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.” And we went on a two hour walk in Central Park in New York City and the conclusion of that was this. He said, “You know, this actually sounds like a really good idea to me, but it sounds like it would be a better idea for somebody who didn’t already have a good job.” He convinced me to think about it for 48 hours before making a final decision. So I went away and was trying to find the right framework in which to make that kind of big decision. I had already talked to my wife about this, and she was very supportive and said, “Look, you know you can count me in 100 percent, whatever you want to do.” It’s true she had married this fairly stable guy in a stable career path, and now he wanted to go do this crazy thing, but she was 100 percent supportive. So it really was a decision that I had to make for myself, and the framework I found which made the decision incredibly easy was what I called — which only a nerd would call — a “regret minimization framework.” So 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.” 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. And I think that’s very good. 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. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus. That’s the kind of thing that in the short-term can confuse you, but if you think about the long-term then you can really make good life decisions that you won’t regret later.
Most regrets, by the way, are acts of omission and not commission. If you do bad things, if you go murder somebody, that would be bad, and that would be an act of commission that you would regret. But most everyday, ordinary non-murderers, when they’re 80 years old, their big regrets are omissions.