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 80 and sort of think, ‘What will I think at that time?’ it gets you away from some of the daily pieces of confusion,” he added.
“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.”
How Bezos turned a blank sheet of paper into Amazon
While Bezos’s decision to start Amazon might look like a no-brainer in hindsight—the e-commerce giant generated roughly $716 billion in revenue in 2025 and now tops the Fortune 500—he said building a company from scratch is far less straightforward.
“That blank sheet of paper stage is one of the hardest stages,” Bezos said.
During the cross-country drive from New York to Seattle, he wrote the first draft of a roughly 30-page plan for what would become Amazon. Yet he recognized the document wouldn’t predict exactly how the business—which started out in his garage—would unfold.
“The business plan won’t survive its first encounters with reality,” he said. “It will always be different; the reality will never ever be the plan. But the the discipline of writing the plan forces you to think through some of the issues and to get sort of mentally comfortable in the space”
Even the company’s name took some trial and error. Bezos initially incorporated the business as “Cadabra,” a play on “abracadabra.” After realizing the name sounded too much like “cadaver,” he changed it to Amazon just three months later.
Even meticulous planning and hard work do not guarantee that a startup will become the next big thing. Bezos said entrepreneurs also need to recognize the role that timing and luck play in turning a small business into something much bigger.
“There are a lot of entrepreneurs, there are a lot of people who are very smart, very hard working, [but] very few ever have the planetary alignment that leads to a tiny little company growing into something substantial,” Bezos said.
Bezos says Gen Z should go to college before starting their own company
Just like the opportunity Bezos saw with the internet, the AI era has presented another major opportunity for new types of businesses. But that doesn’t mean he thinks young people should rush to drop everything and launch a startup.
“It is possible to be 18, 19, 20 years old, drop out of college and be a great entrepreneur,” Bezos said at Italian Tech Week last year. “We have famous examples of that working, Bill Gates, Mark Zuckerberg, etc. But these people are the exception.”
Instead, the now 62-year-old has argued that gaining experience first can improve an aspiring founder’s odds of success. Bezos himself graduated from Princeton University in 1986 with a degree in engineering before his foray into finance—and then entrepreneurship.
“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. “So that would always be my advice, I finished college, and I think it’s been helpful to me.”
Ultimately, Bezos advised striking a balance between enjoying the present while making decisions that will leave you satisfied with the life you’ve built when you look back at 80.
“You should live for the now,” Bezos said to the Academy of Achievement. “I think what you do is you think about the great expanse of time ahead of you and try to make sure that you’re planning for that in a way that’s going to leave you ultimately satisfied.”
The post Jeff Bezos used one simple question to decide whether to quit Wall Street and start Amazon: What will I regret when I’m 80? appeared first on Fortune.
