Success lesson from Jeff Bezos: He asked one question to himself before quitting daily job to build Amazon. What his 'regret minimisation framework' means?

Jeff Bezos did not know whether his idea of selling books online would become a successful business when he decided to leave his well-paid Wall Street job in the 1990s. But he had one way of making the decision: imagine himself at 80 and think about what he would regret most. That one question helped him walk away from a secure career and take the risk that ultimately led to Amazon.

Bezos is now one of the richest people in the world with a fortune valued at $378.1 billion, according to the Forbes. However, when he decided to start Amazon, he was still trying to work out whether leaving a promising career was the right move.

What is Jeff Bezos' regret minimisation framework?

Before starting Amazon, Bezos worked for D.E. Shaw, a New York hedge fund. With the growth of the internet he saw an opportunity to sell books online. The idea had potential, but to follow it meant to give up a stable job, regular income and benefits such as his annual bonus.


To make the decision, Bezos developed what he called the 'regret minimisation framework'. Instead of looking only at the immediate consequences of quitting, he imagined himself looking back on his life at the age of 80.

In a 2001 interview with the Academy of Achievement, Bezos explained how the approach helped him think beyond his immediate concerns.

“I knew that if I failed I wouldn’t regret that but I knew the one thing I might regret is not ever having tried and I knew that that would haunt me every day,” he said.

His then-wife, MacKenzie Scott, was fully supportive of his decision. Bezos said imagining his future self helped him move past the short-term financial considerations and focus on the possibility of regretting an opportunity he had never pursued.

How a business plan eventually became Amazon

After deciding to take the risk, Bezos began preparing for the venture. During a drive from New York to Seattle, he wrote an approximately 30-page business plan for the online bookstore.

However, he understood that a written plan could not predict everything that would happen once the business started operating.

In the Academy of Achievement interview, Bezos described the initial stage of building a company as one of its most difficult phases. He said the process of writing a business plan was valuable because it forced an entrepreneur to think about important challenges, even if the actual business turned out differently later.

Amazon used to have a different name, too. Bezos originally registered the company as Cadabra, inspired by ‘abracadabra’. He later changed it after realising that the name sounded too similar to 'cadaver'.

Bezos' advice to aspiring entrepreneurs

Bezos has also cautioned young people against rushing into entrepreneurship without gaining experience.

Speaking at Italian Tech Week in 2025, he said that although some college dropouts had built successful companies, they were exceptions. He pointed to his own experience, saying he started Amazon at 30 rather than 20.

“I started Amazon when I was 30, not when I was 20, and I think that that extra 10 years of experience actually improved the odds that Amazon would succeed,” he said.