I'm declaring organzitional bankruptcy...ugh

After years and years of trying “this organizational method,” and “that hierarchy workflow”…and, oh yeah, that “app file system” …I have made a mess…

And I’m declaring organizational bankruptcy!

I have files here (hard drive), folders there (Dropbox), and yep, content over there in iCloud.

I’m more than willing to move every single content and media file I own to an auxiliary hard drive, clean off my MBP, and start from scratch on my MBP…


I’m lost on the best way to org things TODAY:

  • Hierarchy?
  • Tags?
  • Folders?
  • In apps?

Any good data bankruptcy lawyers in the house??

BTW - I write a lot of books, which means research items galore…




I am in no way an expert in this matter. But I found myself heading into a similar direction some years ago: data everywhere and nowhere.

I have decided to organize my data in folders if possible. In the long run, all my data lives on my NAS. I have dropped Dropbox, I still use OneDrive and iCloud as temporary locations for some files, but I try to stick to putting stuff in folders on my NAS.

Of course, there is stuff that rests in databases or apps but as soon as data is contained in a file, I will put it into my trusty old folders.

I think you have to find “your way” and to commit to sticking to it.

1 Like

I think different people have different priorities, based on their needs and to the extent to which they need to sync to other platforms (iOS, Windows, etc). What works for me may not work for you.

I personally can’t stand tags, and find it not only a chore but see others dealing with the proliferation of tags, and accidentally creating too many similar tags (then needing to review and consolidate). The only tagging I do is in general categories for my photos in Lightroom, and even then they sit in folders based on date.

I keep my files simple: folders and subfolders, and I rely on search (especially detailed searches with Spotlight-based HoudahSpot). Relying primarily on folders has worked for me for decades.

I only use cloud files to the extent that (a) my iOS devices require it and (b) I need to share files between iOS and macOS.

With storage being ever cheaper, I have no problem retaining most of my files on multi-Tb drives, and having both local and BackBlaze backups.


I think it has to be organic, meaning that I think you have to try something that you come up with, see what works, then prune it. Let it grow naturally. In many different areas of my life I tried to do what others says works, but it didn’t come from me. So when I had a question or had to remember how something works, I had to think about how that person / way would handle it, instead of using my own intuition.
I found that using tags in OF3 with a few simple perspectives reallybworked best.
Create don’t recreate


I keep returning to folder hierarchies, with a good naming convention for files. I prefer names with dates, versions if applicable, and something short that explains what this file is about.

Otherwise discovery (Spotlight and its friends) helps me find what I need.

I find tagging an utter waste of energy.

Prefer not to store data in apps – makes discovery all that more difficult.


Thanks Christian et al…I do agree…appreciated…and see a trend…

Find what works for me, which the current systems isn’t.

I’ll keep playing around with things, and I am going to give gulp tags a go…

Reporting back after done with the bankruptcy lawyers ; )

1 Like

I tag judiciously for quick searching in most apps (Evernote and iCloud-stored materials) but am completely on board with using Folders and Subfolder hierarchy. The trick for me is making sure I’m not going crazy with the number of subfolders, and using a consistent naming taxonomy across all stored files.

One of the challenging parts I find is when folders/files disappear. Whisked off to iCloud land…

I keep almost everything on Google Drive (in 6 folders currently) and have almost no organization other than some simple grouping: archive, media, etc… (Using search) I can normally find anything in seconds. Filing for me is Keep or Delete, then Hazel takes care of anything extra if needed.

I listened to a Tim Ferriss podcast recently, and he invited listeners to consider: What would this look like if it were as easy and simple as possible?

Regarding file management:

  • Keep only files that you absolutely need.
  • Use a good backup system, in case you delete a file that you want to keep later. 3 copies, 2 formats, 1 offsite at a minimum.
  • Use a shallow file structure. Favour lots of top-level folders, rather than deep, nested folders.

You can apply the same logic to task management, etc.

On that note, I should go back and review my own files!

I’m all-in on iCloud storage for actively used stuff. (I have a 200GB account, but that’s only because I have 90GB of photos in the cloud.) In terms of organization, what’s been working pretty stably for me – I’m an academic/college prof – is based on the following elements:

  1. For current projects: For things that have a beginning and end (as in GTD “projects”), I use hierarchically organized folders, with 6 top-level folders that correspond to my GTD “areas of responsibility”
    • In my case: 01 RES (for research publications, etc); 02 TCH (for teaching matters); 03 DPT (for departmental admin); etc.
    • BTW: I use same names in my folders in OmniFocus
    • Subfolders for each project, often starting with the three-letter code for the project folders (e.g., for a course “TCH 2018-19 Digital Ethics” or an article “RES 2019 Autonomy Gaps and Social Exclusion”
    • Sometimes sub-folder codes get added, to separate research projects “RES PRJ…” from research speaking engagements “RES SPK…”
    • This makes it easy to take advantage of auto-completion when search with Spotlight
  2. For reference & resources: Two big buckets of tagged items, one for PDFs of published materials (journal articles, books, scans)
    • Reference resources are often used in multiple projects, so this lets me avoid having multiple copies in each project folder. For example, there are texts that I use every year in a course I teach, so I will tag them with “digitalethics:week3” and then, any annotation I do to those files is always to one and the same file.
    • Another example, a journal article PDF might get the tags “transparency” and “algorithms”, and then I may create a smart folder (saved search) using HoudahSpot or the Finder that I save in the relevant project folder.
    • All my reference tags are colored Orange; I reserve other colors for other sets of tags (Blue for personal; Green for projects; Purple for teaching-related - these are also the colors of my Calendars in the Calendars app)
    • Sometimes, I’ll make an alias of a file (⌘L) and move to alias to a project folder (but this doesn’t work yet for iOS)
    • Hat tip to the Aleh “Macademic” Cherp: Managing project files and good old file folders ; it’s from 2011 (so “OpenMeta” tagging), but his principles are rock-solid.
  3. For inboxes/collection: I chuck stuff into an “Action” folder (like David Sparks does) for sorting “later” (always a challenge to keep these from becoming rats nests, as with any inbox); Desktop might work too.
    • Sometimes I use Hazel & tags to sort this quickly. E.g., for a (very) frequently used reference tag, Hazel watches for any PDF with the “transparency” tag and move it to the bucket of publications.
  4. I’m working on now & to-do’s for the day/week: this is basically a way of making sure I have a quick way to see what I need to work on today.
    • Key tags: “2grade” or “2read” and then “0today” - all of which have a Red color label. In the sidebar of Files app (on my iPad) and the Finder (macOS), these are manually sorted to the top.
    • If there is a project folder that I’m working on, I will often add “0today” to the folder (so that the whole folders shows up)
    • In other cases, I move a specific tag to the top of the sidebar (often I’ll do this with course readings: “digitalethics:week3”).
    • As with inboxes, the trick is to review this regularly, to make sure these lists are current. But it’s sort of like packing your bag before you go into the office.
  5. For archiving I use a top-level “zzzArchive” folder into which I dump completed projects.

Hope this is useful!


Interestingly, @JoelAnderson’s organization scheme mostly mirrors the one that is in Kerry Gleeson’s book The Personal Efficiency Program (1994, 4th edition 2009), which Joel didn’t mention and may not know about, with parts of David Allen’s book Getting Things Done (2001, 2nd edition 2015), which Joel mentioned. I noticed this in the Stack Exchange answer “Tags - best practice for using tags to replace hierarchical folder structure”. The organization scheme that is stable for Joel happens to correspond to what has been recommended by experts for over two decades.

Been there… what I did was I took all Old data and dump it an directory Archive… then from that time frame I build my system of directories to store stuff and stick to it, even when sometimes for one or 2 types of files you would be banging your head were to pu it. On that cases I save it on the directory that will start with the alphabetical letter that comes first, so when thinking where it could be, if my mind give me 2 directories I will use that to try to pinpoint where.

Only eight or ten tags? How do you survive? :stuck_out_tongue_winking_eye:

I am currently at 156 tags. And that’s honestly not any more than I need!

So. there I am… 2 days later, I have completely reorganized the data on my NAS.

Thank you for your input! I am in a different situation (different data with different requirements) but your post has inspired me to change some of my folder structure. I have moved about 10,000 files and I even had fun doing it. Crazy. But satisfying. :slight_smile:

1 Like

This has been really really helpful, and after reading all responses and drilling down with all the great references, I’ve come up with this:

  1. Three heirarchy folders (1) Take Action!, (2) Reference!, and (3) Cold Storage! 3%20folders
  2. A series of tags that describe the file/item per project. I considered different groupings of tags, but really everything I’m doing on digital is project based, from business to health to family to etc…I tend to look at things by project
  3. A big bucket folder of “To Sort” Tons of older items in there that might end up in one of the three folders (#1) or be sent to have have the pixels recycled.

I really appreciate the insights. Wicked helpful!

1 Like

I also think tags are wonderful. I use more than 8–quite a bit more–but there are only about 8 key tags that I really rely on. To avoid the risk of having a proliferation of similarly named tags, like @bowline is concerned about, I developed four hacks that have solved the problem for me:

  1. mostly, tags are applied automatically by Hazel and not by me;

  2. when I apply tags manually, I do so through LaunchBar so I can search the tags easily;

  3. I have a very specific set of broad-based tag groups based on my Areas of Focus, which makes remembering them easier;

  4. I have a very specific naming convention that serves as both a nemonic and a search mechanism (e.g., all my critical tags start with an exclamation point-- !outlines, !memoranda, !template; etc.); and

  5. I have a list of all the tags that I use, which I scan through one a year as part of my annual review.

If that appears complicated, it is not. I spend almost no time tagging files or thinking about tags. Designing the system was painstaking and took time. But that work has paid off with great dividends and now I can find and access files quite swiftly. This is why I’m so eager for iOS and iOS file providers (Dropbox, I’m talking to you) to implement tags more effectively.

1 Like

I asked this in another post, but wondering if anyone has a recommendation for a app to help with tagging?

@iPersuade has some suggestions. I would recommend them, too:

  1. Tagging can be a pain, so doing it automatically has its charme: use Hazel for that if possible.

  2. Applying tags manually can be done with LaunchBar but also… with the Finder (just select a file, hit command - I and enter your tags in the tags field. I also use Leap, which is an awesome way to browse and manage files.

I am a little confused regarding your post in your second topic about tags. I think there are some answers to your question. :slight_smile:

Actually, the exact same apps have been mentioned:


If you want a brief explanation of why Leap.app is “awesome” (to quote @Christian) for helping with tagging, I recently provided one in this post in response to “How and why tagging needs to be improved on macOS and iOS”.