For me, the right way to make that kind of very personal decision, because those decisions are personal, they're not like data-driven business decisions. They are, "What does your heart say?"
And for me, the best way to think about it was to project myself forward to age 80 and say, "Look, when I'm 80 years old, I want to have minimized the number of regrets that I have." I don't want to be 80 years old and in a quiet moment of reflection, thinking back over my life, and cataloguing a bunch of major regrets.
In most cases our biggest regrets turn out to be acts of omission. It's paths not taken and they haunt us. We wonder what would have happened. I knew that when I'm 80, I would never regret trying this thing (quitting a good job to start Amazon) that I was super excited about and it failing.
If it failed, fine. I would be very proud of the fact when I'm 80 that I tried. And I also knew that it would always haunt me if I didn't try. And so that would be a regret, it would be 100 percent chance of regret if I didn't try and basically a 0 percent chance of regret if I tried and failed. That's a useful metric for any important life decision.
-- Jeff Bezos
Jeff Bezos: Ask Yourself 1 Question to Make Truly Important Decisions (and Avoid Lifelong Regrets)
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