I used to have saving turned on for my MSN Messenger chats back around 2001-2004. I didn't lose them. 10-15 years later or so I had a look through them and the cringe was so powerful that I deleted them all anyway.

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.

This made me laugh out loud.

I came across a binder full of short stories I wrote as a little kid, and various homework assignments.

Nope, that thing went straight into the shredder after reading the first page.