Chasing the Workaround
Chasing the Workaround
TL;DR: After walking away from the banking idea, I went looking for what to build — and mostly learned how easily I over-abstract. The fix that stuck: stop chasing “pain,” which is invisible and stretches to fit anything, and start chasing the workarounds people have already built, because a workaround is proof the pain is real, recurs, and already costs something. That pointed me at people’s work, and at a question that turns out to be the thing I’ve always cared about — helping people get unstuck. I don’t have the answer yet but I have a way of looking.
After I walked away, I had to actually go looking
Last time I wrote about catching myself chasing an impressive-sounding idea I didn’t actually want, and what that revealed about how I choose things. Walking away was the easy part to write about. The harder part is what comes after: a blank page, and the genuinely uncomfortable job of finding something real to point at.
This is a note about how that search has gone so far. Most of what I’ve learned isn’t about the world yet. It’s about my own thinking.
Give me a blank page and I’ll abstract until the idea means nothing
My cofounder and I started where a lot of people start — with a feeling. We cared about the moments when someone you’re responsible for is struggling and you find out too late. Pull on that and you arrive at something that sounds profound: it’s really about relationships where you carry real responsibility, where there’s a genuine cost if you drop the ball.
The trouble is that description fits almost everything. A parent and a child. A manager and a report. A doctor and a patient. Every time we tried to narrow it, we just moved the vagueness somewhere else. We’d climbed so far up the ladder of abstraction that the idea was beautiful and useless at the same time.
I’ve started treating that exact sensation — the this explains everything feeling — as an alarm rather than a discovery. When an idea explains everything, it usually isn’t explaining anything. It’s just restating the fact that people have problems.
Pain is invisible; the workaround is not
The turn came when I realized we were hunting the wrong thing.
We’d been chasing “pain.” But pain alone is rarely visible, and worse, it’s infinitely stretchable — you can describe almost any situation as painful, which is exactly why it never narrows anything down. So we stopped looking for pain and started looking for its evidence: the workarounds people have already built.
If someone has rigged up a spreadsheet held together with tape, or sends the same 2 am text to the same person every time it happens, or quietly pays someone to handle a thing — that’s the tell. Nobody builds a workaround for a problem that’s rare or cheap. The workaround is proof that the pain is real, that it recurs, and that it’s already costing time, money, or effort. It’s the fingerprint of a problem worth solving, and unlike a feeling, you can go find it.
That one move changed how we look at everything. We stopped asking people what hurts. We started asking what they’ve already cobbled together to cope — and letting that point us to where the cost is actually real.
That pointed me at work
Workarounds cluster where the same problem hits you over and over, with a real cost each time. That’s not most of life — it’s work. Your job is the place where you face the same kind of stuck week after week, where getting it wrong shows up in your performance, your time, your reputation, and where you’ve quietly built a dozen little systems to get through it.
So that’s where I’m focused: the ordinary, recurring moments where someone hits a wall in their actual work and can’t quite see what the problem is, or what to do about it, or who to ask. Not necessarily the dramatic failures.
And here’s the part I didn’t engineer, which is why I half-trust it: the question I backed into — how do people get unstuck — is the thing I’ve cared about my whole life, long before any of this was a company. I wrote last time that the one thing I never have to force is helping people through their hard parts. It turns out the search quietly walked me back to it.
I’m going looking, with the rules set in advance
I don’t have the answer yet, and I’m wary of the version of me that would now build a tidy story about why I’m obviously right. So I’m doing the opposite of building one.
I’m going to talk to people — startup operators, founders and finance folks first, because I can reach them tomorrow, then somewhere deliberately different, like doctors, to see whether what I find is something structural or just true of people like me. I won’t ask them for ideas or pitch them anything. Instead I’ll ask them to walk me through the last time they got stuck, in detail, and watch for the workaround.
And I’ve written down, before starting, what would make me walk away: if the stuck-moments scatter everywhere with no pattern, if nobody’s built a workaround worth the name, if the cost turns out to be soft. Deciding the kill conditions before you’re emotionally invested is the one thing I took cleanly from my previous startup life at Artie — and it’s the same discipline that let me drop the last idea with confidence.
I’ll know soon, and I’ve decided that’s the point
The honest ending is that I might do all of this and find nothing, and have to cut again. A year ago that would have felt like failure. Now it feels like the job. The entire reason to set the rules in advance is so I get to be wrong cheaply and quickly instead of expensively and slowly.
If you’ve ever caught yourself stuck on something at work and built some ugly little workaround to get through it, I’d genuinely like to hear about it. That’s the whole search I’m focused on.