The resolution to own a new iPhone wasn’t entirely an effect of the massive media hype surrounding the launch. I purchased the first generation iPhone in October 2007, and used it for nearly three years. The last year of use was without mobile broadband. The product lust seemed, for once, entirely justified. The decision to upgrade came on the heels of a prolonged and unusually complex evolution of Apple, the iPhone, the iOS (as it’s now called) and the concept of mobile computing.

To briefly focus on hardware, the 2G iPhone I own isn’t my first. Several weeks after I purchased the original model I began to notice three to four white pixels on the display, largely obvious in videos and startup. It seems, in retrospect, that Apple was keen to keep the then small base of iPhone users as content as possible in those first six months — a delayed trip to the Genius Bar landed me a fresh replacement despite being over the initial warranty period. A year later, they happily exchanged a thoroughly worn pair of microphone headphones. With massive international success, I suspect Apple has dropped such a liberal policy on repairs and replacements.

At my time of purchase, the cost of the phone in the US had just dropped two hundred dollars to $400 on contract. Today, the price is half.

Waiting has it’s benefits. It could be argued that apart from applications, the features that make the iPhone worth owning have all been implemented in successive generations. The 2G iPhone was never blessed with video chat, video recording, the 3G data network, MMS, front and rear facing cameras, an adaptable headphone jack, GPS, a gyroscope, push notifications, or a high-resolution display. Each iteration may have seemed fairly impressive, but leaping three generations one doesn’t simply gain new features — you move to a new product. The product cycle is aggressive. Apple has effectively dropped support for the first generation (a mobile device less than three years old) with the introduction of iOS 4.0.

As with most things, I feel fortunate to have witnessed this evolution. I think it’s notable that much of the software enhancement was driven by an explosion in semi-legal third-party application development. In the first six months, Steve Jobs made it clear that web applications were the future, not native apps. Consequently, a few very talented developers took it upon themselves to break into the system architecture, creating the first jailbreak and providing an unofficial channel for souls willing to void their warranty and open an experience Apple refused to provide.

After a few months of shrugging off criticism, Apple released an interim announcement to the effect that a native application SDK would be released in February 2008. It wasn’t until March that the official announcement came, and it was with the caveat that the OS update would arrive three months later, in June.

I intended to travel outside of the US the following month, and the OS at that stage did not allow a user to lock the phone into Airplane Mode while simultaneously turning on Wi-Fi. Intrigued by the encouraging amount of application development following the ability to jailbreak and eager to use Wi-Fi abroad, I leapt at the chance. The iPhone Dev Team had achieved most of the initial software breaks, though I chose the slightly more popular ziPhone application to open my phone. It was exhilarating. I had access to controls Apple had never intended users to see, access to a Finder of sorts and via the Installer app an entire repository of brilliant applications that changed the way I used the iPhone.

Three months later, with the promise of an updated operating system and official applications from a much broader pool of developers, I restored the phone to its original manufacturer state and watched as new applications flooded the app store. A year on, in the summer of 2009 I broke from AT&T, cracked the phone again, and unlocked it to use internationally. Cydia and Icy had replaced Installer, but jailbroken app development had otherwise continued parallel to official development. The phone became a strange hybrid of sorts with increased capabilities.

Jailbreaking each new iOS release has become increasingly more difficult, and as I move to a legally unlocked iPhone 4, there is virtually no incentive for me to return. It will continue as a necessary tool for people looking to unlock their phones, but despite the recent Library of Congress ruling, it feels as if the jailbreaking community has served it’s purpose and isn’t nearly as prescient as it once was.

Next, Dylan’s “Ballad of a Thin Man” from Highway 61 Revisited. What followed? The same, from Before the Flood. As I considered the odds of two repeating versions of two different songs, I’m hit with the live performance included on Bootleg Series Vol. 7.

Uninspired music library — highly intelligent algorithm — random chance?

Present day, the phone is hacktivated and unlocked so I can use it with an Orange SIM card. The immediate result of this is an absent data plan and much of the iPhone’s core functionality (barring the occasional wifi). At first, this seemed like a tremendous loss — no maps or directions in a new city, lack of on the spot dinner recommendations. Gradually however, it struck me as more a blessing in disguise. Forced to write down directions and addresses in a notebook before I leave home, I’m free to take missteps and make new discoveries. As I spend the large majority of my time as a Web Designer circling the internet, there is liberation in knowing that an email or tweet has no way of reaching me when I’m out. In the middle of a conversation, forced with an unanswered question, the dialog continues in an unexpected direction instead of the quick fix of a Wikipedia entry.

I’ve always had a mixed reaction to new technology, a luddite reluctance mixed with an excitement for new ideas. As technology becomes not only intertwined in our everyday lives, but ubiquitous, I think we need to find the line between automating our experiences and keeping our eyes open to the literal moment.