mentally healthy, before you start trying to work remotely more than a couple of days a week, you need to start finding activities that you can do outside of the house. While everyone’s preferences are different, here are a few ideas to get you started.

Sports activities are always a good idea. It can be anything from weightlifting and running marathons to various team sports such as soccer, airsoft, or basketball; anything that can not only help you maintain an interpersonal network but also improve your physical health and mood as well.

Personally, I lift weights. I find that it helps my mood considerably and reduces soreness from long periods of working at a keyboard.

Intellectual activities such as learning another language, taking classes in interesting subjects, or even participating in book clubs can satisfy your intellectual curiosity and give you something to talk about other than work. I chose to learn a foreign language (Russian) for this.

With performance activities such as public speaking, dance, and learning to play instruments, you can satisfy your creative drive while giving yourself a non-work-related challenge. Public speaking has occupied this role for me.

Religious activities can also give you a ready-made community of similar people. I don’t exactly have this anymore, but I do have a pretty strong and supportive social network of other entrepreneurs and entrepreneurial developers who are a tremendous source of inspiration and support.

You can also just have a group of friends who get together on a regular basis to hang out, but sometimes that’s a bit more difficult as people get older and have children. I’ve found that a lot of my friendships have changed over the years, as happens to most people after 30. I like to get together with my friends when I can, but I don’t rely on it.

There are a ton of options for other activities outside the house that will help reduce your sense of isolation. It’s important to find something that looks interesting to you and try it out a bit before you get started with an ambitious remote work schedule so that you are prepared to make it into a habit once you really go remote.

The first few weeks or so after starting a new routine is the best time to ingrain new habits that you would like to keep, so you’ll want to make sure that you have an activity lined up.

There is another reason why you should try a few options for social interaction before going remote: If you find something you really like, it can end up being what helps motivate you to stick with it.

Remote work isn’t necessarily easier than working in an office, and having something that helps to motivate you can get you through the tough spots. More than once, knowing that going back into the office would severely cut into my study time for Russian kept me going when a lot of other motivation was gone.

Getting Stuck in a Bad Job

Another problem that many people don’t consider when they start working remotely is that it can trap you in a bad job. Previously, we discussed the enormous cost and time savings that can accrue when you start working remotely. However, these advantages can work out to be a bit of a double-edged sword, especially if you start making decisions based on having extra time and money.

For example, let’s say that working remotely saves you 10 hours a week and $500 a month (it should do better than that, but round numbers make calculations easier).

If you buy a new car that has a $450 a month car payment and commit to taking a college class that takes 10 hours a week when you are already close to the edge in money and time, then a potential job loss or even being forced back into the office puts those things in peril.

Such a situation increases your employer’s leverage over you to a degree that you perhaps have to put up with things that you shouldn’t simply to avoid having your entire life thrown into chaos while you find something else.

When you suddenly find yourself with more money or time, don’t default to spending it. Only spend either money or time when you know you have enough surplus to still be intact if things go poorly.

In the previous example, if you have $2,000 a month coming in that you aren’t spending, then a $500 car payment isn’t the end of the world. It’s probably not a good investment, but it doesn’t stretch you into a situation of further risk. Similarly, if the extra 10 hours a week is in addition to 20 more hours of largely unallocated free time, spending 10 isn’t the end of the world.

When your pay (or free time) increases, it’s easy to react by spending them. Instead, you’ll find that you can greatly increase your personal freedom if you invest those gains in ways that can eventually create additional free time and income for you.

For example, when I started working remotely, I spent money on training so I could more efficiently use the tools I needed to write my first book (and this one). Similarly, I used the extra time to write the books.

This investment produced income and opportunities that made it easier to be a lot pickier than usual in regard to my next job. The ability to be relaxed about the job search allowed me to wait for something that better fit my needs, giving me higher pay and more free time than I might have otherwise had.

In addition to avoiding lifestyle inflation when working remotely, I strongly suggest a bit of lifestyle deflation instead. For instance, you can probably save a ton of money by only going out to eat when you really feel like it and then eating the rest of your meals at home.

Further, a lot of the purchases you might have been making so that you could cope with office life (beer after work, for instance) can often be reduced or eliminated entirely.

Since switching back to working remotely, I went from going out to eat almost every day for lunch to doing so maybe twice a week and at cheaper restaurants. I notice no difference in my happiness, and every penny I save is more time to find something else if my job goes away.

When working remotely, you should also be paying attention to what is going on in the office. You don’t want to get surprised by suddenly being downsized or forced to come in.

If you have a sense that something negative is going on, you may want to go ahead and send your resume out. It takes a lot longer to find a good remote job than it does to find one that is on-site due to the smaller pool of potential employers, so you should be quicker to send out your resume than you might be otherwise.

Getting Forced Back Into the Office

It’s not nice, but it can occur: You could suddenly be forced back into the office. A lot of managers don’t like the idea of remote work at all, and new managers can sometimes implement sweeping rule changes.

Additionally, the company may have problems with some of its remote workers and decide to penalize everyone. Finally, you’ll occasionally get clueless managers who want to drag everyone into the office for “synergy” and “collaboration” or who suddenly want you to “earn” your ability to work remotely (long after you “earned it”).

I’m going to give a rather radical suggestion here that a lot of people won’t like: When this happens, send your resume out immediately and be unwilling to accept a counteroffer.

Many people are tolerant of lower salaries, worse benefits, or even longer working hours simply to be able to work from their house, and they negotiated (or tolerated) their current situation in good faith that it would continue.

However, forcing everyone to come back into the office demonstrates two things: It shows that you can’t trust any deal that the company makes with you and that management is callous about breaking such deals.

As a result, even if you personally are otherwise happy with the job, the company is apt to start shedding employees as remote workers with options leave. You may have to go into the office for a little while as you line up the next job, but you should get out as quickly as is reasonable if this happens.

Additionally, as I previously explained, you should be really careful about lifestyle inflation, especially in terms of time or money. In either case, being accustomed to having more means that management has leverage over you in a way that is really unhelpful.

If you are instead building up your savings or building assets that produce money, you’ll have time to wait while you line up better options. Make sure that your plan to work remotely is resilient to changes in management or it will always be at risk. Make sure that you are in a position where a change is an opportunity, not something that you have to fear.

Missed Promotions and Lower Pay

In addition to the other possible negative outcomes of working remotely, there is also the risk that you will be passed up for promotions and pay raises.

To understand why this occurs, let’s examine a couple of ways I’ve heard it expressed from a management perspective. Here are some viewpoints that your manager may have. It’s important to understand these so that you can counter them.

“They work from home, so they are already saving money.” This is absolutely true and utterly irrelevant as well. The other companies out there are paying increasing salaries, including to their remote workers. Nevertheless, this attitude persists. Rather than having this argument with management, you need to be able to point to the value that you provide to the company. This requires clear examples and documentation.

“Why should I pay them more when I can hardly tell if they are working?” This points to a common problem for remote workers. A lack of communication in the office can result in management constantly coming by your desk for status updates, while a lack of communication while remote can cost you your job or seriously hamstring you at review time.

With both of these objections, you’ll notice that communication is of huge importance if you want to better your career in general and is even more important if you want to maintain it at all while remote.

While lots of books suggest that you simply “communicate better,” that advice is not particularly helpful if you aren’t a great communicator already. Instead of giving you rules about things like the length of emails and writing style, it’s often better to have a few simple rules governing communication.

While at first you might not believe that a few simple rules can change the way your manager and your team perceive you, you need to remember that team communication is a complex, interdependent system.

In such a system, a few simple rules change the state of the entire system by changing the way the components interact. For inspiration, let’s use an example from the natural world before diving into a set of rules that can help you.

Have you ever watched a school of fish move? While the patterns may be complex, the individual animals’ behaviors are not, simply obeying a set of four very simple rules. Those rules are:

Get away from anything that appears threatening.

Maintain a minimum distance from everything else.

Match the speed of the rest of the group.

Move toward the perceived center of mass of the group.

That set of four really simple rules produces the complex schooling and shoaling patterns that you see when you watch “Shark Week.” There is no leader of the school, only the interaction of simple rules.

In other words, fixing your communication is not going to require a huge investment from you, nor is it going to require you to change who you are by suddenly talking excessively to people (if you don’t like doing so) or even pretending to be an extrovert. Rather, it requires the conversational equivalent of being a fish. Four simple rules will get you there:

- Communicate problems early rather than waiting until they become too severe to deal with.

- Communicate asynchronously and concisely so that you aren’t a problem for the rest of the group.

- Make sure that you communicate things to others before they need them (but not too early) so that you aren’t blocking them.

- Communicate status at predictable times.

While the above won’t make you a perfect communicator, it can greatly improve the way that your communication is seen.

Simply put, communicating while following these rules does two things. First, it makes sure people have the information they need when it is useful to them, and second, it keeps people from wondering what’s going on.

The latter is especially important for remote workers, as people tend to try to infer information when they don’t have it. That inference has a chance to backfire on you, so it is important to control it so that it doesn’t occur when people are already stressed out.

Giving people information before they ask for it has another advantage. If done well, other people will start to respond to the behavior, usually by not interrupting you to ask for things. After all, it’s less effort for them, and they still get good results.

While being influential on your team in this way may not net you any pay raises or promotions directly, it may help reduce the sort of team dynamics that can keep these things from happening. A team that is less efficient due to interruptions and other information flow problems is less likely to get a raise and more likely to run into performance issues that get the attention of management.

For instance, if a manager with an interruptive management style learns that you always send in a quick note at 9 in the morning, they are less likely to bug you for a status update at 8:55. In other words, your communication style should be adjusted to assume that people in general follow a few simple rules, one of which is avoiding the expenditure of effort when it isn’t required. It’s so easy that even an albacore could do it.

Here’s what this might look like for a remote software developer who reports to a project manager and other stakeholders in addition to communicating with their team. Note how the following practices achieve the objectives previously listed, and then take the bare minimum that might work for you and test it out. You’ll find that outsized improvements are a lot easier to achieve than you might expect.

Every day, send a written status report to your project manager that tells them what you did yesterday, what you plan to do today, what is blocking you, and what meetings you may have scheduled. This is in addition to your scrum meeting if you have one, but should cover the same material.

When something new blocks you, allocate a short period of time to try and get past it, and then raise the issue by email to the person on your team most likely to be able to help you. Copy the project manager on the email so they know what is going on.

Don’t expect a reply immediately, and work on smaller, simpler tasks in the meantime. This means that you should have a set of small, less critical tasks in mind to choose from.

Let your team know when you start work for the day, when you head out to lunch, when you return, and when you are done for the day. Hopefully you have a chat system for the team (and hopefully it allows the muting of notifications).

If other team members need something from you (or are delivering something you need from them), letting them know when you are working allows them to quickly determine whether you are available without having to guess. Setting expectations this way also helps keep other people from abusing your time and attention.

Good communication does two more things for you. First, it ensures that you are clearly communicating your value to the team. Nobody (including your manager) has to guess what you are doing.

Secondly, when the time comes for an annual review or a possible promotion, it provides a thorough paper trail for the management (doubly so if you give these emails the same subject line and never delete your sent items).

Rather than saying “I worked 60 hours a week all year!” you can point to what you actually got done. The latter is more easily tied to the value you provided and doesn’t sound whiny. This allows you to approach salary and promotion discussions from a position of strength, and it does so while removing some of the issues that can make raises and promotions harder to achieve.

Becoming a Second-Class Citizen

One common concern for those getting into remote work is the possibility that they will begin to be treated differently at work. Whether it’s because they aren’t involved in important, but informal conversations, or simply because they can’t talk to the boss on a regular basis, many would-be remote workers are rightly concerned about the quality of their work relationships as a result of going remote.

This concern is reasonable, especially if you are in a hybrid situation where most people work in the office while you work from home. I can also tell you from bitter personal experience that this is an extremely common problem for remote workers, having been on the receiving end of it more than once.

There are three main ways that remote workers may be treated as second-class citizens by their employers. Most of the time, these are unintentional, although it certainly won’t feel unintentional when it’s happening to you.

The first way that you might be sidelined is by not being privy to informal conversations that happen in the office. The second is by not having your time and boundaries respected. The third occurs when you are blamed for problems in which you had no part, simply because you aren’t able to defend yourself.

We’ll break down each of these things so that you can proactively mitigate them.

Missing Out On Informal Conversations

Probably the worst thing about working remotely is missing all the useful conversations that happen in the office (conversely, the best thing about being remote is missing the other kind).

Whether it is finding out that someone got fired or that the company landed a new client or finding out about specific details of project implementation, informal conversations seem to be the lifeblood of most offices. The consequences of missing out on some of this information can be stark.

For instance, if you don’t know that a co-worker was fired or quit, you may waste a lot of time waiting on them to respond to an email when you have a tight deadline looming. Even worse, you might find that suddenly their projects have landed on you or worse still, that management is in a bad mood and will not appreciate the email you are about to send.

I’ve worked at a lot of companies that had at least one manager who was the topic of frequent conversation, usually because of their emotional volatility. You don’t want to find out the hard way that such a person is having a bad day.

Office communication styles vary a lot. While many offices use the best tools they can find and try to keep good documentation on every decision they’ve made and why, you’ll also find offices that are stuck in the stone age as far as their internal processes.

In the latter case, almost no decisions are documented, and everyone relies on their own memory when attempting to recall why a decision was made (or even what decision was made). The results are often terrible even if everyone is on-site. But it’s even worse if you aren’t on-site and are held accountable for your adherence to these decisions when you weren’t even in the conversation.

What’s even more annoying is that even in a modern office that documents things well, hallway conversations and implicit assumptions are still easy to miss.

To compound the problem further, most people can remember what they were told and who told it to them, but usually can’t recall who else was in the conversation. This is especially true when the topics are trivial or when some time has passed since the conversation. As a result, your co-workers may legitimately be completely unaware that you don’t have a piece of critical information.

Thankfully, like the previous discussion on missed promotions and lower pay, a couple of simple rules can help. However, these rules are much more difficult to implement and require a lot more discipline than the rules of communication outlined earlier.

First, you need to make sure that you ask questions early and often. This applies even when you think you know the answer to the question. The idea here is to get people to explicitly state what they want in written form.

For instance, let’s say that you work for a company that does data entry forms for a particular industry. You might ask “Are they going to use this on mobile?” “Will this ever be used in an occasionally connected environment?” and “Will there be a publicly exposed API for this stuff?” even if the answer to these questions is typically “no.”

The reason you ask isn’t necessarily to get information but to have a warning if any of your assumptions are no longer valid. Further, if you are asked to write specifications or report on progress, try to do so in a way that forces your own assumptions to be tested against reality.

Remember that your assumptions are dangerous, especially if you don’t have frequent face-to-face and informal conversations with your co-workers.

Second, you need to make sure that any work products you produce are examined by someone whose assumptions are more likely to be correct. For software developers, this tends to mean code reviews. You want to do these as often as you can without harming the productivity of the team, and start doing them as early as possible.

This check on your assumptions can make any mistakes cheaper and also gets more people involved in checking your assumptions. For instance, if you go over the code with a more senior developer who is still in the office, when they hear something contrary to the way you have written your code, you are more likely to find out about it sooner.

Both of these principles sound easy enough in theory. In practice, however, they are easy to do poorly. Doing them well requires experience, and the best experience is often gained by doing them badly (as I have often done).

Therefore, it’s better to start putting those practices into place well before you transition to a fully remote position, as it is a lot harder to get good practices in place when you aren’t even in the office.

Disrespecting Time and Boundaries

Another common problem that remote workers experience is that the people still in the office will not respect your time and boundaries. In other words, people will (intentionally or not) often waste your work time in stupid ways and then expect you to waste your personal time catching up.

For instance, at a previous job where I worked mostly remotely, only the senior developers had access to certain critical systems. So it was entirely possible to be assigned a bug but be unable to do anything with it because you couldn’t access the system it was on.

This problem was compounded by one of the two senior developers frequently traveling for work and being unreachable during large swaths of the day while the other senior developer was gone for three or four hours in the middle of every workday for karate lessons and worked a lot at night.

This dynamic often meant that I would get assigned a bug in the morning meeting, and by the time I found out that I didn’t have access to the appropriate systems, it was too late. I couldn’t get any help at all until after 2:30 in the afternoon (I started my day at 6:30 in the morning).

The expectation in that environment was that I would just have to work after hours on an irregular basis that was completely out of my hands and couldn’t be predicted. And I would feel bad raising a stink about it because the guy was pretty darned good at karate, and I could tell it was making his life better. But it was making mine intolerable.

The above is a pretty common problem, especially with larger teams that are spread over a larger geographical area. While our team in the previous case was in a single city, no expectations were communicated around core work hours or around making sure that critical systems could be accessed in the middle of the day.

The result was incredibly corrosive to my personal life and meant that I couldn’t reliably work out or meet social commitments without work causing problems. I ended up deciding to leave that job just two months after I started but stuck around anyway for about eight months (because of lifestyle inflation). It was literally the worst job I’ve ever had, and it was mostly remote.

Another common problem for remote workers is that employers will often assume that because you work remotely, your schedule should be flexible enough for you to come into the office at any time with little notice.

This can play havoc with things like child care and other obligations, especially if you have kids who are old enough to need little attention from you while in the house but too young to be left home alone. It’s even worse if you are caring for elderly relatives, have a child with special needs, or have a side business that requires some of your time on a regular basis.

It can be difficult, but you’re going to have to assert boundaries on these things early and often. This means fairly consistent start and end times for your work and also that when you are done for the day, you don’t work unless it’s an emergency. “Emergency” in this case is defined as a short-lived event with serious consequences if it is not handled immediately.

“Emergencies” without bad consequences or “emergencies” that happen frequently are not emergencies and are either the result of poor planning or other people having poor boundaries.

Because many jobs are salaried positions with no overtime pay for “emergency” work, there is no cost to wasting an employee’s time and wrecking their quality of life unless the employee imposes it. This often happens because mistreated employees tend to leave, but there’s no reason to let things get that far. You do have to push back on management if they are demanding an excessive number of hours. If there is no cost to bad decisions, more of them will be made.

You should be ready for these unrealistic expectations when they come. You may even have to leave your job for a different one if it gets bad enough. This is one of the many reasons why I suggest avoiding lifestyle inflation. If you are living hand-to-mouth, you are betting that you won’t run across anyone with poor planning skills who doesn’t value your quality of life.

If you wouldn’t take such a gamble with a cohort of random strangers, it’s unwise to take the same gamble with your co-workers (a cohort of random strangers who you happen to know).

Secondly, make sure that management communicates to you, in writing, what the expectations are around core working hours. Follow these suggestions scrupulously, and don’t allow other people’s insufficient planning to cause work to creep into the rest of your life.

In the job I mentioned above, it took six months to accumulate weight that I didn’t lose for two years, due to stress and inability to control my time. Don’t make that mistake.

Getting Blamed for Problems

The final thing that can be a problem when working remotely is that people will sometimes blame you for problems simply because you aren’t in the room.

While “the shaming of the code” of a previous developer seems to be a time-honored tradition in many offices, it goes a step further when you are out of the office. You may find that you are unfairly blamed for a lot of mishaps, even if you had nothing to do with them.

It’s a bad tendency of humans in groups to break into cliques. Whether it is by social group, religious preference, or simply proximity, this tendency has been with us at least as long as we have been a species. Further, it shows no signs of abating any time soon.

As a remote employee, if the rest of the team is in the office, then you are an outsider. You are considered as much a part of the outgroup as if you had already left the company for greener pastures. While, depending on your team, this may or may not be a problem, you need to recognize that this dynamic underlies every single interaction that you have with the rest of your team.

This problem is very hard to mitigate because you are fighting a core tendency of human nature that has been conserved across all of recorded history. You are just as unlikely to overcome it as any other human being has been, meaning that your odds aren’t particularly good and can be generally rounded to zero. However, there are a few things you can do to reduce the risk of damage from this human social tendency.

First, make sure you communicate with your team on a basic social level and not just about work. When you are just “some dude” who works out of his home in Nebraska and is in the morning standup meetings, you mark yourself as an outsider.

Chat a bit in whatever social chat channels are available. Find commonalities with your co-workers. You need to be doing this anyway to help lighten the social isolation of a remote job, and it also has the effect of humanizing you to your co-workers.

Try to physically get to the office on occasion, even if it’s only once a year. Go to lunch with co-workers when you do, and try to have meaningful conversations about topics unrelated to work. It’s a whole lot easier to screw over a random stranger than it is to do the same to someone with whom you have had positive interactions. You want people to visualize a face when they hear a name.

Never write anything in an ambiguous tone, one that you wouldn’t want plastered on every roadside sign going from your house to work. Reread written communications with your co-workers, thinking about the worst way it can be interpreted, and correct it if you see anything that sounds bad.

Conversely, assume the best when receiving written communications from co-workers, even if the wording sounds bad. Above all, don’t readily take offense if you aren’t completely sure that you should.

If you follow the rules above, you will lessen the degree to which you are considered an outsider by your team. It won’t completely fix all of it, but it will decrease the likelihood of situations where you get blamed and aren’t at fault.

There is one caveat, though: Some situations will be your fault. Readily and quickly admit those. Don’t get people into the habit of having to call you out on your mistakes, or you’ll find that they do it out of habit when you didn’t make a mistake. I learned this the hard way; be smarter than I was.

Smoother Sailing With Smarter
Remote Work

Effective remote work over longer periods of time requires that you realize that remote work has trade-offs, just like everything else in life. While those trade-offs are largely in your favor and can also help your employer considerably, the advantages don’t come without a cost.

There are problems that you are going to have to take care of, and you will have to do so in a proactive manner. You cannot reactively fix any of the downsides listed here, but you can often neatly avoid them, provided that you have good habits that take them into account.

Good social and communication habits will keep a lot of ugly problems at bay. If you really want to work remotely and be allowed to do so for years to come, then you need to start taking steps to do it well before you try to work remotely. If you are ready to do this, I suggest downloading the bonus material for this book (https://simpleprogrammer.com/remoteworkbonus).

Thankfully, the practices that can help you work remotely in a more effective manner can also do wonders for you in an on-site office environment. In fact, I recommend that you start most of these things before working remotely, as they will improve management’s (and your co-workers’) opinion of you in advance of asking to work remotely.

Chapter 6

How To Convince Your Boss To Let You Work Remotely

Once you have a reasonable remote work setup and are prepared to counter objections to remote work, you are ready to start trying to convince your boss to let you work remotely.

Convincing Management Is Not Easy

While it’s tempting to skip directly to trying to convince management of the value of working remotely, I urge you not to skip the preparation. Losing effectiveness because of a preventable issue will not go down well with management. You’ll then have a much harder time convincing them to let you try again.

You should also understand that management is probably not going to let you work in a completely remote fashion the first time you suggest it. You should slowly acclimate them to the idea that at least some people can be effective remotely and that you in particular are one of those people. This is not something that can usually be done quickly.

Getting your boss to agree to let you work from home is a lot like a long sales process. You initially test for indications that they are open to the idea, followed by a very short trial run (or several) in order to build up sufficient proof that you can work remotely.

Doing this with multiple trial runs can also make it easier for you to iron out potential problems that might keep you from being able to work remotely over the long term.

Eventually, once you’ve proven yourself capable of doing so, you’ll pitch the idea of working at home for one or two days a week. This will help you continue building up proof that you can be trusted to work remotely before pitching the idea of doing so more often. The goal is for management to already be comfortable with your remote work before you take the risk of proposing that you do more.

Toward that end, you need to do a little bit more work to make sure that you succeed in convincing management to let you work from home. We’ll be discussing how to do this with a sequence of small steps aimed at gradually increasing management’s comfort with the idea before asking, and asking in a way that makes it easy for them to say “Yes.”

(note: We made a handy guide to go with this process - get it at: https://simpleprogrammer.com/remoteworkbonus).

Before the Trial Run

Before attempting a trial run, you need to start feeling out management to determine how hard it will be to convince them to let you work remotely. If you are really lucky, they are already comfortable with the idea, and you will be able to easily proceed to the next steps in the process.

More than likely, though, your management will be resistant and will have to slowly be coached along.

To get a good idea of how management feels about remote work, start by casually dropping hints in conversation. This is probably the trickiest part of the whole process, as it involves knowing your manager well enough to know what might work and what will produce a bad reaction instead.

Below, I’ve listed some ways to mention remote work to your boss and gauge their reaction. One or two of these will probably work for you, but you’ll have to determine which idea is best, based on your managers.

These are conversation starters that will put you in a position to bring up remote work without overtly suggesting that you intend to do it. Remember, you aren’t trying to convince anyone to do anything; you are only trying to gauge their attitude, learn about their objections to remote work, and then adjust your plan accordingly.

Bad Weather Contingency

“Hey, what’s the plan if there is inclement weather and employees can’t get to the office?”

This one is my favorite approach, as it easily segues into a discussion of how to support remote employees without implying that there will be any. Further, the employees are remote on a temporary basis and not by choice.

This question casts the entire discussion as a way to maintain business continuity rather than a method for allowing employees to skip the commute. This is the safest approach, especially if you don’t know your manager well.

Company X Does It

“My buddy works over at [wherever], and they’ve started to let employees work from home a few days a week.”

This statement can be an effective way to gauge management’s reaction to remote work as well, provided that it seems organically inserted into the conversation at an appropriate time. You have to be careful because if you look like you are forcing the conversation in this direction, this approach will backfire.

Executed correctly, this is a good way to find out what management thinks of the idea of remote working. You might even find that your manager is already trying to figure out how to make remote work a reality.

Volunteering, But From Home

“I’d like to make a branch and try out an idea on [X], but I don’t want to do it on the clock. Can I do it from home?”

Sometimes, if you suggest fixing something on your own time, but from home, you can get a surprising amount of insight into why remote work is not the current practice.

This approach will quickly let you know if your employer has security concerns about the idea of remote work. It also has the nice side effect of showing that you are one of the more engaged employees, as not everyone will volunteer to try an idea out on their own time.

Don’t make a habit of this, though, because it’s easy to volunteer yourself for far more work than you want. This is a tactical, short-term suggestion, not a long-term change in your approach to your job.

Nighttime Issues

“What happens if we have a problem in production at night and you need developer assistance to resolve it?”

While many organizations like to draw a strong boundary between the “production folks” and the “development folks,” in theory, this practice breaks down rather quickly when a production system is offline.

Most companies don’t want to have a critical system down waiting for developers to drive to the office, so you can often get a rough idea of how management feels about remote systems access by using this approach.

Day Off … Working From Home

“If I have a good reason to be home but am able to work, can I?”

A “good reason” could be anything from a doctor’s appointment near the house in the middle of the day, to having work done on your car (or home), to a parent-teacher conference at your child’s school.

Basically, the idea here is to find something that you might have to do during the workweek that doesn’t chew up a whole day but does take enough time that it would be a bit wasteful to drive to and from the office.

Don’t actually schedule the activity yet—the idea is to pose this as a “what-if” and then see the reaction from management.

The Direct Approach

Ultimately, you can also be direct about it.

If you have a good relationship with your manager and they are the sort of person with whom you can be direct, it might just be easier to directly ask them what they think about remote work.

I would generally caution against doing this, even though I’ve done it successfully myself. Think very carefully because this approach can make some managers defensive.

However, other managers will appreciate you being direct with them and may even be willing to lay out exactly what you have to do to be allowed to work remotely. The latter are some of the best people to work with, but the former are what most people have.

The idea behind these approaches is to probe your manager’s impression of remote work so that you can predict their objections for when you later suggest working from home.

While you can just directly ask to work from home, it’s often a much easier process to instead try to mitigate their objections before attempting a trial run. Take note of their objections because the next step requires you to know what they are.

Trial Run

Once you have a rough idea of your manager’s likely objections to remote work, it’s time to start planning a trial run.

The idea behind a trial run is to keep it simple and limited. Instead of pitching the idea of working remotely on a consistent basis, you’ll be pitching the idea of working remotely for a single day (or even a half day if you don’t want to be too ambitious on the first attempt).

Furthermore, you won’t be pitching this as the beginnings of a glorious career of remote work. Seriously, don’t even let on that this is an experiment to prove that you can work remotely in an effective manner. Instead, you will be pitching this idea as a one-off. That is, it’s just a minor situation that came up that could best be solved by you working remotely for a day.

If you have already done some groundwork to determine your employer’s attitude about remote work as outlined in the previous section, you should have a good sense of what objections they will likely raise. These objections tend to fall into a few categories, and you’ll want to have good answers to them before asking.

These categories are as follows:

Productivity - Your manager has expressed concern about your ability to get work done while remote.

Communication - Management is concerned about how your absence will impact the rest of the team’s ability to get their work done.

Security - There is concern about sensitive data leaving the building or about systems being compromised.

Reliability - Management is concerned about you being unable to do your work due to the possibility of an internet outage or other equipment failure.

Jealousy - Management is worried about how other people will perceive allowing you to work remotely because other people may want to do it who aren’t so reliable.

At this point, you should know what concerns management is likely to have. Most of the time, they will have more than one area of concern. While it may seem that multiple concerns would be harder to counter, my experience has been that it is much easier.

I have noticed that when people have an immediate, very negative reaction to something, it tends to be in a single area, while people that cite multiple reasons for something are often trying to convince themselves rather than you.

Before trying to work around someone’s objections to remote work, it’s important to point out that there is a huge difference between what people think and what people say.

If someone expresses that they really hate an idea for a particular reason, then you need to deal with that reason head on because it is probably their true objection. If, instead, they give you a laundry list of reasons, it’s more likely that they aren’t entirely convinced of their position and are simply throwing as many reasons at the argument as possible in the hope something sticks.

We will discuss tactics for dealing with broad categories of objections in a minute, but first we need to decide on a strategy based on how many objections your management has.

With a single objection, the entire outcome is entirely binary. Either you are allowed to work remotely or you are not.

When there are multiple objections, you can often address the easier ones first to gain buy-in from management, and then get them to help you with the others to get the rest of the way. This is more likely to yield positive results because management is involved already.

Once you’ve got an appropriate strategy based on management feedback, you need to figure out how you want to approach management’s objections.

Addressing Management Concerns

If management’s objection is that your productivity may suffer at home, you need to prove that you are effective at your job. Unfortunately, if you are in the sort of organization that doesn’t allow remote work, your effectiveness is probably judged by your presence.

This can mean that you may need to be seen working extra hours. You may also need to increase your level of focus at work. This could be anything from spending less time in idle chatter to very visibly putting on headphones and just working.

Regardless of how you do it, you need to spend a fair bit of time making sure that you are perceived as a hard worker. A word of caution, though: Don’t push yourself to the brink of burnout doing this. You don’t want to set expectations so high that you can’t exceed them while working remotely, and you definitely don’t want to deal with burnout.

If management is concerned about communication, you should start actively improving your communication with your team, using the same methods you would use if you were working remotely. The idea behind this is twofold.

First, following these practices consistently will improve your communication with the team significantly—especially if your communication has been on an ad hoc basis before. Secondly, it will establish a communications system that works just as well remotely as it does on-site, which makes it a lot easier to argue for working remotely.

Security is another thing that can really get in the way when trying to work remotely. It’s also very likely almost entirely out of your control (and possibly even out of your manager’s control).

If one of your manager’s concerns is security, you should probably involve them in your planning a bit earlier. You should be trying to get security concerns out of the way long before you start trying to work remotely. Security concerns will waste a tremendous amount of time otherwise and can completely derail you. Try to get them to lay out their specific concerns and what it would take to overcome those problems. The security landscape is always changing, so you’ll have to do a lot more work if this is on your list.

However, this work will not only make you a better employee (security is always a concern), but if you ask a lot of security-related questions, you tend to come across as more security-conscious anyway.

With all the security threats out there, overcoming security-related objections is not something you can do just once. You’ll have to have an attitude change, and your approach will have to constantly be improving to stay ahead of likely threats.

Your manager may also be concerned by the reliability of your home internet connection, home computer, or other assets required to do your job (such as the speed of your internet connection). This is best mitigated by detailing your backup plans if things go wrong, as described previously. These plans don’t really have to be perfect, but they should be thorough.

The goal of having these plans in hand is to change the conversation from being about what could go wrong to how you will handle things if something does go wrong. The latter is a much easier conversation to have because it assumes that you will already be working remotely rather than being a discussion about whether you can or not.

Management may also be concerned about how other employees will react to you working remotely, even if it is only for a single day. This is also a very tricky issue to navigate, as the jealousy of other employees is really not your problem, even if your manager is trying to make it your problem.

Even worse, any overt plans to mitigate this are likely to backfire because they usually end up tangled with personnel issues above your paygrade. You don’t ever want to find yourself in a position where you are saying something negative (even if it is true) about one or more of your co-workers during a discussion of remote work. Your manager may be concerned that morale will break down if some employees work remotely and others are required to come in, so you’ll want to set things up where things are less likely to become adversarial.

They may also be well aware that some other employees simply can’t be trusted to work from home, as it does seem to be difficult for the unmotivated, the unscrupulous, and the easily distracted.

This problem ties into performance. To get around it, you need to work with your manager to craft a set of expectations that must be achieved while working remotely. If you do this, the manager can point to this list of expectations when other employees approach them about working from home.

This gets rid of an annoying personnel problem for management and also gives them something to motivate the other employees rather than something that introduces jealousy to the team.

There is a common thread in all the approaches to convincing management to let you work remotely: You have to understand what problems the manager is anticipating and why they are anticipating them, and then you have to short-circuit that expectation. You shouldn’t approach management about a “trial run” of remote work until you have a good idea how you will counter their objections.

Scheduling the Trial Run

With your answers to likely objections in hand, now it’s time to schedule your trial run. Pick a reason for staying home that is plausible. Don’t make something up—lying only gets you caught, and it takes a lot more effort anyway. The following are excellent candidates:

Doctor or dentist appointments close to home, but some distance from the office. If you think management might be resistant to this, an appointment for a colonoscopy, “female issues,” and other touchy subjects will do wonders to get them to change the subject and go along with you.

Parent/teacher conferences, school registration, school events like plays, or just eating lunch with your kid (if you have one).

Veterinary appointments for your pet (the less outlandish this sounds, the better).

Visiting relatives or friends from out of town who want to grab lunch and will be near where you live.

Showing your house before a sale, doing home repairs, or waiting for deliveries or inspections. If you rent and strangers will be going into your residence, you really should be there. Obviously, make sure that you aren’t waiting on your internet provider …

Needing to be home so you can leave early for a long trip.

Being home to prepare for a religious observance (especially if that observance means lots of houseguests, large meals, or restrictions on when you can work) or so you can start early on the cooking for a national holiday. Thanksgiving in the U.S., for instance, is a great excuse for this.

Car repairs.

Jury Duty.

You get the idea. You probably have an opportunity coming up that you can use for your trial run. Trial runs are easier if they are scheduled in advance and both sides understand expectations.

While it can be tempting to try this when you (or your kid/spouse/cat) are sick, it’s a lot easier to make a good impression without all the stress. Besides, a sudden illness is not predictable and could occur when you are really needed in the office. For the first time you work remotely, you want to limit what can go wrong.

How To Conduct a Trial Run

Once you have permission to work remotely, on that day, make sure that you actually get a lot done, communicate well, and that you quickly handle any problems that arise. Not only does this make a better impression with management, but taking the single day trial run seriously will also help you iron out any problems that you didn’t know about before working remotely.

While you should have a solid plan, bear in mind that very few things go entirely according to plan no matter how well you prepare. For instance, at my previous job, I was well-prepared to work remotely when I started this process. I was also blissfully unaware of the tiny, cheap network hub that sat in the floor between my workstation and the network jack.

This hub was not on a backup battery and would get bounced several times a day due to small power fluctuations. The short network outages were unnoticeable at the office but resulted in a disconnection of my remote desktop when working from home. In hindsight, I should have known it was there, but these sorts of small issues are easy to miss. You’ll probably run into one or two issues like this yourself.

The point isn’t to plan to such a degree that nothing can go wrong; you just want your plans to limit the really big, destructive things that can happen. The rest is simply a learning experience. Because you are only doing this for a single day, small problems are probably not that big a deal, and in the worst case, you can usually recover the next day.

When working remotely, make sure that you communicate a lot. It’s easy when working remotely to forget about the rest of your team, but resist this temptation. Make sure you stay ahead of any issues that might arise and also that you communicate on a social level as well using whatever tools the rest of the team uses. You want to counter the notion that you are sitting at home watching TV before it ever arises, and being reachable makes a huge difference. This is especially true if you respond quickly, as the pattern for someone who is distracted by TV is one of slow responses if they respond at all.

When you return to the office, try to have a quick conversation with your manager to touch base and find out what you did well and what you can improve. Remember that it’s a lot easier to convince someone to let you work remotely on a regular basis when they’ve had some input on the way that you do it.

Also, make sure that you touch base with your team. In particular, you want to make sure that your communication was sufficient to keep from being a bottleneck but not so overbearing that you got on people’s nerves. It’s important to get a feel for this, as co-workers can create huge problems for remote workers (and often do). It’s far better to have them on your side from the start.

Multiple Trial Run Days

Once you have successfully conducted a trial run and gotten feedback, now it’s time to do it again. This next time will be a lot easier than the first time. Not only will you be more comfortable asking, but you’ve also set expectations for how you will work remotely.

While it’s tempting to skip directly to asking to work remotely on a regular basis after a single day of remote work, it’s ill-advised for a number of reasons. Most important of all, you really need to prove that you can consistently work from home, both to your manager and your co-workers.

A single day isn’t enough to do this, and it’s not enough to make sure that you are well-prepared for the realities of remote work, even if you’ve done it in the past. Before asking to work remotely on a regular basis you need to have a few things in order.

You also need to have at least some experience mitigating the things that will go wrong over a longer period of time. For instance, while you might work a day or two from home without experiencing an internet outage, as you work remotely more often, the possibility that this remains true approaches zero.

You will eventually have a problem while working remotely, and it’s better to handle it as part of a “trial run” day than to have it happen after you have already secured regular remote work.

In addition to this, you need to make sure that you can work effectively in your remote space. While you can get away with it for a day or two, a workspace with ergonomic issues will often make itself very apparent if you work remotely often enough.

For instance, I thought I had a pretty good remote work environment for a while, but after working remotely a few times, I discovered that the layout of my office had major problems with glare from one of the windows during the summer months.

I also discovered that my slightly-too-high keyboard was a recipe for shoulder and neck issues. Had I been working remotely on a regular basis, these issues would have harmed my productivity significantly until they could be resolved.

Because I had multiple “trial run” days before asking to work remotely a few days a week, I discovered and mitigated these issues before they could become major problems.

The point of having multiple trial run days spread over a period of months is to find issues like these before you start working remotely. While you may be lucky and not encounter any problems, you are more likely to succeed if you assume that problems will happen and plan for them.

Additionally, you should look for any recurring patterns that you develop while working remotely to make sure that they are congruent with your goal of being able to work remotely.

For instance, if you discover that you frequently are listless and unfocused in the afternoons, you need to deal with this before regularly working from home. You might mitigate this by working harder in the morning or by taking an extended lunch break and working longer in the evening.

Pay careful attention to any habits that look like they may be forming when you are in your trial run period, as these tendencies often become unconscious habits that are hard to break once you are into a routine of working remotely. This can be anything from oversleeping to spending too much time goofing off while you are supposed to be working.

You might get away with these things when working remotely for a single day, but they will be a big problem when working remotely more often.

The final reason to have multiple trial run days is to train your management and co-workers on how to deal with you as a remote worker. Rather than simply leaving the office and forcing them to deal with a sudden change, you can gradually acclimate them to a more remote-friendly workflow.

Unless they are fairly experienced working on a distributed team, this transition is a learning process for them too, and it is best that it be as seamless, painless, and unremarkable as possible.

Above all, you don’t want your transition to regular remote work to be a jarring experience for the rest of your team, as such experiences can produce passive aggressive behavior and other problems from your teammates if you aren’t careful.

Proving Your Results

Once you have successfully worked remotely a few times and have ironed out all the problems that appeared, you need to start the process of convincing management that you should be allowed to do so more often.

This is a nerve-wracking part of the process, especially for people who tend to be a bit more shy and reserved, as you have to commit to a course of action. Up until now, while you have been slowly moving toward being able to work remotely, most of your moves have been fairly low risk, and it has been relatively easy to recover from mistakes.

However, the stakes are now higher. You want to pitch the idea of working remotely at least one day a week, on a consistent basis. This is far more difficult than the occasional “one-off” remote workday because it will require that other people regularly change their expectations to accommodate you. If you aren’t comfortable with being direct (or even confrontational), this can be a very difficult process.

If you’ve been occasionally working from home with some success, you should have a rough idea of how effective you are. Now you need to get management to have the same viewpoint.

There are a few approaches you can use here. First, when updating management about your progress on remote workdays, make sure that you highlight how much you got done without the time and stress of the commute and interruptions.

You should also make sure that if you are going to work any extra hours that aren’t strictly part of your job, you only do those at home. After all, if you have the ability to work remotely on occasion, you can probably do a little additional work remotely. Make sure that you note what you got done with your periodic forays into remote work after hours, and make sure that management knows about it.

You should also be dropping some hints to management that you feel like you are more effective working remotely. Use these hints to gauge their reaction, and see what approaches seem to produce better reactions.

At this time, you should also be trying to figure out how your manager’s manager evaluates them. Try to determine how you can express your improved work in terms that help your manager.

It’s far easier to appeal to someone’s self-interest when asking for things than it is to appeal to your own interest. If you can prove that you are more effective working remotely and in a way that helps your manager, they are more likely to go along with your ideas and less likely to change their mind later (if you don’t screw up).

The tricky part with all this is that it is really difficult to directly ask how your manager is evaluated and get an accurate answer. Instead, you are going to have to observe their behavior and see what actually motivates them. Don’t ask; observe. Try to form a mental model of your manager’s behavior.

For instance, a manager might tell you that they are evaluated based on how stable their team’s code is, but under pressure they’ll tell you to cut corners to hit a delivery deadline.

In this case, they are more concerned about delivering results quickly than they are about the long-term stability of the codebase, and it shows in their actions. You need to watch your manager’s behavior enough to find out what they really value versus what they say they value. Once you know that, then you make sure that you highlight the results from remote working that most closely mirror your manager’s real priorities.

Pitching Recurring Work From Home

Once you feel like you have effectively proven to your manager that you are more effective at meeting their goals while working remotely, it’s time to ask to be allowed to work remotely on a consistent basis.

Initially, you should try for only a day or two a week unless you really have a good reason. You should also be careful about which days you choose. It’s best to avoid weekdays with the following characteristics:

Days where lots of things tend to go wrong. At a previous job, this tended to be Mondays because problems built up over the weekend and had to be resolved Monday morning when support came in. These tickets would filter up to development by midmorning on Mondays.

Days where management tends to have company-wide meetings. Because of the problems that often occurred on Mondays and because upper management liked to take Fridays off for golf and the like, meetings tended to be on Wednesdays.

You probably also want to avoid taking Fridays as your remote day, because managers and other employees often assume that you are not really working, but starting the weekend early when you do that.

You probably don’t want multiple consecutive remote workdays, at least not at the beginning. Remember that people are still adjusting to you being out of the office; you want that adjustment to be as easy as possible.

As a result of the considerations above, most of the time when I’ve worked remotely for a few days a week, it has tended to be on Tuesdays and Thursdays.

This means that my remote days didn’t interfere with problems that occurred over the weekend and that I was physically present in the office for most large meetings. You’ll need to observe your own organization to figure out which days are the best ones to work remotely.

When it comes time to ask, simply ask. Don’t beat around the bush, and don’t be circumspect. Consider one of the following scripts as an example:

“You know, I’ve been thinking. Since I’m getting more done remotely, I’d like to try to work remotely one day a week and see if I can’t get this project completed more quickly. I was thinking Tuesdays might be good for that, since we don’t tend to have many meetings that day.”

“Would it be possible for me to start working remotely on Tuesdays so that I can get started a little earlier and get some focused work done before John comes in to the office? That would allow me to get some uninterrupted time for some of the more difficult tasks before he needs anything from me. That would help me have things ready for him to QA before he starts working and would help me stay ahead of him for the rest of the week.”

“I’m struggling a bit with the interruptions from Bob when he comes in to talk to John on Tuesdays when they are trying to wrap up QA’s sprint. I know the talks are necessary though—would it be possible for me to work remotely those days so that we aren’t disrupting each other?”

There are a few things to note in all the approaches above. First, you express why being allowed to work remotely would be a good idea either before you ask or very quickly afterward. Don’t give your manager time to come up with excuses not to let you work remotely before you give a reason to allow it.

Secondly, you state the advantage in terms of how it helps the team or productivity. Third, you suggest a specific day for the remote work rather than just saying something general like “let me work remotely on a regular basis.” This will help shift the discussion toward which day(s) you work remotely rather than whether you are allowed to at all.

If you’ve set things up properly, this discussion won’t be as difficult as you might think. You’ve already proven that you can work remotely in an effective manner on an ad hoc basis.

Now, you are just making it official and recurring. If this conversation doesn’t work out the first time, keep doing single day trial runs for a while longer, and keep working on convincing management. It may take a few tries to truly convince them, so don’t give up too early.

However, you may also find that management simply won’t let you work remotely. There could be any number of reasons for this, but sometimes people are just impossible to convince no matter how much evidence you have.

If you find this to be the case, I would suggest that you start applying for remote jobs elsewhere. Life is too short to be stuck in an office, and you’ve already done some of the leg work that proves that you can work from home. We’ll be discussing how to look for remote jobs later.

How To Learn From Failing At Pitching

Like anything in life, if you try to pitch the idea of remote work, it may not work the first time. This is especially true if you aren’t particularly good at reading social cues, don’t organize your arguments well, or have poor timing.

That’s completely fine.

Don’t let the fear of failure keep you from trying. Instead, learn how to fail gracefully and recover. You’ll get better at pitching ideas more quickly by failing and recovering than you will by trying to avoid failure.

When you fail to convince management to let you work remotely on a regular basis, you need to analyze what went wrong to determine what to do next. There are several likely scenarios related to the management concerns we discussed earlier.

If you failed to convince your manager that you were productive enough to be allowed to work remotely, then there are a few things that could be wrong. First, you could have simply not been productive enough while you were at home. It’s also possible that you failed to effectively communicate your productivity to management.

Your boss may simply not like the idea of remote work and is using “lack of productivity” as an excuse. Regardless, you have two things you need to do here. The first is to make sure that you are productive enough and in the way that management is expecting. Secondly, you need to make sure that you are effectively communicating about that productivity.

If you are being sufficiently productive, you should be allowed to work remotely, provided that your boss isn’t using it as an excuse. For the latter case, you need to find out what the real reason for their reluctance is and address that.

If they are concerned about your communication, there are two possible scenarios. Either you didn’t communicate enough and someone else’s productivity was harmed, or you did communicate enough and one of your co-workers threw you under the bus.

In either case, having a copy of the relevant communications on hand is very useful for diagnostic purposes. You should double-check to make sure that you did communicate effectively. If not, you need to correct this before moving ahead.

If, on the other hand, one of your co-workers threw you under the bus, you need to make sure that your manager sees the communications that occurred. As a friend of mine often says, “if they want to throw you under the bus, make sure their head goes under one of the tires.”

If this happens to you, make sure that your manager is aware of the facts—it only takes one person like this to make it impossible for you to work from home, and some people have a very nasty tendency to backstab when their co-workers aren’t around. Make it apparent to management when this happens to you so that someone covering their own backside doesn’t get to impose the cost of a commute on you.

If management is concerned enough about security that they won’t let you work from home on a regular basis while they allow it once in a while, something else is going on.

It may be that there are legitimate security considerations that they don’t consider to be a major problem when you just occasionally work remotely. If this is the case, you need to figure out specifics about the concerns and mitigate the problem.

Security can also be an excuse, especially if you are already being allowed to work remotely on an ad hoc basis. You’ll need to dig a bit to find the real reason for management’s reluctance and then address that.

It’s also possible that they are concerned about the reliability of your internet connection and home computer. These concerns can usually be handled by simply showing them your contingency plans in the event of an outage.

If you show them that you’ve considered everything that can go wrong to a degree that exceeds what the people in the office have thought of, it goes a long way toward convincing them.

Management may also be concerned about how your co-workers will react to you being allowed to work remotely on a regular basis. Bear in mind here that management still has to appear to be impartial and can’t look like they are playing favorites.

They may have legitimate concerns about one or more of your co-workers working remotely. Even though it “shouldn’t” be your problem, it still is your problem. Worse still, if you press your luck with management here, you are more likely to irritate them, which doesn’t help your prospects.

Instead, your approach should attempt to help your manager out by more clearly specifying what is expected from a remote employee. When the other party asks to be allowed to work remotely (since you are allowed to do so), they will be presented with these same requirements.

If the other party really wants to work from home, this may force them to improve their own performance. If they are unwilling to do the work, management has a very good answer for why they aren’t allowed to work remotely. This answer can deflect most accusations of favoritism before they begin.

Convincing management to let you work remotely is a delicate and long-term dance. It can potentially take years. When (not if) you fail to convince management to let you work from the house, the way you handle that failure can determine whether it is permanent or just a small setback.

It’s a Sales Process

When pitching remote work, never forget that while for you it is an engineering process, for everyone else it is a sales process.

It’s easy to focus on simply delivering results, but that’s almost never enough to really convince other people to let you work from home. Instead, being able to deliver is only a tiny part of a much larger sales process.

You have to convince other people that allowing you to work remotely is both sustainable and advantageous if you want to be able to do it over the long term. Organizing this goal as a sequence of smaller goals of increasing commitment and complexity is the best way to pull it off while limiting the risk of failure.

It takes longer, but it tends to work better.

Chapter 7

Creating Good Habits for Remote Work

Once you have convinced management to let you work remotely on a regular basis, you need to make sure you establish healthy routines for remote work.

There are a lot of concerns that you need to address over the long term. Generally speaking, these can be divided into two broad categories: those revolving around you and your home such as your health and your social life, and those related to the office such dealing with management and co-workers.

When it comes to the former, you need to make sure your routines help you avoid social isolation, keep you from getting sloppy with your health and physical appearance, and limit home interruptions.

With regard to office concerns, your remote work habits should help you deal with management, handle having to go into the office efficiently, and keep your skills sharp through regular training.

In this chapter, I’ll show you the biggest issues you’re likely to face—in terms of your home and yourself, as well as the office and colleagues—and, particularly, how good habits can help you deal with them. Afterward, I’ll give you detailed, in-depth instructions on how to come up with your ideal schedule to make your life easier.

While you can certainly use all of the time and money you save from working remotely to watch TV and go to restaurants close to home, you are probably better off making some other big changes to your life as well. It’s worth rethinking a lot of your normal routine when working remotely, as it’s an excellent opportunity to truly change your life for the better in a big way.

Creating Good Habits: You and Your Home

It’s best to try and establish a good routine for yourself as soon as you start regularly working from home. While you can certainly change your work habits later, it’s a lot easier to change your habits at the same time as you change your schedule. The quality of your daily habits while working remotely will determine your long-term success.

Working from home, there are several issues that can affect your work—and your life in general—that aren’t as present when working in the office. Let’s take a closer look.

Diet and Exercise

You should make sure to get at least some exercise every week. Exercise does several things for you.

First of all, it improves your health in general, which is important regardless of where you work. It will also generally get you out of the house and interacting with other people who aren’t your co-workers. These relationships are worth your time.

Exercise will also help you burn off a lot of frustration with work, which is still common, even if you are working remotely. I drastically improved my deadlift single repetition maximum weight during a particularly bad period of a previous job simply because I would go lift every time I got irritated.

Try for at least two workouts a week. and make sure they are intense enough to make you sweat, but don’t overdo it unless that’s something you find enjoyable. Like most things, there is an 80/20 rule with exercise. Twenty percent of the effort will achieve 80% of the results.

You should vary your workout so that you build strength, improve your cardiovascular health, and increase your flexibility. All three of these are beneficial in order to stay healthy.

If you are in particularly poor health, like many office dwellers, you may want to start out by simply walking a little every day. If you aren’t used to working out a lot, that’s OK. Just start by doing something small. If you get a little better every day and continue practicing, eventually you will become one of those healthy people who work out.

Also, be careful with your diet. When working from home, it’s really easy to get into the snack food more often than you might otherwise. Try to keep unhealthy food out of your house if possible. When you are stressed out from work, it’s easier to avoid excess snacking if it requires a trip to the grocery store.

While getting into a really solid diet routine is far out of scope for this section (there are thousands of books on the subject, and some of them are even good), generally just avoiding lots of carbohydrates and heavily processed food is usually enough to keep your health from rapidly declining. For a more thorough discussion of how to truly fix your diet for optimal health, see a professional.

Avoiding Isolation Over Time

One of the biggest problems with long-term remote work is how easily you can end up feeling socially isolated if you aren’t careful. While you will commonly hear that working remotely can be isolating (especially when talking to people who don’t like the idea), you won’t really understand how isolating remote work can be until you’ve experienced it for a while.

This is especially a problem for people who live in so-called “bedroom communities” outside of major cities where most other people are commuting into the office. Communities such as these feel surprisingly empty during working hours.

If you are like many of us (myself included), you probably have spent some time making sure that your house is a comfortable place to be. While this a reasonable goal, it can work against you when you are working remotely, as you have fewer reasons to leave the house.

I strongly suggest that you find a good reason to leave your house during the workweek for at least a few hours a week. Whether this means going to a gym, going to lunch with nearby friends, or just running errands during the day, it’s really important to get out and move around a bit.

It’s also a good idea to network with other people in the area who are working remotely. Try to go out to lunch once a week with another remote worker, both to get some social interaction and to build your personal network. Remember that at some point, you’re going to be looking for another job, and it’s a good idea to know other people in the area who work for companies that already allow remote work.

The first time I had a job where I worked remotely most of the time, I didn’t follow this advice. Instead, I didn’t leave the house except to run the occasional errand on the weekend. After a few months of this, I started getting very stir-crazy and tended to talk too much when I did talk to people.

While it’s not the end of the world if you do end up a little socially isolated, you’ll definitely enjoy the remote work experience a lot more if you regularly get out and interact with other people.

Additionally, you should make a regular habit of talking with your co-workers and other friends over chat about nonwork stuff. While you may be at home all the time, that doesn’t mean that you can (or should) be completely focused at all times.

People in the office aren’t completely focused on their work at all times, either, so it is reasonable to have some downtime when working from home. Just make sure that the way that you communicate is appropriate and allows other people to respond without disrupting their own work.

Also, be very careful about how frequently you are perceived to be chatting. Keep conversations brief enough to give you (and others) a break, but don’t spend all day in chat. Remember that chat conversations are easily archived and viewed by management even if you don’t think your manager will look.

Finally, make sure that you spend time with your family. It’s really easy when working from home to spend too much time in your home office. If your family is home during the day, make time for brief conversations with them. Remember that you are working from home, not serving a sentence in solitary confinement.

While you shouldn’t watch a full-length movie with your spouse while allegedly “working from home,” it’s entirely reasonable to talk for a few minutes here and there during the day. You can be normal and have normal conversations, just don’t forget that you have to get your work done.

Managing Home Interruptions

One consistent problem when working from home is managing interruptions. While in an office this tends to be someone else’s problem, at home you have to deal with it yourself.

Interruptions come in various forms, with the most egregious ones being the easiest to deal with and the more subtle ones likely to be a frustration for a long time. Some amount of interruption during the day is probably unavoidable in a home office (just like it’s unavoidable in a regular office).

There are a few common sources of interruptions in the home environment:

- People leaving or entering the building

- Small children and babies crying

- Loud noise from other occupants

- Loud noise outside such as leaf blowers and loud conversations

- Deliveries and door-to-door salespeople

- Phone calls, including telemarketers

- Random friends and family dropping by

You’ll notice something about all of these things: You don’t have true control over any of them. However, there are a few things you can do.

First, you need to make sure that the other occupants of your dwelling (if they are old enough to understand) have a way of knowing that you are trying to work. It can be as simple as closing an office door, but you need to have some way of signaling that you need to focus and cannot deal with an interruption.

This gets a lot of the simple problems out of the way, and when combined with good noise canceling headphones, can often do away with with most interruptions.

Additionally, if there are small children or infants in your residence, you need to make sure that you are not the caregiver. It’s really easy to take “just a minute” to go take care of a child and end up losing an hour or more of work time.

While your job isn’t your only focus in life, it does need to be the main focus during your work hours. Further, if you are trying to work full-time from home while caring for a child, you probably aren’t doing very well at either task.

Phone calls are also a problem. In general, my telephone is set on silent all day while I’m working. Co-workers know to contact me using email or other means.

I do not allow telemarketers to randomly interrupt me during the day. I suggest you do the same not the least because the model of interrupting people while they are working to try and sell them an extended car warranty is a really bad one anyway. If you have a cellphone, you can probably program it to only let calls from certain people ring through.

You are also going to have to make it clear to random door-to-door salespeople, family, and friends who drop by that you are at work and don’t have time to chat. A lot of people don’t really understand that remote work is still work and that they are putting your job in danger with interruptions. Make sure you communicate this clearly, and set good boundaries.

Loud noise from outside will be an issue in certain environments. In leafy suburban neighborhoods, leaf blowers and lawn mowers are frequent irritations during the day, while in more urban environments, mechanical noise, construction noise, noise from traffic, loud music, and noise from passersby can often be irritating.

Truly rural environments may include noise from heavy equipment and animals. In short, there isn’t really anywhere you can go to get away from it, so you’re going to have to take some steps to deal with it.

First of all, a lot of this noise occurs on a regular schedule. Lawns are often mowed on certain days, construction is usually daily for months, and even roosters start crowing at fairly predictable hours. You may simply have to adjust your work schedule so that you are doing something else when the noise is occurring.

For instance, most of the people around me and I use the same lawn service. When they are mowing, I go to a coffee shop.

It’s a little bit more tricky if there is continuous outdoor noise during work hours, however. About the most you can do is take a laptop to the interior of your residence, as far away from the noise as possible, and try to cover it up with background noise (if you can find anything that isn’t distracting).

The point is, you are going to get interrupted when working from home, and it will happen a lot. You need to identify likely problems and have a plan for dealing with them just like you have to have a plan for dealing with every other failure point.

Interpersonal Issues

You will also find that the interpersonal dynamics of your most important relationships change a lot when you work remotely. For starters, because most people don’t understand remote work, they will think that you aren’t really working.

The reality is that you’re going to have to be able to work hard and bring focus to bear on what you actually do if you want to be able to work remotely over the long term. Other people are not likely to spontaneously understand what it really entails, so you’re going to have to deal with recurring issues surrounding this if you want your transition to remote work to be a smooth one.

The following are some common assumptions you’ll face. Sometimes, people say these things, but most of the time, they imply them with their actions. We’ll go through these and explain what to do to counter this behavior in a way that should avoid extensive conflict. However, there will be some conflict.

Some of these assertions are extremely self-serving for the people that make them while being destructive to you personally. As a result, you may find yourself pushing back on other people, but you can usually do so in a way that doesn’t create destructive conflict, and you may actually improve some of your personal relationships once you set boundaries with other people.

One common assumption is that remote workers are available for chores—such as child care, pet sitting, or running errands—during the day. Relatives and close friends will often assume that since you work from home, you can do things for them during the day. And on occasion, you might even be able to.

Nonetheless, when it is on a regular basis and disrupts the workday, you simply can’t. It’s better if you point out early on that you can’t do things for other people very often during the day because you are actually working and are expected to show progress in your various work tasks.

For most people, simply expressing that will get the point across. However, for others you may find that you have to be a bit more blunt. In the latter case, it’s best to tell them “no, and stop asking.”

It’s also pretty likely, especially early on, that you actually will run errands for family members and the like during the day. It’s a small thing and is part of being a good member of your social circle.

Where it gets you in trouble is not having a good sense of when you have spent too much time on tasks for other people. You need to figure out for yourself what amount of help you can afford to give other people and then make sure that line is not crossed.

For instance, early in my remote work career, my wife frequently wanted me to go to the grocery store during the day and pick things up, often on short notice. On occasion this is fine, but when it happens three or four times a week, it starts eating all of your free time.

When I expressed that without being stressed out or exasperated, it was fairly easy to convince her that running to the grocery store all the time wasn’t tenable. Had I waited until I was already overloaded at work (and in trouble for not getting enough done), it likely would have led to a conflict. Fix these problems early, and you won’t have to fix them often.

Another common thing you’ll experience is that other people often believe that you can just take a break at some random time in the middle of the day with no warning.

Whether it’s because they show up at your house uninvited or because they call you on the phone (or message you on social media), some people simply don’t have good sense about what remote work is really like, especially if you work in a technical field that they don’t understand. System administrators and software developers often experience this sort of behavior from their close friends and family.

I’ve found that the best way to deal with this is to simply stop responding to people during business hours. You probably wouldn’t be able to respond to them if you were working in an office, so it is not at all unreasonable to avoid responding while working at home.

Similarly, if they just stop by, be polite, but tell them you have to get back to work. Remember that in every interaction, you are training the people you interact with how to treat you. Generally, being firm is enough to make sure the boundary is respected and that you are still friends with the other party.

When it comes to assumptions, people might think you can take care of small children while working.

Just say no. You might be able to occasionally change a diaper or something when working remotely, but you can’t be on call for small children. It simply doesn’t work. You might be able to take care of a 10-year-old, especially if the child is fairly self-reliant and respects the fact that you need to work.

This may cause a bit of friction, especially with your significant other. Many times, when one partner is able to work from home, the other partner assumes that there is no longer any need to pay for child care. This can lead to significant arguments, as child care isn’t cheap. This is especially annoying if you ended up taking a pay cut (or skipping a pay raise) as part of your negotiation to work remotely.

However, the fact remains: You cannot effectively care for small children while attempting to do real work from home. You’ll either neglect the work, or you’ll neglect the children. Given that you probably don’t want to have something awful happen and end up in jail, you’re almost certain to neglect the job.

The way to handle this is to point out how much you need to be able to concentrate and how expensive and difficult it will be when you lose your job for lack of performance and have to suddenly search for another job while trying to find day care at the same time.

This may not completely diffuse the argument, however. You’re going to have to stand your ground on this one. Just remember that the other person is trying to do the right thing, but they don’t understand the constraints you are working under.

When it comes to significant others, another odd situation could come up. When your significant other’s employer finds out that you work remotely, they might assume your significant other can now work more because they “don’t have to get home as early.”

I’ll start off by telling you that your working arrangement is no one else’s business, but most especially not the business of your spouse’s employer. Failing that, your spouse needs to stand up for themselves. Yes, they do have obligations at home, and no, it’s not relevant at all that their spouse happens to be in the house.

This can be a tricky thing to negotiate as well, as your spouse suddenly finds that they have a conflict at work because of a change in your job status. However, it is deeply unfair to penalize someone because of their spouse’s job situation.

Furthermore, a lot of times managers don’t realize how ridiculous this sounds until it is expressed that way. Before planning to start working remotely on a regular basis, it may be worthwhile to have a long discussion with your spouse about this issue so they are prepared as well.

A frequent refrain heard from the masses of captive cubicle cattle is that you are lucky that you work from home. This is usually thrown out any time that you are less than totally positive about something in your work environment or mention that your work is challenging.

It’s a very annoying assertion because the reality is that you probably had to put in significant effort to be allowed to work remotely, and you certainly have to put in a lot of effort to maintain remote work. You might have been “lucky” enough to get a boss who liked the idea from the start. Beyond that, it was all hard work.

You should probably correct people that say this and do so early and often. They need to realize that it isn’t a matter of luck. It’s a matter of planning ahead and proving yourself. This statement is equivalent to telling a bodybuilder that they are lucky, when the reality is that they put in the work—even if they did happen to have some genetic advantages, the effort is nothing to scoff at.

When your friend realizes the effort you put in to get this alleged luck, point out that they can do exactly the same thing. A lot of times, these sorts of statements are indicators that people wish they had what you do but don’t know how to start. You’ll be far less irritated by hearing this all the time if you realize what it really means.

When you are told that you are lucky in response to some legitimate criticism of your work environment, make sure that you don’t take that to mean that you don’t have a right to complain.

Suddenly allowing people to work remotely doesn’t absolve a company of their basic duty to take care of their employees. Otherwise, a lot of companies would do so. It’s a sign that they are on the right path and nothing more. Even fully remote companies have their problems.

You’ll also hear the assertion that any job you can do from home isn’t a real job, whatever that means. Just ignore these people. If you find your work meaningful and helpful to other people, you don’t need anyone’s approval to do it. In truth, the very fact that you are working remotely and getting paid to do so puts the lie to this notion.

You’re going to hear a lot of things from people who are stuck going into an office (or worse still, a retail store) about how easy your life is. And they are right. The point of this entire exercise is to actually make your life easier, better, and more fulfilling. Nobody else’s perceptions really count. Don’t let yourself be goaded into having to defend making your own life better.

So far, we’ve seen some of the issues at home that a good routine can help you with. Now it’s time to take a look at similar issues with the office and its people.

Creating Good Habits: Office, Management, and Colleagues

Although you have begun working from home, that doesn’t mean that dealing with the office and its workers is now a thing of the past. The dynamics have changed, but that only reveals that you need to have good habits in place so that you can deal with issues and situations such as the following.

Soliciting Feedback

While interpersonal feedback and expectations can be annoying and distracting, there is a kind of feedback that you need to have a plan for recieving: feedback from your co-workers and management. You should be regularly soliciting feedback so that you can spot problems and correct them before they become a real issue.

Being proactive about gathering feedback is important for remote workers. For starters, you aren’t in the office every day, so it’s really easy to miss things that are becoming a problem in the office.

The issue is further compounded by the lack of informal interactions where you can pay attention to other people’s body language to find out how people feel. Even if you are regularly in video meetings with the rest of your team, it can be easy to miss subtle clues that you would have picked up had you been in the office. People also tend to do a little bit more acting when they are on camera.

As a result, you need to reach out to your team. Tell them you’d like to get feedback on how you are doing when you are remote. Depending on the team, there are a couple of different ways to do this.

If you just started working remotely while the rest of the team is still in the office, you might consider simply being direct and asking what is working and what isn’t. If you phrase it by asking what they think the biggest problem is, people will often tell you. Many times, they’ll offer suggestions for how to fix it as well.

On the other hand, if you are in a fully remote team, this strategy will come off as a bit odd. Instead, you may need to get this feedback with informal conversations. For instance, you might ask, “What’s the best way to make sure that you know I’m working on the email you just sent me?”.

If the rest of your team is remote and is used to the work environment, they probably already have pretty good coping strategies for dealing with the idiosyncrasies of the rest of the team. It’s easier to borrow these than to invent them.

You should be more direct with your manager when asking for advice. You should never go into an annual review and be surprised by your manager’s perceptions of your work. However, this can easily happen when you are working from home.

What I’ve done in the past is to simply send an email directly asking what I’m doing well and what can be improved. Point out to management that you really like to work from home and want the process to be better for everyone, but that you want to make sure that you don’t have a blind spot in regard to your own performance.

Usually, if you don’t do this too frequently or at a bad time, you can get some really good feedback. Even if you don’t, it’s important to involve your manager in this process so that they feel invested. Don’t forget to do this—I’ve had nasty surprises in the past when I’ve failed to do it well.

When You Have To Go In to the Office

Even though you are working remotely on a regular basis, there are probably going to still be times when you are required to go into the office. Whether you have to do so a couple of days a week or just once or twice a year, you need to be very cautious about how you handle your office visits.

While your work at home is highly visible to you, it isn’t as visible to the people in the office. Therefore, you need to make sure that you present yourself well whenever you are in the office. There are a lot of factors here, and you need to get them right so that you can protect your ability to work remotely.

A lot of people fail to do this and create a bad impression that causes them problems later. Let’s discuss a few things that you need to make sure that you handle office visits well.

First, you should make sure that you dress well when you go in to the office. People are exceptionally good at seeing patterns (even if there aren’t any). If you present yourself professionally when they do see you, they’ll often assume that you are being professional when they don’t see you.

While this doesn’t protect you if you really screw up, it does have the effect of keeping people from looking at you too critically. Think of it as a sort of camouflage. You don’t want to be different from a hard worker in the office, because then your co-workers will start looking for other things that don’t align with being a hard worker.

Also, when you are in the office, make sure that you spend quality time with your co-workers, including going to lunch. Because the home environment is isolating, you need to spend extra time overcoming that. Repair relationships, build new relationships, and make sure that you have a good idea of the political situation in the office when you go in.

If you don’t, office politics will give you a nasty surprise when you are just trying to get work done at home. Be especially aware of new co-workers and managers—you need to establish good working relationships with them as well.

Time Off and Errands

When working remotely, you’ll probably still need to take days off and occasionally deal with errands and other obligations during the day. You need to make sure that your team is always aware of these things, as the last thing you need is to have your team waiting on you while you are drinking margaritas with your best friend on your day off.

Even though you may have applied for the time off with your manager, if the manager isn’t in the office and the team doesn’t know, it’s still a problem for you.

Remember, if you are working remotely, you don’t want anyone in the office (especially an authority figure) to be thinking “this would work just fine if they weren’t remote.” Do everything you can to keep that thought out of their minds even if it occasionally feels like you are justifying yourself too much to them.

Also, be sure to set an automatic response in your email client (and chat clients if possible) to indicate how long you expect to be out of your home office and who to contact instead. Make it really simple for your co-workers to know that you aren’t working—you don’t want them guessing about this.

Training

When working remotely, it’s also important to keep your skills up to date. While your company may have some training opportunities in the office, a lot of companies don’t do a good job of training their remote employees on the latest technology. You probably should handle this yourself.

Generally speaking, you can get a lot of good free information using resources like YouTube and free online tutorials. You can also opt for some of the more expensive video training websites, but keep in mind that the information on these sites is often dated due to their slower production cycle.

Try to spend at least a few hours out of every workweek learning new things on your employer’s time. You shouldn’t be doing this on your own time unless you are trying to take your career in a radically different direction. Remember that learning new skills and techniques will make your work for your employer better and will often improve your productivity. Your employer should be paying for that, not you.

It’s also important to have a realistic training schedule. Try to pick a technology to deeply focus on every quarter or so, and really work on learning it well. It’s easy when working remotely to gain shallow knowledge of a variety of different platforms, especially if you find it interesting to learn new things.

Avoid broad but shallow learning, as this is a career mistake that limits your options. Remember that if you like working remotely and want to do so even after your current job, you are better off being a specialist in a particular technology, rather than a generalist.

Specialists can more easily set their own terms, whereas generalists usually can’t do so as easily. Structure your training so that it not only provides more value for your current employer but that you also build deep knowledge that the next employer is going to want even if they have to put up with you working remotely.

And now that we have seen what kind of issues can affect your remote work—related to both home and office—and how having good habits can really help, it’s time to see how you can build your ideal schedule. A schedule suitable for you and your individual needs is a major booster for productivity as well as quality of life in general.

A Day in the Life: Building an Ideal Schedule

When working remotely, it can be tempting to simply wear your pajamas and plop down at your desk like you would on a Saturday morning when you are playing games. You can get away with this for a while, but it’s not a good habit to get into.

I’ve known very few people whose work discipline was solid when they were dressed for sleep with their hair sticking up. While you should have taken steps to make sure that work doesn’t leak into your home life and cause problems, you need to do the same thing to make sure that home life doesn’t leak into your work.

Everyone has a different ideal routine when working remotely. Before we get into how to discover yours, I’ll show you what I do. I think mine works pretty well for me, but I’m always experimenting.

I wake up at 5:30 in the morning most days and have the coffee pot programmed to have a fresh batch of coffee ready at 6. During the first 30 minutes, I have time to get cleaned up, get dressed, walk the dogs, and do my daily planning.

Once the coffee pot starts, I’m usually in the kitchen practicing Russian using Pimsleur—I used to do this in the car, and the kitchen was the best place to fit it in my schedule once I started working remotely again. Once the coffee is done, I pour a cup and head downstairs to the office. I finish my Russian practice by 6:35 or so.

After that, I sign in at work, check my email, and start sending emails with any questions I have. Then I send a message to check in with my project manager and co-workers. At this point, I have a little over an hour to handle smaller work tasks while I dump coffee into my system.

At 7:45, I sign out and take my daughter to the bus stop, returning to my desk at about 8:05. When I return, I get another (usually the third) cup of coffee and sign back in. The first hour of the day is preparation for what comes next.

For three hours after returning to my desk, I play my music loud and work in short, extremely focused bursts, taking short breaks only to use the restroom and get more coffee. At 11 or shortly after, I sign out for an hour.

During the hour I’m signed out, I work on my own personal projects and eat lunch. Usually that is writing podcast outlines or content for books (this section was written during lunch). When the hour is done, I return to my desk, briefly check my email, and check back in with my team, then I try to get another three hours of extreme focus in.

Once that is done, it’s a little after 3, and I’m usually pretty tired. For the next hour or so, I handle smaller, less difficult tasks, and try to get ahead of anything that might be a problem in the next few days. Just after 4, I’m roughly done for the day, and I sign off.

I stay at the computer, however, usually working on my own stuff, but keeping my email and chat open in case someone needs me. At 4:45, my daughter returns home, and I disconnect from work entirely. After that point, I don’t respond to emails or chat messages unless it is an emergency.

Once my daughter is home, I tend to either go lift weights in my home gym or go upstairs for a bit to handle various home tasks. After I’ve made sure that she has started her homework and has had a snack, I tend to return to my own work while keeping the door open in case she needs anything.

At 6, my wife returns home and real family time starts. My time is fairly unstructured at this point and tends to alternate between working on my own tasks, playing games, and the occasional bit of TV. By 8:30, I’m winding down and programming the coffee pot for tomorrow. I spend another 30-45 minutes practicing Russian, and then read until I get tired. I’m usually out by 9:30.

My routine is ideal for me because I spend time every day on my major priorities. In addition to work, I am usually working on one or more writing projects, often have consulting programming projects, and have a podcast (which also requires a lot of writing and research).

Every day has dedicated time for these things, and I’ve shuffled my schedule so that I conduct these tasks (and my work) in a way that lets me fit everything in.

You might look at this and think: “Wait a minute, he’s only truly focused on his work tasks for six hours a day.” That’s entirely true. The other two hours of work are for administrative tasks and for making sure that the next part of my tasks are lined up.

You probably have a similar distribution of work (or worse) during your normal workday, but don’t explicitly allocate the time. By explicitly defining my “admin time” and my “heads down, working” time, I’m able to retain an appropriate level of focus for both.

I also avoid getting completely burnt out and exhausted by making sure that I don’t work more than three hours at a time in a highly focused mode. I also found that it was critical to have distinct periods of time during the day when I work on my own things, as I don’t plan to be a salaried employee for the rest of my life.

What I do during lunch and after work reflects that. I spend some time every day working toward a life where I am my own boss. Similarly, I have also highly prioritized learning a foreign language because it matches with other strategic objectives that I have, which I also spend time on every single day.

Now that I’ve gone into some detail on the schedule I’ve built for myself, I’m going to upset you by telling you not to copy it wholesale.

I built this schedule based on my own experience and by carefully setting goals, taking detailed notes about my energy level and productivity during the day, and considering the fixed requirements of my schedule (such as the time my daughter needs to leave and the time she returns).

There is almost a 100% chance that my schedule is not ideal for you. Never fear, however, as you can do the same thing I did and build a very workable schedule for yourself using the approach that worked for me.

There are five phases to the process of building a “perfect” remote work schedule for yourself. Be aware that whatever schedule you design will be fairly ephemeral—any slight change will cause you to have to rework it if you want to achieve your goals over the longer term.

Your goal in building up an ideal schedule is to make the most effective use of your focus and time and to use your body’s internal clock to your best advantage. Toward that end, you’ll need to collect data on the following and continually adjust until you get something that works well.

Here are the phases that you will go through:

You will determine your chronotype. Your chronotype simply tells you when your most effective working time is. While you probably think you already know what this is, your habits the night before and many other factors can play a huge role in this. It may be worth altering your nighttime routine so that you can more effectively leverage your chronotype for maximum efficiency during the day.

You will list your goals for the next six months. These will not just be your work goals but also your personal goals. These include things like diet and exercise.

You will collect data regarding your mood and efficiency during the day, trying to get a picture of how your personal energy and focus levels for certain tasks vary. You will collect this data while noting your caffeine and food intake because these matter a lot.

You will take note of fixed events during your day that impact your schedule and cannot be avoided. This also includes meaningful interactions with your family, friends, and social circle, as those are not “optional” if you want remote work to be a sustainable part of a healthy life.

You will then construct an “ideal week” work schedule that allows you to work on your goals during the week at the best time based on your energy level.

After accomplishing these tasks, you’ll be well on your way to much better productivity while working from home. While you might try to simplify the process (I did initially), if you really want to maintain optimal performance, you’re going to need to do some extra work to see that this happens.

Let’s now take a closer look at each one of these five elements.

Your Chronotype

Almost all of us have come to the conclusion that we are either a morning person or a night owl. Some of us are even right about it on occasion. However, it’s really easy to be wrong about whether you are truly a morning person or not, simply because most of us don’t really test it.

If you think you aren’t a morning person (or if you think that you are, for that matter), think back to when you decided this. Did you decide it because you hated getting up in the morning in middle school or high school after you stayed up too late watching TV? Conversely, did you decide that you were a morning person because at some point you adjusted to getting up early and taking in a half pot of coffee before lunch?

If either those things sounds familiar, you don’t actually know what your chronotype is. Sure, you might have a good guess, and it might even be correct. However, if you really do some testing, you might also find that you get a result that you don’t expect.

I’ve observed a number of people who go through this process, certain that they aren’t “a morning person,” only to find out that they are actually extremely productive in the mornings but lack the discipline to go to bed early enough for it to matter.

I’ve seen others who thought they were morning people, only to find out that they were really more effective in the afternoons and evenings—they had spent years getting up early because they were “supposed to.” In either case, these people are missing out on significant improvements to their productivity and better use of their time.

To get started, take a couple of days and try to live as if you are a different chronotype. For instance, if you think you are a morning person, try going to bed later, getting up later, and working in the afternoon.

Similarly, if you don’t think you are a morning person, try going to bed earlier for a few days and working first thing in the morning. You’ll probably have to do this for a few days, but you’re certain to learn something interesting.

When I was young, I didn’t think I was a morning person. Even though I grew up in a rural environment and had to get up very early, I still wasn’t really noticing that my energy levels were better first thing in the morning than they were in the evenings.

This was partially because I was doing a lot of manual labor and partially because I was staying up too late playing video games most nights. As a result, during my early adult years, I was convinced that I was not a morning person.

That all changed when one of my jobs basically required me to get up and start the day early due to working with overseas contractors. I learned that not only could I get up early but that my productivity was far higher before 9 in the morning than it was at any time afterward.

Experiment for a couple of days, and test your assumptions about what time of day you have the most energy. You might be surprised. Make sure to allocate time to get enough sleep when you do this—your results will not be informative if you don’t. This can seem like a waste of time, but it will pay off in the long run, especially if you learn that you’ve been wrong.

Your Goals

Now that you have a rough idea of your chronotype, get back onto your normal schedule. While you should fix your schedule eventually, you want to make sure that any long-term change you make is both low stress and wildly successful. This will make it easier to make the changes stick over time.

At this point, you need to start doing a little bit of planning regarding your long-term goals. Working remotely is fine, but the real goals are to improve your quality of life, to allow you to achieve things that you wouldn’t otherwise, and to reduce your overall level of stress. So, it’s a good time to take a minute and start making longer term plans.

There are three main areas you should probably consider:

- Physical and mental health

- Career growth goals

- Family and relationship goals

These are all areas that tend to suffer when you are stuck in an office both because of the environment and because of the tremendous amount of time you waste in traffic. Once you are working remotely, you have the opportunity to start fixing some of the things that were damaged by being forced into an office.

Let’s break these areas down a bit more so that you can understand how going into an office might have created issues that you never considered.

Your physical and mental health might have suffered. Are you heavier now than when you started working? How do you feel about running a mile now compared to when you started working? Do you eat more junk food now than you used to? How’s your sleep? Are you tired all the time? Are you miserable in your career?

Your career growth can also be harmed by being in an office, especially if you want a career that is different from what you are currently doing.

Do you want training in something but suspect that management will react badly to the suggestion? Have you avoided learning something that you want to learn because you know you will have to use your personal time to do it? Do you feel comfortable asking your manager for training that might one day put you into a position to replace them?

If any of these questions make you cringe, it’s worth addressing them when you start working from home (and if you want to do that, you should download the bonus material for this book from https://simpleprogrammer.com/remoteworkbonus ).

The health of your family and other relationships can also be damaged by working in an office. When was the last time you had lunch with your best friend (or your spouse) during the week? When was the last time you had to tell a spouse, child, or friend that you couldn’t attend something that was important to them because you had to work?

Worse still, when was the last time you took time off from work to do something important with one of these people, only to be stressed out because you were missing work? Have your children ever said “I think Daddy/Mommy works too much”? Do you have aging parents that you can only see once in a blue moon because travel has to fit around work?

I realize that the questions above are probably extremely uncomfortable to ask. However, the fact is these major areas of life can be improved for most people. The good news is that if you are able to work remotely on a regular basis, you are in a better position than most people to fix these areas of your life.

However, there is some bad news: I can only advise you on generalities, and you’re going to have to work out the specifics for yourself based on your own situation. Further, depending on how complicated some areas of your life are, it may be worth seeing a professional to get some help. But I can offer you some general guidelines.

For physical health, there are three main factors to consider: what you eat, how often you exercise, and how well you sleep. For optimum mental health, you need to take care of your physical health as well as consider a few other things.

In particular, you need to make sure that you regularly get a chance to unplug from work and participate in activities that you find meaningful. You also need to ensure that you have proper boundaries in your interpersonal relationships and that you manage stress in a way that is healthy.

For career growth, there are a few issues to consider. First and foremost, are you being effective at work? Second, are you actually happy doing what you are doing, and if not, what would you be happy doing instead? What are your goals 5, 10, and 20 years from now, and what can you do right now to start moving toward those goals? What skills and knowledge do you need to acquire for your next step?

As for family and relationship goals, do you get enough time with your spouse or significant other to have a meaningful relationship? If not, what would such a situation look like?

How about your children if you have any? Could their lives be improved if you spent more time with them, allowed them to be involved in more after-school activities, or simply helped them get a deeper understanding of their schoolwork?

How about your close friends? What if you could spend more time with them?

It’s hard to get into specifics with these issues because everyone’s life is different, and everyone has different areas that they need to improve. Further, giving advice is hard because sometimes it’s beyond the paygrade of someone who isn’t a professional.

Simply put, you probably shouldn’t be taking advice from a random guy on the internet on this stuff. Instead, what I suggest is coming up with a single goal for one of the three areas listed above and then planning out how to improve it within the next three months.

While you could take on multiple goals at once, you’ll get better results by fixing a single irritating, but easy area of your life first and then seeing how that changes things. You will often find, for instance, that a lot of work stress goes away when your personal relationships are healthier, or vice versa. Take a single goal or pain point of your own and follow along.

So let’s start with a single goal. Since I (probably) don’t know you personally, we’ll take an area that has been a struggle for me and try to come up with a way to improve the situation.

My biggest issue at the moment is how frequently I end up eating things that aren’t optimal for my health. I’ve got some food sensitivities that can be a royal pain, and I tend to eat far too many carbohydrates when I’m stressed out.

Further, these food sensitivities create additional stress in my life because they tend to upset my stomach and make me feel gross in general. I’m avoiding specifics out of courtesy to the audience, but I suspect you can imagine.

To fix this, what I have to do is to make sure that healthy food options are available and easy for me. This tends to mean that I need to spend a fair amount of time every weekend on meal preparation.

There are four main components that are required to make sure that you can correct an issue with your life. These are as follows:

Daily and weekly habits. You need to be addressing the issue on a regular enough basis that the process fades into the background noise of your life. While I don’t mind bulk cooking for the week (I actually find it relaxing), I don’t find deep meaning in it.

It’s something that needs to be done, done well, and done consistently for the benefit of the things that I do find meaningful. In this case, I realized that I need to prepare food in bulk on Sunday afternoons (weekly habit) and that I need to put food in the refrigerator to thaw every morning so that it’s ready in time to cook dinner (daily habit).

There is also another hidden assumption here, and that is that I will have the supplies on hand that I need before I start cooking on Sunday. This means another weekly habit of getting a grocery list together and going to pick it all up (I do this on Saturdays).

Removal of obstacles. You also need to make sure that you aren’t damaging your progress toward your goal. This means getting rid of things that can cause a problem.

For myself, with the diet, this meant that I stopped buying salty, carbohydrate-loaded snacks for myself. Instead, I kept snacks around that don’t cause problems for me. Essentially, instead of stocking potato chips, cookies, ice cream, and high-carbohydrate breakfast food (such as muffins), I now make sure I have a steady supply of mixed nuts, beef jerky, pickled eggs, sardines, and the like.

I generally don’t need a lot of snack food, but keeping these on hand makes it easier to eat something that doesn’t cause problems for me.

Tools. You may find that you need to spend a little money making it easier for yourself to fix a bad habit. In my case, the purchase of a vacuum sealer and a pressure cooker made bulk cooking a lot easier and faster.

You should spend some time thinking about how you can make your desired habit change easier—you don’t get bonus points for making this stuff harder, so don’t.

The feedback loop. You need to track what you are doing and carefully monitor the results. Ineffective habits are worse than useless in that they are discouraging and waste time. You need to collect whatever data you can to be sure you are headed in the right direction.

In my case, I could tell that the frequency of stomach issues was lower, and I saved a ton of money on junk food. The point of the feedback loop isn’t necessarily to make sure that you are complying with your habit (although that helps).

Rather, it’s to make sure that you are actually improving your quality of life. This makes it easier to justify maintaining the habit long enough for it to become something you don’t spend a ton of time and attention on.

With some goals in hand, we’re ready to start the next phase of the journey, which is the process of collecting data so that you can make more informed decisions.

Data Collection

Now it’s time to collect some baseline data to see what can be improved. While the initial data that you collect will be fairly extensive, you can usually get rid of most of it within a fairly short period of time.

Major problems show up very quickly if you are paying attention. Initially, I suggest doing a single week of tracking in Excel using multiple worksheets. You should try to write an entry every two hours that you are awake on one spreadsheet.

The leftmost column should be the day of the week, with the next column to the right being the hour block. For instance, if you get up at 5 in the morning, then you’d have a row for 5-7, 7-9, etc. On each row, after the hour is denoted, track the following items:

- What, if anything, you ate

- What you did during that timeblock

- Who you interacted with during that timeblock and how

- Any relevant physical sensations (hunger, headache, nervousness, etc.)
Any physical activity you did

After that, rate the following on a scale of 1-10 (with 10 being the best) in terms of how you felt emotionally during this period in the following areas:

- Your level of fatigue

- Your level of focus

- Your level of anxiety

- Your level of irritation

- Your level of optimism

Add a blank cell after that for any commentary, and then set recurring calendar reminders in your calendar of choice to fill in this info every two hours that you are awake for a week.

Yes, this sucks and is a lot of work, but it’s important to collect this information as well as you can so that you dig into it. You’ll be ditching the spreadsheet after the first week, so don’t worry if this seems like a lot of work. It’s a short-term thing.

In another sheet in the same workbook, make an entry for each day, and track the following:

- When you woke up and how you felt upon awakening

- What you had for whatever meals you ate during the day

- How much alcohol you had as well as the amounts (and time of consumption) of any other substances that might have altered your mental state (this includes coffee, cough syrup, and drugs, whether prescription or not)

- Your level of financial stress

- What you planned to do that day

- What time you went to bed and what you did before sleeping. Also note how long it took you to fall asleep.

- Any workouts or other exercise (even if not traditional exercise such as heavy yard work)

- Whether you woke up during the night

- Any physical symptoms you were experiencing (headache, stomach ache, or allergies, for instance)

With this data in hand after a week, patterns should start to show themselves. For instance, you will probably find that you consume more caffeine (and more food in general) after a night of poor sleep.

Similarly, you may find that alcohol and television before sleep results in worse sleep and a worse next day. Similarly, you may find (as I did) that when you do a lot of writing during the day, you actually have a more pleasant day in general. You might also find that you feel extremely drained and unproductive (or inspired) after interacting with certain people.

Don’t overanalyze the data once you’ve collected it. This is not enough information to grasp broad trends in your quality of life. Rather, it’s an exercise in determining the things that make your life demonstrably worse or better. Pay special attention to anything that might be related to the goal that you chose in the previous section.

For instance, when I did this exercise for myself, I noticed that staying up late (or drinking alcohol) before bed tended to cause me to feel awful the next day. This was true for as little as a single glass of beer or going to bed only an hour later than normal. The next day, I tended to consume a lot more caffeine while spending the entire day fighting my fatigue. I was also more easily irritated and ate more junk food.

Then the following evening, after all that caffeine and frustration, I tended to have a hard time falling (and staying) asleep. On top of that, I found that I played video games more often, watched more TV, and tended to skip workouts as well.

The first time I did this exercise, I learned that I probably shouldn’t drink any alcohol during the week, that I should go to bed as early as I can manage, and that I should moderate my coffee intake if I didn’t sleep well the night before.

You may well find behavioral patterns in your own data that are insightful as well. Once you have this data in hand, I strongly suggest that you continue journaling. However, you don’t need to be so thorough. Instead, every day, simply keep track of three things.

First, keep track of the positive things that happened that day along with the things that you got done. Second, keep track of the negative things that occurred (or things that need improvement). Finally, write down a reasonable list of objectives for the next day.

Keeping a journal like this will give you a lot of useful information as you continue your journey while not requiring an exorbitant amount of time from you. As a bonus, this practice also gives you a convenient list of accomplishments should you need one later on (for instance, at your annual review at work).

Over time, you may even find that you can get away with tracking this information over a weekly or monthly period. I’ve kept a monthly journal myself.

The real point of this kind of tracking is that you will periodically get a hint that there are things you can improve in the way that you approach your work. If you keep a journal, simplistic as it may be, you’ll already have a lot of information on hand to help clarify whether your idea is a good one or not.

I spend 5 to 10 minutes once a month on journaling how the previous month went, and it has been one of the most powerful and low-maintenance self-improvement tools I have. If you want a little more detail on how I approach this, I did a podcast interview with OK Productive that really gets into the details.

Fixing Your Schedule for Good

When you are working from home, it’s easy to accidentally miss a meeting or other work event where your absence is likely to be noticed. Since you are no longer in an office with other employees who will stand up and walk to the conference room for a meeting, you’re going to want to make sure that you have a good way of keeping track of meetings, appointments, and the like.

You should also keep track of fixed items in your schedule here even if you think you will be able to remember them. It can be useful, especially when you are stuck on a call, to get a reminder that your child’s bus should be dropping them off in the next 20 minutes, that the garbage can needs to be taken to the street, or that it’s time for your yoga class.

It’s also useful to include reminders for things that need to be done on a particular day, including following up with other people.

Proper organization of your schedule is simple. Get everything into your calendar so that your computer (or phone) can remember. There is a tremendous amount of mental overhead involved in trying to remember this stuff, and it’s really not necessary.

I tend to use Google calendar for my personal calendar so that I can add additional calendars for any project that involves other people. Being able to share calendars is useful in certain cases, but I don’t like to share my entire calendar (it’s nobody else’s business).

Google calendar also allows me to toggle which calendars are visible to me when looking at the interface, which makes it easy to create speculative calendars for planning purposes but also easy to keep them invisible when they aren’t in use.

It’s also handy for your spouse or other family members to share their calendar with you, as it makes it easier to see what obligations other people in your household have. This can help avoid situations where you and your significant other both schedule appointments and aren’t there when the bus drops off your children, for instance.

If you haven’t already internalized the habit, it’s a good time to start putting things on your calendar to keep track of fixed and recurring events so that you can quickly look at the events for a given day and find out what your real commitments are. Things like annual doctor’s checkups, elderly relatives coming into town, or your dog’s next vet appointment are easy to forget.

Remember, your boss is expecting you to be productive when working from home, and they probably aren’t going to form a good impression if you consistently fail to meet your expectations because you forgot.

Similarly, when working remotely, it’s a good idea to tell management when you plan to be away from the house well before you are out. Being proactive about this helps avoid situations where your manager is frantically trying to reach you by phone (all the while cursing the fact that you aren’t in the office). Ignore this advice at your peril.

While not everything can be planned out in advance and communicated to management (if needed), management will often give you the benefit of the doubt if they otherwise believe you to be well-organized. You need to cultivate and protect that reputation as much as possible, and keeping your commitments on your calendar will help you do that.

Your Ideal Week

Now that you have some of the fixed items in your schedule listed on your calendar, it’s a good time to start thinking about what an ideal week looks like for you.

While you mostly will not experience an ideal week in reality, if you plan well you can often get pretty close. The idea is not for this to be a fixed schedule but rather for you to brainstorm about when you can do your most effective work in various areas.

This will help you in a day to day sense as you plan out when you are going to work on various tasks during the day. It will also make it easier for you to avoid situations where you attempt to do difficult work when you aren’t in a mental state that makes it easier.

For instance, back when I regularly commuted into the office, I quickly learned that trying to do challenging software development work between 1 and 3 in the afternoon was probably not a good idea. Not only was I typically tired during that part of the day, but it also tended to be a time period with lots of other recurring interruptions.

It was also a bit late in the day to be trying to dump coffee in my system in a vain effort to be focused. Instead, I learned to use that time period for things like documentation, writing unit tests, testing code, reviewing pull requests, and other tasks that were not (usually) as intensive as some of the more difficult development work that I had.

When I consciously took control of my schedule and started scheduling my work for when I was in a better mental state to do it, my productivity skyrocketed while the number of hours I had to work actually decreased.

To lay out your ideal calendar, make sure that you have your notes from the data collection exercise earlier. Make a brand-new, separate calendar from your main calendars in your tool of choice (I use Google’s calendar for this).

First, block out times for sleep, and make them recurring. Also block out times for your meals, and do the same. Next, block out time for any recurring obligations that you have. For instance, if you are taking a class after work, allocate time for it and make it recurring. Also make sure to allocate time for regular exercise, meditation, and whatever else you do to try to stay sane and healthy.

This is backward from the way most people work out their schedules. However, if you want to have a sustainable remote career, you have to put your nonwork needs first, and then fit your work around those.

If you do it the other way around, it’s really easy to neglect your own needs, so we should start with making sure that our own needs are met first. Your work will eventually suffer if you don’t take care of yourself—taking care of yourself will make you a better worker.

Now that you have all that stuff on your calendar, you will block out time for work. However, instead of simply making a block entitled “work” and moving on, you need to allocate time to your main work activities. These vary based on profession, and you’ll probably find that they change over time. For instance, here is the set of major activities I had at a previous job:

- Programming

- Mentoring junior developers

- System architecture and design

- Software testing

- Writing documentation

When I did the data collection exercise described earlier, I discovered a few things. First of all, my optimal times for writing code and designing systems were between 6 and 10 in the morning and after 4 in the afternoon. The other activities were a necessary part of my job but were not the main things that management valued. Therefore, the other tasks had to fit around the optimal coding times.

With the data you have collected previously, you should have a rough idea of when you are most capable of doing certain tasks. While you will continue to refine this based on experience over time, you should have enough information to at least get started.

However, you need to be careful about how you prioritize your work activities. While your manager will likely tell you that everything is important, there are some tasks that they will prioritize over others.

In my case, while I was expected to write documentation and mentor junior developers, neither of those tasks ever came up during my annual review. Therefore, it was reasonable to act as if these tasks were lower value, since doing them well didn’t get me a raise, while doing other activities poorly probably would have hurt me.

Given that your work environment likely has similar dynamics in play, I strongly suggest you take a similar approach. Find the most important activities that are expected of you, and schedule them first. Give them time blocks that correspond to optimal work time, and then schedule the less critical activities during the other available time in your workday.

The point of this exercise is to give you a rough idea of what your typical day should look like. In reality, most days won’t be perfect, but you can use this calendar to plan your day for optimum efficiency.

If you do this correctly, not only will working from home be easier, but you will give the impression that you are working far more than you probably are. This is especially true if you didn’t go through this exercise when you were going into the office.

Keep this calendar up to date as you gain more insight into your optimal working time. When you have a particularly good (or bad) day, compare the work you did that day to what you had scheduled on your ideal week calendar.

You will often discover surprising insights. I certainly did. I learned that I felt more energized on average when I did at least some writing every day, and I also learned that I’m terrible at database performance optimization late in the day.

Keep this calendar on hand and refer to it often, adjusting as needed, and it will be an extremely helpful tool in your toolbox.

Habits Determine Your Long-Term Success

The key to being able to work remotely over a long period of time is to build up healthy habits and maintain them. There are many risks to a remote worker’s ability to work from home, with issues related to the situation at home or one’s personal health as well as issues related to the office and the people there.

Managing your work relationships and how you are perceived in the office is critical to your ability to be an effective remote worker. You’ll also find that a lot of social relationships change when you start working from home, and you will need to manage those relationships so that they don’t make your life more difficult.

Building appropriate remote work habits is your responsibility. While your employer and your social circle might be able to help, the responsibility for results rests on you alone.

But that’s a good thing—it means you can have control over your life. The difficulties in making a change are transitory; the benefits are long term.

Chapter 8

How To Get Your Organization Ready for Remote Work

When you finally convince management to let you work remotely, you’ll probably inspire other employees to try to work remotely, as well. Depending on the size of your organization, this may make things interesting, to say the least.

As an organization gets more and more remote employees, the way that it has to function will change considerably. An organization with enough remote employees will often find that becoming remote creates a lot of opportunities to rework their internal processes. It’s a good idea to approach this challenge in an organized manner.

While we’ve previously discussed how to get your boss to let you work from home, another area of concern needs to be covered. If management is truly on-board with the idea of leveraging a remote workforce, there are things they need to know.

Allowing remote work is a bit of an intimidating process, as there are a lot of unknowns and surprises along the way. Consequently, it’s much simpler when management has a list of things to consider. This makes it easier to make decisions quickly and helps to avoid simple, foreseeable errors that hurt team morale or productivity. The last thing you want is for your company to fall behind the competition, but at the same time, your company still has to function today.

In this chapter, I’ll show you how to prepare for remote work from the managerial side so that your company can be the front-runner that forces everyone to react.

Why Remote-First?

The number of people working remotely continues to climb. In the future, not only will companies be expected to allow at least some remote work, but the expectations around how that remote work is conducted will continue to become more complex.

In short, an organization that starts building infrastructure around remote work today will be ahead of their competition in a few years. Further, having solid remote work practices will help them compete for employees today.

In many fields, salaries are one of the largest expenses on the balance sheet. Moreover, the price of good help continues to rise, especially when a company needs to hire that help close to the office. A company that can effectively hire and retain remote employees has a significant advantage over those who cannot or will not do the same.

If you want your company to be effective in a world that is increasingly remote, it helps to go “remote-first.” Remote-first is a set of organizational processes and principles that places priority on asynchronous communication flows and location-independent processes.

By going remote-first, you not only make your company a better place to work for your remote employees, but you change your organizational processes in ways that will also help your on-site employees and employees in satellite offices (or out visiting clients), as well.

Many of these process changes are useful even if your company has no intention of regularly allowing employees to work from home, as these processes are built with the assumption that resources (such as network connections, employees, and the like) will not always be perfectly available. These strategies work because they more closely represent reality than strategies made without these assumptions.

In the rest of this guide, we will discuss some of the principles that your organization needs to have in place in order to truly leverage remote workers. Rather than simply being an organizational quirk, remote workers can become a huge advantage for your organization, provided that you plan accordingly.

What Does Remote-First Mean?

Remote-first sounds like a gimmick. Because of this, we need to clearly express what we mean when we use the term.

The definition of remote-first is simple, but not always straightforward to achieve. Simply put, it means that remote employees are not an afterthought. Processes are built from the ground up with the assumption that not everyone is face-to-face, or even in the same time zone.

Remote-first respects personal working styles, disabilities, and personal schedules in a way that the standard 9-to-5 job does not. The strategy is designed to be inclusive of people who may not have a life situation that allows them to commute to an office.

CircleCI, which has a wonderful blog post on this topic, suggests a few items that demonstrate what a real remote-first strategy looks like in practice:

- Videoconferencing by default

- Accessible, structured, and documented team meetings

- Document, document, document (aka, nothing is word-of-mouth or from memory)

- No hallway conversations (unless you document them)

- Planned together-time

These notions are good starting points, and I’ll elaborate on them with some thoughts of my own.

However, a consistent theme appears when considering all these points: You do not engage in processes in a way that places remote workers (or workers who were simply out that day) at a disadvantage.

Rather, you create a paper trail for every decision that is made and make sure that employees get the chance for face-to-face time when possible.

The above contrasts with “remote-friendly,” which is another term that you’ll see in use. Remote-friendly companies allow some employees to work remotely at least some of the time. That’s basically all that it guarantees. They don’t make significant changes to internal processes to make sure that those employees are successful.

What this means in practice is that while these companies have remote employees, those employees are almost certainly expected to travel to the office to conduct certain activities.

In addition, it tends to mean that remote employees are at a significant disadvantage in terms of their ability to know what’s going on in the office. They frequently get blindsided by things that were decided in hallway conversations, or on conference calls where they couldn’t hear the speaker. Remote-friendly is only barely friendly for the typical remote worker.

However, there is hope. When an organization allows some employees to work remotely, they have a good starting point for beginning to shift toward being a truly remote-first organization. Few companies (although the number is increasing) start out as fully remote organizations—most seem to get there only after having spent significant time as a remote-friendly company.

Changing processes in a running business is not a quick or simple task. Rather, it’s usually a sequence of “good enough” compromises that drive the organization toward an end goal. These changes will not occur overnight in most organizations, simply because the mission of the organization is its mission.

Remote-first is (and should always be) second to the main purpose of the organization. It doesn’t help an organization at all to forget its primary purpose and implement remote-first if doing so ends up causing layoffs. As a result, this process will take time.

There is a continuum between remote-friendly and remote-first organizations. Along the way, certain organizational changes will need to take place in stages to enable continued improvements. These are defined below:

Remote-Hostile - The organization does not allow any remote work, including in cases of emergencies, adverse weather events, and the like. Productivity tends to be measured by “butts in seats.”

Stage 1 - The organization allows remote work under certain conditions, but never on a recurring basis. The ability to work remotely could be denied on any given day.

Stage 2 - The organization allows some employees to work remotely on a regular basis, but doesn’t allow anyone to work remotely all the time. The ability to work remotely could be taken away at the whim of management or if remote employees become annoying to the rest of the organization in some way.

Stage 3 - The organization allows one or more employees to work remotely all the time, but has not changed communication processes to accommodate these individuals. The remote workers could be told to either come into the office or submit their resignations at any time.

Stage 4 - The organization modifies its process for meetings, reviews, and other collaboration to accommodate remote work. Remote-only employees have meetings that are built with them in mind, but their project management is not.

Stage 5 - The organization modifies its methods of process planning and project management to accommodate remote work. However, it may take some time after onboarding before an employee is allowed to work remotely or has everything they need to do so.

Stage 6 - The organization has modified its onboarding process with the assumption that new employees will be remote. However, no steps are taken to ensure team cohesion over distance.

Stage 7 - The organization is truly remote, and has practices around periodically bringing employees together to make sure that team cohesion is maintained.

As you can see, the journey to truly being a remote-first organization is not a short one. If you’ve been following along, your organization may already be well into stage 2 and might even be at stage 4 or later. However, after stage 2, the truly difficult work begins.

In general, most organizations currently don’t get to stage 7 (although they may still have a lot of those characteristics). In any organization, you can usually only push remote work so far before one or more stakeholders starts pushing back. If you aren’t the CEO, you need to be very careful about testing the waters politically before moving on to the next step.

At each step, you may need a new strategy to continue moving forward. Don’t be discouraged if you only make it to stage 3 or 4 (or even just stage 1). Every step is an improvement for your team and is capable of being leveraged to be able to take the next step.

The whole process may take years to accomplish. For instance, below are some good examples of what you may want to emphasize at each step:

Remote-Hostile - Emphasize business continuity and employee retention (people don’t want to lose sick days to bad weather).

Stage 1 - Emphasize remote work for meeting specific goals or for employee morale.

Stage 2 - Emphasize the wider hiring pool and potentially lower costs of hiring if you are in a high-priced area. Mention just the larger hiring pool if you are in a more stagnant, lower-cost area.

Stage 3 - Emphasize improving the productivity of both the remote workers and in-office workers (due to fewer blocks and interruptions) of changing processes to asynchronous and well-documented ones.

Stage 4 - Emphasize the need of project management to step away from micromanagement and interruptive meeting schedules to improve productivity and the quality of estimates. Frequently, project managers want time estimates from employees, yet interrupt them so frequently that it’s impossible for employees to guess how long a task will take.

Stage 5 - Emphasize that, since remote work is an option, employees should be trained with the assumption that they will be working from home in order to reduce the cost and risk of their transition to remote work. Mention that since processes are already designed with remote workers in mind, the onboarding process may best be handled from the perspective that the employee is likely to end up working remotely.

Stage 6 - Emphasize that some face-to-face team time would improve collaboration, make certain training situations easier, and make employee retention easier.

Stage 7 - This is where you ultimately would like to be. Your objective here is to make sure that management continually realizes how valuable remote work is for your organization. The goal here is to make sure that management stays happy with having a remote workforce, so that they don’t decide to suddenly force everyone back into the office.

At each phase, there are specific things you need to do to help you transition to the next phase. The biggest roadblocks to success in making your team remote will come after you’ve had some initial success.

The problem isn’t just that upper management is liable to be reticent to go along with you (they probably will be); the problem is that your strategies have to evolve during this process. Many managers will try what worked last time when they find themselves in a vastly different situation; don’t do this.

Because remote work represents such a (potentially) profound change in your business processes at each phase, you’ll find more success exploring new opportunities that open up rather than trying the same arguments over and over.

How Meetings Need to Occur

Meetings can be one of the most painful things to deal with when working remotely. There are four common antipatterns to remote meetings that are extremely annoying and unproductive for remote employees.

These antipatterns not only make it more difficult for the remote employees to get their work done, but they also have the nasty side effect of turning remote employees into second-class, uninformed employees.

First, haphazardly scheduled (or totally ad-hoc) meetings are extremely difficult to organize with remote team members. They may not be at their desks, and it can often be hard to quickly determine if they are. As a result, meetings scheduled quickly by disorganized managers often disrupt remote workers.

While meetings like this are also disruptive to on-site workers, those workers usually find out about the meetings before the remote workers do, and they don’t have as much risk of technical problems.

While it is recommended that remote employees do what they can to make sure their equipment stays working during the course of the day, the fact is that meeting software seems to always have a few quirks that need to be overcome. It’s easier to let remote employees get on the meeting a few minutes early so that they can make sure the system works for them before the rest of your staff joins the call.

If you don’t give remote staff adequate time to make sure their equipment is working before the start of a meeting, this can often lead to remote workers being completely left out of critical meetings, getting incorrect information from their coworkers, or having management come to resent them because it reduces the manager’s ability to just start a meeting without planning ahead.

From long experience, I can tell you that ad-hoc meetings are some of the worst meetings you’ll have as a remote employee, as you are often not given time to get to a stopping point in your work, get more coffee, or even go to the bathroom before they start.

Second, meetings that are scheduled with half the team in a conference room while the remote employees listen in on a speakerphone are also not particularly good for the remote employees.

Many conference rooms have terrible acoustics, especially if management is more concerned about the appearance of the space than the functionality. Conference rooms with wooden floors and no sound-absorbing materials on the walls are very common.

Speaker phones that pick up every stray noise in the room while failing to pick up speech are also a huge annoyance. When I’ve worked remotely at companies with these sorts of conference rooms, I didn’t even bother trying to pay attention in meetings. With this kind of audio quality, something as simple as someone doodling close to the phone meant that I couldn’t hear anything useful anyway.

If I did hear something, I could often only hear the voices of people close to the phone, or people loudly discussing something irrelevant at the far end of the room. It’s a common problem.

Third, meetings that do not respect employees’ time are a scourge of remote workers. While they also waste the time of the people who are in the office, those people were clearly seen attending the meetings. The remote workers were not, even though they were there, as well.

Remote workers are generally expected to prove that they are efficient by actually getting things done, so wasteful meetings are especially harmful to them. While this dynamic doesn’t sound so bad, over the long term, it can lead to excessive hours and terrible work/life balance for remote employees.

When combined with all the problems that usually occur with wasteful meetings (bad management, lack of clear direction, inconsistent priorities), it can very quickly lead to burnout.

I’ve left two partially remote jobs that consistently wasted my time, as I found myself working considerably more due to inefficiency. By the end of both jobs, I was losing more time to work while working remotely than I would have spent driving to the office every day.

Fourth, many meeting organizers aren’t considerate of the schedules of their remote employees. In some cases, this means that remote employees find themselves stuck in meetings either well before their workday should really begin, or well after it should end.

Meetings may also be scheduled in such a way that it makes it hard to pick up children from school and meet other obligations. While this can be a problem in the office as well, remote employees who complain about this sort of inconsiderate planning are more likely to be treated as if they are just whining.

It still is a major issue when an employer consistently makes it impossible for you to take your 7-year-old to the bus stop next to a busy highway, but because many managers think you are “lucky” to work remotely, they may believe that you have no right to complain.

While such meetings are not always avoidable, they usually can be planned so that they occur at a time that allows everyone to attend and doesn’t put an undue burden on anyone.

So, given the four most common antipatterns of meetings involving remote employees, it’s pretty simple to determine how meetings should be conducted for most companies with remote employees. A few general guidelines can help your team considerably.

Give at least an hour’s warning before any meeting unless it’s a critical emergency. Give your remote employees time to prepare, as well, and remember that there is latency built in to most ways that you might attempt to contact them.

If you have more than a couple of emergencies in a year (and you aren’t in an active war zone), they aren’t emergencies; they are managerial screwups. Fix them and keep them from happening again. Yes, this is phrased bluntly, but if you don’t fix this, you’re going to lose more than just your remote employees, eventually.

Have remote employees put things on their calendars. For instance, have them mark down their available time, or when they need to pick up their child at the bus stop. Don’t schedule things over these or too close to them.

Allow people to have work/life balance, including remote employees. Don’t establish your remote employees as second-class citizens by treating their concerns as somehow less than those of the folks in the office.

Fix your audio issues. If your conference room is prone to echoes, this needs to be corrected. Remember that while the happiness of remote employees may not be your top priority, bad acoustics in your conference room are going to make you look like an amateur to any strategic partners, customers, or investors who get stuck in a conference call with you, as well.

Meetings should be limited in scope and should generally have only a few people in them. One person talks, and the rest listen until it’s their turn to talk. If you are getting a lot of side conversations going in a meeting, you either have the wrong people in the meeting or have the wrong scope for the meeting.

Regardless, your remote employees can’t hear what they need to hear, and you are probably making things difficult for many of your on-site employees as well. This is especially true for employees with hearing problems, or who have conditions that make focusing more difficult for them.

Avoid frequent status meetings with unrelated teams. This includes daily stand-ups. If the team members are not working on the same project, most of the content of the meeting is a waste of time for the people on the other teams. Additionally, make sure that people take unrelated or otherwise superfluous discussions out of the meeting so that they don’t waste everyone’s time.

For the on-site worker, there is an incentive to talk at length about useless trivia on their project, simply to look busy. For the remote worker, this just simply wastes more of their time. Prefer to help the people who get things done over those who simply signal getting things done, and you’ll be a better manager.

Be conscientious of time zones. There’s usually not a good reason to stick a West Coast person in an 11:30 a.m. meeting, simply because someone on the East Coast thinks the meeting is convenient at 2:30 p.m. While you may occasionally do things like this, doing it consistently establishes a hierarchy among your employees, whether you intend it or not.

Meetings should generally be considered to be headset-first, rather than chair-first. What I mean by that is that you should assume meetings will be conducted using a webcam and a headset, with in-office people in chairs being a second thought, rather than the other way around.

Not only will such a strategy keep you away from setting up meetings that are bad for the remote team, but it should also force you to plan ahead sufficiently so that your remote team is prepared when the meeting starts. The on-site team members end up with better meetings as a side effect.

As a manager, try working from home as well. You’ll quickly find a laundry list of things that should improve to help your team. You’ll find that employees don’t tell you everything that’s on their mind, but if you are able to simulate their experience, you can often learn a lot.

Once you find an area that is a problem for remote employees, involve them in the process of fixing it. Remote employees have a tendency to avoid complaining because they are afraid that a complaint will cause them to lose remote work privileges, so it’s important to make sure they understand that this isn’t the case at all.

When conducting meetings with remote personnel, the golden rule applies. Don’t put your remote employees in a situation that you wouldn’t want to be in while on-site. It takes some thinking, but a little preparation for the reality of remote work will help you considerably in setting up effective meetings for your team.

How Project Planning Changes

When your organization starts to have more remote workers, you’ll find that project management styles have to adjust to accommodate the new reality. There are a few common patterns of project management that will have to be changed, as well, if you want your organization to be effective with remote workers.

We’ve already discussed meeting antipatterns at length, and there are similar dynamics that occur with project management. This is probably no surprise, given that many meetings are necessary for successful project management to occur. However, there are a few things that project managers on a remote team need to contend with if they wish to be successful.

First, project managers should generally avoid asking for status updates at the last minute. With remote teams, and especially remote teams distributed across a wide area, attempts to find out project status at the last minute are doomed to failure. Not only will you disrupt your team, but you may have to wait a considerable amount of time for a response, especially if the current local time for your team member is well outside of normal working hours.

You need to either collect project status information once a day during a recurring quick morning meeting, or you need to make sure that your team has appropriate tools on hand to be able to make project status information available to you without you having to contact them.

If you’ve been managing everything with a desktop tool that doesn’t support multiple concurrent users, this will not go well for you. Generally speaking, you’re going to have to start using online tools that allow other team members to update their tasks, and that don’t waste their time with project management minutiae.

While many online tools do allow remote workers to keep their status up-to-date, far too many are built so that they take too long to update. In extreme cases, this tends to mean that employees will put off making their status updates, and you won’t have the information you need when you need it.

I once worked for a company that managed all their bug tracking and project tracking in a slow, error-prone desktop application that they built in-house. For more than a decade, every time management wanted more information, they solved the problem by adding more input fields.

I updated my task list twice a month at most, because it wasted so much time that it wasn’t worth doing until people were really upset about it.

It was especially not worth doing when I was mainly being evaluated on my ability to get real work done, rather than my ability to fill in a stupid form to keep the project managers informed so they knew who to blame when we didn’t meet yet another deadline. I guarantee you that you will cultivate the same mentality on your own team if you manage things the same way.

As I mentioned before, the way you conduct meetings has to change when you are handling project schedules for a remote team. If you are managing people working on disparate projects, this means that you need to have separate meetings for the teams on those projects.

Far too many project managers make the mistake of forcing everyone into the same meeting, even though most of the meeting is a waste for most of the people there, simply because it is easier on the project manager. While on-site workers may be engaged, remote workers are less likely to pay attention.

Remember, they know they aren’t being evaluated based upon meeting attendance—they still have to prove their productivity. Don’t set up your meetings in a way that makes their goals in opposition to your own.

However, in addition to changing your interactions with the team, the team also needs to change their way of interacting with you as a project manager. Assuming that you have good systems in place that allow your team to keep you up-to-date without an exorbitant amount of effort, you have every right to make sure that they do so.

One of the best ways of ensuring this is to make sure the team knows that keeping the software up-to-date means that you won’t be interrupting them (and that you’ll help shield them from being interrupted by management, as well). Instead of trying to sell this workflow as a way to make your life easier, explain it as a way to make their lives easier.

Project managers (and managers in general) will also find that they have to train their own managers on how to interact with remote teams. This can be a tricky balancing act, like most work situations where you find yourself between your management and your team.

Like the team, management can be trained to interact appropriately by making sure that systems are in place that give them the information they need when they need it, and without having to interact with you.

If you make sure your team is reporting project status and progress efficiently, try to make sure that information is easily available to management as early as possible. This may be as simple as sending a daily email with project status or could be as complex as surfacing that information in your project management system.

You probably should also avoid giving management too much detailed information, especially if your team is working on a technical project and your manager is nontechnical, as too much technical detail tends to make some managers call for even more details. If they do, they probably aren’t going to ask you—they’ll bother your team directly instead.

If management starts interrupting your team, the team will eventually believe that keeping things up-to-date in the project management system is no longer worth their time, making your job much harder. While generally, I don’t recommend gatekeeping behavior, this is one place where you probably should engage in it, simply to keep everything running smoothly.

From your manager’s perspective, it’s hard to tell what a remote team is doing. It’s also very tempting (especially if the team gives too much technical detail) to directly contact the team members for information. This is a waste of time for management as well as a disruption for the team. Generally, management will only want summary details that show that the team is meeting objectives.

This means it is absolutely necessary that management get a different view of project status than the one you use (or the one that developers work with). Ignore this at your peril. While the same is often true of normal project management with on-site staff, the added complexity of remote staff means that you have to get this right if you don’t want management interfering with your team.

For instance, at a previous job, we all used the same in-house project management system (and I use that term as loosely as you could possibly imagine) to track what was going on with the team. Everyone had the same interface, so when developers had to put details in for other developers, that meant that upper management also saw those details.

This led to some interesting problems. For example, one developer put in an entry, listing the HTTP headers he had used for keeping track of details needed by the application. A senior manager saw that entry, and started calling developers individually to try and figure out why we hadn’t switched from HTTP to HTTPS yet.

The truth is, he didn’t need that detail and didn’t understand enough of what was going on to be able to effectively react to it. The lack of a separate report for him to read resulted in hours of wasted time for most of the team, because he called an emergency meeting to talk about payment card industry (PCI) compliance.

Trust me, you don’t want this kind of thing happening, because even with the interruptions, he still expected the team to be on schedule.

Cohesion

When managing a remote team, you have to make sure that you maintain team cohesion. While this is also important in an office environment, once a team starts working in different offices, a number of factors make cohesion more difficult.

Here are some things that can come as a surprise to anyone running a distributed team. It’s not that any of these things are unpredictable. What makes them unexpected is that they aren’t anticipated by people who aren’t used to a fully remote environment.

Employees who don’t know each other well are more easily offended. They don’t know their coworkers as well, so it’s easier for them to misinterpret emails, comments made during meetings, and other interactions in an uncharitable manner.

Employees may not have a good idea of what their coworkers do during the day. While we often think that management may assume that employees are not working much when they are remote, it’s easy to forget that their coworkers may form similar incorrect impressions. This can create friction on the team.

As remote employees, we are often judged by what we accomplish. Our on-site team members are often judged by their presence and the appearance of accomplishment. This can lead to situations where one’s coworkers’ best interests and our own best interests don’t overlap very much.

The normal human interactions in an office simply don’t happen when people are remote. While in some offices, this can actually reduce conflict and miscommunication, it also tends to mean that teams don’t bond as quickly or as well. As a result, team members and management need to take deliberate actions to foster positive interactions between team members.

It’s easy for remote employees to feel like they aren’t really part of the team. This can make them more likely to decide to leave. I’ve turned down job offers that paid more because I really liked my team, as I’m sure many others have done. Had I been isolated and remote, the money and benefits of a different job could have swayed me.

Remote employees who are stressed out may not feel like they can talk to their coworkers or manager about it. This can mean that problems fester unseen, even if they could have easily been fixed. Situations like this are often only noticed when things are so far gone that they can’t be corrected.

To help with group cohesion, you need to get everybody into the office at least a couple of times a year, if possible. Sure, it’s expensive to pay for hotel rooms, per diem for lunch, and airline flights, but that expense is tiny compared to the cost of the kind of turnover and bickering that the problems above can cause.

Aim for a few days at a time, and make sure that you have at least some activities planned that aren’t work-related. Also, make sure that when the remote employees return home, they get a few days off (or at least a reduced workload). Remember that travel is tiring and also interferes with everything at home. After a weeklong trip, your employee is probably a day or two behind on home obligations.

While this won’t fix everything, it makes a few things easier. For one, it humanizes team members. Rather than just experiencing their coworkers as digital avatars on a chat channel somewhere, they will experience their coworkers as real, flesh-and-blood human beings.

There is a dynamic here that is easy to miss; as methods of communication become more limited, they also become more strident and harsh. Two people who angrily honk car horns at each other and raise their fists might have no conflict at all had they met in an environment that allowed them to talk like human beings. Something similar goes on with teams in professional environments.

Getting your team together allows more of the sort of complex interpersonal interactions that will make them more capable of communicating well with each other later on.

Additionally, bringing the employees together allows you to observe them. Most people are unaware of how much information they “leak” in social settings. You can quickly determine which employees have good rapport and which ones do not by observing them in social settings.

In a team of any size, even a few hours of interaction will show you who dislikes whom. Further, and perhaps more useful, observing such interactions will also show you which people in your organization can serve as a bridge between cliques on your team.

These are the people you talk to when you need help heading off problems on your team. They often have unique insight into why certain personality conflicts and interpersonal clashes occur, and they are in a position where those clashes probably bother them, as well.

If you are looking for people to promote, these are some of the best choices, as they neatly avoid the appearance of taking a side in whatever conflict is going on in your team.

Office Stipend

When working with a remote team, it’s important to pay for at least some of the equipment that team members use. Having an effective remote office is not cheap. Computers used by remote workers can cost several thousand dollars, as can the desks, monitors, chairs, and other equipment.

While some of your remote employees may be willing to purchase their own equipment, a lot of them won’t want to spend enough to make sure they have suitable equipment.

At one company where I worked, the office didn’t pay for any equipment for their remote employees. Here are a few things I noticed.

A lot of the remote employees had extremely slow computers. The office mandated a particular VPN client and wanted total control over any machine that was connected to their network. As a result, employees earning six-figure salaries bought $400 laptops so they could work from the house. Nobody is going to let your head of information security control their gaming computer.

The drain on productivity was staggering and easily cost more in the course of a year than what simply buying decent laptops would have cost. This was especially true when equipment failures occurred at critical times (and all times are critical if your productivity is low enough).

Many of the employees who worked remotely also failed to invest in appropriate network infrastructure. As a result, many of them were working from home offices with cheap internet connections and cheap wireless routers.

While you might not judge someone for liking the stuttering jerky motions of a 1980s TV character like Max Headroom, that premise doesn’t apply when your quality assurance (QA) analyst is exhibiting the same sort of behavior in a video conference due to a spotty internet connection.

That same office didn’t provide phones. This meant that when something went wrong in the office, you got contacted on your personal cell phone. Besides being inconvenient and extremely annoying, this resulted in several people simply keeping their phone in “Do Not Disturb” mode most of the time.

It turns out that people resent getting called by people from work when they are out to lunch, asleep in the dead of night, or watching TV on Saturday morning with their children. If you are calling an employee’s personal cell phone, you can easily stoke such resentments, even if you don’t mean to.

Back, neck, shoulder, and hip problems were also common on this team. This tended to result in more absences from work and significantly more complaints during work, most of which I got the pleasure of listening to … These pains were a result of suboptimal working conditions, which often consisted of setting a cheap laptop on a kitchen counter and then trying to work an eight-hour day on it.

If you are looking to save money on equipment purchases by having your team work remotely on their own equipment, you are going to get a rude awakening. While tax law theoretically allows remote employees to write off some of their expenses, in practice, most accountants don’t allow them to do so.

Such behavior has a nasty tendency to trigger an audit, and is often not worth the trouble. As a result, employees are liable to cut corners in order to reduce expenses. You can expect most of the negative results of these “savings” to fall on you.

While you can certainly save money on employee-related expenses by allowing employees to work remotely, you probably shouldn’t try to save any of that money on the tools that employees use to get their work done. This tends to backfire spectacularly while making you look cheap in the process. There is literally no upside here.

Your employees probably also have at least some decent equipment at home that they would like to use. For instance, I’ve pretty much always had a decent computer and a desk at home for doing contract work, so it’s often a waste of time for an employer to purchase those for me (unless they want to control the computer with domain policy, in which case they need to provide one).

However, until recently, I’ve had a tendency to purchase cheaper office chairs; this would have been a very good purchase for an employer to make on my behalf.

Since you never really know what hardware an employee can provide for themselves, the best strategy is to provide a stipend for office equipment and to make employees list what equipment they intend to provide (if any) and what they plan to buy with the stipend.

While you may need to be prepared to suggest decent equipment for your employees, approaching things this way allows the employee to deal with the unique situation in their home office.

This could be anything from space constraints that require them to have an unusual desk, to needing a better video card due to already having a large multi-monitor setup—that would be me; I love the setup, except when I have to pay for all the hardware I need to drive it.

Stipends also make it easier for employees to personalize their workspace. This can often make a home office feel less isolating.

While I would typically point to some research that backs up this assertion, I don’t really have any. I can, however, offer that I and a number of friends of mine have noticed this effect. At the very least, it’s an interesting phenomenon that might apply to your employees, as well. Personally, I believe that being able to make at least some choices in your work environment helps you become more attached to it. This sense of control can make people happier (or at least make them more content). This makes them happier in their work and more likely to engage with coworkers in a positive way, which reduces their sense of isolation.

Handling Time Zone Differences

When dealing with remote employees across multiple time zones, things can get interesting really quickly. While a difference of a single time zone probably doesn’t matter too much, larger differences in time can be fairly disruptive to a team.

Once your employees are distributed across three or more time zones, a few issues become apparent. Here are some things that you’ll often observe in distributed organizations:

For each time zone you add, you lose two hours of the day when everyone can attend a meeting without annoyance. Your people farthest to the east will be annoyed at late meetings because it makes them get home late, and your most westerly employees will be annoyed with early meetings because they force them to get started earlier.

If your employees are scattered across more than four time zones, you’ll find that the ideal meeting times for certain team members line up with the ideal lunch time of other team members.

If your employees are spread across six or more time zones, you’ll find that they segment based on location, simply due to communication issues. If this disconnect occurs across a team, you’ll often find that the team has performance problems due to interpersonal squabbles.

Large time zone differences lead to disconnect. If disconnect occurs between teams, you may be able to largely avoid the problem, provided that the team members who are required to work together are within similar time zones.

If your employees are 10 or more time zones apart, meetings are terrible for everyone involved because the only times when everyone is awake are also terrible times to get work done (during the early morning or early evening).

From the above observations, a few rules emerge that will generally help you avoid time zone-related problems.

Any group of people separated by more than a few hours will generally function poorly as a team, simply because of the communication issues arising from vastly different schedules. Don’t try to make them into a team unless it is absolutely necessary.

If you simply need shift coverage (for instance, in support and other customer-facing roles), make sure that you have a process in place to “hand over” any work from one group to the next. This should be a fairly formalized process conducted near the end of one shift and near the beginning of the next. Try to make sure there is at least some overlap in coverage so that your employees have time to communicate.

A group in disparate time zones can be very useful if leveraged appropriately. While you may not want a team of software developers to be widely separated by time zones, having a QA team working in a vastly different time zone from your development team can be hugely helpful.

Such an arrangement allows the development team to deploy without being concerned that they will break things while QA is testing, and it also means that the developers will have QA feedback available when they return to work in the morning. If you time this well, such interactions can be a beautiful thing.

No single group in your organization should regularly expect to have their personal time or their lunch breaks interrupted by a meeting with a remote team (or remote team members). This dynamic almost always eventually results in resentment, and one could easily assume that one team is management’s “favorite” compared to the other. It’s best to avoid it as much as possible.

If you have a team distributed over a wide area, this probably means that management will be subjected to meetings at annoying hours. While this is unfortunate, it probably can’t be helped.

Someone needs to communicate with the other team, and that person is likely in the management hierarchy above them. However, if you build your systems of communication in such a way that assumes all communication is asynchronous, managers can at least make these interactions as efficient as possible.

Finally, the challenges of widely distributed teams mean that you may want to avoid them, unless you have a good reason to have one. Time zone differences of more than four hours are periodically painful, while differences of 10 hours or more are almost always painful. Unless you have a good reason, you are usually better off avoiding this situation, even if you save a little money in the process.

Treating Remote Workers Fairly

It can be difficult to treat remote employees fairly if you also have an on-site team. Not only are the on-site employees in a position to be noticed more frequently by management, but they often are in a better position regarding information asymmetry in the office. This seems like a subtle thing until you have been on the receiving end of it.

There is an implicit difference in the amount of power that a remote employee can wield when compared to someone who is in the office, especially if management is also in the office.

This is especially true if the in-office employees regularly eat lunch and socialize with management. This tends to be what people think of when they consider whether remote employees are treated fairly.

However, a lot of other more subtle things can occur. For example, sometimes, remote employees live in places where none of the people around them have the same profession (or even speak the same language).

While working for one company that had a few remote employees, along with a few employees who worked remotely part of the time, I noticed something interesting. One of my remote coworkers was extremely talkative during our morning stand-up meetings, which slightly annoyed some other members of the team and made the meetings longer than they needed to be.

When I thought about it, I realized that this employee was working in a fairly remote location, surrounded by people who largely were not programmers (and who largely didn’t speak English). Things were better after we all made an effort to talk to him outside the morning meeting.

Situations like this can occur if you aren’t paying attention, and can be just as unfair to remote employees as situations where management shows favoritism to particular people because of proximity.

Being fair to remote employees can often mean that you have to expend more time and attention making sure that their needs are met than what you spend on people in the office.

For one thing, there is a significant communication barrier in place that keeps you from detecting problems early. In addition, the remote employees are often regarded as “lucky,” simply because they get to work from home. This often serves as an excuse to dismiss their other concerns.

Be very careful about thinking of your remote employees as being lucky, and do what you can to make sure that your other employees don’t react as if their coworkers are lucky, either.

They are simply working in a different set of circumstances—no one refers to the in-office employees as “lucky” because their work isn’t sitting in their house in a room dedicated to it. If you think about it a bit, every working situation has both advantages and disadvantages.

The concept of “luck” as an explanation for being allowed to work from home is corrosive to team morale and is best avoided if you want to be fair to your remote employees. The corollary to this, of course, is that if you don’t want to be fair to your remote employees, the problem tends to be self-limiting, since they’ll choose to go somewhere else.

Besides the difference in social dynamics, other situations arise that can be useful for making sure that your remote employees feel valued and treated fairly. Don’t think of these things as things you “have to do,” but rather as opportunities.

When you buy lunch for employees who are on-site, try to do the same for your remote employees, as well. While this takes more work, it also requires you to coordinate this benefit with the remote employee. They will notice the extra effort.

Make sure that when you schedule things for the on-site team, you are also considerate of remote workers’ schedules. You may be tempted to assume that your remote employees have more flexible schedules, but that may not be the reality.

This assumption may even be accurate, but a little consideration will not only show the employees that you care, but can make their lives easier.

Make sure that you regularly keep in contact with your remote team members in the same way that you would keep in contact with people in the office. Even if it is simple chat and pleasantries, take time out to make sure that you communicate informally with your remote team members.

While you might not think that this sort of small talk is valuable, it often allows both you and the remote employees to convey useful information that might not be communicated otherwise. Much of human communication works better in informal contexts, especially one-on-one.

Be aware that your remote employees may have different priorities than your on-site employees. While the prospect of a salary increase, promotion into management, or more visible work might motivate on-site employees, remote employees may not find much motivation in such incentives. While raises, improvements in title, and more responsibilities may sound nice to employees in the office, they may come with extra burdens that remote employees have no interest in whatsoever. For instance, being promoted into management may mean dealing with more personnel issues, rather than simply working on a task. Similarly, there may be expectations attached to a raise that make it not worth the trouble, especially for people who are already financially secure. I’ve worked in several companies where fairly small raises and titles were offered, with the expectation that one would start working 60 hours a week for them. If someone is already trying to get away from the average office environment, an incentive structure that aligns with forcing them into more of it is unlikely to motivate them.

You will need to modify incentives that you use based on the motivations of your remote employees. Really, you should be doing this with your on-site employees, as well, but there is less room for error when considering remote employees.

Above all, whenever you do anything with a remote team, spend some time considering how it will be perceived by the remote team members. It’s easy to forget to do this, but you do so at your peril.

Remember that remote team members may have different goals, and be motivated by different incentives, and take that into account before you start changing anything.

When the Office Is “Down”

Eventually, unless your company spends an inordinate amount of time, money, and effort on their availability and uptime, there will be problems connecting to your systems from remote locations. This can be especially difficult for remote employees who can’t connect to critical systems while the people in the office can. This situation is almost unavoidable.

To understand how to treat remote employees when they can’t connect to systems at the office, consider what would happen if your systems were in the cloud and your remote employees could access them, while the people in the office could not.

Would you blame the office employees for “having to come in and try to work in someone else’s building”? Would you tell them that they probably are “idiots who just don’t know enough about networking to keep the system running”? Would you insist that they stay later after the internet started working again to catch up?

You probably cringed at those suggestions. There are a lot of unspoken social norms about how to treat on-site employees, largely gathered from years of real-world experience with what happens when on-site employees are mistreated.

Most of our safety regulations and discussions of the rights of employees came about due to “bad things” happening in an on-site environment. Remote work is something new, and we as a culture have not really made enough similar mistakes in regard to remote workers.

Consequently, social norms are not as well established when interacting with remote employees. While you probably disagreed with every suggestion in the previous paragraph, similar approaches are routinely applied to remote workers, and most people don’t even blink. This isn’t their fault—it’s simply that history hasn’t caught up with us yet, leaving us with instinctive reactions that produce bad results.

When the office is unreachable and it isn’t the fault of the remote employee, it doesn’t serve any purpose to blame them for it. Similarly, if the company isn’t paying for the internet connection and the equipment used to connect, it’s best to either start doing so, or to accept that the employee is probably doing the best that they can with the resources that they have.

This tends to mean that unless the remote employee negligently (or purposefully) caused the failure, you really shouldn’t blame them. It also means that you shouldn’t treat them as if they are at fault.

Demanding that the remote employee work after hours to catch up after an equipment failure is probably not a good idea—it comes across as if you are blaming them, whether you intend to or not.

Having a remote workforce is an investment in the future. It’s an investment in creating a better, more flexible work environment for your employees. That is all for naught if you subsequently blame the employee for equipment and network failures that they were unable to prevent (or that they couldn’t afford the cost of preventing).

Security Concerns

Security is also something that concerns any employer. Whether it is the theft of trade secrets, breaching of network resources, or the use of critical infrastructure for inappropriate purposes, nearly every employer considers security to be a critical problem that needs to be handled effectively, lest the business be destroyed by the next random hacker who comes along.

In many environments, employees spend a lot of time training to avoid creating security issues. The way that employers handle security may be as simple as requiring all employees to sign a Health Insurance Portability and Accountability Act (HIPAA) waiver or as complex as having intensive audit processes and requiring continual training for employees.

Regardless, if you haven’t considered security, you should probably stop reading and go handle it—you can’t have a sustainable remote team without taking security seriously (and it is dangerous to try).

I can’t stress it enough: If you aren’t scared about the security landscape right now, it’s because you haven’t been paying attention. This is doubly true if you are a security professional. Massive breaches are a common occurrence, with millions or tens of millions of dollars in damages. Ignoring security is about as outmoded as ignoring the internet itself. Your business will not survive if you do.

If the previous paragraphs scared you (or if they reinforced what you already know), then you probably wonder how you should handle security when you have remote team members. You may feel relatively safe when considering the security of your own office, but remote employees add another dimension to consider.

While your average programmer in a cubicle is working on a machine that is largely controlled by your IT department, the story is a bit different for remote workers. Your user experience designer in the IT room doesn’t have a computer that is likely to be stolen during a break-in, and probably won’t allow their children to use their work computer. Do you have similar assurances regarding your remote employees?

If you are like most employers, you are probably a little uncomfortable with the lack of control that such a situation creates. If a computer is not always in your custody, you simply don’t have control of it. Consequently, you can only trust machines such as these to a limited degree.

Further, if the computer in question doesn’t belong to your company and you can’t enforce security policies on it, then you are crazy to trust it. In an office environment, this means that you can’t trust the random laptop that one of your coworkers (or salespeople, *cough* *cough*) brought into the office.

In a remote environment, if you aren’t providing employees with their own computers, that means you may never be able to fully trust any machines that they are attempting to use.

While this sounds grim, there is good news. Lots of projects are conducted using machines that aren’t fully trusted. This pattern is very common in distributed software teams, especially in the open source community. Absolute trust of a machine is not always necessary in order to get good results from a team member.

If you assume that a remote computer can’t necessarily be trusted, your processes will need to be changed to accommodate that. If your organization stores any sensitive data at all, then you probably should have processes in place that assume that any single machine might be compromised.

In essence, most of the security considerations that occur because of remote workers are really things that you should already be handling anyway. Having remote employees forces you to do so before being forced by compliance requirements.

There are, however, a few issues for remote employees that you will need to handle with a robust security policy. Not only do you have to do your best to prevent these issues, you also need processes in place to periodically audit to make sure that these problems haven’t occurred.

You also need procedures in place for the inevitable case when a security policy is ignored or circumvented. These items below are true even if you provide your employees with a company computer.

Stolen Equipment

Your employee’s car or home may be burglarized with a company laptop or other devices present. These devices may be stolen. If they have sensitive data on them that was not encrypted at rest, then this small theft may constitute a serious data breach.

Generally speaking, your employees should never have sensitive data on their company laptops. However, in some (extremely narrow) cases, that may be necessary. In these cases, you need to make sure that employees are only keeping data that they absolutely require and getting rid of it as soon as they no longer need it.

Similar concerns exist in office environments, as well. However, offices, especially large corporate ones in expensive parts of town, are far less likely to experience a burglary than a home or a car.

As a result, you need to take extra steps to make sure security policies are applied (and kept in place) on any devices that a remote employee will be using. This is not only limited to computers. Tablets, phones, external hard drives, and the like can also cause a breach if stolen.

At a minimum, you need to make sure that the devices require authentication to use, encrypt their contents at rest, and have appropriate patch management applied to them so that someone can’t use a known vulnerability to get into a stolen device.

You also need to make sure employees promptly report stolen equipment. It’s surprising how many organizations have a very blame-oriented culture and then are surprised when employees don’t report problems.

Local Network Security Breach

Another major risk for remote employees is that their home computer network security may be compromised. Whether it’s because of their activities on their own computers, or because someone else in the building is not being careful, there is always the possibility that someone’s home network is insecure.

You will want to make sure that any devices used to connect to your network have a fairly strict firewall policy, have local scanning for viruses and other malware, and that communications between that device and your office are encrypted.

Illegal and Unprofessional Activity Conducted on the Computer

When employees are working from home, there is always a risk that the computer will be used in illegal or unprofessional activity. This could be anything from buying drugs online, to pornography (legal or otherwise), to software piracy, to harassment and threats toward other people.

While these things could also be a problem in an office, it’s a greater risk when someone has company equipment at home. People at home often feel a lot more comfortable doing things that they wouldn’t do in an office.

Besides the extremely negative results of this behavior, this could also result in problems for the company, as people engaging in these behaviors tend to end up with a lot of malware on their computers from visiting dodgy websites.

It’s also entirely possible, especially in the case of particularly egregious behavior, that it could even result in the seizure of the computer as evidence by law enforcement. And it gets progressively worse if the employee did something illegal from your company’s internal infrastructure.

To protect the company, you will need to monitor computer usage on any machine that the company owns, even if it isn’t connected to your network. In particular, you need to look for patterns of behavior that indicate the machine is being misused.

However, you have to do this without damaging the employee’s ability to work effectively or ruining morale. This is a very difficult balance to maintain, and frankly, I’ve seen very few companies do it well.

Content filters and regular scans for malware will help, but the thing that helps the most is vetting your employees before hiring them. Beyond that, your main goals are to catch unauthorized behavior early, and to limit the systems involved if it occurs.

Computer Used by Unauthorized People

When you send a computer home to be used by an employee, you probably don’t want their spouse, children, or random strangers using the machine. Not only is it possible for those people to mess up the machine, but there is a strong possibility that sensitive or proprietary data is on the computer (or will be in the future).

This makes it extremely risky to allow your employee’s family and friends to use the computer. Even if they don’t mean to do anything nefarious, such a situation only requires a keylogger to be installed. Keyloggers are often slipped in as the payload in malware, and could also be installed on purpose by a malicious member of the employee’s household (or a neighborhood kid who happens to be visiting and sees an unlocked workstation). Once that happens, the machine is no longer secure.

As a result, you need to make sure your employees understand that they can be terminated for allowing use of company equipment by unauthorized parties. You also need to make sure you have appropriate policies on the computer that cause it to lock (or sign out) after being idle for a certain period of time.

Furthermore, you should also enforce fairly regular password resets so that the employee’s family can’t just memorize the password once and have access to the machine. Additionally, you need thorough malware scanning, just in case someone does manage to log on to the machine without authorization.

Computer Damaged/Broken

When employees are working from home, there is always the possibility that a component in the computer will break. While computer repairs are annoying and sometimes expensive, that’s not the biggest issue. The biggest issue is the potential for data loss, especially if an employee isn’t backing up their data on a regular basis.

While I haven’t experienced this happening with a remote employee, I got to witness firsthand just how messy such a situation can be. I worked with a guy who was not the best about keeping his stuff on a server that could be backed up. Instead, he kept everything on his local file system.

As luck would have it, his hard drive died right before a major deadline. The company had to spend several thousand dollars to recover critical code that had been written over the previous several months.

They were not able to recover everything, and the project launch date ended up slipping by several months, costing the company two customers (it was a product that cost about $20,000 a year at a minimum).

Computer failures are cheap compared to what happens when sensitive data is lost during a computer failure. To prevent this, you need to have agreed upon storage locations on the machine itself, and data in those locations needs to be backed up on a regular basis to servers that you control.

Additionally, if there is any way to do so, you also need to have regular checks to make sure people have updated internal systems recently. If they haven’t, management needs to know. There is no excuse for losing expensive data due to a hard drive crash.

Insider Data Breaches and Data Exfiltration

Finally, if you have remote employees, you need to be extremely careful about access permissions for any sensitive data. This may require more than simple audit permissions around data changes. After all, having remote employees means that there is a screen in someone’s home that has your data on it.

Even if the data isn’t copied digitally, it could still be copied manually. Worse still, there aren’t a lot of ways to stop someone who is manually copying sensitive data out of the system—you just have to hope that you can catch them quickly. To do this, you need to have thorough and complete audit trails around access to sensitive data.

This means that each time the data is accessed, even if it isn’t altered, you need to know who did it. Additionally, if possible, you need to drastically limit who can access sensitive information. If a person’s job doesn’t require access to production data, they shouldn’t have it.

This can be anything from computer code, to trade secrets, or even customer lists. You should also log any failed attempts to access sensitive systems and alert system administrators when such attempts occur. These practices will make it far more likely that you will catch someone before they do much damage.

Also, make sure that any terminated employee’s access to systems is quickly revoked and that the hardware they are using is quickly returned to the office. Be especially careful with this returned hardware—don’t assume that you can trust it.

It’s entirely possible that the former employee could have installed a keylogger or other malware before returning the machine. A full operating system install is probably a good course of action.

Dealing with data breaches and avoiding data breaches could be book topics themselves (and, in fact, they are), but these general guidelines should be enough to point you in the right direction.

Remote-First Is Hard, but Worth the Effort

If you are planning on having remote workers in your organization, it behooves you to consider that these employees arrive in your organization under a very different set of assumptions and problems than those experienced by on-site employees.

As a result, as an employer or manager, you have to think about remote employees differently than your on-site employees while attempting to treat them equally. It’s difficult to do both, but it’s required if you want to receive any benefit from a remote workforce.

Remember, your competitors are eventually going to embrace remote work. The trends clearly point in this direction, and the number of remote employees is constantly increasing.

If you manage to build your remote team effectively, it can help you compete against your rivals in the market. However, to be truly competitive, you will have to drastically modify the way you work with your employees in order to achieve any competitive advantage.

Doing so will change your entire business, while ignoring the trends will weaken your business, and eventually kill it. It pays to do this well.

Chapter 9

The Ultimate List of Remote Work Resources

Whether you are just starting out on your remote work journey or you have been doing it for years, you’ll find that having appropriate tools for the task is a critical part of maintaining your productivity.

Further, as your remote career progresses, you may find that other opportunities open up for you. It’s entirely possible that you’ll decide to start a business from a remote location, that you’ll travel the world while working, or that you’ll need to look for more jobs.

Even if you stay right where you are, it’s often helpful to have resources and communities of remote workers just like yourself. Not only will this help you stay sane, but it can make it a lot easier to get good answers to the kind of unique problems that remote employees face every day.

In this guide, I’m going to list some resources that can help you along on your remote journey. As you’ll notice, I’ve broken these tools down into rough categories so that they are easier to find when you need them.

In addition to remote work resources, I’ve also included resources that will be helpful if you decide to go a step further and start a career as a digital nomad.

There are a few reasons why these are included. The first is that there is a lot of overlap between the lifestyles of a standard remote employee and that of a digital nomad.

The second is that a lot of material on remote work focuses on people living in nice, suburban environments with reliable power, phone, and internet connectivity. Your situation may not be like that or may not always be like that.

Finally, remember that digital nomads are frequently moving around, having to deal with a large amount of uncertainty in their working environment. As a result, their ideas are often really helpful when you do have to travel as part of your remote career whether that means travel into the corporate office or travel while working.

Automation

As a result of time zone differences, traveling, or simply wanting to do less manual work, you may find that when working remotely, you need to automate certain tasks or be automatically notified if certain events occur.

While you could “simply” automate many things using simple scripts (many programmers have), it’s often not the best use of your time, especially when it comes time to modify these scripts due to changes. As a result, it’s usually more time efficient to use a service that handles most of the work for you.

Currently, there are three really good contenders for this on the market. Depending on what you need to do, different tools offer different options.

Buffer allows you to schedule social media posts. Not only is this helpful if social media is part of your job, but it’s also very handy if you use social media for any kind of side work. Buffering posts will allow you to make sure that they go out when they should whether you are present or not.

IFTTT (or If This Then That) can do several things for you. First of all, it can react to incoming data such as RSS feeds, emails, or events from other tools. It can then perform simple actions on your behalf based on that data, such as posting to Twitter when you publish a new blog post.

Zapier is another useful tool for automation, and it is the most complex. Not only does it have the power of IFTTT, but it can connect a huge number of applications.

Automation applications can save you a ton of time and effort. For instance, consider Zapier. I use it personally to automate a number of pieces of our podcast workflow.

When a card is moved in our Kanban board (KanbanFlow), a Zapier workflow not only makes sure that I get relevant tasks assigned to me in my to-do list application (Nozbe), but it also creates files for our outbound emails around the episode in my dropbox.

In addition to simple workflows, Zapier also lets you build complex, multistep workflows, which can be really handy if you are dealing with something complex enough to need a custom script.

Book Suggestions

If you are looking to make a “long term thing” out of remote work, it behooves you to learn from the people who have done so before you. While it’s entirely possible to learn everything yourself for free, such an approach can also mean that you end up learning simple things in hard ways.

Books, in whatever form, are a great way to take a shortcut in the learning process so that it is less painful, expensive, and time consuming. Thankfully, there are a ton of good books out there that are either directly related to remote work or contain lessons and information that are useful for people who would like to work from home.

Deep Work - This book isn’t strictly about remote work. Rather, it’s about how to cultivate the ability to focus without distraction. The skill of extreme focus will help you tremendously when working remotely.

It Doesn’t Have To Be Crazy at Work by Jason Fried and David Heinemeier Hansson - If you are interested in remote work, it’s a fair bet that it’s because you’ve been exposed to some of the crazy corporate culture of overwork. In this book, the authors discuss how businesses can run without the insane “hustle,” 80-hour work weeks, and constant compromises on quality of life.

No Excuses: The Definitive Guide To Managing a Remote Team - This free guide to building a remote team is packed with good advice on outsourcing and building a remote team. In particular, the sections on management and building business process templates are very useful.

Remote: Office Not Required by Jason Fried - In this book, two of the people who started Basecamp discuss the phenomenon of remote work and explain how they got it all working to build a successful company. This book is full of good ideas about running your own business, and it’s also helpful if you have to talk to your manager about how to run a remote team effectively.

The Art of Staying Productive Even Across Distance - Written by Wrike, this free book discusses simple techniques to make you a master of remote collaboration. I’ve successfully used a number of them myself and highly recommend this read.

The Remote Jobseeker’s Handbook - If you don’t think your current employer will let you work remotely, you could always just go for a remote job. This book helps you build an action plan for finding a remote job. While I didn’t use the material personally, several friends have, to great success.

The Ultimate Guide to Remote Work by Wade Foster - This free guide by Zapier shares how to build remote teams and talks about the challenges the company faced as they scaled.

The Year Without Pants: WordPress.com and the Future of Work by Scott Berkun - This book goes behind the scenes of the company behind WordPress (Automattic, Inc.) and discusses how they were able to build their organization. Remote work is part of it, but the rest is about how to build a dynamic, effective organization. Of special interest are the sections about managing creativity.

Working Remotely - The Telecommuter’s Guide to the Galaxy - This book goes heavily into remote work practices and how organizations might want to implement remote work.

Your Brain at Work - While not specific to remote work, this book focuses heavily on how to overcome distractions, maintain focus, and work more effectively. It’s a good read.

I don’t necessarily recommend reading all these books end-to-end like I did. Rather, it’s often better to have them on hand to have quick reference material when you run into a problem or need advice on a situation.

Blogs

While working remotely, it helps to keep up to date on things that may impact your work, especially in regard to industry news that may make you more efficient or help you avoid problems. Not only are blogs a good source of ideas for how to improve your remote work experience, but they can also be the best way to find out about things that cause you problems.

I learned about a lot of the tools and software in this guide by reading blog posts. In addition, blog posts written by remote workers have often warned me about software updates that could have caused me problems. On more than one occasion, a timely blog post has kept me from installing a Windows update that would have broken my system right before a critical deadline.

This has been especially serious when a Windows update would have broken things that I needed as a remote employee that on-site employees usually didn’t need.

There are a few blogs that cover remote work as well as some others that are blogs of companies that use remote working as a strategy. These sites often have very useful tips on making sure that you get the most out of working from home.

Buffer Blog - Not only is Buffer one of the tools I recommend for automation purposes, but they also know how to run a remote company. They don’t write a ton of stuff on remote work, but what they have is quite good.

Doist Blog - In addition to tips on remote work, this blog is absolutely packed with tips on productivity that you will find useful as well. Being a good leader is the best way to keep your remote job from becoming a dead end job.

Know Your Team Blog - While not entirely focused around remote work, this blog has a lot of good information on how to be a better leader.

Lifehacker’s Remote Work Content - While it feels sparser than it used to, Lifehacker’s remote work section still has a lot of useful tips and tricks. It’s a good resource, especially if you combine it with some of the productivity discussions on the rest of the blog.

Miro Blog - This blog covers a lot of interesting things, remote work among them. It also deals with agile, productivity, and creativity.

Nodesk - A curated set of resources for remote workers, digital nomads, and traveling professionals.

SignalvNoise.com - While this blog does cover some topics around remote work, what I really find endearing about it is their approach toward making a more sustainable life and workplace. The principles they describe are good even if you are stuck going into an office (maybe especially so).

The Remote Work Blog - As its name suggests, this blog is heavily focused on remote work. It also includes a fair number of posts about becoming a digital nomad, which may interest you depending on your situation in life.

Blogs are a great resource, provided that you are judicious in what you read. They can serve as a constant source of new things to learn, which will help you grow.

However, I caution you to be careful that you don’t replace doing with reading. Blogs are great resources if you read them as you need things.

Career Resources

As time goes on, you’re going to want more from your remote career than simply doing the same thing from the house. Whether it’s a change in position, a change in job, or you’d like to get promoted, you’re going to eventually need career guidance.

At the very least, you’ll need good advice on how to update your resume. When working remotely, it’s easy to be lulled into a sense of calm complacency because of the less stressful environment.

However, at some point, your job situation is going to change. When that happens, you will need to be prepared lest you find yourself forced back into an office job. Lots of things can happen to your job over time. Whether it’s downsizing, new management that doesn’t like remote work, or you simply wanting to do something else with your career, at some point your current job will end.

Good preparation in regard to your career will help you make sure that you can keep working from home in the future.

Prosper Career Coaching - While not focused on remote work, what this site does focus on is still critical. They help managers become real leaders. If you’ve ever been in a situation where you were promoted into management without any help, you might want to see what they can do for your company.

Resume.io - If you are like me, you hate messing around with your resume, especially when you want to make it look good without the usual slugging match with Microsoft Word. This site will help you with templates, and its very quick workflow will help you quickly create a resume that will get the attention of hiring managers.

Communities

Remote work is often a lonely experience, especially if all of your co-workers are in an office. Furthermore, networking is extremely important if you are going to be working from home.

Most of the best job opportunities I’ve had have come from my personal network of friends, former co-workers, and family. If you want to keep your career health while getting good advice from people who are in similar situations, the following communities are a great source of tips, tricks, and contacts.

This list of communities includes several groups that are built around the idea of being a digital nomad. While this may not be what you are looking for, I still encourage you to check them out. Digital nomads have figured out how to do a lot of work under pretty serious constraints, and the things they’ve learned may be useful to you as well.

#Freelance - If your notion of an ideal remote working arrangement includes working for yourself, the #Freelance hashtag on Twitter has all kinds of good resources from a variety of different people.

Hacker Paradise - If you are seriously considering becoming a total digital nomad, this site has a lot of advice on places that you might consider going to. Their blog also has a number of articles that have useful application even if you never try to work while traveling.

Reddit/Telecommuting - Sometimes you just have a question and need some advice from people who are doing the same thing. This reddit community is great for discussing the issues faced by remote workers.

Conferences

Conferences offer a lot of opportunities that you can’t get anywhere else, especially if you work remotely and seldom go into the office. Besides the vast amount that you can learn by attending a conference, such events are also excellent opportunities for face-to-face networking with other people.

While conference attendance may be something that you considered optional when you went into an office every day, it’s a really good idea to treat it as mandatory when you are working remotely.

Further, conferences are a great place to find out about larger companies that have a remote work strategy. These companies will often have a booth at conferences or will have a number of people attending (including speakers).

While you may or may not like working at larger organizations, jobs such as these do have advantages, especially in terms of pay and benefits. It can be really helpful to know which companies have good remote working environments if you are looking for another job.

Even better, if you have networked effectively with their employees or managers, you will have a distinct advantage over other people applying for the same job. Remote jobs are often competitive, so any advantage you can get will help.

Running Remote - While I haven’t managed to make it to this conference, I’ve heard lots of good things from people who have managed to attend. Hundreds of remote first leaders gather together to discuss the practical realities of remote work as well as to network, and some of the attending and sponsoring companies are very impressive.

The Remote Work Summit - This conference is a bit more HR-centric and talks a lot about topics like building an effective remote culture. Best of all, in the true remote spirit, you can attend online.

Nomad Summit - I’ve talked to people who have attended this one. This conference is focused on digital nomads and takes place in various exotic locations. Recent ones have included Playa del Carmen and Chiang Mai.

Education

Even if your employer offers training as part of your job, you probably should still be learning things on your own time. While you should certainly take advantage of any free training offered by your employer, there are a lot of issues with relying on only that training.

The first is that employers are generally only going to pay for training that is actually useful to them. If your career goals are different from your employer’s goals, this will not be optimal for you.

Secondly, if you are training and are in the middle of a course, what happens to your progress when your job suddenly changes? It’s incredibly frustrating to spend a bunch of time training, only to have your job suddenly end in the middle. It also makes it a lot more difficult to prove to your next employer that you actually understand the material, especially if you didn’t complete your training.

I’ve done a lot of contracting and worked at a lot of companies. I will never allow an employer to control my training again. I did that once, and it was a royal pain to get the next job using the technology I had been learning. I had to do a bunch of work between jobs and pay for training myself. It would have been much easier had I never relied on my employer. I strongly suggest that you do the same.

Codecademy - If your future plans include learning to code (or getting back into coding after an extended break), Codecademy is a good place to start. While you may not dream of being a software developer, having at least some ability to code can help you be more productive by allowing you to automate repetitive tasks. A surprising number of jobs can be made more effective with just a little code, so this is worth looking into.

Coursera - With more than 3900 courses and specializations, there is something on Coursera for just about anyone.

Khan Academy - Whether you are trying to fill in some gaps from your education or just decided that you really want to learn organic chemistry this year (I won’t judge, but I didn’t like it the first time), Khan Academy has a ton of material available for you. They are a nonprofit whose goal is to provide a free, world-class education to everyone.

Lambda School - If you aren’t a software developer and would like to be one soon without trying to learn it all on your own, Lambda School may be a good choice. While it does cost money, you don’t have to pay them until you start getting paid.

Skillshare - With thousands of available classes on a wide variety of subjects, this site can teach you a lot of valuable skills for your career, covering everything from design, to business, to photography.

Udacity - offers nanodegrees on a lot of subjects along with career coaching and mentoring. Best of all, you can work at your own pace and fit the work around your existing schedule.

Workplaceless - If your team is struggling to make remote work a reality, this site has a lot of training that will help you do it. This includes training for workers and managers, helping them build an action plan for the process of transitioning into a remote company.

Equipment

While much of the equipment used in a remote office can vary greatly, especially over time, there are a few things you should make sure to have in order.

Of these, you are probably going to find that your office chair, headphones, and conferencing equipment are some of the most common sources of annoyance. It is worth it to spend a little extra money on these things.

For instance, you may be sitting in your chair for eight or more hours in a day. In a year, you could easily spend 2,000 hours in a chair. Going cheap on your seating is an excellent way to develop chronic back problems and is not a good place to try to reduce expenses. Similarly, cheap conference equipment can annoy your co-workers (or your boss) and is probably not a good idea.

It can also be very helpful to invest in a good set of noise canceling headphones. Even though I work remotely, I still can’t really block out all the ambient noise. In particular, when the neighbors are having work done on their house, I can often hear the equipment in use as well as loud conversations outside my window.

Compounding this problem is the fact that I have a Jack Russell hound mix living in my house. When stuff is going on outside, she jumps like a Jack Russell terrier and lands like a hound. She can do this for what seems like hours at a time. Had I not invested in some good headphones, my productivity at home would be limited by outside noise.

Bose Noise Canceling Headphones - These are probably the No. 1 reason that I stayed sane the first few times I worked remotely (back when my office was near a busy hallway in the house). While noise canceling headphones don’t do a great job of blocking out things like human voices, they do block out a lot of repetitive background noises, which still helps a lot.

Herman Miller Chairs - These are some of the best chairs for use in a remote office. I had one before and will eventually get another one. They aren’t cheap, though, unless you buy them used from a company during a bankruptcy sale.

Owl Labs Meeting Owl - These are impressive smart conference room cameras. While the price point is not justified for use in a home office, they can do wonders for the average small-business conference room setup.

Job Boards

When you start looking for your first (or your next) remote job, you will need to find job boards that either specialize in remote work or that easily allow you to filter your job search criteria to find companies that will let you work from home.

Once you’ve experienced the far superior work environment that you can have at home, going back into an office will sound like the worst thing ever.

However, if you lose your job and can’t get something else quickly, your financial situation may force you back into an office. It’s a good idea to constantly be keeping your eyes open, just in case.

AngelList Remote Jobs - Billed as the largest job marketplace for remote work (probably accurate), AngelList has a huge number of open remote job positions on its board. I highly recommend it if you are looking for a remote position.

FlexJobs - This job board specializes in finding flexible jobs. This includes both remote and on-site jobs whether full-time or part-time.

Jobspresso.co - This job board has thousands of remote jobs and also has a mailing list of more than 100,000 potential remote workers. This kind of reach is handy if your company is looking for more remote employees.

LinkedIn (remote jobs) - You can also search for remote jobs on LinkedIn. This is where I made the connections that landed me in my current position, and the application process is very simple.

Moonlight - Moonlight is a community of remote software developers, built around finding flexible remote work.

Remote.co - Not only is this a job board for remote jobs, but it also contains a ton of resources to help both companies and individuals with the process of remote work.

RemoteHub.io - This is probably the most straightforward of the remote job boards out there, and it has a nice instant application process for certain companies on the site.

Stack Overflow (remote jobs) - Stack Overflow is an extremely popular site for software developers, and they also have an excellent selection of remote jobs. I’ve applied for several remote positions I found here.

We Work Remotely - This is a job board mostly for software developers (and tech-adjacent jobs) that offers an impressive array of positions at a number of prestigious companies.

Workaline - This is a huge database of remote work opportunities across a wide variety of disciplines. They routinely post over 200 new remote positions every week.

Working Nomads - This is a job board of remote positions aimed more toward digital nomads. It’s especially nice because it has a lot of positions that aren’t technology-oriented. This can be helpful if you are technical, but your spouse isn’t, especially if you both want to work from home.

Podcasts

If you are like me, you may find that long hours spent working in silence end up feeling a little oppressive, at best. If you need something to listen to and aren’t in the mood for music, podcasts are a great way to absorb more useful information while you work.

They are also great for those times when you are forced to go into the office whether you are listening to them in traffic or using them to drown out the ambient noise in the office.

I have at least 30 podcasts on various topics that I listen to while working, so take it from this podcast junkie—you can learn a lot from them without a lot of effort. Podcasts represent around 80% of the new things I learn. Here are some I’d recommend.

21st Century Work Life - This podcast goes into depth discussing the new work paradigm of the 21st century, including things like artificial intelligence, remote work, and distributed teams.

Complete Developer Podcast - This is my podcast. While geared toward software development in general, both of us work remotely, so that perspective tends to come through on a lot of things. Also, we have a substantial amount of good material on productivity and building the best version of your life as a software developer.

Distributed Podcast - This podcast discusses the musings of Matt Mullenweg, the co-founder of WordPress. He built a 900-person company with no offices and employees scattered across 68 countries, so he has a lot of good material here.

Ok Productive - This podcast is not necessarily built around remote work, but a lot of the productivity tips and hacks they discuss on the show can be extremely valuable for remote employees.

Modern Work Podcast - This podcast features in-depth interviews conducted with digital nomads and other remote workers. The podcast host travels and works full-time as a freelancer. She’s also the author of the Digital Nomad Survival Guide.

Rework - This podcast is about better ways to run your business. Hosted by the founders of Basecamp, it offers insights into ways that companies can improve how they run, including lots of advice on having a remote work environment.

Wide Teams - This podcast features interviews with remote workers in various fields. The personal anecdotes of the people being interviewed are often very insightful and useful even if you are in a different industry.

Yonder - Aimed at helping companies transition to a more flexible, “free-range” workforce, this podcast is full of useful tips. They also have a number of helpful articles on the site.

Tools

Working remotely is great, but productivity can be tricky to manage. While you may not be the person who makes the choice about which productivity tools to use in your office, you might have influence over such a person.

If that’s the case, then choosing good tools for your team is one of the primary ways that you can make sure that remote work remains sustainable. The best tools for the job vary a lot, but here are some great ones that can help in a variety of situations.

Asana - A web project management tool that is widely used in remote organizations.

Basecamp - A web-based project management tool focused on simplicity.

Brain.fm - Custom-generated music tailored for your brain. The idea here is to drive you into an appropriate mental state for a particular task.

Clockify - Free time tracking software for teams to manage hours across projects.

Clubhouse.io - Project management tool specifically designed for software teams.

Deel - Compliance, payments, and invoicing tool.

Evernote - Note taking and knowledge management tool that works for teams. I use it as a digital filing cabinet across all my devices.

G Suite - Google’s office suite of tools for business. These are built to allow real-time synchronization, so they work well for remote teams.

Monday.com - Team Management and Kanban board. I’ve worked at several places that used this, and it’s always been handy without getting in the way.

Nozbe - To-do list tool. I use this one to manage every to-do list I have and even have special workflows in Zapier that push things into the tool in response to events.

RescueTime - Helps you optimize your use of time during the day by letting you block distractions, track time automatically, and set goals. It’s great for breaking your habit of spending too much time on Hacker News.

Slack - One of the most popular chat applications out there, nearly every remote company has a slack channel. It’s good for both teams and one-on-one chatting. We use it to keep in touch with our podcast audience.

Toggl - Neat little time tracking application. I use it both for tracking billable time as well as time spent on nonbillable activities. It’s inexpensive and well worth the low price.

Trello - Kanban board for managing projects and teams. It’s very helpful for custom internal processes (such as content editing workflows) and offers a lot of integrations with other tools that you might be using as well.

Video Conferencing

Even if most of your meetings can be handled effectively with your various workflow tools, there will still be times when you want to be able to talk with co-workers face to face. Video conferencing is critical to your success as a remote employee.

While video conferencing software (and the hardware it works with) don’t always allow it, I try to always have both my camera and microphone on when I am on a call with my team. While this isn’t strictly required, I find that helps reduce the number of misunderstandings that occur on the team. Having good and reliable video conferencing software will help you maintain your connection with your team.

Video conferencing software is one of the most critical tools you will have. Every time you are in a face-to-face discussion, your video conferencing tool of choice is as critical to communication as your own face is when you are in the office.

While you may not be the person who chooses the software that your team uses, you should advise whoever makes that decision to use good software. Far too often, I’ve worked with teams using the cheapest video conferencing software they could find, only to end up wasting hours dealing with its various quirks and problems.

This is a bad place to skimp because any failure of this software can easily waste time for your entire team. Get it right with some of the tools below.

Hangouts - Chat and video conferencing application provided by Google. We use this for all face-to-face conversations for the podcast as well as our quarterly meetings. It is extremely reliable for us.

Microsoft Teams - An alternative to slack and many other chat and video conferencing programs, Microsoft teams integrates nicely with Outlook and other office tools. I’ve used it on a number of projects with great success.

Skype - A free chat and video conferencing tool used by default in many organizations. It does work pretty well in general, but the newer version is not as stable as the old one.

UberConference - Free software for conference calling. It’s especially nice because you can set up and join conference calls without messing with PINs.

Zoom - Video conferencing software that is especially effective for large groups, including for webinars.

Tools Make Work Easier

If you want to be successful in remote work, having good tools and resources makes it a lot easier to be successful. The stability of any remote work environment is heavily dependent on your ability to effectively use technology to get your work done, communicate with your team, and manage problems as they occur.

While you can work remotely with very minimal tooling and few resources (and I certainly have), it ends up being a lot more stressful than it has to be.

While you are working remotely, be sure to take time every few months to evaluate how well you are doing. Pay special attention to anything that seems more difficult or frustrating than it did before, as small problems can add up over time to make remote work difficult.

When you run into something that is making your work less pleasant, see if you can find a tool that will help you get around the problem. You’ll often find very inexpensive solutions for common problems, as you aren’t the first to have them.