1. Photo apps like iCloud Photos, Google Photos, and Photo Prism are getting much better at auto organizing/cataloging what photos are and surfacing them together in much more interesting ways. More photos is now a plus instead of a minus. 2. You can always delete, but if you never record you can't go back and record (often).
So I take a Marie Kondo "Keep what Sparks Joy" approach and delete anything I find that I do not care for when I find it. I also sometimes pick an area of stuff I have and try to aggressively delete things I don't care for.
I find that horrifying. I would probably scramble to delete that as soon as possible. Don't know about anyone else here, but having my junk float around the internet is mortifying. I delete unused accounts as soon as the thought of it pops into my mind.
I learned that the nostalgia is not about the files by itself but my life context at that time. I don't miss old code or Old OS's. I miss that sense of wonder when I was less experienced and more naive, and everything was new.
I'm learning the same - whenever I feel nostalgic about playing an old SNES or PSX game, I've realized that it was just about that time in my life, and usually just watching a clip on youtube or listening to the soundtrack is enough to scratch the itch, rather than actually playing the game again
I'm sure your parents or someone from their generation have actual, physical photo albums from their past - and that the experience of browsing through these photos brings back things that they haven't necessarily _forgotten_ about, but that they wouldn't have brought into active memory unless they were browsing through them.
Over the years I have experienced and built many things that I do not deem "important" to me, yet when I see them mentioned (even in writings by myself), it takes me back to that point in time - all the feelings, learning and discoveries that it brought to life.
An example is scrolling through a list of my repositories on GitHub. Some of the projects on there I have "forgotten" about, but with the mention of it I am instantly brought back and remember a whole lot more details - motivations, feelings, the ecosystem...
Legally it’s very helpful if you create a paper trail of your work
I never really regret deleting something, but that could be because I try to keep my life simple, within reason, and focus on the future.
I also recognize, as you point out, that there are limits to this -- sometimes there is a genuine need to keep a record. As a programmer, my work is all tracked in git. For a creative professional, I assume that a basic requirement of that sort of job is an excellent backup system.
I.e. photos and important documents are only about 50GB so very easy to keep. This would be the things that I wanted my family to keep, If I died.
Then theres random projects and files that I keep in yearly archives, just to look and remember what I was up to x years ago. That's also not huge amounts of data (1-2 GB per year).
And then theres data which I didn't create. E.g. movies, game installer,... Where a loss wouldn't really be a big problem.
In day to day life these past record could as well not exist, but you still get to go look at them if you're willing to make the effort to do so. Also being willing to lose these items if something catastrophic would happen relief a lot of the archiving burden.