Regret Minimisation

How it works

Jeff Bezos used this framework to decide whether to leave his Wall Street job and start Amazon. He projected himself to age 80 and asked: “Will I regret not trying this?” The answer was obviously yes — he’d always wonder “what if.” The reverse question: “Will I regret trying and failing?” Almost certainly not — he’d be proud of having tried.

The framework works because it cuts through the noise of short-term anxiety and reframes the decision in terms of what actually matters over a lifetime. Most people overweight the risk of failure in the short term and underweight the risk of regret in the long term.

Case study: How Jeff Bezos decided to start Amazon

In 1994, Jeff Bezos was a 30-year-old Senior Vice President at D.E. Shaw, a quantitative hedge fund on Wall Street. He was well-paid, well-respected, and on track for a traditional finance career. When he saw that web usage was growing at 2,300% per year, he had an idea for an online bookstore.

Bezos used what he later called the “Regret Minimization Framework.” He projected himself to age 80 and asked: “Will I regret not trying this?” The answer was obviously yes — he would always wonder what might have been. Then he asked: “Will I regret trying and failing?” The answer was no — even if Amazon failed, he would know he tried. He would not regret the attempt.

He resigned from D.E. Shaw and started Amazon from his garage. The framework didn’t predict success. What it did was clarify that the asymmetry of regret pointed toward action: the regret of inaction was certain and permanent, while the regret of failure was tolerable and finite.

Real-world examples

Career pivots. Should you leave a stable career to pursue something you care about? Short-term thinking emphasises risk. Regret minimisation asks: at 80, which will you regret more — the financial risk, or spending decades in a career that didn’t matter to you?

Relationships. Should you tell someone how you feel? The short-term risk is rejection. The long-term risk is always wondering what would have happened.

Creative projects. Should you write the book, build the app, start the podcast? The short-term cost is time and possible embarrassment. The long-term regret of never trying usually dwarfs the short-term cost of trying.

When to use it

Use this framework for irreversible or hard-to-reverse decisions — career changes, relationship decisions, creative commitments. It’s less useful for everyday decisions where the stakes are low and the time horizon is short. Reserve it for the “fork in the road” moments.

Common mistakes

The main mistake is using it to justify impulsive decisions. The framework is for considered decisions, not rationalisation. The second mistake is assuming all regrets are created equal. Regret from inaction (not trying) tends to grow over time, while regret from action (trying and failing) tends to shrink. This asymmetry is what makes the framework work, but it doesn’t mean every risky choice is the right one.

Try it now

Think of a decision you’re currently wrestling with. Project yourself to 80. Which choice will you regret more — making the leap, or staying where you are? Be honest about the answer.

Related models

These models complement Regret Minimisation — they address similar situations from different angles.