Unsurprisingly given his many later accomplishments, Jeff Bezos was a pretty successful guy even before he founded Amazon. As a Princeton-educated computer scientist, Bezos spent the early part of his career working in banking and presumably making a bundle in the process.

As Bezos explained in a 2001 interview, this reality complicated his decision to leave his successful career in banking to pursue his wild dream of building an online everything store. Was he making a mistake to leave a well paid, secure gig for a highly uncertain foray into entrepreneurship?

Cushy gig vs. wild dream

"I went to my boss and said to him, 'You know, I'm going to go do this crazy thing and I'm going to start this company selling books online.' This was something that I had already been talking to him about in a sort of more general context, but then he said, 'Let's go on a walk,'" Bezos relates.

After two hours strolling Central Park and talking, Bezos's boss impressed upon him that, even though his business idea was solid, he had a lot to lose. "He convinced me to think about it for 48 hours before making a final decision," Bezos reports. "So, I went away and was trying to find the right framework in which to make that kind of big decision."

His wife said she was happy to support him either way, so she couldn't be the deciding factor. What could be? Bezos settled on the idea of "regret minimization."

A regret minimization framework

"I wanted to project myself forward to age 80 and say, 'Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have,'" explains Bezos. "I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. 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. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision."

He went for it and the rest is, as they say, history.

Research backs him up on at least one major aspect of his big decision -- as Bezos suspected, science says that we tend to regret actions not taken far more than we regret failed attempts.

But Bezos isn't just saying you should always dive into every risky but promising new venture. Instead, he believes that his regret minimization framework can help anyone sift through their own personal goals and values to make a weighty call.

"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 claims.

If you're facing a tough call in your life, it's worth a try. You might also want to have a look at other people's common regrets to help you avoid your own second-guessing, or check out other expert advice on how to make truly difficult choices.

How do you approach the toughest decisions in your life?

Published on: Jun 13, 2016