Give me file hierarchies, or give me chaos.

IN “HOW DROPBOX Remains Relevant,” Khoi Vinh explains why Dropbox owes much of its success to subtly faceted, user-focused design:

Even in an age when the biggest operating systems in the world actively eschew file hierarchies, Dropbox is thriving—its service matters deeply to countless users. Why? In part it’s because the company works hard at making file hierarchies useful, that they focus on the outcomes of file management and not just on the files and folders.

Absolutely. Dropbox sweats the user experience details as commendably as it masters the considerable engineering challenges required to reliably sync files everywhere a user may need them.

But there’s another reason Dropbox succeeds. And it isn’t despite its emphasis on old-fashioned file hierarchies. It’s because of that emphasis.


⇛ ALTHOUGH Khoi may well be right that “smart passive management of design assets and working files seems inevitable,” I, for one, do not look forward to the day I no longer have direct access to my files and the ability to control where and how they are stored. To my way of thinking, passive management of file assets is okay for screwing around with iPads, where we’re mainly watching TV on Netflix or obsessive-compulsively checking the popularity of our Instagram uploads. But for real work, and even for passionate hobby work (like managing family photos), give me files and folders any day.

Stay with photos a moment. Consider snapshots. For my money, apps like Photos (and, formerly, iPhoto) that “save” me from the “inconvenience” of knowing where my images are do me no favors. Thanks, but no thanks. Let me save photos where I want to save them, not where the system thinks I should save them—typically on a laptop’s rapidly filling solid state hard drive with minimal storage capacity.

Dropbox, with its emphasis on good old-fashioned hierarchies, is superb at automatically saving one original of each photo I take, whether shot with a phone or a fancy camera. No loops, no duplicates, no confusion. In contrast, Photo’s cloud sync options, designed to spare the user the trouble of thinking, always trip me up. Like when, after syncing my phone to my home desktop computer, I tell Photos to delete the photos I’ve just sync’d from my phone. Photos obeys my command, and then instantly restores the photos to my phone from the “cloud.”

Why would a system expect a user who has deleted files to want those files restored a moment later? In what universe of scenarios can that possibly be what the user expects? [Your system may work differently from mine. Your deletes may stick. If so, good on you. You may have checked a different box in a hidden drawer of a preferences dialog, possibly in the app preferences you can set in the app itself, or possibly in the app preferences you set in the phone’s Settings app, or possibly online—say, in iCloud, or possibly in the iCloud settings in the phone’s Settings app. This is simplicity?]

Because my phone and iCloud restore photos as soon as they’re deleted, my Camera Roll is an unwieldly monster—despite my applying common sense, logic, years of design and computer using experience, and hours of conversation with a rapidly dwindling circle of friends—not to mention the hours I’ve spent scouring the web for hints. The whole situation reminds me of an article I saw on the cover of PC World years ago: “Plug ‘n Play: How To Make It Work.” (Hint: If you have to learn how to make it work, it ain’t plug ‘n play. And that’s kind of how I feel about the current state of passive file management.)


⇛ SYSTEMS designed to relieve you of thinking too often end up forcing you to think, and think, and think, without ever solving the problems their supposed simplicity has created for you. How much easier would photo maintenance on my phone be if Photos, like Dropbox, used file hierarchies? I could solve the problem myself in a second, with the click of a checkbox, if only Apple weren’t committed to chasing a future where nobody needs to know anything about how their computer works—and, as a result, some of us have no clue what to do when the computer doesn’t work quite right.


⇛ I UNDERSTAND that these are difficult problems to solve, and that confusion and frustration are the price consumers pay for innovation that may benefit them in the long run, once all the kinks are out. I’m not anti-innovation or anti-Apple.

But I’m a web person. I like files. I like editing a CSS file without necessarily having to edit an HTML file. I like fixing a problem by replacing a corrupted file with a clean one. Maybe I’m set in my ways, but I don’t consider it a hardship to open a folder or replace a file. I wouldn’t be quite as happy with a web where I didn’t “need” to “bother” writing CSS.

In the same way, I like deciding where files go—saving an image for Project A in a Project A folder, a text document for Project B in a Project B folder (and all of it in Dropbox). I’m glad Adobe Lightroom maintains a picture of my photo folder hierarchy in a sidebar of its interface, enabling me to see where my files live, and instantly choose a group of photos by date (instead of, say, scrolling through thousands of files visually). When it’s time to get dressed in the morning, I don’t throw myself into a giant room full of clothes. I pull socks from my sock drawer and shirts from my shirt drawer. I’ve been doing this since I was five years old. It’s not a challenge.

Khoi ends his excellent Dropbox piece thusly:

Maybe we’re all just set in our ways, but people seem at least resigned, and more likely just plain comfortable with managing their files. It may not be what future workflows are built around, but for working designers, the future is hypothetical, and Dropbox works today.

To which I say Amen. And add the hope that, so long as my career lasts, I can keep using a workflow I find easy and comprehensible.

Don’t make me think.” Absolutely. But, equally, don’t treat me like an idiot. Folders über alles.



Also published in Medium