In 1994, Jeff was at a crossroads.
He’d recently been promoted to senior VP at an investment bank (the youngest in the firm's history), and was earning handsomely.
But something gnawed at him:
The internet was growing 2,000% a year, and he couldn’t stop thinking about quitting to start a virtual bookstore.
So he ran the idea by his boss.
“Sounds like an amazing idea”, his boss said, “...if you had nothing to lose. But risking senior VP?”
He gave Jeff 48 hours to decide. To avoid making the decision on a whim, Jeff went home and created a framework to guide his thinking:
🥅 “The regret minimization formula”
The idea’s simple: Project yourself forward to when you’re 80, and think, “Which decision would I regret least?”
Suddenly, Jeff’s choice was obvious. He left his firm, started Amazon, and now, 30 years later, Jeff Bezos is the world’s 3rd richest man.
Of course, not every decision turns us into billionaires, but this framework's still useful: figure out what you'd regret most later, and do something about it right now.
The only question is....what *will* you regret in the future?
Luckily, author Daniel Pink has some clues.
In his research for The Power of Regret, Pink asked 19,000 people around the world what they regretted most.
And to Pink’s surprise, all of them basically said the same four things:
1) “I didn’t put in the work.”
Pink calls these foundation regrets, and they're exactly what they sound like: regrets about neglecting basic, foundational things — like your health, finances, or relationships.
Maybe you didn’t save money when you could’ve. Maybe you skipped workouts or kept putting off sleep. These regrets hurt because deep down you know you could've avoided them.
The fix here isn't complicated: Step back, reprioritize, and get the basics right again.
2) “I was too scared.”
These are regrets about playing it safe when you had the chance to take a risk. Bezos’s decision fits this, but they can be smaller things too. Like approaching someone interesting, speaking up in meetings, or trying a hobby that scares you.
They sting because you'll never know what might've happened. And usually, the real 'risk' was smaller than it felt at the time.
A practical fix? Treat courage like a muscle. Train it. Write down things you want to try but haven't because they scare you. Start with the small ones.
3) “That didn’t feel right.”
Your boss leaves the room, and you criticize him behind his back. How do you feel afterward?
That's moral regret.
To avoid this: Boundaries!
Make clear “I don’t” rules. e.g., I don’t gossip behind backs. I don’t accept jobs purely for money. I don’t work for companies making people's lives worse.
4) “I should’ve reached out.”
You know you should message a friend but don’t, afraid it’ll feel awkward. Gradually, the relationship fades. That’s connection regret — the one I’m trying to work on.
My framework: If you think of someone, reach out. If a random memory with someone pops in your head and makes you smile, text them!
🤔 What if I let myself be happier?
Bronnie Ware was a nurse who cared for people on their deathbeds. The biggest regret she heard repeatedly? “I wish I’d let myself be happier.”
Notice how they phrased it — "let myself." We tend to think happiness is something we'll finally earn after we hit a random future milestone: after a promotion, after the next job, after some $ number.
So we postpone it, or worse, sabotage it daily by getting annoyed over things we'll soon forget.
But in doing so, it’s easy to forget that happiness is something you allow yourself now.
And maybe that's the real takeaway here:
If you already know what you'll regret later, why not do something about it?
