Notes - "Linking your thinking" or "Folders, Notes, and Files" Apps

Use whatever works for you. I don’t like to drift too far from the Mac’s file system. I get nervous even using Notes.

This all said, I’ve got two comments about history to add.

First “new-era linked tools” aren’t really that new. I used a “thought processor” linked subdocuments tool called Houdini in the early 1990’s. It was written by Neil Larsen who also wrote a very nice outlining program called MaxThink around the same time. In the mid 80’s I used a program called Kamas which I’ve always felt was a precursor to the way Scrivener handles subdividing documents.

Second, the hierarchical directory file systems, that I first discovered with UNIX in 1980, to me was the greatest development in organization in my lifetime. Until then it was all basically flat. The only saving grace was that storage was expensive so not that many files could be stored on-line.


Ooh, that’s very interesting to hear about.

Thanks! Much appreciated.

I work with a lot of seniors in my computer repair business and I’m amazed how many of them don’t use folders. Most all of their documents are simply in the downloads folder.

I started my computer journey with DOS 3.1 and if you didn’t have the file system in your head you couldn’t do anything.


My “not a computer person” coworkers are all like that. One lady I work with has to get a PDF from every transaction she does. She has thousands of PDFs all in one folder that go back 6 years, from when she started. It drives me insane, I tried to get her just to file them by year and she won’t. She has to think about it and find the time. I said I could do it in 5 minutes, but nope.

Some of my “middle aged”managers kept all their files on the Desktop. How they found anything when they 3+ times the number of icons that can be displayed remained a mystery. Each time I had to work on their Mac I would create a dated folder and drag everything into it. And when I came back it would be covered again.

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Here’s my take on the second greatest development in organisation: tags as first-class metadata in modern filesystems. First time I heard about that was in Longhorn (later Vista) that reviewers said it had a “database-like filesystem”. Probably OS X already had something built-in back way back then. I’m not sure why current macOS has such anemic support for tags in the Finder, I think it could be pretty powerful.

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That’s happening with college students since 2017 or so: they were raised “mobile only” and smartphones don’t have a file system. Everything lands on the desktop and they search for what they need.

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That’s interesting; i’ve never been able to figure tags out, or labels in Gmail for that matter which is essentially the same thing. Is it genetic that some people have a preference for tags and some people have a preference for folders?

I think there are two modes of operation here. Thinking and archiving. Some of us are less thinkers and more archivers, hence I prefer the “Folder, Notes and Attachments” approach. I marvel when people show their amazing zettlekastens built with Obsidian, DEVON or whatever but I simply don’t have the time to reflect on all the stuff I am storing. (Now the question would be: why are you archiving it for, then? but that’s another question)

My important take: whatever system you use, for me it’s mandatory to use the same vault, database or repository for both things. Currently this means having all my files in a filesystem hierarchy and using different apps on top of the same folder so I favor apps that support this kind of storage. Obsidian, DEVONthink, Notebooks, Eaglefiler, and of course anything that opens an arbitrary file all coexist nicely and perhaps Noteplan, Agenda could be make to work like this approach, which negates Evernote, Notion, Roam, or whatever is cloud based.

Edit: as a side note, I am still using Evernote (still paying a grandfathered, unsupported license). When I’m processing my Inbox I just drop stuff there without any organisation after archiving it in my local folder structure. Amazingly, Evernote search does not require much effort to allow you to find things so it’s a nice backup resort.


I grokked tagging when using iTunes around 2004. I was worried that I would not be able to locate the mp3 files I was importing into it and a friend of mine told me: “So what, forget about the folder the file is in, just use tags and smart playlists to locate your songs”. And it has been like that until this day. This means I am vendor-locked into iTunes (and Macs) but there are worse things, imho.

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I never could get into tags for multi-dimensional filing. I only use them for automation/processing. For instance, I have “Sticky” that I put on the files I want to keep on my desktop. Any not so marked get filed elsewhere automatically by Hazel after a couple of days. Any statements that come in get tagged “To Process” so I know I need to look at them. After a few days anything still in the Downloads folder gets marked with an “Old” tag telling me I should move it elsewhere. That’s it.

I’m afraid that if I were to start adding tags based on content that I would end up being overwhelmed with tags, and there is no system in place to create hierarchies of tags. I rely on the ability to search contents which Finder does fairly well and DevonThink (which I also have) does excellently.


I’m all tags and folders all the time. To make sure that my tagging is consistent across all my apps, I’ve documented them in a spreadsheet.

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The initial impetus behind the Documents folder (inspired by Windows) and implemented first by Microsoft’s applications) was that users only had to look in one place for any file. Some applications even created dedicated sub-folders in Documents on installation.

I remember one company for whom I built installers spending huge amounts of time trying to decide whether to automatically create a sub-folder in Documents, or not. We went with Not.

The assumption, based on my ancient memories from the 90s and late 80s, was that users would rely on Search, which would be exceedingly rapid, and that indexes made by the System would also make search both rapid and precise.

Spotlight while useful, has never met those initial assertions.

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And then when applications like Act! start hardcoding the Documents folder for the location of their database that causes problems. Microsoft now decides to forcibly include the Documents folder in OneDrive. When you sync any database folder to the cloud, the database corrupts. I’ve had to create another Documents folder in the user’s folder before OneDrive has synced to fix that.

Other programs shouldn’t use the Documents folder for their user program data. There is %localAppData% and %AppData% on Windows and ~Library/Application Support on macOS for that.


I don’t think it’s age related, more based on your thought process.

The biggest ding against file systems is that (without duplication, and what kind of animal wouldn’t have a single Source of truth) is that you can only put a file in one folder.

Tags or labels allow you to apply multiple contexts to a file e.g. March, 2024, Energy, Bill, £200+

To be honest with search improving by the year, for work I’ve given up (for example) using multiple folders in email, once an email is completed, it goes in the @Completed folder from where, once a month, it gets “archived” by year.

If I want to look for anything I’ll search for it by who sent it, a subject line or even by month.

Files are saved by project (in a GTD context of a project) and archived by year. Search again allows me to find what I need.

They “allow to apply” but also “force you to apply”, otherwise the system falls down. Tagging optimizes retrieval by making classification more difficult by adding the complexity of managing, curating and enforcing a taxonomy of tags. That’s not to say I don’t find tags useful (I do!)

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I use tags in Obsidian for process terms and overall Areas of Focus in the GTD sense. Obsidian does support hierarchical tags so that really helps. I’ve never used tags in the finder at all.

The one place that I use a lot of tags is in my Lightroom database. I use tags for process, subjects and other large groups and it makes it a lot easier to find a set of pictures when I am looking for stuff.

If I have to resport to search I know I am in trouble. I depend on a logical folder naming scheme for finder files. Even my Obsidian system has a lot of folders and documents are placed in them as the primary way of accessing them.

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I do the same thing. Using folders makes it a lot easier to find and use your Obsidian files in other apps, which is the whole point of the “files before apps” philosophy.

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I recently discovered that you can’t share your Documents folder over your LAN if you are signed in to iCloud. This is the case even if you don’t keep your Documents folder in the cloud. (Same applies for Desktop) What the heck is that about? I’ve strongly considered adding a “Docs” folder and moving everything in Documents into that.

Oh, and I find Spotlight, especially when invoked from Finder, to be really good. Back in my Windows days (which finally ended when I retired 8 years ago) Windows search was so awful that I used a third-party search program, and I eventually even brought in a Mac mini from home, kept all my documents on it, because it was so much better at searching.

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If you can keep things logically organized over decades, more power to you! I can’t. My Archive folder on my server has 526,000 documents in it, some date back to the 1980’s. There are 32,000 documents in Documents.