6 Red Flags That You Need To Start Cutting Your Losses

Written By John Sonmez

There’s a stigma in our society about quitting that causes us to cling on to projects long after they should be let go.

Quitters never win. Quitting lasts forever. Champions never quit.

You’re never a loser till you quit trying.

No one wants to lose. No one wants to be a loser.

Well, at least most people I know feel that way.

With all this mindset and advice to never quit, it sadly makes sense that we stubbornly refuse to take a step back, look over our projects, and admit that it’s time to cut our losses.

More importantly, that cutting our losses is sometimes the best decision.

So, how do you know when you are just experiencing a challenging dip or when the time has come to move on?

6 Red Flags to Indicate That You Should Be Cutting Your Losses

It’s hard to tell when those make or break points are coming if you are in the thick of working on something.

Still, there are a number of big a-ha’s, or red flag moments, that you may be able to identify as you are wading through the weeds, that will help you clarify what your next steps should be.

It’s No Longer Fun and/or Interesting

When you started on this project, you were totally “in it”.

Like a new relationship, most new experiences have a glowing honeymoon period where everything is new and fun. No matter what the reason for your excitement, you couldn’t wait to dig in and do the work.

Maybe you showed up to the office earlier. Maybe you earmarked special time in your schedule to devote specifically to it. Maybe you went out and learned a whole new coding language, because you knew it would make the project better.

Eventually, the day comes where you have to check out of the hotel and return from your idyllic honeymoon experience. Back in the real world, you have to learn to navigate this new relationship, and it just isn’t as grand.

The good news is this is natural. Every project (and relationship) experiences this blah type of feeling, when the motivation is waning and the tasks become tedious.

Maybe you start arriving at the office 5-10 minutes closer to your original start time. Maybe you start finding excuses and other things that you “have to do” during that special time. Maybe you slack off on keeping up with changes to the new coding language you learned.

The Red Flag Moment: You’ll know that this is a red flag moment not because you aren’t 100% in it anymore, but because you continuously aren’t in the moment. A few days to a week of the blahs is totally natural, but if you are hitting 10+ days with no moments of uptick or engagement, the time for quitting may be near.


Short Term Fixes are Causing More Long-Term Problems

Every big project is going to involve some rolling up of the sleeves.

It may feel like you don’t want to work hard anymore, and that may be what others say when they accuse you of giving up too soon.

Yet there comes a point when working smarter is no longer possible, and all you are doing is working harder.

You could be constantly implementing fixes to solve small issues and push the project to launch. Updating different features, with minimal testing on the interactions with future implementations. You are worried that the integrity of the project is becoming compromised, in a quest to finish.

The Red Flag Moment: You begin to realize, and you might be the only one, that everyone is simply chasing their tails trying to get code out. But that solutions are barely a temporary fix, and the laundry list of problems they are causing is quickly getting longer. Everyone is more focused on launching than they are in the long-term viability.

Other Things Have Taken Priority

Similar to the honeymoon period, when you start a new project, it is the most important thing in your world.

That’s part of what makes it so exciting in the beginning – everyone focusing on one thing together. Everything else falls to the wayside. You can’t even think about another project or your boring old daily tasks. It’s all about the new project, all the time.

Eventually, your boss begins to ask where the TPS reports are again. You spend longer in the break room, talking to Bob about his new project. Before you know it, everyone is shifting their scrum boards to help debug the new program.

The Red Flag Moment: It isn’t empty excuses and waning interest causing you to divert your attentions. It is actual better work that you recognize needs you.

You Are Blindly Hopeful

No one likes to admit when their baby is a little bit ugly.

Often, they can’t see it themselves.

With this new project, the short term fixes may be accumulating at a rate faster than anyone can determine the repercussions. The users may not be engaging, or worse, they aren’t interested in purchasing.

But you have a vision…a dream.

You know what this little engine could do, and you are determined to “think I can” your way up the mountain. Ain’t nothin’ gonna stop you now.

The Red Flag Moment: You can’t find a single flaw in your project. As things progress, every new iteration is going to have hiccups and obstacles to overcome. If you refuse to see them, even when others point them out, you may be more obsessed than you want to admit.

You Don’t Want To Admit You Were Wrong

This one is hard to differentiate from Blindly Hopeful.

Yet, with Blindly Hopeful, you can’t see any faults. It’s all rainbows and unicorns. If this were someone else’s work, you’d be the one on the outside looking in, shaking your head that they can’t just cut their loss and move on.

The touchpoint here is that it isn’t the project, it’s you.

The Red Flag Moment: You begin to get defensive, constantly justifying your actions to anyone who asks the simplest question. You argue, not only to convince them, but also to convince yourself.

Cutting Your Losses

You Ignore The Red Flags

Did you know that the earliest recorded use of the phrase “red flag” indicated a warning that a flood was coming?

In Philip Thicknesse’s A Year's Journey through France and Part of Spain, 1777 : Volume 1, he notes a red flag being raised higher and higher at the harbour in Calais to match the rising water levels.
The first few levels meant that something could be wrong, and residents should stay aware. As the levels went up, and the red flag became more prominent, it was a sign that everyone should head for the hills, or face the possibility of drowning.

The same thing happens when we ignore the red flags in a project we are working on. One or two may simply mean that you need to keep an eye on the issues. However, if too many start piling on, you may just drown.

The Red Flag Moment: This one is usually the one that hits the most people, cause it hits you like a brick wall. Suddenly, one day, you look at your work, and can mentally calculate the 8-10 huge issues that make the viability an impossibility. It isn’t that the final product is threatened, it flat out can’t happen.

Should You Stay or Should You Go?

Seth Godin has a principle that is often referenced in business and tech circles, known as The Dip.

The Dip is “a little book that teaches you when to quit (and when to stick)”. It’s premise is simply that in every project or business or endeavor, you are going to experience a multitude of different dips. Temporary setbacks that will leave you questioning whether it is worth it any longer.

The key is figuring out whether their challenge is a dip in the eventual line graph to success, or if it is a crucial red flag warning you to get out before the village drowns.

Cutting your losses is sometimes essential to your long-term success. Paying attention to important issues that come up, such as a slew of incompatible features or a highly defensive conversation, may be what separates you from the losers.

It isn’t that the winners never quit. It’s that they know when to quit, and they know when to stay in and fight.

Of course, there are more than 6 red flags that you need to start cutting your losses. What are some of the red flags you’ve experienced? Did you get out while you still could? Or did you hold on for too long?