Stop demanding certainty before shipping

Happy Sunday!

I was thinking this weekend about the entrepreneurs I know who are actually doing well. Almost none of them are the ones who would have looked impressive in school.

They're the ones who try a lot of things. They ship, they watch what happens, they ship again. The volume itself is the strategy.

The pattern that keeps showing up is this: action produces information. Sitting and thinking, without acting, mostly just produces more thinking.

You can be the smartest person in the room and still not know which version of your offer converts. That information doesn't exist yet. It has to be generated.

The only way to generate it is to take the shot.

I'm not saying methodical doesn't matter. It does. You have to actually look at what came back from each shot, learn something, and feed it into the next one.

But on the input side, it's volume. More shots equals more surface area for luck to find you. Fewer shots equals a smaller target for it to hit.

The over-thinkers I know are usually trying to reason their way to a level of certainty that the situation just doesn't offer. They want the answer before they've earned the data.

The ones who are winning skipped that step. They took the cheap version of the shot, saw what happened, and kept going.

I know this sounds like it contradicts the payback-math posts I was putting out earlier this week. It doesn't, but I want to name the tension.

At the agency level, the client is paying us to make the most informed decision we can with their money. A little caution is the whole point. They didn't hire us to fire shots.

At the founder level, when you're still figuring out what to build at all, the data doesn't exist yet. The only way to get it is to ship something and watch.

Different scales, different rules. Big bets get modeled. Small bets get fired.

The mistake I see most often, and have made plenty of times myself, is applying agency-level caution to founder-level decisions. Demanding certainty before posting a piece of content, sending an email, taking a call.

That caution feels responsible. It isn't. It's just slower fiction.

The people I watch pulling ahead aren't smarter. They're firing more shots at smaller targets and reading the results honestly.

That's the whole thing.

What's a shot you've been over-thinking this week? Hit reply and tell me. I read every one.

Talk soon,

- Raymond

P.S. The opposite of overthinking isn't carelessness. It's volume.