I still have data going back to around 95 though, and I like that. Pictures and chat logs from way back when I first met my wife. Old games I played as a teen. Some of the code I wrote way back when I was first learning and some of my first open source contributions.
I did lose a lot along the way, though. Sometimes I wish I could still see some of that earliest stuff. And things that have been lost on the ephemeral 'net - old BBS discussions, usenet topics, my teenage livejournal, etc. that I didn't copy and save.
The tough part is that it gets hard to manage.
While I do pull forward the most important stuff each time I get a new PC, a lot of the rest is sitting in old backup formats from various backup software that I might not even be able to restore anymore. It's always nice when I think of something I used to have and can go dig it out of one of those backups, but I don't know that I will always be able to.
And it can be really hard to find something. I've tried various organizational schemes over the years, but that just means that some things are organized one way and some are organized another, and it's even more difficult to find things. I suppose I should go through and re-organize everything into one consistent standard structure, but that's what I've always done before and it just becomes like the XKCD about adding yet another standard.
Anyway, the digital clutter still works well enough for me. It's sort of a cozy old home filled with sentimental things instead of a sterile empty monastic cell.