At 80, looking back at your life — which choice would you wish you'd taken? That's the core of the regret minimization framework. It's the question Jeff Bezos asked himself in 1994 before leaving a successful career to start an internet bookstore. The answer was clear: he could live with trying and failing. He couldn't live with never trying.
The Weight of What If
Big decisions come with a specific kind of weight — one that logic alone can't lift.
You can feel it already — the future version of yourself asking "what if I had?" Not trying feels safe today, but the wondering never quite goes away. The path not taken stays alive in your imagination, becoming heavier with time, not lighter.
"It's not practical." "The timing isn't right." "There are too many risks." Sometimes those concerns are real. But sometimes they're fear wearing a sensible disguise — and telling the difference matters more than any spreadsheet can capture.
While you're deliberating, the window is closing. Some decisions have an expiration date, and not choosing is itself a choice — often the one with the most second-guessing attached. Waiting feels neutral but it isn't. Time is making the decision whether you do or not.
If a big decision is weighing on you right now, it might help to think it through before time decides for you.
Why Regret Cuts Deepest
The regret minimization framework works because it bypasses the noise that keeps decisions stuck.
When the fear behind the decision is specifically about choosing wrong, that's the deeper pattern of fear of regret at work.
When Regret Drives the DecisionYou might already know the answer. Sometimes the hardest part isn't figuring it out — it's trusting what you already feel. It can help to figure out what you'd miss out loud.
Use the Regret Framework
Four steps. Simple to understand, powerful to apply honestly.
Name the Decision
Be specific. What exactly are you choosing between?
Project to 80
Imagine looking back at your whole life. What do you see?
Ask the Question
"Will I look back and wish I had tried this?" Not "will it work?"
Trust the Answer
If yes — the fear is real but temporary. The what-if would be permanent.
This framework is most powerful for big, fear-blocked decisions. For decisions stuck in other ways, a broader decision making framework might help.
Finding a Framework That WorksPicture Yourself at 80
If a big decision is sitting on your chest, walk through these.
The question is simple, but sitting with it honestly takes space — and most people don't have a place to do that. thisOne is a thinking partner that helps you work through big decisions by asking the questions that cut through the noise. You talk through what you're facing, it helps you separate fear from real concerns, and the picture gets clearer. Not advice — a conversation that helps you see which path matters.
The Bigger Picture
Most people don't look back with pain at their failures. They carry the weight of what they never attempted. Trying and failing is survivable — the failure fades and life goes on. Not trying? That wondering stays permanent.