Rainblog

Our office is full of iPads, but it looks as if for one new owner the honeymoon is already over. Our sales director would really like to take a Keynote presentation from his desktop to his iPad (where he has an iPad version of Keynote), but the iPad doesn’t want to make it easy for him. And the language he’s been using is terrifying.

Apple’s suggested methods for getting a file off your desktop and onto the device apparently include “mailing it to yourself”, “putting it on a website”, and using iTunes file-sharing. The first two options smack of desperation. As for the last one, if you’re the kind of person who says “I need to move this file from here to there, so naturally I’ll use my music player software”, your mind must work in a very strange way.

For a company that prides itself on design and usability, Apple has some strange blind spots. I’ve written before about the bizarre issues involved in syncing an iPod, where every application ends up inventing its own method for sharing data with the desktop. The fact that the iPad launched without a good, transparent way of moving data between the desktop and the device is odd enough, but it may even be a deliberate choice. Apple recently went after the makers of the ebook reading software Stanza and GoodReader, forcing them to change their apps so that they could no longer browse the device’s filesystem for content transferred there using a USB sync utility.

It’s still not clear why Apple insisted on the change. The official statement says that Stanza violated the developer agreement by using private APIs. Insisting that developers use only public APIs is fair enough, but Apple could easily have made the filesystem accessible through a public API. If they don’t, is it because unrestricted filesystem access might permit piracy or does Apple feel that users need to be shielded at any cost from the mind-destroying horror that is a modern hierarchical filesystem? Has Apple chosen not to simplify moving content between devices as a matter of policy, or is it because they haven’t yet found a good, user-friendly way to manage the process?

During my time at Sony, I once saw an informal demo by Jun Rekimoto, a man who probably comes up with a dozen brilliant UI solutions before breakfast every day. At one point in the demo, he showed how to transfer a file between two computers by tapping on the screen of one with a lightpen, then walking across the room and tapping on the screen of the second. Of course the file wasn’t really “in” the lightpen; the transfer took place across the network, and the business with the lightpen was largely sleight of hand. But it was also a brilliantly simple metaphor that was instantly understandable. You pick up the file here, you put it down over there.

Apple needs to get over whatever odd scruples are holding them back and make data transfer between devices work like that. You need to be able to walk up to your desktop machine with your iPad or your iPhone in hand, and move files between the two with a single, simple motion. The whole business should just work - like Jun’s demo, and like everything else on the iPad - with a simplicity and obviousness that could easily be mistaken for magic.

But in the meantime, I’m afraid you’re going to need to keep mailing files to yourself. 

One of the things that used to drive me crazy about working on Windows boxes was that there were so many different ways to do the same operation. In most applications, copy and paste was done with control keys: Ctrl-C, Ctrl-V. But the indispensable putty followed the X-Windows model: left-click copies, right-click pastes. The equally useful Trillian used a hybrid; left-click copies, Ctrl-V pastes. And I never did quite figure out how to copy and paste in DOS boxes, but I think it involved the entrails of a chicken and a signed authorization from the Pope.

Any time you find yourself doing the same basic operation four different ways, something’s broken.

Which brings me to the iPod/iPhone.

I finally cracked and bought myself an iPod Touch, as a replacement for the elderly Palm Zire 71 that I’ve been carrying everywhere for the last six years. The Zire, incidentally, still works fine, but for a variety of reasons I felt it was time to move on. I’m now in what you might call the ‘honeymoon period’ with the Touch, if by ‘honeymoon period’ you mean the span of weeks in which you discover that your new bride is an incredibly flexible contortionist who has read every page of The Perfumed Garden, but also smokes foul-smelling cigars in bed and wakes up at four every morning to sing baritone arias from German operas at the top of her voice. In short, there’s good news and bad.

One of the glorious things about the Palm was the ease of syncing the device with your desktop. You sat it on its cradle, you pushed the button, it ground away rather slowly, and you were done. There were quirks but, by and large, Palm really delivered on the promise of no-brainer bidirectional syncing.

The iPod is a different story. To coin a phrase, “how may I sync thee, let me count the ways”.

Generally, syncing data from Apple’s built-in applications - Address Book, Calendar etc - is simple. You hook up the iPod, and iTunes syncs things for you. It’s when we move on to third-party apps that the insanity kicks in.

Two apps that I added to my iPod immediately were SplashID and SplashMoney. I’ve used them so long on the Palm that there was no question that I’d buy the iPhone versions when I made the switch. They both sync wirelessly with the desktop: you start the desktop app, then open the corresponding app on the iPhone and press the sync icon. Pretty straightforward.

I also knew that I wanted OmniFocus on my iPod. I’ve been using it on the desktop for a while, so the idea of seamlessly syncing to-do lists to a portable device was very appealing. OmniFocus actually offers a bunch of ways to sync. You can do it in the cloud, through MobileMe or WebDAV or you can do it over wi-fi in the same way as the Splash apps: the desktop app runs as a server, and the iPhone app connects to it.

I’m an outline junkie, so I had to have an outliner. Until Omni Group delivers OmniOutliner for the iPhone, the best game in town looks to be CarbonFin. The way you sync with the CarbonFin iPhone app is as follows: you sign up for their Outliner Online website, which lets you upload outlines from your desktop in OPML format. When you hit the sync button on the mobile device, it pulls your outlines down from the web. A bit clunky, but it works.

A few weeks back Hog Bay Software were giving away copies of WriteRoom for free, so naturally I grabbed a copy. Like CarbonFin, WriteRoom offers a website-based syncing method, with the interesting quirk that you actually use your Google username and password to log in. It also offers syncing over a local wi-fi network. In this case the iPhone app acts as a server, and you use Safari on the desktop to connect to it. My first thought when I realized this was “Awesome, my mobile device is running a web server.” My second was “Wait, what the fuck?”

GoodReader uses a similar mobile-device-as-server model. It also offers direct web download. And it supports USB-based sync, using a separate desktop application that you have to download from a partner site. Most of these methods are more or less straightforward, but each one is presented and documented in its own way.

Finally, there’s Kindle for iPhone, which uses something called WhisperSync, Amazon’s proprietary name for what appears to be another web-based syncing model. Amazon figures you don’t need to know the details and they’re right, but it’s a little unnerving because you don’t know exactly what it’s doing and when. Is this book on my device, or is in the cloud? Amazon thinks you shouldn’t need to know or care, which is fine if you live in a world of permanent ubiquitous connectivity, but may prove problematic in real life.

So, half a dozen apps, a dozen ways of doing things. And here’s the real kicker: remember that one-touch sync that Palm had? You can forget about that. To sync my new iPod, I need to start iTunes and SplashID and SplashMoney and OmniFocus on the desktop, fool around on a couple of websites, and then run all the corresponding iPod apps, one after the other. As the man said, this ain’t rock’n’roll, this is genocide.

In an ideal world, there would be one method by which all apps (including third-party apps) could sync their data over USB, one method by which all apps could sync data over wi-fi, and one method by which all apps could sync data through the cloud (Apple would want to make this MobileMe, I would want it to be possible to use a private WebDAV server instead). Instead of having to manage each app individually, there would be a single uniform interface where the user could kick off a synchronization. But in bizarro iPod world, everyone is free - or obliged - to invent their own way of doing things. The result is anarchy.

My feeling is that Apple dropped the ball on this one. I haven’t read the developer documentation, but the sheer number of different approaches taken by the third-party developers argues that they never offered the necessary underpinnings that would allow uniform solutions. For a company that has long prided itself on promoting ease of use by design, that’s a pretty grievous failure.

Suddenly, the Windows copy-and-paste clusterfuck seems modest by comparison.