No one regrets playing by the rules

Early in my career, I chased every shiny opportunity—late nights at startups, random gigs abroad—while neglecting simple habits like saving or exercising. I imagined I’d regret playing it safe, but what hit me was the hole in my foundation. A small health scare and an unexpected expense reminded me that I’d built my life on sand.

I remember the chill of a winter morning when my old car broke down and my bank account teetered. All those grand adventures didn’t feed my security needs. That day I realized most regrets aren’t about missed thrills but about ignored basics. They’re like a roof that leaks quietly until the whole ceiling caves in.

So I took one rule to heart: secure your foundation first. I started paying myself with a tiny automatic transfer to savings. I began a ten-minute morning stretch instead of waiting for a two-hour gym trip. These micro-habits sounded trivial, but over months and years they formed a bedrock I’d never regret.

Behavioral economics even calls this ‘modern portfolio theory’ for emotions—diversify your emotional assets, balancing joy with responsibility. I’ve come to see that no one fills their eulogy with ‘I wish I’d saved more,’ but everyone sighs if they didn’t. And that small shift—honoring did-it regrets over didn’t-do regrets—changed my life.

First, jot down your key life foundations—health, savings, skills—and underline any you’re neglecting. Next, for each big choice before you—changing jobs, signing a lease—ask whether it strengthens or weakens those pillars. Finally, embed one micro-habit, like a 10-minute walk or $10 transfer, into your weekly routine. Block the time or set the alert, and follow through. Give it a chance this week and watch how small moves power big results.