Comment by TOGoS

I have similar inner battles.

I think the key is to come up with a system that takes your natural tendencies into account. Result might not be perfect but it will be less of a disaster than if you had no system at all.

Things like 'slow recycle bin' (where you throw stuff that you probably won't need to look at again, but you might) help with this.

e.g.

I have a lot of 6-quart sterilite bins where I keep various tools/components/junk. Most of them contain specific things and are labeled accordingly. There are also some that are labeled "random crap from my pockets". Not ideal to have "random crap" bins but at least I know which ones they are, and the option is open to go through and better-organize them later.

I have periods where I carefully curate my digital photos and archive them using a specific file structure. Sometimes I don't keep up, so as a backup, I dump all the raw photos to a big hard drive and generate manifest files with filenames, sizes, and bitprint hashes that I keep in Git. This part is of course somewhat automated or it would never happen at all.