How do you handle files that don't really belong in one place?

Cool Workflows
1

I’ve been thinking a lot about file management on the Mac, and there’s one point where my own system always seems to get awkard.

Some files just don’t have one clean home.

A PDF might be part of something I’m actively working on, but also something I want to keep around as reference. A note from one meeting can end up mattering across a few different projects.
Something I downloaded for one purpose can turn out to be useful weeks later for a completely different one.

That’s usually where folders stop feeling quite right for me.

I can put the file somewhere, of course. I can even make a pretty reasonable folder choice. But once a file spans more than one context, I’m never fully convinced that location is doing much beyond delaying the moment I have to search for it later.

Finder tags seem like the obvious answer, but I’ve never been sure how well the hold up once work gets busy and the system gets a little messy. I can imagine a small set of tags working well, but I’d love to hear from people who’ve actually kept that going over time.

So I’m curious what people here really do.

Do you mostly accept the limits of folders and rely on search later?

Do Finder tags actually stay useful for you?

Have you found some other Mac workflow that handles this better?

I’m less interested in the ideal setup than in what still works after a few months of real use.

2

This the trade off of folders (only one location) verses Tags (can be linked to multiple things)

Tags are better for the scenarios you’ve discussed and I’d suggest that a Folder organisation is wrong for your requirements.

However under macOS and APFS so long as your files aren’t going to change over time (e.g. meeting notes) you can copy to multiple folders without taking up any significant additional disk space.

Alternatively taking notes in something like obsidian allows you to tag to multiple projects.

3

I don’t have an answer, because I’m struggling with file management myself.

But I do have a question: isn’t the file manager you’re developing supposed to solve this problem? :thinking:

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4

I’ve discovered in organizing and using pdfs I use as research that, yes, sometimes they apply to more than one article or project.

  1. I clearly label files first.
  2. I have a spreadsheet listing publication data and a partial path for the file.
  3. I pick a single home for a file.
  4. I use aliases when I am actively working or gathering resources to start drafting/outlining.
5

I consider Finder folders as static containers and Finder tags as dynamic indicators. Files are placed in a (sub)-folder following a project hierarchy. By example, you might well imagine the differences in files that I store in Documents/Finances/taxes/taxes 2025/submitted versus Documents/Finances/taxes/taxes 2025/resources. Once a file is placed into a Finder folder, I rarely move the file from the folder. I may, near the end of a project, tweak the name on the folder as the use-case demands. Separately from this, I have a distinct set of Finder tags as below. They track the status of a file or folder.

Finder 20260426-085424@2x

Finally, in those cases where a file is a resource for two or more projects (static final locations), I have no hesitation about duplicating the file or making an alias link to the file in one core location. I duplicate a file when it is a static (e.g. read-only) resource. I would alias a file into different locations when it may be a working document for editing in more than one application. The latter option is an exceptionally rare occurrence – one that I mostly try to avoid.

In summary, one solution to your conundrum may be to separate the context of a file using the concepts of static final location versus active current state. Use folders for the former, keeping them generally individually-distinct and immutable over time. Don’t be afraid to duplicate files that are truly static (immutable) resources – data storage is cheap (versus the pains of re-remembering how you initially stored a certain file that you need in a different project). Use tags for the latter, allowing them to overlap and change as needed over time.

EDIT: Added caveat to don’t be afraid to duplicate files.

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JJW

6

I have a related issue where a lot of my files have a defined company location and can’t be moved, eg all our finance and HR files have their own sharepoint sites, albeit synced to my machine.

So I use my task manager as an “anchor” for all my projects, and then use Hookmark to make a link to everything I use on that project, irrespective of its actual location.

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7

This is where I find Devonthink helpful. I use replicants to have a file in multiple folders.

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8

The reason I don’t duplicate files is that I annotate PDF journal articles a lot.

There needs to be a single authoritative copy

9

Would an alias to the one original do the job?

10

Yep. See above. I use aliases.

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11

Yes. Exactly. I had the caveat in the details and added it now also explicitly to the summary.

–
JJW

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12

I’ve started using notes with links to source documents. For example, I administer a family member’s special needs trust. I need to handle various tax and legal filings, financial account management, disbursements, etc. The trust was established via the estate plan of another family member, which, in turn, has links to yet another family member’s estate plan. I can store the legal agreements underlying these various arrangements in a single place, but can access them from the individual notes I’ve set up for each aspect of trust administration. The notes link to lots of other things, too: financial institution web portals, IRS forms and instructions, contact information, etc.

I store the documents in DEVONthink and keep the notes in NotePlan, but any system that facilitates the combination of document storage, notes, and linking would work.

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