Another take on file naming and organization

Found this interesting article:

I’m not at all sure that the scheme would work for me. The idea of encoding categories into file names is intriguing, but I think the overhead of typing [category][suubcategory]-other_stuff for each filename would be more than the benefit, at least for me.

Since I am nearly exclusively on MacOS / iPadOS / iOS, using Finder tags is a much more natural approach for me at least.

I tag folders with tag that starts with ‘@’ to distinguish those tags, which I use for automatic filing using Hazel and a custom script. I could see having category tags that start with another special character and so forth…

Food for though for those of us always searching for the “best” way to organize things.

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The best way to organise files is universally defined as “not the way you’re doing it.” :joy:

I do actually use something similar to that format, but only for a specific subset of files. Most of my stuff would fall under the “miscellaneous crap” category.


I’ve found that there’s not much payback from spending time nursing anything but the simplest file naming convention. In other words, one size fits all. In my case:

yyyymmdd topic - source

In as few words as possible.

Where a file is located (folder in a well-maintained hierarchy) is more useful to me than what the file’s name is.

I don’t tag, because there’s no payback for that either. Names and tags are no substitute for a great file search like FoxTrot Professional Search.

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What do you like about Foxtrot over, say, DEVONthink, HoudahSpot, etc. ?

I read the article but I am a bit confused. Why iCloud folders are different that the main folders on the HD?

I’m not an expert on how FoxTrot does it’s job, but I understand that it augments Spotlight data with its own additional index of keyword data and file metadata. FoxTrot also provides a lot of fine tuning of what gets indexed. It also has add-on features to provide the index contents from the Mac to an companion iOS app or share it on a server. It has a robust set of search rules. Finally, it is very fast – both at creating the index and at displaying results.

Houdah Spot is a nice front end to search Spotlight - but it’s just a front end.

I don’t think DEVONthink is in the same category of Mac-wide search, since its search is limited to whatever is in the currently open databases. (The companion DEVONsphere Express can search across the local machine, but I find it slow and clunky.)

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Foxtrot Serach has an iOS companion which is fully integrated with the desktop.
Also Foxtrot will let you use a 2nd Mac such as a laptop to search the index of your main Mac.




Zero chance that anyone who actually uses a computer productively has the time and focus for a file system like that.

Interesting that he doesn’t show you any screenprints of his files.

Perhaps just a clickbait story?

I think the power of this idea is not the exact naming convention but the concept of having the same structure in all your tools (your second brain, your digital cabinet, your email, your todo app, whatever). So you automatically know where to put something in some place with the confidence that you will surely find it.

I happen to like but with a less sophisiticated structure.


Agreed - that is a lot more practical. Moreover once the system is set up, the time to apply a number to any given file is minimal.

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@quorm: I don’t argue with you. The mental effort to apply categories and subcategories to every file vs applying a date/time stamp and descriptive text in the filename has dissuaded me in the past from these kind of schemes. The trick however is in making sure that your folder organization allows you to find things, and that is also sometimes difficult, with duplicative folders in different locations cropping up through entropy.

@pantulis: I read through the johnny.decimal stuff; thanks for the link.

What I liked:

  • It is more concise than full text category and subcategory names, which makes for less typing and also makes it easier / less distracting when adding this information to non-file items like emails. I suspect having [43.18] appended to a subject in an email is going to be less of a problem for the recipient(s) than [Finances:TaxaReturn2020] would be.
  • It enforces a filing system, and if you create your areas and categories well, there is (hopefully) less danger of misfiling things.
  • If you embed the area/category into a file name (eg [42.18]) it become easy to have Hazel parse that information and automate filing.

What I don’t like:

  • Sometimes this is too rigid of a scheme, to at the least I would likely have some sort of bin for “unfiled” files, although this is not too much of a deviation from the “rules”;
  • It adds, I think, too much cognitive overhead by having to keep a listing of what the numbers translate into for the areas and categories, which might become a pain in the butt over time;
  • Despite the concise and relative unobtrusive nature of the numbers vs words idea, I still tend to think that drilling down into my file system is easier if I look for a folder called “Taxes2020” under the folder “Finances” than having to look up in my notes the folder [42.18] to work on a tax return.
  • The description was a bit confusing. Under 42 -> 18, do I ONLY create folders, or only create files, or both? I got the idea that under 42 -> 18 I would create TaxReturn2020, TaxReturn 2021, etc, because 42 is the finances area and 18 is Taxes, but I wasn’t total sure how I would actually do all this in practice. I found the description a bit confusing, but that could be just me.

It’s interesting that “Johnny” simply numbers folders under the main headings. Stephen Wolfram does something like this with his files; there’s a lengthly but interesting post on his blog from some ago about how he organizes everything. He pretty much saves everything in a “Wolfram Notebook.” Not being a Mathematica user, I think that this is basically a document that Mathematica can process that is an amalgam of Wolfram Language commands and free-form text. It appears that in a given folder which is created for a given topic he is working on, all files are simply named in sequence with a two digit number. He claims that he rarely has enough files in one folder to make searching through them for the specific information he wants a problem. I suspect this would not be a good solution for me.

@MitchWagner has nailed this one.

Just to nitpick or critique a bit:

“Hey Kristy, where can I find the payroll schedule?”
“Twelve dot oh-three.”

Thanks, Kristy.

If these are the queries you receive, there is a larger issue because the name of “Twelve dot oh-three” is “12.03 Payroll schedule for 2018”. This is not a good advertisement for being able to find things.

Nothing is more than two clicks away
Except they are:

  1. open 10-19 Finance
  2. open 12 Payroll
  3. open 12.03 Payroll schedule for 2018

There is more detail here which mandates never creating a folder in a J.D folder.

There’s also the issue of saving a file in the wrong place and having difficulty finding it. I would think if one were going all in on JD, one would add that at the beginning of the filename.

Personally, if I adopted this system, I would use a hyphen or underscore rather than a dot to avoid confusing filename parsers that might misinterpret the dot as the beginning of the file’s extension.

But I would never adopt this system. If I had the need to do something similar, I would use a mnemonic system that doesn’t rely on remembering or looking up equivalences for section numbers. (I also would not name a folder “…spreadsheet”, because it isn’t - but following their example.)

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You never get away from eventually drilling down into folders; that’s inevitable with a hierarchical structure.

We are in agreement viz numbers vs letters. The advantage, as I noted, is that adding [43.12] to an email subject is less confusing or obtrusive than adding [Finances.TaxReturn2020], but the numbering scheme adds more cognitive work to recall or look up various numbers.

Using a single letter (“F”) of course is a problem if you also have an area named Food. The advantage to numbers having no association with the topic is that there is no incentive to have the Food area numbered 12 or 42, so the same lack of association that makes it more work to remember the numbers makes it easier to assign them.

One of the ways I avoid “drilling down” for frequently accessed folders is to assign a tag to the folder itself. Those “folder tags” start with an @ sign to distinguish them from other tags that I use for searching and categorizing. I can open any such tagged folder instantly through my own scripts in Alfred, and there are a very small number of them reflecting folders I need to open very frequently. Not a perfect scheme but it helps me a lot.

I totally agree about not using the “.”, and would use something else, probably a hyphen as you suggest. My file naming scheme presents a date in YYYY-MMDD format, with alternative formats of YYYY-MM or YYYY-MMDD-HHSS when needed, followed by a descriptive file name, with NO special characters. All spaces are replaced with an underscore (very useful as I do a lot with scripts and in the shell where spaces in file names is a royal pain), and of course the extension starts with a period.

I don’t rename every file this way, but pretty much anything that needs filing/archiving and most working documents will have this format, and I have my own script that can process a file name into this format, using a supplied date, or pulling a date out of the file name itself (eg if I named the file YYYY.MMDD.extension, with spaces and the date at the end and with a period in it, which is faster to type), or with the file’s creation date or content creation date. Thus it is very quick for me to select a bunch of files in Finder, fire off a KM script that renames the files, and queue them up for filing.

We as humans are so different in the ways we do things. It is just a natural thing.

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I have three loose guidelines for filename and organization:

  • When I name a document, I try to think of the names I’ll try when I’m looking for it. I’ll throw in the name of the project, the type of document it is, and so on. Then if I look for the document, later, if I have trouble finding it, I’ll remember whatever keywords I tried to find it with, and failed, and add those keywords to the document name, so it’s easier to find next time.

  • One folder per project – that is, one folder per article. Folders are organized into a higher level folder called Current. When I’m done with a project, the folder gets moved to a higher-level folder named for the year.

  • I also have folders for my personal blog, and for a civic association I volunteer.

  • So for example, if I’m doing an article about Acme Corp. using SuperCloud Software for payroll management, I’ll name a folder “Acme SuperCloud payroll” and individual documents might be called “Acme SuperCloud payroll interview notes,” etc.

  • Article drafts include the date in their name, rather than V1, V2, etc. Easier to keep track of the sequence.

I’ve been refining this system over 30 years; it works well for me.


I date certain files “YYYY-MM-DD-subject” such as journal files, project notes invoices etc. others get a basic category first such as “CSS styling whatever”, “GTD using contexts” etc…

It really depends on how I need to find them going forward. Dates are important for some, categories for others. This plus a sensible (for me) folder system where I mirror Omnifocus, Devonthink and system filing set ups as much as possible seems to work reasonably well.


Adding to this, one thing I’ve found useful, if you only have a small number of active current projects, put their folders in the Finder sidebar.


The folders-in-the-sidebar tip is useful. Another option for quick access to important folders and files is Default Folder X, which provides features that macOS should provide.


Agreed - and Trickster overlaps somewhat with the cabilities of Default Folder X.