[georgemcbay]

Though it is impossible to quantify, I think as a society we're probably starting to lose a lot of potentially great second acts from people who made early mistakes due to the way everything is tracked, monitored, and easily searchable these days.

I wish I had some good practical advice on this subject, but my only advice would be things already said here: freelance, or stick to companies small enough that there isn't much HR bureaucracy in place yet.

FWIW, in my teenage years (I'll be 40 this year) I did quite a lot of "freelance, unofficial security work" and I know a lot of other people who did, some of whom are relatively famous (within certain communities anyway) who did the same and pretty much the only difference between them/me and you is not getting caught, or being located in a jurisdiction that didn't care enough to press charges at the time. So good luck, man.