I Have 20 Years of Digital Files. What Do I Do with Them?

If you have no specific plan for your "data" and cannot recall any important value extracted from it in the past 5 years (2 if you're <30), then it's just digital hoarding. It was a popular disease in the days before the internet when some people visited each other with hard drives and synced "new data". Music they will never listen to, videos they'll never watch, guides they never read. They even tried to download the internet, for a while.

The proper way to deal with it is not sorting or filtering. The proper way is to precisely extract what you actually used (like in: "it happened in June") in the recent years and then hard-delete the rest. Give it ten minutes, then just do it.

When later you remember that you had something but now it's gone, think about the tradeoff between searching through the pile vs searching through the internet and how rarely you refer to the pile compared to efforts spent on maintaining it.

Gift link: https://www.wsj.com/tech/personal-tech/computer-digital-file...