I remember reading the compendium of human-interface writings Apple put together in the 1990s. There was an exploration of ways to show age in software. They were changing the color and adding other aging effects to old files in the Finder.

I think part of that thought has stuck with me. I like storing things in directories by year. It is a structural reminder that a lot of the value of what I'm doing is tied to this moment in time. I can search back through "over the years" to find things, and it addresses this question of guilt.