How to Find a Problem to Work On
advice and observations after a year in the trenches
22.09.25 4:00am
Throughout this last year helping run prod, I met a ton of people who are, like me, interested in changing the world with technology. Most commonly, people want to start a startup. They give lots of reasons for this: most commonly, they're actually lying to themselves about these reasons and it boils down to relatively personal feelings about ambition and impact. It remains the case that there are certain people that are really good at startups, and it is the right answer for these people.
The obvious next question is which startup to start. There is plenty of literature on this topic of “finding a problem” which you may read (eg this YC slop). I don't think it's very helpful. However, I have spent the last year searching for a problem, and watching a bunch of others do it, and have now happily left the process behind. I've concluded that it's all bollocks, and this post will explain why and give some more practical advice.
There's a concept in decision theory called the “explore-exploit tradeoff”. This also comes up in reinforcement learning and game theory and a bunch of other fields: basically, an agent can always either be searching for more solutions (exploring) or executing a known solution (exploiting). Search forever and no progress is made, exploit forever and you may overlook a better path. When I told him I was in search of a problem, my friend Isaak told me to explore more. He explained that if I just took a step back from what I was working on and started exploring, I would find something that truly excites me.
The problem with trying to explore more is that “finding more problems to work on” is not a real activity. You cannot start doing it at 9am, and stop for tea at 5. You cannot work overtime on it and find even more. I have seen incredible people try to “find more problems to work on” for weeks, and achieve absolutely naff all. Invariably, you go back to whatever the first idea was before you started. Everyone who I've spoken to who did this has said it was a waste of time.
In reality, there are only two ways to get new ideas for what to work on:
Unfortunately, Doing Nothing doesn't always work - most of the old generation of startup literature on this topic (e.g. this PG essay) suggests focusing on solving problems you experience in your everyday life, but I think we've outgrown that as a society - in other words, it's been patched. I've written before about how all the problems in college sophomores' lives (food, dating, cabs) have been solved. The problems in e.g. a large corporate finance team's lives are not as obvious. Moreover, if you are not an expert in a problem, it is hard to understand how to solve it, and expertise in these non-obvious problems takes effort. It is not hard to be an expert in web apps; it is hard to be an expert in jet engines.
Becoming an expert in a real-world problem rarely comes from reading a book. If you could read books about the problem, then it would be academic, and these are not the sort of things startups do - you can get funded to do a PhD instead. Talking to people who are already experts is a good plan, but if the existing solutions to the problem are really bad, it's quite likely that they don't actually know anything - remember, if they really had all the answers, they would be doing a startup themselves.
So there it is - if you're looking for an idea, either Do Nothing or Do Something. If you don't have one yet, don't feel pressure - if you yourself aren't completely convinced it will work and (crucially) actually right about it, it almost certainly won't. There are very few accidentally great successes, and you shouldn't bet your life on it happening to you.
I'm not sure if I have all the answers with healthcare yet. I may not have found out all the secrets this summer, but nobody does when they start. The process of finding an idea to work on doesn't stop when you have the idea, since nothing comes out fully formed. The best I can hope for is confidence that I'm working on the right thing, and that I know enough to have an edge over everybody else. I think I'm nearly there.