The decisions founders can’t stop thinking about

This is a great example of the pattern I’m exploring. The difficult part often isn’t choosing between free and paid — it’s knowing what evidence would actually change the decision.

A useful question is: “What signal would make me change my mind?” If that signal never appears, constantly reopening the decision is usually just uncertainty looking for relief.

The goal isn’t to make every decision permanent, but to create a clear rule for when it deserves another review.

A decision keeps looping when it has no reopen rule. Record the choice, the assumption that justified it, an expiry date, and the evidence that would reopen it. Competitor behavior is not automatically new evidence; it only matters if it crosses a trigger you named in advance.

This is exactly the kind of pattern I'm interested in. Sometimes it's not the decision that's unresolved, it's the uncertainty around the tradeoff. Has anything in your own data changed since you made the decision, or is it mainly seeing competitors take a different approach?

One pattern I've noticed is that founders often revisit the same decision because they're trying to reduce uncertainty with more execution. Sometimes the bottleneck isn't a lack of evidence—it's deciding what the existing evidence actually justifies.

I keep coming back to this one thing: should we limit access to AI features unless people pay for a subscription, or make them completely free to get more people to use them? I decided weeks ago that it's better for business to limit access, but every time I see a competitor giving away free AI features, I start questioning my decision again. It's not that I have any new information, it's just that I keep wondering what would happen if we gave it away for free - would it actually help us grow faster?