How Jeff Bezos decides which risks to take

Jenny Blake’s new book on making a career change, “Pivot,” includes a chapter on fear of failure, and how not to let it paralyse you professionally.

Blake pivoted multiple times in her career — most notably, she left Google after the publication of her first book to launch her career-coaching business. It was, she readily admits, a scary process.

To help illustrate how she dealt with her fear in a productive way, Blake includes a lengthy quotation from an oft-cited interview with Amazon founder and CEO Jeff Bezos, on his “regret minimization framework”:

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

“And 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.”

Bezos has made embracing failure an integral part of business at Amazon. Business Insider’s Eugene Kim has reported that Bezos “says nine times out of ten, you’re going to fail. But every once in while, you’ll hit a home run that in business terms is more like 1,000 runs. ‘Given a ten per cent chance of a 100 times payoff, you should take that bet every time,’ Bezos says.”

Bezos is hardly the only successful person to use this strategy. In a recent video interview with Business Insider, Tony Robbins said that whenever he’s hesitant about doing something that scares him, he imagines himself at age 85, sitting in his rocking chair and looking back on his life.

At that point, he asks himself, would he experience greater regret over having done the scary thing or opted out?

The key here, of course, is that you genuinely have to ask yourself which you’ll regret more: taking the risk or not. In some cases, the answer really might be “not.”

But if you do make a “mistake,” in that you take the risk and it doesn’t work out, it doesn’t have to be something you regret.

“If you experience failure fallout, mine the wreckage for underlying strengths and key lessons,” Blake writes. “When you mine the learning, the experience stops being a failure and becomes the seeds of something new, a strength-in-waiting.”

Disclosure: Jeff Bezos is an investor in Business Insider through hispersonal investment company Bezos Expeditions.

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