What’s the Problem, Again?

4 Simple Rules for Avoiding Death Spiral Projects

At times in my career, I’ve found myself working on projects that I would describe as “going through the motions.” While these efforts often began with the best of intentions — “make the customer happy”, “rewrite our client/server software for the Web”, and so on — over time they became death spirals for one primary reason: I lost sight of the problem I was solving.

Wait, what was I working on?

By following a few simple rules about What, How, Why and When to solve a given problem, you can avoid the same fate.

What: Make Sure There’s a Problem

There is one fail-proof antidote to the poison of death-spiral projects. Do not let a day go by without asking yourself…

“What is the problem I’m working on?”

It seems obvious, but in my experience it’s rare for an entrepreneur or creative person to stop what she is doing and do a self check-in on what exactly is the problem being solved.

After coming up with an answer to this question, decide if the overall problem is big enough to justify continuing to put effort into solving it. Sometimes a problem can be solved with a quick and dirty approach rather than the big project you have planned on the horizon.

How: Make the Overall Problem Smaller

Now that you’ve got an important and large problem to solve, ironically, you need make it smaller by breaking it into chunks. Creative people often avoid taking the time to break down a problem into it’s sub-parts, favoring just getting started #mvp #hustle #killyourself.

But if you break a problem down, your mind can consider a more focused and doable solution from day to day, without having to consider massive boil-the-ocean solutions that are beyond your reach. I like to do this by just using indented bullet points in a text editor. Example:


Once you have a break down, choose the smallest and most achievable part of the problem to attack today. I love the feeling of solving a tiny little piece of what I know to be a larger problem every day. This is hard if you allow yourself to just jump into the big problem solving without following this rule.

Why: Make the Problem Matter to You

To me, solving problems with software or design is a personal matter. I get very immersed in a problem and always look to solve it very deeply. However, if the subject of the problem or the potential benefit don’t ultimately matter to me, I will allow the core issues to linger and my solution will be half-hearted.

Like Sisyphus rolling his stone up a hill, solutions provided by people who don’t care about the problems they solve are bound to roll back down the proverbial hill of needing to be solved again.

This guy is on the The Struggle Bus

The only consistent way I’ve found to avoid this scenario is to surround yourself in problem “sets” that speak to your skills and passions. For me, these are problems relating to building solid, scalable digital products efficiently. So, I surround myself with challenging businesses, customers, and engineers in the software space. I imagine that, while I might be good at solving problems as a nurse or a pilot or a teacher or a food critic, it is not what I am ultimately motivated to do and I would not excel.

When: Is the Problem Actually Solved? If So, STOP and Find Another One

Another strange observation I have made is that teams and creative individuals never seem to be satisfied with their solution. The recent emphasis on iterating on a solution over and over again has caused many to get stuck in a rut of perfecting a single problem, which they believe needs to be solved more accurately, efficiently, and with greater value generation.

Sure, iteration can be good, but in many cases there is too little time and too much competition to justify whiling away on a single problem. Just identify it, make a solution work, and move on!


With some simple rules in your mind as you go through the day, you’ll find your problem solving abilities will expand as you make more effective and efficient choices in what, how, why and when to solve the problems you are best suited for. Best of luck!

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