Ask HN: In your career, what are you most embarrassed about?

Getting used to a salary off the bat. My first job offer out of college was >250K, and I stopped living frugally too early.

Staying too long in a comfortable job and not leaving solely on my own terms.

I majored in Latin, thinking that teaching jobs would be easy to come by when, in fact, they weren't. That cost me around 6 years, with the dubious benefit that I was fluent in a dead language and that I nearly know the etymology of a fantastic number of words in English.

Not starting soon enough - but then again would have missed out on a helluva ride. Embraced, enjoyed, and lived each phase to the fullest. Feel a little behind now but if I didn't then I'd probably procrastinate, so it's a nice fire-under-my-ass. :) All in all despite not getting straight there, no regrets because the journey itself has been great!

I find the best entrepreneurs aren't embarrassed by much of anything and seem to embrace their mistakes.

Not firing someone incompetent I'd hired (as a favor) as soon as it became obviously necessary, who later went on to embezzle a lot of money.

Not sticking up for myself.

Don't wait for some theoretical FU money.

The people who have FU money, if they didn't inherit it, seem to have incorporated my first point into their lives. (Not that money is necessarily the outcome.) Also, sticking up for yourself does not equal being an ass to other people. For myself, treating other people nicely/respectfully is inherent to my own well being. And I actually do worse at it when I am not taking care of myself.

As for the "I should never have made the mistake" aspect. My intellect, and/or my intuition, could read the situation. But lack of will power, conditioning, health, or whatever -- something held me in place.

I didn't get the PMP cert after it cost me the offer from google.