I have my original gmail address from 20 years ago still and even old youtube videos my friends and I uploaded from ~18 years ago.

The cringe is rough but at some point the cringe becomes so bad it loops back around to me just feeling nostalgic and grateful that there's proof I was able to do things, create, be silly, whatever without worrying about appearances so much.

Also, I figure if I ever become a megalomaniac then old youtube videos of my teenage self doing parkour should go pretty far in humbling me (although, honestly, I think 13 year old me was way cooler than I am now, so I guess it could backfire).

Sometimes I feel bad that I lost years of chat history from then too, but you made me realize that might be a good thing.

I'm in a similar boat, I previously saved a bunch of AIM chats from my school days but only tiny fragments made it to present day. From those fragments I gather I wouldn't want to re-read much of it. :D

I always had enough storage to more or less never be concerned about deleting stuff. I have almost every backup of every phone, computer, relevant app, forum private messages, emails, and so on going back ~25+ years. I found my Yahoo Messenger chat logs and I had the exact same cringe reaction. I didn't delete them but one thing's for sure, my writing style and thinking have changed so much that those artifacts are unrecognizable.

This was very unexpected to me because in my mind the changes only happened as I became a young adult. The evidence of these decades of logs shows the change continued to happen as an adult.

This made me laugh out loud.