I don't really regret keeping anything I deemed worthy from high school, it's kind of fun to see that stuff. But I've pretty much thrown everything away from undergrad that I thought I would revisit "for fun". Now it's my MBA stuff that I'm working through. I kept a lot of good stuff, and now I'm down to just a few things that I still think I might find utility from. I'm sure in a few years that stuff will be gone too.