The other day, whilst sitting in the waiting room of a doctor's office, awaiting the inevitable bad news to come down the pipeline (you're dead, you're dying, no that rash can't be treated), I attempted to do something daring with my iPhone 3GS. I attempted to work. I say attempted, because what dawned on me -- separated from my laptop, a netbook, or any viable computing system -- was that I couldn't really get much of my work done on Apple's bundle of joy. It wasn't the first time I tried to get work done on my phone, but it was one of the first times that I really thought about how frustrating the experience is. What follows is my heartbreaking tale of staggering lameness. Or staggering tale of heartbreaking lameness. Your pick.
Before I even got to the "work" part of my experience, I realized I had serious problems. AT&T's service is never anything to write home about in New York City (in fact, it's usually embarrassingly bad), but I found that my 3G connection seemed especially weak in this Manhattan doctor's den. Oh, I had five bars all right, but trying to load just the iPhone-formatted version of Engadget tested my will to live. After nurses denied my requests for assisted suicide, I resigned myself to dealing with the network issues. Honestly, a lot of what I do during the day (namely, hanging out in a chat room and commanding the team to help me pick the perfect pizza toppings) doesn't require the highest-test connection -- though I certainly put pedal to floor at times.

So, stoically accepting the fate of thin 3G, I set about firing up the apps I would need to actually tend to Engadget. First up, I required an IRC session. That's no problem, because the App Store is filled with useful tools for chatting with good buddies. I prefer Mobile Colloquy, so away I went, happily bounding into the Engadget chat room to direct the editors and get the latest gossip about Gyllenspoon. Of course, it took an exorbitant amount of time to actually connect, but once I did it's a reasonable experience... save for one big issue. The iPhone keyboard truly sucks if you're trying to type words it might not be familiar with. You know, like tech terminology which isn't exactly part of its native dictionary. Additionally, typing quickly during a conversation with lots of people is severely hampered by the inaccuracy of the on-screen keyboard.

I would have left it at that, but my work requires that I use a bunch of web tools, look at lots of news sites, and have a feed reader open... basically, things that would require some level of multitasking. Imagine the frustration of having to constantly break the connection in chat to go look at a site or work on a post. It's frustrating, let me tell you. The idea of jumping into and out of applications -- of having to actually quit an app to move to another one -- is

"We don't work like this on our computers -- why does Apple think we want to work like this on our phones?"

an incredibly outmoded and foreign idea in 2009. Additionally, the email experience on the iPhone is brutal -- and to get anything done in a day as Editor-in-chief of Engadget, you need your mail. As a Gmail user, the way the native iPhone mail application handles messages is counterintuitive at best. Google presents a lovely browser-based solution for email, but it is markedly hampered by the browser environment itself. It's slow and inaccurate to navigate, though obviously better if you need to bounce between an open page and your mail. Funnily, the Safari experience provides better multitasking than the phone itself. Adding insult to multiple injuries, the system of notification for SMS, calendar events, or even push IM messages (which still gives you limited options) is intrusive, productivity-stalling, and frankly upsetting. It doesn't aid productivity if you're constantly being hammered with pop-ups.

The whole, painful experience set me thinking. Is this really what Apple wants me to be doing with my phone anyhow? The company has added lots of features -- like decent Exchange support -- so that its phone will appeal to enterprise and business users, but can these users really get what they need out of the device? Basic functionality, like calling people, email, and certainly document editing still feel inelegant and clunky due to the onscreen keyboard, and the lack of multitasking makes moving around through those typically important tasks difficult to say the least. The experience on an Android device, S60, the Pre, a BlackBerry, or even Windows Mobile just makes more sense. Let me say that again: those experiences make more sense. Now I'm not saying the execution of those experiences is better across platforms, but the philosophy of letting users multitask is more natural to us. The iPhone doesn't even have a method for switching between recently used or favorite applications.

We don't work like this on our computers -- why does Apple think we want to work like this on our phones?

Well that's the thing -- maybe they don't really care about how we work. Maybe they don't want us to work at all. If you take a look at the App Store, it's fairly obvious where the cash is going -- and it's not to productivity or enterprise apps. Where is it going? To Doom Resurrection, frankly (sorry, not for me -- I hate games on rails). At the end of the day, it's nice to stick the "we love business users" line into your PR, but it's quite another thing to make it real.

Keep this in mind: I'm not a Wall Street lifer -- I'm a guy in new media who needs to get things done. I should be part of Apple's target market.

So, what's the fix here? Well for Apple, the solution is simple -- the virtual keyboard problem is annoying, but not a deal breaker necessarily. The lack of multitasking is. The fact that Apple won't let end users decide to run down their battery with these dangerous, experience-ruining background tasks is galling, but the fact that the company doesn't seem to recognize how important the concept is is even worse. Giving users the option to select even a few apps to juggle would alleviate this problem instantly, but you've still got the hurdle of notifications which are difficult to manage, and an email platform which feels woefully behind the curve. Until the company finds some new paths to beat in those departments, the iPhone -- for all its apps and all its uses -- still doesn't hit the sweetspot for a lot of users who need to work.

For me? Providing this heart holds up the way doctors say it will, I'll be keeping a keen eye on Android developments. But seriously guys... put a keyboard on those things.

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Editorial: Taking the iPhone 3GS off the job market