I don't believe in big decisions | Always Draft

I don't believe in big decisions

01 Jun, 2026

I don't believe in big decisions. The ones that look enormous are usually a long chain of micro-choices that we bundle into a single moment after the fact.

One big brave moment? Nah. Maybe in Hollywood or AI-slopped LinkedIn posts.

This is hard to believe, so you can try it by walking it back from something big you chose or something you did. There would have been a set of micro-choices leading up to it (going to the place or party, booking the taxi, talking to your friends about doing the thing before you act upon it, and so on). And before that you had already been thinking it over for a while. Earlier than that, you had cleared a bit of room in your week just to make space to think about it (this might even be losing sleep thinking about the thing).

TLDR: There is always an earlier step, which means the outcome got built a little at a time rather than gambled in one sitting.

Annie Duke's Thinking in Bets is the best practical guide I have read on this. Treat decisions as a run of small bets under the pressure of uncertainty and never judge the decision on the result... this is the most important part. I used to play a lot of poker which made it very easy to pick up other books on this topic, but Annie's book is truly for anyone and everyone.

With small bets you can limit your downside. This means mistakes are cheaper to make and Shane Parrish puts it well (I'm paraphrasing): the real test of a decision is how cheaply you can be wrong about it. When an error is expensive, people freeze and defend the call they already made. Make the error cheap and the same people start moving, testing, and adjusting as they go.

So to everyone out there working in customer decisioning / customer engagement / customer value management / customer lifecycle marketing / customer growth... or whatever label the corporate world can't agree on: you are responsible for LTV and interventions or treatments will come and go. All of it is a long run of small, recoverable bets that compound into lifetime value.

In practice that changes how you run the work. The temptation is to save up for the big swing, the quarter-defining campaign or the model rebuild, then launch it rarely and defend it once it is live. The teams that compound do the opposite: they put lots of small treatments into market, keep each one cheap enough to be wrong about, and read the result honestly. That last part is where most of the edge sits, because a treatment is only worth keeping if it actually delivered a result, rather than riding the coat-tails of a result already in motion (the age old difference between correlation and cause).

Cut the losers early, let the winners run, and the wins stack up into LTV the same way the micro-choices stacked up into the decision.

The same is true of you, outside of work. The life you want gets built the same way, from a long sequence of small, cheap, reversible moves, most of which you can walk back if they do not land. Lived like that, the whole thing feels lighter and a little braver, because you can start before you are sure and correct as you go.

END.