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.