The other day, I ran into a bit of difficulty with getting my daily blog post up. I’d written the start of a post on my iPad, with the intention of finishing and polishing it up in the morning, possibly on the subway on the way to work. Imagine my surprise when the file, which was stored on Dropbox, utterly failed to appear on my phone. And on my work computer. And everywhere else. I addressed this problem by simply writing the rest of the post in Drafts, which synced back to my iPad, copy and pasting the text into the document there, and proceeding with my typical blog workflow. [1] Nothing was lost, thankfully, but the sinking sensation of knowing that something isn’t where I thought it would be brought back a lot of bad memories from the bad days of syncing across devices.

Back in the day when I had a desktop and a laptop, and Dropbox but a gleam in some developer’s eye, I tried syncing a Yojimbo database between two machines. The only supported way to accomplish this was to use .Mac [1], which cost the princely sum of $99 a year. My poor college student self couldn’t afford that. It was expensive enough buying the Mac mini and the iBook G4. So, I found a workaround—an app called SyncTogether, that promised to be a surrogate .Mac for my local network. For a while, it worked, but then it didn’t. Synchronizing became a pain, with pop ups asking me which of two seemingly identical items I wished to keep in Yojimbo. Somewhere along the line, the synchronization database became completely fouled up. Wanting to start from scratch, I dove into the terminal and tried to rm -rf my way out.

The result permanently fouled up any attempt at future synchronization between my mini and my iBook forever. After trying a tool that allowed me to access the desktop Yojimbo database via the web, I gave up on the app entirely.

Comparatively speaking, Dropbox farting and failing to move files around was a mere annoyance. After all, I got my blog post finished and out the door. It was a bigger annoyance the first time it happened, trying to share an important work-related file with my bosses, falling back to e-mailing the file as an attachment. Dropbox usually works so well and so seamlessly that when it fails, it feels like a betrayal. Meanwhile, when the various Apple sync services fail to work, we brush it off as “Well, what did you expect. This is the company that gave us iTools/.Mac/MobileMe.” For what it’s worth, iCloud hasn’t failed me yet, but I don’t use it for document sync. That’s what Dropbox is for. It syncs the text files I live in, the TextExapnder snippets that help me work faster, and the 1Password database that I can’t do anything without. [2]

The more reliable something is, the more we come to rely upon it, and the more frustrated we get when it fails, even in a minor way. It’s a danger of this modern, connected life, the digital equivalent of the dog eating your homework. [3] And, that does happen—John Steinbeck’s first draft of Of Mice and Men was eaten by his dog, and he had to rewrite the entire novel from scratch. While writing a fiction piece a few years ago, TextMate, my text editor at the time, crashed before I could save. Attempting to use an iOS note-taking app on my phone nuked my entire Notational Data folder. At least I was able to restore everything from Dropbox’s backup when that happened.

And, thinking about it, with Dropbox letting me recover three years worth of text files makes me a little more inclined to forgive it for failing to synchronize now and then. It really could be much, much worse.