I was in Silicon Valley just before the start of Dot-Com with nearly a decades experience running a couple of software startups (in Texas, not in a high tech city) working at Apple and left to go back home thus missing out on enormous opportunities. I thought Apple would go out of business and figured no point in sticking around. What a doofus... I never looked around and asked, would my experience be useful somewhere?

My career was OK but who knows where I might have wound up.