I've made a point to actively hunt down and eliminate my earlier digital selves, with a few treasured exceptions. Old cringey high school attempts at poetry? Gone and happily forgotten. Few thousand words of decent post-based Sci-Fi RPG? Archived. Also in re-reading some of that stuff, I realize how much of himself young OB put in his writing. The RPG I mentioned was set in a mid-future specialty hospital that catered to patients harmed by cybernetic implants. I was writing from the perspective of a doctor who was once a patient, and in reading some of his dialogue, his thoughts, I really see a lot of my adult self. I was definitely projecting an ideal future version of myself into the story. Maybe I'll edit together some of the better/worse bits and post them.
I've gone in and scrubbed a lot of my older online crap that was floating around. I've not done anything online that would prevent me from being hired or anything like that, but I've been more and more concerned about online identity and what that means. Live a life offline and keep it offline. I'm concerned about people now who do stupid kid stuff and now have a real "Permanent Record(TM)" that will follow them forever.