How I Decide When to Jump — Even When the Math Doesn’t Add Up

There’s a certain kind of decision every founder runs into.

The data’s inconclusive. The market case is shaky. And the upside? It's there — probably.

But there's no clean model to justify the move.

So you hesitate.

You collect a few more opinions.

Maybe you build a backup spreadsheet.

And before you know it, the moment’s passed.

Here’s what I’ve learned:

Some of the best decisions I’ve made as a founder didn’t look logical at first glance.

But they felt aligned — and they created momentum.

Over time, I stopped relying purely on spreadsheets and started using a simple filter to help me move when the path wasn’t obvious.

🧭 The “Weighted Trust Bet” Framework

When I’m weighing a decision under uncertainty, I ask three questions:

1. Do I genuinely want to do this — or am I just reacting to something else?

If I’m trying to fix, avoid, or prove something, I pause.

If I’m pulled toward it with real interest, I move.

2. Do I trust myself to handle what happens next?

This isn’t about whether it’ll “work.”

It’s about whether I have the capacity to adapt and learn if it doesn’t go to plan.

3. Will I get feedback fast?

If I can get real signal in the next 30–60 days — from users, team, or market — then it’s usually worth the risk.

If I get a "yes" on two out of the three, I go forward.

🧠 Bonus Filter: Future Regret

When I’m really stuck, I’ll ask myself:

Not: “Will this succeed?”

Just: “Will I wish I’d moved?”

That question tends to surface the right answer quickly.

📌 Final Takeaway

You can’t spreadsheet your way into every good decision.

Founders aren’t just operators — we’re pattern recognizers. And sometimes, a move only makes sense after you make it.

So when the ROI isn’t obvious, but the opportunity feels real, try using clarity, trust, and feedback speed as your compass.

It won’t guarantee success.

But it will keep you moving in the right direction — faster than most.

Best,
—Peter