Would 80-year-old you regret this?
Regret Minimisation
Project yourself to age 80. Will you regret NOT doing this? Jeff Bezos used this to leave his job and start Amazon.
Jeff Bezos was a senior VP at a hedge fund with a clear career path. He wanted to start Amazon. His framework: project yourself to age 80, looking back at your life. Which choice would you regret more — trying and failing, or never trying? The answer was obvious. He quit the next day.
The method
Identify the decision. Project yourself to age 80, sitting in a rocking chair, looking back at your life. You are healthy, clear-headed, and reflective. Ask: if I don't take this path, will I regret it? If I do take it and it fails, will I regret it? Most often, the regret of inaction is larger than the regret of a failed attempt.
Why we get this wrong in real-time
Present-day decisions are dominated by loss aversion — the pain of a potential loss is roughly twice as strong as the pleasure of an equivalent gain. At 80, you've exited most of those immediate loss scenarios. The calculus changes. You see more clearly what you would have valued, what you were afraid of that didn't matter, and what you sacrificed in the name of safety.
The asymmetry of regret
Research consistently shows that people regret their inactions more than their actions over long time horizons. Short-term, we regret what we did. Long-term, we regret what we didn't do. The framework exploits this asymmetry: it fast-forwards to the time horizon where the regret calculus inverts.
What it is not
Regret minimisation is not permission to be reckless. It does not say 'do everything with upside and ignore downside.' It is specifically for decisions where the downside of failing is survivable and the upside is meaningful. It is not a framework for high-stakes gambles with catastrophic failure modes.
In practice
You're a senior engineer at a stable company. Someone offers you a founding engineering role at an early stage startup. Risky, lower initial salary, could fail. Project to 80: 'I turned down the chance to build something from scratch because I was comfortable.' vs 'I tried, it failed after two years, I learned an enormous amount and moved on.' The second story doesn't sting. The first one does.
TL;DR
Most action-regrets fade. Most inaction-regrets compound. Fast-forward to 80 and ask which decision you'd live with.