Sometimes things aren’t going badly, but I’m still not sure I should keep going. That’s a strange kind of tension. I’m not stuck. I’m not failing. But I’m also not totally convinced anymore.
The current idea works. We’re making progress. But then something else shows up: a better business model, a stronger pull from the market, a clearer opportunity. Suddenly I’m asking: should I switch directions, even if this one isn’t broken?
Here’s how I try to think through it.
First, I talk to everyone in the company to get clear on where we actually stand. What are we optimizing for right now? What resources do we really have? How much time is left, and what’s the burn?
Sometimes just doing that unlocks clarity. If we only have six months of runway and we’re trying to build something that takes twelve, then it doesn’t matter how promising the vision is—it’s not going to work.
But most of the time, it comes down to conviction.
Doing a startup means I have to believe in what I’m building—deeply enough to push through everything that’s not working yet. If I’m seriously considering a pivot, it probably means I’ve already lost some of that belief. The right question then isn’t just “is the new idea better?” It’s “which one do I believe in more?”
So I pressure-test myself:
What would I regret more in three years?
If I had to rebuild conviction in this idea, could I do it?
Would a pivot now bring me closer to the kind of company I want to build long-term?
Once I answer those, the decision usually isn’t that complicated.
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