Jeff Bezos used one simple question to decide whether to quit Wall Street and start Amazon: What will I regret when I’m 80?

For aspiring entrepreneurs, one of the hardest parts of starting a business isn’t necessarily coming up with a great idea. It’s being willing to walk away from a stable career—and take a chance on something that might not work. Even Jeff Bezos, now with a $357 billion net worth, once faced that dilemma. 

Before building Amazon, he had a lucrative job at a New York hedge fund, and as the internet began taking off, Bezos saw an opportunity to build something big by selling books online—but he was still hesitant to leave his career behind.

“The framework I found which made the decision incredibly easy was what I called—which only a nerd would call—a regret minimization framework,” Bezos said in a 2001 interview with the Academy of Achievement that resurfaced on social media.

“I wanted to project myself forward to age 80 and say ‘Okay now I’m looking back on my life, I want to have minimize the number of regrets I have.’”

His then-wife, MacKenzie Scott, was “100% supportive,” Bezos said, but one of his biggest challenges was resisting the short-term temptations, like leaving an annual bonus on the table. Only when he thought about his long-term future did the decision become clear.

“If you can project yourself out to age........

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