All of us feel that way to some degree. I shouldn't have wasted my time with certain people when there was no real attachment, or worse, they'd eventually and delightfully backstab me. I shouldn't have said this or that, or instead, should have said it because people can't guess what I think or feel. I should have used my time better instead of procrastinating. I should have spent more time with my friends... the real ones, those who were always there. I shouldn't have ignored problems just because they'd "eventually work [themselves] out" while I was busy playing with my latest techno device. I shouldn't have paid what amounts to 15% of my current life savings in taxes, when no one here cares about tax evasion and information on how to do it is readily available online. I shouldn't have lent money to this person who had just moved to a new place with zero funds left, and whom I thought was really close to me, yet later decided I was too much of a problem and ran a two-month scheme from the shadows to get me kicked. Or that "friend of a friend" who was supposedly balls-deep in debt but later scammed us all by disappearing.
The thing is, you learn these things as you go. Only time will show you which one of two choices was, or would have been, the best. Only the experience of getting fucked over by others at least once will teach you how to avoid getting fucked over in the future. If you're thinking you made mistakes or bad decisions, remember that's only in hindsight. At the time, you did whatever seemed the best idea with the knowledge and resources you had. If they ended up being good, that's great. If they didn't, apply that knowledge to avoid getting burnt again in the future.
And if you could somehow tell all of this to your 2009 self, do you think he'd listen? I know mine wouldn't.
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