Are You Making These Terrible Mistakes When Asking For Advice?

Written By John Sonmez

Lots of freelancers and creatives adhere to a “I never dole out free advice” mantra when asked if someone can pick their brain for a few minutes.

Think – when was the last time a person asked you for programming advice? If you could “just take a look” at their blog? Explain to your mother that it is Google that keeps changing their logo, and why you have no control over it.

I’m a horrible offender with my poor brother-in-law. He’s a programmer, and even though I work extensively in this world, I couldn’t begin to tell you what language he specializes in. He spends a lot of time writing code and managing his outsourced team. I still ask him to help me write webhooks for my payment processor.

I can feel him virtually pressing his fingers against the bridge of his nose, slowly hissing air through his teeth, cursing for a brief millisecond his choice in bride. If only he had married that girl five years ago, whose sister is an accountant.

I recently received a request from a friend to give some writing advice to an acquaintance of his that had recently started out in the field.

From the first sentence of the conversation, to the last, I could have predicted every single word.

The requests for free advice and help are always the same. I used to flippantly respond to questions like “How did you get a column on Forbes?” with this GIF…


…but eventually I stopped. I think too many people believed it to be true.

What’s Wrong With Asking For Help?

There are lots of reasons that people lack the awareness and manners to ask for advice in a way that is advantageous to their end goals, yet doesn’t make them come off as a total jerk in the interaction.

Business Advice

They don’t have “real-world” experience

The internet and various technologies have broken down the walls and barriers that used to stratify working classes.

No longer do you have to go to university, put in five to ten years in an entry level position, suck up to bosses and prove yourself, to eventually pull yourself up to a lower-mid level management position.

Instead, you can take classes online to learn your skills. You can start a blog to build your profile and prove yourself. Heck, if you’re a Zuckerbergian-wunderkind (or a late-in-life wunder-bloomer) you may just be able to buy and sell the planet within the same five to ten years that others a collating report copies and executing strategies that they learned in their 101 level classes.

As anyone who has ever seen The Social Network can attest, this may seem like an ideal path to riches and fame, but there are a lot of drawbacks as well.

Learn those soft skills that folks in your field with decades of experience seem to be able to integrate inherently.

There’s a reason they can do that.

They are oblivious to how much of a burden their request is

With this particular email request I received, every email was something new for me to answer.

How did I get to where I am in my career – as if there is a quick two paragraph hack, and it isn't a huge question that would take an entire blog post (if not book) to answer.

What should this person do, in their current position, to get to where I am – as if building a decade worth of experience and expertise is something someone can simply replicate.

Would I be willing to share my contacts and put them in touch with some of the editors and publications I’ve written for – as if throwing my reputation under the bus for someone I barely knew, who had sent me three short messages all asking for something, is a gamble I’d be willing to take.

Consider when you are making these asks, what is the person on the other side going to have to do or give up to help you. Is is their time? Their reputation? Their trade secrets and connections?

They are simply selfish jerks

I like to see the good in people.

It is a life skill that tends to serve me well, but occasionally bites me in the ass.

That’s why I prefer to see these poorly executed requests for help as just that – poorly executed. But with good intentions; from good people.

Sometimes, however, when you are a nice person, people like to take that opportunity to treat you as their personal doormat.

They’ll keep coming back and draining you for time, information, and maybe even money or resources.

Perhaps that is why they are so willing to play fast and loose with your reputation and career. They don’t respect you, because they don’t respect many people.

These wonderful denizens of human society will usually only reveal their true colors when you call them on it.

I once got a request to explain how I set up our editorial agency, as this person was hoping to set up a proofreading service that was an exact copy of one of our service offerings.

When I told her that I would be happy to share generally, but was not going to tell her how to replicate my business, she replied that there is plenty for all of us, so I shouldn’t feel threatened. In some weird, syrupy, passive-aggressive way that I have previously only seen in the hallways of my high school and various Disney channel musical movies.

I thought that was adorable. Chuckled to myself for at least the next five days whenever I thought about it.


Are You Making These Mistakes? Helping Those Who Are?

We’ve all found ourselves on one side or the other of the advice table in our lifetime.

I have an open door policy for people earnestly asking for my help and advice in progressing their writing and entrepreneurial careers, because once upon a time, people took the time to have an open door policy with me.

Still, I’ll dole out the tough love on these requests when they are terrible. Though it stings a bit, letting folks know how their request is an imposition or flat-out ridiculous will help them in the long run.

I try to keep the same rules I teach to others in mind when I am contacting folks that I need advice or help from.

I have yet to meet anyone who is so far advanced in their field and career that there isn’t some relationship that would be advantageous to their future. For many years to come, it is up to us to help those that follow us and continue looking to those who lead.

Just need to make sure we do it in an way that ends in a win for everyone.

And doesn’t make you come off as a jerk in the process.