Jeff Bezos describes using a regret-minimization framework to decide whether to start Amazon, imagining himself at 80 and realizing he'd regret not trying more than failing. A second speaker turned down a higher-paying accounting job to stay in a less satisfying role that let him pursue insurance work part-time, a risk he later felt grateful for taking.
Chapters
For me, when I thought about, you know, leaving my job and starting this company, I knew there was a good chance that it wouldn't work, but I also knew that when I was 80 years old and thinking back over my life, I would never regret having tried and failed, but I might regret having never tried. And when I thought about it that way, it didn't actually seem like that big of a risk.
I remember when, right before we got into this insurance thing, I had the opportunity to take a new accounting job and paid more money, was a bigger role, had like a 5-year plan to take over and run the whole company, the family wanted to retire, etc. And, uh, we had to sit down and really think about it. And I declined that job to stay on a job I disliked because it gave me the opportunity to get into insurance part-time. Super thankful that I took that risk, if you will.