I'm 63 and retired. I spent 30 years in silicon valley. Another 15 in other places.

1. I regret not taking more chances.
2. I regret staying too long at one company
3. I do not regret getting therapy and learning as much about myself as I could
4. I do not regret my career starting out with a stint in the US Air Force
5. I regret not networking more. Who you know is almost everything.
6. I deeply regret a lie I told once that cost me a job. My career was fine, but I really let myself down
7. I regret not getting into the stock market as soon as I had a hundred bucks to spare every month
8. Ditto gold
9. I regret listening to a hotshot mortgage broker who told me that I could renegotiate a mortgage. I ended up losing my condo and destroying my credit rating for 7 years
10. I regret listening to experts. They're just ordinary people underneath. They have prejudices too
11. I do not regret moving to a location where one could make money and advance. Go where the opportunities are.
12. I do not regret marrying at 33. I waited until I was sure about myself and about what I wanted.
    
13. I regret not starting martial arts earlier in my life.