It is an endeavor! For books and movies, others made good suggestions for tools. For music, reminders, notes and photos I find it's worth paying for icloud. It

It is an endeavor! For books and movies, others made good suggestions for tools. For music, reminders, notes and photos I find it's worth paying for icloud. It works quite well on windows too these days so subsequently I use it to store most of my files too[1], except files which are too big or copyrighted. There's a compelling argument to use a file server instead of the cloud because it's really the only way to have everything in one place. So first of all you need to decide to use cloud or your own drive/file server. For file organization, I tried to organize so many times but it was too big of a job to start. So I finally decided to do it by year. I have a documents folder with folders such as "2023". Inside that I simply make a folder for anything such as "taxes" or "CV". For some years everything is in one "unsorted" folder. It's low friction to throw stuff in there as you find it, and not too overwhelming to sort through one year at a time. It tends to be fairly easy to remember what year things are from later. I have a limited number of exceptions that make sense to use different organization, for example a top level folder called "gitlab" My biggest piece of advice, as someone who struggled to get organization done for years is to be very deliberate when moving stuff and delete things from the old location as soon as you've confirmed the move and backed it up. Use a tool like rsync that can give you piece of mind that nothing was missed. If you don't delete it, you'll end up like me and finding duplicate files later and wasting time making sure it's really a duplicate before deleting it. Same goes for backups. Put your old ones on a drive and put that in a closet or delete them if you're sure you didn't miss anything. Going forward, you'll keep your new system backed up and you don't need the confusion of nested old backups-of-backups later. [1]I also have some of these documents in google drive (from before icloud was good), some on a file server (from a period of a few years where I thought I wanted to self-host everything). It's on my to-do list to get everything into icloud only except for files which are too big or copyrighted, then figure out a good system to mirror icloud to my file server so that I am back to having one single drive to backup and trusting that everything is there.