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On Small Bets And Compounding Kindness

A practice for improving the self by shrinking the promise and enlarging the receipt.

Article20182 min readSelf ImprovementRegret MinimizationPractice

Shrink the promise, enlarge the receipt. You can promise a continent or you can deliver a footbridge. One teaches you to wait for applause. The other gets your neighbors across the river.

I learned this on a railway platform in spring, the benches varnished and the schedule honest for once. I was late, and still somehow early, in the way a person is when they've been putting off a small task that has grown large in the head. I had been promising grand reforms. But the train didn't care about my declarations-only whether my ticket was in my pocket and my feet knew where to go.

flowchart LR
  P[Big Promise] */}|Delay| W[Waiting]
  W */}|Excuse| R[Regret]
  S[Small Bet] */}|Action| E[Evidence]
  E */}|Trust| O[Options]

The mathematics of this are plain. When you make smaller changes, you minimize expected regret because the cost of correction is bounded. You also claim more observations per month, which compounds faster than eloquence. Jane Austen knew this in her bones-every letter and glance in her pages is a small bet that changes a future.

Anthony Bourdain would add that the small bet should taste like something. Cook one onion properly and you’ll sense your posture improve. Obama might tell you that the long arc only bends when your hand is already on the lever, steady and humble. And Orwell would warn you that the enemy of all this is political language: slogans that absolve us of doing the work.

Here’s a token I draw when I’m tempted to overpromise:

The technique is not joyless. It’s the opposite. Small bets create the merriest kind of luck because they leave doors ajar. They grant strangers permission to help. They allow a team to disagree without drama-no one is defending a manifesto, only a step. Even cats understand this: mine inspects a room perimeter first, then chooses a sunlit square; the reconnaissance is the work.

When you practice small bets, you begin to see opportunities in plain sight. The unsent email that could close a loop. The label that would spare a junior teammate confusion. The name that would make a feature legible in two years when the original authors have moved on. None of this is glamorous, and all of it is mercy.

Regret shrinks when correction is cheap, and correction is cheap when you keep your units of change humane. If you must make a large promise, let it be to maintain this discipline. Deliver the footbridge. Wave your neighbors across. Then build the next one.

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