Do you work on interesting problems?

Do you work on interesting problems?

When I’m interviewing candidates, I always leave ample time for them to ask me questions about Simple Thread, how we work, all of the intangible things that are not listed in a typical job description.

Recently a candidate asked me, “What kind of projects do you all work on? Do you work on interesting problems?

It’s a perfectly reasonable question, and it was actually a great interview overall, thoughtful conversation with comfortable back and forth. But for some reason on this day, the question kinda stumped me. I didn’t know what to say.

After an awkwardly long pause, I said, “Uhhhhhhh, yeah, I think so. Yes! But also, I think I can find almost any problem interesting.”

And once I started talking, I regained my wits and discussed our typical projects, highlighting a few that sound cool and interesting. But it got me thinking, do we work on interesting projects?

What is an interesting project?

Part of the reason the question temporarily baffled me is that interest is in the eye of the beholder. So when somebody asks me if we work on interesting problems, I start weighing what they would find interesting.

I might answer it a bit differently depending on the audience, e.g., software developers or visual designers or potential clients or old friends from college. They all have different ideas of what’s interesting.

That said, there are some characteristics that are universally interesting:

  • Problems at the edges of what’s feasible with current technologies
  • Working in a hyped technology (machine learning, quantum computing, etc.)
  • Solving Big Important Problems™ (health, education, ecology, etc.)
  • Problems requiring insane quality, e.g., ultra polished visual design

Basically anything that makes you think, “Whoa, how’d they do that!?!”

What are boring projects?

But then I thought about the projects I’ve worked on that don’t match the criteria above. Are they not interesting too?

Well, to me they’re interesting. Most problems have constraints, and figuring out how to solve the problem as best as possible within its constraints is interesting.

Maybe it’s because I worked retail and food service jobs before I became a software developer. Or maybe I’ve just heard too many stories of struggle from my extended family. But for whatever reason, even after multiple decades in this industry, I still feel extremely lucky to have a career where I use my brain to solve logic puzzles.

Every project has moments where the constraints cause a problem, a little puzzle for your team to figure out. Maybe you can craft the perfect solution to exactly fit the shape of the constraints. Maybe you need to reshape the problem to be one that is solvable within the constraints. Maybe you can backtrack and reshape the very constraint itself! That’s the profound joy of working in code and digital design; they are nearly infinitely flexible building materials.

I’ve worked on projects that might sound boring to a lot of people. Optimization projects. Technical debt pay down projects. Rescue projects. Replatforming projects. But with the right mindset, solving these puzzles was extremely interesting and rewarding.

Are any projects boring?

So that got me thinking. Could I think of any project I’ve worked on that I found boring? Because if the answer is no, I’m not sure I’m a trustworthy voice on this topic.

First I thought maybe it was related to constraints. Maybe solving those little puzzles was the fundamental source of interest.

But no, I’ve worked on some projects that were virtually unconstrained. We had a generous budget – relative to the problem being solved. We didn’t have any crazy technical hurdles to overcome. The deadlines were reasonable. The problem was well understood. The project was just about doing the work, delivering code, testing, getting feedback, iterating, adapting, etc.

So why weren’t those projects boring?

I got to tell you, this question bothered me. It nagged at me, tugged at my brain all that day. That night as I lay in bed and tried to sleep, my thoughts returned to it.

Sure, the projects I’m thinking about were fun in part because the teams were great, the tech stacks were pleasant to work with, the environment was good to work in, and the projects mattered to our stakeholders. Wait, what was that last one?


The projects mattered!


Aha! As soon as I had that thought, I knew that was the idea my brain had been circling all day. The problems we were solving mattered to somebody.

Problems that matter.

It’s not always sufficient, by itself, but it’s the big correlation I couldn’t see. If I understand why the system we’re building needs to exist, why the problem we’re solving will improve the lives of people out in the world, why anyone cares about this problem at all – I can usually find a way to make it interesting.

And using that lens, I thought back over my career. Yes, I have worked on projects that weren’t interesting. They were projects where you could tell the client stakeholders weren’t engaged – not the business users, not the subject matter experts, nobody really cared about it at all.

If nobody actually cares about solving the problem, that is a boring project.

I’ve seen this most often in large enterprises where something is being dictated to the team from above. It’s a system they don’t want to use, solving problems they don’t care about. Or sometimes, you’re working with the head of a business unit who doesn’t really care about this part of the business. They’re just putting in time here on their way higher up the organization, solving a problem because they’ve been told to solve it. But they don’t know and don’t care, not really.

A similar problem can show up in small start-ups – e.g., if they don’t have a great product-market fit yet or they don’t really believe in the direction their VC overlords are pushing. You can feel them thrashing around, unsure of the problem and the solution. They care, but they have no idea if a specific solution actually matters.

Yes, we work on interesting problems!

When I reflect on all of our projects at Simple Thread over the years, I can’t think of any that didn’t matter.

Many of our projects form the core software that our clients run their businesses on or revamp how a team does mission critical work or provide the SAAS platform for their main product. These projects matter immensely to our clients.

Until I started thinking through our project list in response to that candidate’s question, I’m not sure I realized how much of an impact we are having on our clients. These projects matter, and I’m proud of that.

So yes, the next time someone asks me if we work on interesting projects, I can say, “Absolutely! We work on interesting projects that make a huge difference to our clients.”

If you need help with a project that matters to you, please reach out. I’m always happy to listen.

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