How Mac experts organize their files

Computers are the ultimate file cabinets. My own Mac stores oodles files of all types—my photos, my music, and thousands of text and Word documents. That said, a stack of papers in my home office’s To Be Filed box could make a grown man cry; I’m afraid the files on my Mac are organized no better. Macworld Senior Editor Dan Frakes literally shuddered as I described how I store all my articles for Macworld in a single folder, with no other taxonomy in place.

The point of organizing your files is to make it easy to find them again. There are numerous approaches to both organizing and then locating files. I set out to discover how experts tackle both tasks.

John Siracusa

Macworld Senior Contributor, podcaster, and verbose OS X reviewer John Siracusa organizes his files “by category, from general to specific.” Mostly. “I tend to use more nesting for things I create myself than for things I get from elsewhere,” he says.

When it comes time for John to find his files again, he uses “the Finder, Open dialog boxes, and the Terminal…about equally.”

One feature he doesn’t use is OS X’s All My Files feature. “I have way too many files for All My Files to be useful to me,” he says. Nor has he yet availed himself of Apple’s new attempts to simplify file organization: “I haven’t started using Mavericks Tags yet, but I plan to.”

While some Mac users I spoke to aren’t overly concerned with where their files are specifically, John definitely cares. He turns to Spotlight only when he “can’t find something the old-fashioned way, or when I want to answer an open-ended question like ‘How many images did I create last month?’”

Speaking of the “old-fashioned way,” here’s how John approaches the Finder: “I mostly use List-view windows sorted by the various dates (Added, Modified, Created), rooted at the top level of some major subsection of my files (for example, my Dropbox or Pictures folder). Selectively disclosing the contents of a few folders within List view helps me work with a handful of deeply nested files without being overwhelmed by all the other files I’m not working with in the same hierarchy, and without requiring constant navigation or multiple windows.”

He relies on a couple of third-party utilities to help manage all his files, too. “I’ve been using Default Folder since the days of the classic Mac OS. I try to avoid system modifications like this if I can help it, but Default Folder is indispensable,” he says. John also added the few files that he opens the most often to his  Quicksilver catalog. That way, he can trigger those files  quickly—and he keeps that list of files very short. “I find this much faster than doing the same kind of search using Spotlight,” he says.

Katie Floyd

Katie Floyd is a litigator and the cohost of Mac Power Users Podcast. She lives by nested folders.

Katie says that she tries “to stick to Apple’s preferred organization method by keeping all my documents in the Documents folder, Photos inside iPhoto, media in iTunes,” and so on. “However, I’ve created a symbolic link to this folder in my Dropbox account…. This way I have access to all my files wherever I go.”

While she’ll occasionally launch a file by name using launchers such as  LaunchBar or Alfred, she says it’s usually faster to dive into her nested folder structure, ‘because I’m very particular about filing all my documents in their proper places.’”

Like John, Katie doesn’t use Mavericks’s tagging feature, “but now that tags are built directly into the OS, I’m more interested in them. So I may in the future.” She doesn’t use All My Files, either.

Also like John, Katie uses third-party utilities to keep her files organized. “I use Hazel to automatically name and file many of my files. I have dozens of Hazel rules set up, but I have several specialized rules set up for my Desktop, Downloads, and Scanned folders so that Hazel will look at these documents to determine what they are, based on their type, content, or other criteria, and will then automatically name and file them for me.”

And Hazel isn’t the only app Katie relies on for keeping her files organized. “I also store many things in Evernote, rather than directly in the Finder. I consider the Finder to be storage for documents and files that I’m working on or may need to edit one day, while Evernote I use more for reference documents.”  This approach, explains Katie, “keeps all these items out of my Finder and cuts down on the clutter.” 

Federico Viticci

Federico Viticci runs MacStories. He likes Hazel, too. “Hazel is the key element of my workflow. Moving files and sorting them is boring, so I let Hazel do that for me with rules for renaming files using variables (such as dates, which Hazel can automatically extract from a PDF) or AppleScript.”

Federico relies on Noodlesoft’s $28 Hazel to apply discipline to his file management: “Like many others, I’m guilty of saving temporary files to my desktop thinking that, sometime during the day, I will clean it up and trash them. It never happens, and for that reason I have created a Hazel rule that automatically removes files that are more than three days old.” Those files are safe to remove, Federico says: “If they’re on the desktop for three days, they’re not that important—it means I’m just lazy.”

Like Katie, Federico relies on nested folders synced via Dropbox. One example: “After moving away from iPhoto, I set up a Hazel rule that runs on my Mac mini server and  automatically sorts photos in Year/Month subfolders in my Dropbox so that photos are available on all my devices.”

Federico also uses a smart strategy to ensure that date-named folders sort effectively: He uses a mixed filename style (like “11 – November”). “In this way, folders are sorted alphabetically, but they retain the readable name of the month.”

Federico puts the folders he uses daily in the Finder’s sidebar for quick access. And like Katie, he stores a lot of documents in Evernote, and uses a keyboard launcher (Alfred) for quickly finding specific files by name.

Like the other experts I spoke to, Federico doesn’t use All My Files. But he’s already started experimenting with Tags in Mavericks. “They’re growing on me,” he says. When he had several files for a project scattered all around his drive, he found it “really convenient to be able to keep [them] in their original locations…and still view them in a single tag screen.”

Casey Liss

Casey Liss is arguably the most famous of the three hosts of Accidental Tech Podcast. But, in his own words, his file storage setup is “pretty unremarkable.”

“I tend to treat the desktop as a temporary dumping ground; files don’t live there for more than an hour or so,” Casey says.

Rather than leave his desktop cluttered with icons, though, Casey has a single folder that files get shuttled into quickly. “Instead of dumping files onto the desktop like most do, I dump them in my Incoming folder. I try to hold myself to keeping files there no longer than a week”—although Casey admits that “currently I have 11 files in there, the oldest of which is about a year old. So, yeah. Room to improve, I’d say.”

Casey makes light use of folder-level grouping in the Documents folder, and stores some documents in Dropbox—”a near-wasteland that would be upgraded to wasteland status if more stuff was there.”

He prefers not needing to rely on Spotlight to find files. “I want to be able to find a file without searching for it…. Thus, I care enough to have at least a vague notion of where something is.” His solution? “I just get files into the broadest container that effectively files it and call it a day.”

He uses neither All My Files nor Tags, though he echoes that now-common refrain: “I intend to explore Mavericks Tags, but I haven’t really found a compelling reason to use them yet.”

What have we learned?

Obviously, there are plenty of strategies you can consider when you’re determining how best to organize your files. But the operative descriptor there is “your”: You need to find an approach that’s all your own—one that you can stick to.

Casey is content to clean up his desktop on his own with his Incoming folder, and he uses the broadest organization scheme possible (like me!). But Federico and Katie prefer to let Hazel handle routine clean-up, and to rely on Evernote for storing certain kinds of less-frequently needed files. John uses many-levels-deep nesting for his files so that he always knows where to look.

As you follow a file organization system that you can stick with, you should always be able to find your files. But if we’ve learned just one thing, it’s this: Nobody except for Federico Viticci uses Tags…yet.