It's not what you do and mess up, it's what you don't do that will plague you when you are old and looking back on your life.
"When you think about the things that you will regret when you're 80, they're almost always the things that you did not do. They're acts of omission. Very rarely are you going to regret something that you did that failed and didn't work or whatever," says Bezos in an interview with Axel Springer CEO Mathias Döpfner, published by Business Insider on Saturday.
It's not only true of professional decisions, but of life too, says the 54-year-old entrepreneur, who is currently worth $130.5 billion according to Forbes.
"I'm not just talking about business things," says Bezos. "It's like, 'I love that person and I never told them,' and you know, 50 years later you're like, 'Why didn't I tell her? Why didn't I go after it?'
"So that's the kind of life regret that is very hard to be happy about when you're telling yourself in a private moment that story of your life."
Bezos is himself embodiment of that willingness to act.
He famously left a Wall Street investment banking career to start selling books online with a little website called Amazon. In hindsight it was a lucrative decision. At the time, however, Bezos, and his wife MacKenzie, were taking a risk — one that not everyone agreed with.
"I was working at a financial firm in New York City with a bunch of very smart people, and I had a brilliant boss that I much admired," recalled Bezos in a commencement speech he gave at his alma mater, Princeton, in 2010. "I went to my boss and told him I wanted to start a company selling books on the Internet. He took me on a long walk in Central Park, listened carefully to me, and finally said, 'That sounds like a really good idea, but it would be an even better idea for someone who didn't already have a good job.'"
Bezos did think about the decision carefully.
"That logic made some sense to me, and he convinced me to think about it for 48 hours before making a final decision. Seen in that light, it really was a difficult choice, but ultimately, I decided I had to give it a shot," said Bezos in his speech.
"I didn't think I'd regret trying and failing. And I suspected I would always be haunted by a decision to not try at all," he explained. So he "took the less safe path to follow my passion, and I'm proud of that choice," he said.
In addition to that mindset, Bezos says having supportive and loving people in his life also helped inspire him to take risks.
"MacKenzie, you know, she had married this stable guy working on Wall Street, and a year after we got married, I went to her and said I wanted to quit my job, move across the country and start this internet bookstore. And MacKenzie, of course, like everybody I explained this to, her first question was: 'What's the internet?' Because nobody knew. This was 1994," says Bezos in his interview with Döpfner.
"But even before she could say 'What's the internet?' she said, 'Great — let's go!' Because she wanted to support it and she knew that I had always had this passion for invention and starting a company," says Bezos.
In addition to his wife, Bezos credits his parents and grandfather as major influences in his life, giving him strength.
"My mom had me when she was 17 years old, and she was still in high school, in Albuquerque, New Mexico, and this is in 1964. I can assure you that being a pregnant teenager in high school was not cool in Albuquerque, New Mexico, at that time. And so it was very difficult for her," says Bezos. "My grandfather went to bat for her, and then they tried to kick her out of school, and they're incredible, so the gift I had was I that had this incredible family."
Feeling supported and loved afforded him the confidence to take bold actions, Bezos says.
"When you have loving and supportive people in your life — like MacKenzie, my parents, my grandfather, my grandmother — you end up being able to take risks," says Bezos. "Because I think it's one of those things, you know, you kind of know that somebody's got your back. And so if you're thinking about it logically, it's an emotional thing."
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