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.
I get what you mean because I was the same way. I prefered a folder structure but I recently came around. Thing is that you don't need to remember all tags. It will just help it narrow the field in a search but everything tagged health will be in the health bucket (folder) and everything in bank is in bank. if you filter for everything in bank and health you will get a smaller return to find what you want so basically remember more tags will help you find the item but just remembering a few will be good enough.
Bingo. I really wish Explorer, OneDrive, and Microsoft’s office stuff would support tags. It would actually help me in the workplace unlike the CoPilot initiative.
Don't have an agenda and already mentioned it here but consider looking at "Tagspaces" newer versions got a little enshittified, I forget right now what version I parked at, but I think you can still find older builds that have almost all the best features for free. Your files / tagging infrastructure will not fall apart if you switch OS or ditch the app which I think is really important for longevity. It would be really easy to code something new that's compatible with the tagging structure if you ever wanted too.