Life Isn't Chess. It's Poker.
JA Westenberg
We confuse good decisions with good outcomes and punish ourselves when luck goes wrong. Thinking in bets means estimating probabilities and judging choices by expected value, not results. That helps you learn, take smart risks, and accept uncertainty.
18 Nov 2025
When you frame a decision as a bet, you're forced to explicitly acknowledge that you're operating under uncertainty. You have to assign some probability to different outcomes, however rough. You have to think about expected value rather than guaranteed results. My friend made a bet that had, let's say, a 70% chance of working out well and a 30% chance of not working out. He lost the bet. That doesn't retroactively make it a bad bet.
The world contains more uncertainty than we're comfortable acknowledging. We want to believe that if we just think hard enough, gather enough information, and make the right choice, we can ensure success. We want to believe that good decision-making guarantees good outcomes. But it doesn't. Sometimes you make the best possible choice given the information available and things still go sideways. Sometimes you make a questionable choice and get lucky.