Organizing My Mac

Hi all,

Like many of us, I have been using the Mac for many years. I am curious about setting up the main user folder.

The basic default for files/folders would be in the Mac created Documents folder. This seems to be the default location for various purposes and some application files.

Personally, I do not want my main files mixed in with these default application folders, so I created a folder inside the Documents folder called “MAIN_FILES” and all of my documents and folders go into sub folders inside this “MAIN_FILES” personal folder.

But now I am rethinking this set up. I think it might be best to leave the documents folder alone and let all the default files and folders go inside there.

Instead, I am thinking that I will:

1 - move the “MAIN_FILES” folder - to the root of the user folder.
2 - not use the “MAIN_FILES” folder at all, and instead move its contents (the sub folders) to the root of the user folder.

Q: Does anyone have suggestions or preferences how Best to organize our files/Folders?

Thanks in advance - Dave

I created a docs subfolder within Documents. I wanted more control and it’s also a carryover from when I was on windows. Personally, the Documents folder gets too cluttered for my taste. I stick with this for backup and potential sync purposes.

I always get confused about the “Document Folder”, especially I have 3 Mac . Do they merge into one Document Folder like or iCloud Folder (eg. PDF expert, there is only one PDF expert folder for all Mac and iOS) but I think I see different “Document Folder” for different Mac.

Due to the confusion, I do not set this as the default folder for saving documents. I generally default to saving to the iCloud folder that the app created , such as Pages

Long time ago I symlinked my “Documents”, and “Desktop” folder to same name folders in Dropbox, thus ensuring everything was always available on every device. It also meant software using Documents folder as default location, could continue to do that.

I did switch off “Desktop & Documents Folders” in iCloud Drive to go ensure nothing strange happens.

This has worked well for me for years and everything was always available to me regardless of device and location. Still think this is ideal for standard file management.

I have been re-thinking some of my strategies when I started using Devonthink as I have taken certain folders out of the old structure and loaded them into Devonthink.

I am using Devonthink much more now and like the power and convenience, but will have to see how it keeps working for me when I move more and more over and the total database size might cause syncing to become a trouble. Alternative for me would then be to index existing folders in Dropbox into Devonthink instead of importing them

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My setup is similar to @simonsmark. I use Dropbox so that everything is always available no matter the device. Essentially, the top level Dropbox is my Documents folder. Recently, I’ve turned off iCloud Desktop & Documents Folders and stopped using iCloud Drive. See this post on iCloud problems with sync.

I use a modified version of The PARA Method:

My organization structure is like this:

1 Projects
2 Areas
3 Work Areas
4 Resources
5 Archive

I reflected for a while on my long-term ‘areas’ that rarely change. For example, Finance, Health, Home, Pets, Writing etc.

I usually change all the app preferences to save files in my preferred folders rather than their defaults.

This setup has worked well (so far) for me.


I use Default Folder X to quickly find and navigate to recent and favourite folders within my filing structure.

Also have been consistent with a file naming convention over the years, which helps find stuff.

2022-01-27 (From/To/Project/Photoshoot)-(What/Subject)-(Version No/Photo No)

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I use the Documents folder, with iCloud syncing turned on.

Within that, I have 5 main subfolders, numbered so they go to the top.

  1. Projects (for things I am at least semi-active on)
  2. Filing Cabinet (for bills etc)
  3. Resources (books or other things I want to keep access to)
  4. Archive (mostly old projects)
  5. School (to keep work stuff in a silo)

I’ll add/remove other folders as I want, but gradually whittle back to these.

I also have a totally separate “Local Documents” folder in my User folder which I mainly use for projects that have large files or otherwise seem to dislike continuous syncing.


Don’t overthink it is my first thought about this. KISS.

The Documents folder is the virtual variant of a file cabinet.
Make one folder called “Work” and one called “Private”, and put your belongings in there, in subfolders of course. The difference between Work and Private things are the most common “aha experiences” my clients see when I suggest this.

Furthermore; Because stupid vendors like Microsoft don’t use the Library/Application Support as they should, they put their crap (settings files etc) in Documents as well. I always hide them from the users (with Terminal command “chflags hidden”).


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I have done and still do basically what you describe. In Documents I have a folder for all my data. In it ar sub folders for the Filing_Cabinet, my Active_Projects and folders for organizations that I will eventually have to send off to another person. That keeps things separate enough for me.

I put my main user folders into the sidebar so I can get to them easily.

I would suggest putting MAIN_FILES in the sidebar of Finder, that way no matter where it really lives, you’ll know it’s there in the side bar.

Consideration: if you move it out of Documents, it no longer syncs to the cloud (if you have that turned on). Could be a consideration for cross-device work, and as a pseudo-backup.

Thought: put things where you will look for them first when you need them. I don’t intend to be flippant, but that is the ultimate goal. I hang the dog leash in the front closet because that’s where I look for the dog leash. Same can be said for files.
This is what motivated my recent post trying to get some clarity on PARA.

I’ve also found Trickster to be very helpful, as it allows locating files and folders through a third dimension (time or “when”) (with folders providing access by “where”, and tags providing access by “what”).

I struggle with this but have found some systems that work for me:

Good Finds” are for those quirky things I’ve found and want to keep but have no project or real relevance to anything except that I like them. Like this image, which has sat in that folder for 16 years now:

Presentations” archives pretty much every single presentation I’ve ever given and each folder within it has a number so I know when it occurred in relation to the rest.

I call my “File Cabinet” type folder “Paperwork” but it serves the same purpose as others have described.

When I was taking classes, I organized my coursework by quarter, course, and assignment and I can always find stuff when I need it.


This is a great tip!! I don’t use Terminal very often… is there a tutorial on how to hide a specific folder?

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Glad I could help.

You just write the folder or file name after the command.

Eg: chflags hidden TheFolder

To show it again, the flag is nohidden

Some tips:

  • Be in the same location as the item you want to hide. If not you have the specify the entire path, eg
    chflags hidden hidden /Volumes/Macintosh\ HD/Users/carlsson/Documents/TheFolder

  • The Terminal differs between capital letters and lower case.

  • When you are in a specific folder you only have to write the first letters and then press Tab, the whole name will autofill. So if you are in you Documents folder and want to make your “The folder with a long name or so” invisible, just write “The” and press tab, and it will fill in the rest for you. (Until you have two items that starts with “The”…)

(I am no Terminal power user by any means, but I have catched som things during the years.)


Another reason I suggest everybody to use the Documents folder: The shortcut to reach it is CMD+Shift+O.
Ie, it’s very easy to reach it with your keyboard.
Putting items in the dock or sidebar of Finder windows is also great of course. :slight_smile:

I have a “30Day” folder. Everything I’m working on is in that folder. If anything is not modified in that folder after 30 days it gets archived to an archive folder with the format “creation date-major category-minor category-title” so a file would look something like this: 20220128-companyX-projectY-widget-proposal. The archive folders are per date:


This is all automated using hazel. Hazel adds the date, moves the file, creates the archive folder if it doesn’t exist.

The logic: I tend to remember when something was done which narrows down the search. The major category and minor category also narrow down the search. I can usually find what I need very quickly. Archiving by date allows me to offload old content on to external hard disks.

This does not include media which is in a separate folder but similarly formatted. It also doesn’t include teaching and preaching notes which I class as being evergreen although they are created with the same format, just not archived in my main archive.

I keep everything on iCloud Drive after jumping out from Evernote. Tried Apple Notes but syncing was so frustrating that I decided it was not worth it to put everything inside a system that does not have an easy way out, so needed to be on some kind of filesystem. Also happen to have a hefty iCloud Photo Library so the choice was easy.

Now, on iCloud I have two file cabinets, Personal and Work. To work with these two, I have them indexed into separate DEVONthink databases. I have first hand experience on the pains of this setup and my tip is: dont do like I do unless you are ready to diagnose the different latencies between CloudKit and iCloud Drive. But it is convenient for me.

Source code repositories are always stored in some kind of Git repo, so they live in ~/src

As for the folder structure, I use my own “Johnny Decimal” taxonomies. The beauty of these is that once you start memorizing numeric prefixes if you manage to keep the same structure on your file cabinet, your email folders and your task manager everything just flows.

I’ve had everything in ~/Data for years. Separate from everything apps might create automatically. Nowadays it’s more of an archive as I moved active work to Dropbox then to icloud.

I never store anything in Documents myself, and always set apps to save stuff at other places. When I have a computer that I use both for work and privately, I have two folder ~/work and ~/private and inside them I have sub-folder for various thing. On the level ~/work/X I have 5 folders, inside them additional levels … probably 8-12 levels deep. I’ve been doing this for the last 20-30 years and it works very well for me and my work. Privately I have only 3-5 levels.

A really interesting topic, and thanks for some great ideas!

If I can add one question, I am setting up an additional external hard drive to my back up plan (per Sparky’s plan, Scarif). This will be the drive that collects everything, past and present. Anyone have a similar drive, and if so how did you organize it?



Hi Mike,

I have a similar type drive and I can recommend a few things. One of the large capacity (4 to 8 TB) spinning drives is very good for this and quite inexpensive. Also it might be a good idea to “back up the back up” and have a second duplicate version of this drive.

  • For this type of usage I leave these drives mostly unattached/disconnected, and only update them once in a while since your main data is already being backed up in other places - (using either carbon copy cloner - Arq or chronosync etc.)

Quick story: the drive that I use for this purpose actually went down a while back.

Why was laughing?

Because I did actually have a “back up of the back up” that was current. I was able to get a new drive formatted and copied everything from the secondary drive to the brand new primary drive no problem.