Dilemas of organizing on new Mac

I’m a Mac idiot. Worse, I’m from the PC world and I tend to overanalyze things. I say I’m a Mac idiot because while I’m far from new to computers, I’m new to Macs. This probably makes me fairly dangerous to my poor unsuspecting Mac.

I need to organize files. I know there are a thousand Mac forums (can anyone recommend their favorites that are helpful to newbies like me?), but everyone here has always been so delightful and helpful, I thought I’d ask your opinions first.

Smart folders? Labels? Leave everything in current locations or make folders like I did on the PC? What works for you? There seems to be so many options with the Mac that I’m overwhelmed - Gah!

My main concern is for my writing. For my fiction writing, I could make a folder called Writing, then make separate folders for each novel or short story within it. But what about query letters, the synopsis, crits, agent lists, etc? Folders, none, labels? My PC file system is huge - spindly. I need a better method.

Why must I be a geek and a writer? LOL!

Spotlight, the Mac search tool, is pretty good and can save you from yourself when necessary. You’ll still want to organize things a bit, but it’s not the end of the world if you don’t.

I organize files into folders by client or project, with subfolders for administrative stuff vs. the project contents. I’ve found that it’s easiest to keep the hierarchy as flat as possible, so I don’t have a “writing” folder. I also keep application-specific packages – like Scrivener projects or DevonThink databases – at the top level, even though they might be related to particular projects. I’ve found that makes it easier when things turn out to be relevant to more than one project.

Some people swear by them, but I use labels and smart folders ad hoc for special situations, not as my main structure.

Hope this helps; welcome to the Mac world!


There are ways of doing this with smart folders, spotlight comment metadata and so on, but to be honest, I just use folders. Lots and lots and lots of folders, with up to ten levels of heirarchy in some cases. It sounds like you’re using a similar system on the PC, so I’d just stick with that if I were you.

A few tips and tricks that may help organise it a little better:

  • Column view is most useful when dealing with a large taxonomy structure

  • You can navigate through column view using the cursor keys

  • You can set a window to “always open with” the current view type by pressing cmd-J while in the open folder (so set a folder to view as columns, then press cmd-J, check “always open in column view” and voila)

  • Prefixing your folder names with numbers can be useful for maintaining their position (e.g. my own writing folder is called “1 Writing”, which forces it to the top. Folders that contain previous drafts are often called “Z Old Versions”, which forces them to the bottom)

  • Type a letter or number, and the first folder whose name starts with that letter/number will be selected

Since it appears you were well-organized on the PC, why not just replicate your folders on the Mac? You may do that with the Migration Assistant, putting the folders in the Documents folder.

Apple makes it easy to switch from PCs. Hundreds of video tutorials are available on the main Apple web site: apple.com/mac/
and especially useful for you is Switch 101; apple.com/support/switch101/

Like Katherine, I rely on Spotlight to locate files and use color labels or smart folders only rarely. Both DevonThink and Scrivener are excellent tools for keeping project data and drafts organized.

The interface metaphors in a Mac still emphasize office standards: desktop, folders, and files; but the modern way to go is to think of your data as a “cloud” and just supply “tags” to the pieces, so you can find them quickly. Look on this forum for “tags” and “tagging” and you’ll find much discussion of software that enables that process.

I agree with the general advice given here so far. The Mac has a lot of nifty tools for finding and organising your data, but when it comes down to the actual human level organisation, good old folders remain the best way to do things.

My home folder is kind of set up the way I saw it in a blog on organising, but with a few personal modifications. I have a folder called Archive which is where I store everything I’m done working on, and things that I’ve collected. Software PDF manuals, ebooks, archived web pages, all of that stuff. My archive is organised roughly by descending life categories. There is a section for writing, a section for software development, documentation, and so on. The reason for putting this in a separate location than the system provided Documents is that, as with “My Documents” on a PC, lots of programs tend to trample in that directory and automatically store data there. Since everything I have is carefully organised, I’d rather not have other programs disrupting that without my express permission. So I just ignore Documents altogether.

I also prefer to keep things organised by project and category rather than media type. Consequently I don’t really use the system provided folders like Pictures. I’d rather just store media that is relevant to a project with that very project, in the Archive. Then I know where everything is, and structure is not duplicated in multiple media-based hierarchies.

Then I have a Working folder on the same level as Archive. That is just what it sounds like. Things in progress: Everything from two-minute projects to projects which will take years to finish. Lately I’ve been using DropBox, and it has in most regards become my Working folder. Dropbox keeps all registered computers synchronised with one folder. So that means my current projects are up to date no matter what computer I’m sitting at.

There are a few other minor folders in my organising philosophy. Downloads, Outbox, and Pending. Downloads is self-explanatory, Outbox is where I dump things that are going to other people or web sites, and Pending is just a collection of aliases (Shortcuts in Windows terminology) to projects in Working. Since Working contains everything I am actively doing that isn’t finished yet, I find it efficient to also have a separate collection of immediate or high-urgency work items. Note it is all aliases though. All physical files in progress stay in Working. I’m just storing “bookmarks” to these files in a convenient place.

I also use the “prefix” method on my project folders, but I just use a simple numeric date and time stamp for this. This has two primary advantages: 1) I can know roughly when something was created just by looking at this number, and 2) I can see when it was created in context with its siblings by default sort by name. Consequently, the date stamp is in a descending pattern, with years at the front and time at the end. Sometimes I delete this once I archive it. It depends on the nature of the project, usually.

Now for some Mac specific stuff. I use a neat little program called Hazel (also discovered via this blog) to keep some of the more temporary folders tidy. Downloads and Outbox are ruthlessly culled. If something hasn’t been touched in three hours, it gets deleted. This way, I never have to worry about these folders getting cluttered with old stuff I never bothered to sort, and it forces me to sort on a regular basis. Everything stays organised. There are no “misc” or “temp” folders on my system! I also use Hazel to track the age of projects in Working. I use labels for this. Items which have been there for 30 days get a blue label; after 90 days a yellow label; 180 days orange; and 360+ red. At a glance, I can look at the Working folder and see how active things are. Whenever a file or folder is edited the label gets reset. I can also identify when a project has died due to inactivity. Perhaps I never finished it, but perhaps I never will finish it because it became obsolete or I’m no longer interested in it enough to continue. Might as well archive it at that point. I go through Working on a weekly basis and sort finished projects to the Archive. This keeps that area clean and focussed.

Some people might want another top-level folder for ongoing projects which will never end. I do have a few of these, but as of yet, not enough to consider them as cluttering the Working folder.

Even somebody highly organised like myself sometimes forgets where a file went, or more often where some content went. I’ll often remember a phrase of something but not the file name, and Spotlight comes in very handy for these events. But to be perfectly honest, I very rarely use saved searches, spotlight, or any of the add-on third-party tools for making these more useful. I’ve found that the above described system is so intuitive to me that I rarely need extra help in finding things. It’s nice to know the Mac comes equipped with tools for organising, but for the most part, I just stick to files and folders.

Back when Spotlight and Saved Searches came out, there was a lot of talk about single-folder file dumps, tagging, and so on. But in my experience, these models just don’t work too well on a file system. There are simply too many files for one human to tag them all in such a way as to provide meaningful search results. Programs like Leap attempt to help solve this by providing a second layer of organisation above the folder+file organisation, but like I said, I’ve never really found a good use for them. They would all take many days of setting up, and in my smaller scale tests I found I always gravitated toward direct access.

One other tool that I use is called LaunchBar. Trying to describe it (or its free companion, QuickSilver) in a sentence would be difficult, but specific to this conversation: I use it as a way to access and manipulate nearly everything by keyboard. No mouse, no hundreds of Finder windows. I can get at a download in about two key-strokes average, and I can sort items very rapidly using it’s ability to copy, move, and alias files. I prefer this method because it lets me slice right through a hierarchy like a knife. In a sense, it doesn’t matter how much clutter exists (though I still keep things clean), because you can quickly isolate the path with a few keystrokes per directory. Since it “learns,” frequently used paths become one keystroke combinations.

Heh, me too. Ethan Schoonover’s (pre-OmniFocus) screencast on taxonomy, perchance? :slight_smile:

That would be the one. :slight_smile: It’s too bad it has languished in the past year.

Tagging can be a useful supplement to traditional folder hierarchies and direct access via Finder/PathFinder, but it’s not necessarily for everyone and file system tagging is the most difficult type to setup and get working.

For people who want to try tagging, I think the key to getting a tagging system to work is to tag things once (as they are created), and to only tag old stuff as you find it and work with it. I won’t say more than that (since I haven’t tested this hypothesis yet myself; I’m still using a traditional folder setup for file system navigation/browsing), but I think tagging can be a good supplement to folder hierarchies once you get into the flow of it. Leap for browsing and Default Folder X for Spotlight comment tagging as you save is probably your best bet.

Another good reason to keep a separate “Current” or “Working” documents folder is for easier backups. I want to make sure that the documents I’m currently working on are backed up daily – which is reasonably easy now that I’ve upgraded to Leopard and have Time Machine. However, Time Machine only backs up to my hard drive. If my building burns down or becomes inaccessible (as happened to a lot of lower Manhattan residents after 9/11), I also have a backup of my recently edited/pending documents on a flash drive attached to my keychain, something I can be sure I’ll always have on me. Still, it doesn’t have much space, so I certainly don’t need a backup there of the whole Documents folder (which also contains archives of all my writing – I have that backed up elsewhere, and it only needs monthly updates, as old projects “graduate” to the archives).

I could use Drop Box of something similar to synch this stuff online, but I only use one computer, so that seems like overkill.