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Mountain Lion’s New File System

Apple has been working on its file system and with iOS it had almost killed the concept of folders—before reintroducing them with a peculiar restriction: only one level! With Mountain Lion it brings its one folder level logic to OSX. What could be the reason for such a restrictive measure?

Classic folder systems don’t perform too well. One reason is that organizing folders is engaging in the tiring discipline of information architecture. Information architecture is hard brain work. Just like a chess problem, it seems obvious once done, but takes considerable mental energy to figure out a clear and simple information architecture. And mainly, you just don’t want to do it all the time. Tying folders to an app and reducing them to one level could solve a lot of these problems.

Folders-in-folders don’t work

The folder system paradigm is a geeky concept. Geeks built it because geeks need it. Geeks organize files all day long. Geeks don’t know and don’t really care how much their systems suck for other people. Geeks do not realize that for most people organizing documents within an operating system next to System files and applications feels like a complicated and maybe even dangerous business. Remember that autoexec.bat file?

Folders tend to grow deeper and deeper. As soon as we have more than a handful of notions, or (beware!) more than one hierarchical level of notions, it gets hard for most brains to build a mental model of that information architecture. While it is common to have several hierarchy levels in applications and file systems, they actually don’t work very well. We are just not smart enough to deal with notional pyramids. Trying to picture notional systems with several levels is like thinking three moves ahead in chess. Everybody believes that they can, but only a few skilled people really can do it. If you doubt this, prove me wrong by telling me what is in each file menu in your browser…

Folders-in-folders are hard to deal with. Just as physical folders-in-folders are prone to creating a mess, digital folders-in-folders represent a steep mental hurdle for most of us. Most people don’t want to bother with folder structures. They get confused when they’re forced to deal with settings in a text editing application. People expect things to just work.

Even geeks can’t handle folders in folders

I am a geek myself, and even a specialist in organizing complex clusters of information, but my own file systems always sucked. Picture this: I have a degree in philosophy and have worked for almost 15 years as an information architect. I enjoy playing chess, reading Kant, and thinking about the correct order and hierarchy of words all day long and yet I hate, always hated, and always will hate thinking about organizing files. I just want them out of sight. I used to blame that on my laziness. But maybe it’s not just that. Thinking about how to deal with files prevents me from working. And this annoys me.

Some might argue that the reason why I hated naming and organizing folders on my computer was not in spite but because I am an information architect. As an amateur you might still believe in the perfect order of your words, the perfect philosophical system, the perfect file system.

The more experience you have dealing with notional systems, the more you know that there is no perfect information architecture, but only better or worse compromises. And making compromises is tiring.

The beauty of search and sort

It is possible to fill books with how horrible iTunes is, but finding a song among 1’000’000 in there works incredibly well. Without folders. How come?

The iTunes music library was Apple’s first step into a new file system paradigm. And besides all the mistakes they made with iTunes later on, they solved the basic problem: How to organize thousands of files without folder system. The solution was search and sort.

To find one song among a million, all you do is type in either the band, the album or the song, and sort the list accordingly. It takes no more than a couple of seconds to find what you are looking for.

If you prefer to find your music through the iTunes folders than through search and sort, then, of course, you are the file system king and you don’t need a better way to organize your files on a computer.

Seeing how well the file system worked, Apple decided to integrate the search and sort paradigm step by step into the core interaction of the finder. Search became the new finder.

Default folders help

I was relieved when Apple introduced default content folders in the left side Finder panel:

OS X default folders

The default content folders are: Documents – Downloads – Movies – Music – Pictures. The choice of those categories, as obvious as it may seem now, are also based on a series of compromises (Do we need a texts folder? A “Work” or “Private” folder? Are Photoshop “documents” not often “Pictures”?), but they are all pretty good compromises and adding a folder is easy. I don’t know about you, but before Apple introduced the default folders my document filing system was not nearly as obvious.

Curious to see how well they worked, I dropped my intricate file structure and tried to just use the defaults (with the additions of “Sites” and “Dropbox”). Putting everything into “Documents” freaked me out—it took some bungee jumper’s deep breathing. I’m not even sure if I can find my files quicker now, because I’ve been using Spotlight for this so my workflow didn’t change. However, what matters is I don’t need to think before putting a file away anymore.

Not having any more deep folder structures is generally a big relief. But it still makes me nervous. Enter Document Library.

The Document Library

With the introduction of Mountain Lion, Apple is about to make a major change to its file system. Your files will be tied to the app they were created in. Each application comes with its own little file browser, the Document Library:

Mountain Lion’s Document Library

The Document Library has its pros and cons, and, like so many tech people, I was quite skeptical at first. Not about anything specific, just skeptical in a general, dickish way.
Geeks think in our own little boxes. If one comes up with a new pattern for a common interaction, others will naturally be generally skeptical. That’s usually a healthy attitude for usability issues. But that’s not the real reason why geeks are skeptical. It’s because we are smart asses. We are the people that put salt and pepper on the pizza before trying it, because we just know best.

I was convinced that the Document Library is going to be like those annoying templates we never use in Word or Creative Suite. Template choosers feel like old Flash splash screens: nothing but an annoying hurdle for noobs.

But not in this case. What makes the Document Library better than a template chooser is iCloud, with its one level folder structure. The problem is that the concept is not obvious enough. Yet. We know Apple—they will substantially invest in explaining how to use it with ads. They’ve been doing this for years now, and it’s one of the reasons why Apple products are perceived as easy to use.

I am not sure I’d like the Document Library and iCloud’s new file system paradigm if I hadn’t been forced to understand it. I had to as part of developing iA Writer. Getting our heads around how iCloud is supposed to be used, the following three arguments killed my skepticism:

  1. I don’t need to type file extensions into Spotlight any more. In general, documents belong to an app. While there are often several apps that can use the same document, we usually have a preferred app for each document type.
  2. I don’t need to drag documents into the app. I can navigate from app to app, and handle the documents right there.
  3. I don’t need to put files away. The OS does it all for me, and my documents are always at hand in the app that they belong to.

These are all simplifications in the file handling that might go unnoticed to the amateur, but they are substantial simplifications—as long as the user accepts the new paradigm.

That paradigm change alone would not suffice to make file handling easier, because there is still a major problem: getting files from one device to all your devices. Enter iCloud.


iCloud makes sure that my documents are always on all the devices I use. In real time.

Having all documents accessible without sending them via e-mail gets rid of a stressful question: where is the latest version and what is it called? This, in combination with the OS X Versions feature, is a giant leap forward in cross-device file management.

iCloud is mind-blowing. Or more accurately: iCloud would be mind-blowing if it worked 100% of the time. Which it doesn’t. It’s more like 99.9% of the time. This is not good enough for a core part of a new file system component. With over 400,000 customers, this keeps me awake at night. 0.1% of 400,000 is 400.

Now, if you scale that to the total number of Apple users, you’ll see why Apple does not yet fully support iCloud on all its own software. I fervently hope that Apple squashes these bugs.

In Apple’s defense, this is a brand new, highly complex technology, and it is continually getting better. We’ve found the latest “one level folders” change to be a major improvement.

On the surface it’s only a file system with folders, and technically they’re not even real folders (but that’s besides the point). But in practice, it is real-time syncing of files and folders across all your devices, and technically this is a big deal. Here’s an example to illustrate why this is tough:

Imagine that you have a document open on both your iPhone and your Mac. Now change the name of the document and put it in a folder. Let’s up the ante and rename the folder. How is the Mac going to know that the open document now has different name, and is in another place which also has a different name? Yet somehow it works (most of the time).

1-level Folders in iCloud

As a developer of iCloud-powered apps we had to quickly work out why on iCloud we are only allowed one level of folders. Why the restriction? If you’ve made it this far it’s quite clear. They wanted to avoid the folder in folder conundrum and guide the user to use a simple structure.

iA Writer on iOS: File System

Folders are not a feature that beginners muddle through but pro users require. No one can deal with deep folder structures. Our brain is simply not built for them.

On the other hand, a reduced one level structure is very easy to handle. Here is what I came up with for my own folder structure in the iCloud Document Library:

  1. Notes
  2. First Drafts
  3. Edits
  4. Archive
  5. Trash

For me these are:

  1. Quick thoughts, funny things, random sentences
  2. More detailed sketches of thoughts
  3. Texts that I am currently working on
  4. Published texts
  5. Things I’m not ready to fully erase yet

Having a long list of files per app works well enough, if you have good search and sort functions. So, pragmatically, you don’t really need folders. But…

Having a basic structure that mirrors our mental model, such as (for me) the editorial stages documents go through, is still a big help. With a basic file structure, the files always seem in the right place. And that is the real benefit of folders in an operating system.


Realizing that deep folder systems only create chaos, I went with Apple’s default folder structure, and located files via Spotlight using document extensions.

The Document Library removes the need to narrow your search using extensions, and the need to think about where to put your files.

The ubiquity of iCloud and the Versions feature removes the need to manually version files using different file names.

The iCloud Document Library folders, restricted to one level, guide us to use a simple hierarchical system that mirrors our mental model. This makes them easy to understand, gives us peace of mind that the files are in the right place, and relieves us from our OCD compulsion to over-organize.

We need folders. More for our peace of mind than for pragmatic reasons. We like to know that things are in the right place. Few people can think three chess moves ahead, and maybe even fewer people can picture notional hierarchies that are deeper than one level. In spite of the outraged geeks that will hate Apple for being this authoritarian, it makes a lot of sense to restrict the folder depth to one level for geeks and casual users alike. We need folders, and we need folders in the cloud, but we don’t need folders in folders.

All this will be for naught if Apple doesn’t succeed in explaining why the new file system works like it works. But if Apple is good at one thing it’s marketing.

PS: Why not just use Dropbox?

For those who prefer Dropbox and cite it as an example of how to Do Things Right™—Dropbox is great. At iA, we use it as our internal file system. An amazing service, but…

  1. Dropbox does not allow you to access the same document from different devices. This makes syncing a lot easier.
  2. Dropbox is a couple of versions ahead of iCloud
  3. The Dropbox API has its own (sometimes quite bad) hiccups

Remember that if you have problems with iCloud (or Dropbox for that matter) it doesn’t mean that everyone is having the same problems. We are pretty sure that Apple is going to find and fix the remaining problems. Why? Because they have to. Without iCloud the whole new file system paradigm goes down the drain. The clock is ticking.

PS2: Folders on iA Writer for iPad and iPhone

At first it seemed iCloud wouldn’t have folders at all. So we built iA Writer’s file system around the initial no folders concept. Then Apple introduced folders, but only one level deep. When this happened, we put all of our energy into implementing that strategic change into our iOS apps as soon as possible. Why?

  1. The Document Library in Mountain Lion allows you to create folders. These folders need to be mirrored on iOS, or the folder structure is destroyed every time you access iCloud using your iOS device.
  2. Folder syncing between OSX and iOS needs a lot of debugging. If you don’t have folders on your iOS app the files in folders will not be visible.

In other words: The Document Library on OSX is almost useless, if your mobile iCloud apps don’t support folders.

iA Writer for iPhone, iPad, and Mac

Update: I hope that you realize that…

Mac OSX Lion still has the normal file browser. What happens with iCloud is a direction Apple OSX is heading into. But it’s not forced upon you:

Use Mountain Lion and its built-in apps like TextEdit and Preview for a few hours and it is very clear that this is how Apple wants users to deal with documents and app content. It’s a radical change from the nearly 30-year-old file-system-centric approach to data management on the Mac. The old way: go to the Finder, find the file you want, and open it. The new way: go to the app and open the document from within the app. Conceptually it works just like iOS—your files aren’t in the file system, but rather “in” the app you used to create them. This is the future, but Apple isn’t forcing it upon us. The feature is prominent, yes, because Apple wants us to use it. But it is far from mandatory. Don’t want to use iCloud document storage? Then just keep on managing your files exactly as before. Apple’s not dragging us to the future; they’re enticing us to walk there on our own. —Daring Fireball

Some people mentioned that professionals need folders for client projects working in a team. I hope you don’t organize your team repository only on your own machine. Mountain Lion is not going to replace GitHub or whatever you use to organize your client projects (we use GitHub and Dropbox). iCloud is for personal use, it’s not a team work file system.