Stop Optimising for the One Thing
The best deals I’ve been involved in didn’t come from a plan. They came from a call I nearly didn’t take.
I used to call that luck. I don’t anymore.
Nassim Taleb has a name for it — positive optionality. Stop narrowing toward one outcome. Expand your surface area so that good things have somewhere to land.
Most people do the opposite. Lock in early, cut everything that doesn’t feed The Goal, grind in a straight line. Feels disciplined. And it works — until it doesn’t, because you’ve built a strategy with no peripheral vision and no room for the unexpected.
The Maths Nobody Checks
Rory Sutherland made an observation I haven’t been able to shake: most people chase goals where the cost of entry already outweighs the prize.
A hundred people in the world make serious money from tennis. Everyone else is funding the dream through years of coaching and lost income. The prize is real. The odds aren’t.
I see it in property constantly. Everyone wants to be a developer, a syndicator, a high-end agent. The money’s real there too. But the cycle windows are short, the cost of entry keeps rising, and the people actually capturing the upside almost always got lucky with timing and didn’t realise it.
The goal looked achievable from the outside. The maths said otherwise.
The Honest Question
Morgan Housel writes that most financial decisions are identity decisions in disguise. People don’t want the outcome — they want to be the kind of person who achieved it.
If that’s the goal, the cost of entry is irrelevant. You’ll keep paying it regardless of the return.
So ask yourself: would you still do the work if the specific outcome never came?
If yes — the maths don’t matter much. If no — they matter a lot.