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The Clarity of Regret 👴🏻

In 1994, Jeff Bezos was a thirty-year-old vice president at quantitative hedge fund D.E. Shaw. Bezos was one of the youngest SVPs on Wall Street, and part of his job involved doing market research for potential investment opportunities. One day, he came across a piece of information that changed everything – he learned that Internet usage was growing at 3200 percent year over year, and he decided he wanted to start a company on the web. He had the idea to create an online store, beginning with books.

Bezos told his boss, David Shaw, that he wanted to leave the company to take a chance on his idea, and Shaw promptly took young Bezos on a two hour walk through Central Park to discuss things. After listening, Shaw said, “I think you’re onto a good idea here, but this would be a better idea for someone who didn’t already have a good job.” He asked Bezos to consider things for a few days before settling on a final decision.

Bezos was then in a difficult position. His mother had given birth to him at seventeen, and his adopted father, Mike, fled Cuba for the U.S. with nothing but the shirt on his back. Bezos’ parents had sacrificed a lot for him, and by all conventional measures he was living the American Dream: valedictorian in high school, followed by Princeton and a prestigious finance job. What’s more, Bezos’ new wife, MacKenzie, said she would support whatever decision he made. It was an impossible choice to make, and he was torn.

In order to decide, Bezos came up with a simple mental model that he would use for years to come. He called it the “regret minimization framework.” Bezos imagined himself as an eighty year-old looking back on his life, wanting to minimize his regrets. How would that man think and feel about the choice young Bezos was about to make? Suddenly, the right option was clear:

The regret minimization framework is powerful. And while I recognize that it is a privileged way to be able to view things, it’s largely in line with how I want to live.

With that in mind, there will be some changes to this newsletter in the new year, which I’ll write about in mid-January. Until then, I’m going to enjoy some time away from writing a weekly email.

Thank you for following along with me in 2021. I wish you a healthy and happy end to this year and start to the next.

Pete's Picks ✅

1. What I'm Reading: The Courage to Be Disliked, a crash course in the psychology of Alfred Adler via a dialogue between a young man and a philosopher.

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Cheers,

Peter