I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not trying.
If you think about the long term then you can really make good life decisions that you won’t regret later.
Am I going to regret leaving Wall Street? No. Will I regret missing the beginning of the Internet? Yes.
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.
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.”
