this post was submitted on 21 Feb 2025
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idk, it seems I'll have a similar set of problems I already have with organizing files. If I have health expense documents, is that "health", "me", or "money"? What about travel expense receipts? Or [pick any two categories that may overlap]?
That's why I prefer using tags or labels: they don't force you to make a mutually exclusive choice.
I like the "no more than ten" principle though; when organizing a file tree I try to aim for up to 5 or 6 items in a given directory, as I tend to notice the friction when choosing among more than a handful.
It's obviously not for every body but I hate tags because they are so random and I would forget what I used. I've been successfully using the Johnny decimal guide for a few years because it's intuitive for me. Your examples are obvious for me: health expense goes into "Receipts > Health" and travel expense goes into "Receipts > Travel." If I had to use tags I would think of "health, personal, money, receipts, bank, medication, etc." and it would be a real mental struggle to categorize everything and remember all the tags I have ever used. Also I use Joplin and Obsidian which make this kind of organization easier.
The "no more than ten" principles forces me to put everything in the most generic category I can think of. And if I need more than 10, it's a new project or a new something. But I agree it's not for everyone, it just happens to be suited with how I'm organized and how I think.
This is why you need a tagging system that limits your choices and can easily sort across folders by tags. I prefer Tagspaces because it just adds the tags directly to the end of filenames so I never lose the tags and if I am on a system where it's not installed I do always have the option of just manually adding a tag. I keep things in folders too and 8/10 times the folder structure does the trick, but boy it's nice to have those tags when I'm either looking for something or need to see a lot of similar things all at once. Never more applicable than tax time. Can pull up receipts w2s, loan stuff, medical stuff all by just pulling the (tax) tag.