Bear does this really well with its hierarchical tags.
Most filesystems can do this with hardlinks (but the UX mostly sucks).
I ended up with a box, in the box there are large plastic envelopes, and each envelope is labelled.
I have:
- "assets" (cars, warrantees, service records, purchase invoices etc)
- "health" (all medical related things)
- "insurance" (everything insurance related)
- "guns" (I like guns... so licenses, legal paperwork, etc etc)
The best thing is, this is a box. So worst case, even if I misfiled something, all I need to do is rifle through a box. The box is portable and universal, and if my wife needs something, I can easily guide her to where to find it.
The benefit of file structures is that things have to have a place, you can't not put something in a folder, so for car insurance, it might be in "insurance" or "cars" but it's definitely one or the other. With tags, it could be "insurance", "finance", "cars", "automobiles", "vehicles", "veihcles", etc.
Any tips of how to funnel some strictness into tags so that they're actually usable?
Your operating system must behave way different from mine. Hardlinks in both Linux and macOS are merely "named inodes" and only when all references to the inode are removed is the storage actually subject to reuse
A flat structure seems less organized, since you are “mixing” stuff, but as long as there isn't too much stuff inside, going through stuff one-by-one is faster than you think. If I do have a lot of stuff in a section, I either split into several sections in the top structure (so 13 is life insurance, 14 is other...), or go one level deeper (not preferred, but I do it when it's very clear and there is too much stuff, like photos, which btw sorting chronologically works best for me).
It is really not much of an issue having 50 top sections. It makes the organization transparent, and indexing, sorting and going one-by-one remains easy.
In reality you just decide. One feels better to your brain. And you tend to remember that.
It helps of course if you remain consistent. In the systems we design we’ve realised that most people want the insurance close to the thing being insured.
So in our life admin system we have health, pet, home, motor, and travel insurance as IDs alongside your records for those things. Seems to suit most people.
And don’t forget you’ve got your index as a fallback. I don’t remember most of these numbers but I just launched Bear, typed `insurance` in the search field, and there they are. Now in three clicks I can get to my home insurance which, turns out, is at `12.12`.
Haha, nope. Different brains work differently. One day I genuinely prefer one, a week later another.
One observation from over the years which matters because I keep separate sustains for personal (including freelance work) and employee office work. I usually can pick just one place and remember it for the latter whereas personal is a land of struggle and experimentation.
The "Obsidian way" that many people recommend is notes that are as small as possible to maximize this kind of effect, but that's not how I like to do it. I prefer bigger notes with lots of headings (that can be nested up to 6 levels), and lots of links within a note and between notes to specific headings. I find this to be a nice blend of hierarchical navigation and link navigation.
Non-text files (like receipts or pictures) get linked from the relevant note or section, and many types of media can be viewed inline in the WYSIWYG editor.

The whole vault is in my iCloud drive, so the files are available on my phone.
It doesnt take so much “scale” if one has deficient short term memory/recall/adhd or is (as youve elegantly put it) “too retarded”. (hey - samesies)
Tags/content classifiers/ontologies are I think the solution here, but require continuously grooming your data to ensure it’s classified correctly - a time investment.
My opinion is that modern ML classifiers are helping,l - Ive found some help with tools that recently added auto-tagging - and I think the real magic bullet will be augmenting this capability with relevant personal/activity context. An algorithm can infer much of the contextual relevances that are missing from the current tools if it can match some incoming information to any or all of the areas/topics/projects/horizons/decimal-things that users of organizational tools have decided are important to them.
As a result I’m a heavy search user. I find 90% of the time I can quickly find what I’m looking for with a few keywords.
For the OP, health insurance policy, I’d type “health insurance policy” into my google drive. Then it pops up, wherever it was.
This of course means you name things with something that makes sense to you. Don’t leave it with whatever name when you downloaded it by default.
This also is a huge help with links. I need to find the latest xyz ticket (which I previously viewed) and I’ll type in xyz… and boom, there it is. This is why I don’t clear my browser history very often!
Over-reliance on hierarchy has been identified as a double edged sword of these organizational systems. Hierarchy is only useful when the hierarchy itself matters, e.g. when "grab all documents about this" is a use case, keeping such documents together matters. If the use case is finding one particular document, we have better tools than hierarchy for that, and any time spent on organization is more or less wasted when a good file name and simple storage rules do the work better, and are irrelevant for modern retrieval methods.
I use Paperless to catalog all my PDFs, Obsidian for notes and Gmail for email, Todoist for tasks and Cloze for CRM, all of which support tags.
Classification is a vexing problem I've tried to grapple with.
The Dewey Decimal system is a really good example of people trying to get a handle on it. It's not easy. "Arduino Cookbook" is in the Electronics section (621.3810285536 to be precise, although the decimal system doesn't usually get that crazy in its specificity), whilst "Getting Started with Arduino" is in 005.133, more that half a library apart.
As one commentator put it, a book is rarely about one thing. People have criticized the Dewey system, so they throw the baby out with the bathwater and declare their bright shiny new wheel to be the solution.
Except, of course , they skip over the same fundamental problem that Dewey had: books don't really fit into a taxonomy.
One solution which may work for small personal systems is to not bother to use a hierarchy. Put car insurance in one folder, then file all folders alphabetically.
Getting more sophisticated, if you have a hierarchical system, consider indexing. I found an old address book that I had lying around. Add entries into that. Sure, entries won't be in strict alphabetical order, but hopefully you won't have a system so big that you can't find anything.
Indexing is "the" solution, because you don't have to try to figure out where in the taxonomy something is. You just look it up. Indexing also allows you to construct different "views" of a subject, thereby allowing you bypass taxonomic choices.
Being a computer geek, you could keep an index file on computer. You can then simply grep it.
Using your example, you could describe the insurance for your Citron as 21.2.8. Or, you could call it automobiles.citron.insurance. Which looks a lot like automobiles/citron/insurance. How is this any different from just using a folder structure?
Calling a folder citron instead of 2, gives room to have N amount of folders at that level instead of just 10, which I think is the constrain that made this system manageable.
So in Johnny's system, I assign 21 to automobiles. My VW van gets 21.1, my Citron is 21.2, etc. and the insurance for each car gets a .8 so 21.1.8, 21.2.8, etc.
And I assign 13 to Money. Insurance belongs under money so 13.5 is insurance and life insurance gets 13.5.1, E&O insurance gets 13.5.2, etc.
I also need a top folder for Medical for doc visits, vaxes, ER visits, Surgeries, the kids' allergies and stuff.
So where all this is going is two months later, where is the health insurance policy? Is it under medical or under money? Is the car insurance under Automobiles or Insurance under Money?
Back to my head exploding - this is my issue - I can never remember which branch of the tree to find a specific leaf? Does my annual car tax belong with the Money or with the Auto branch? If I want to see the tax for all the cars at the same time, I put it under Money - Taxes - Auto but when I need to know the last time I paid the tax on the VW, I will assume its filed under Auto-VW-Car Tax.
This is why I can never find anything. All due respect to Johnny but I'm too retarded to use it properly.