The new mobile office

We all have workflows that we like to keep, as interruptions to them tend to make us less productive. Changing how we work, when well planned, is likely to ultimately increase our productivity, yet in the short term, the time needed to design and implement that new workflow will actually slow us down. Eventually, the new flow will make us more productive, but the transition time is often so painful that we default to not changing, even when we know what we're doing now is not optimal.

I've been preferably a Mac user for about 12 years now, and primarily a mac user for 7 years. I'm so tied to this workflow that when I changed employers just over 3.5 years ago, I made it a point to negotiate what computer I got to use as part of my hiring package. You can think me a diva, but frankly, Windows is a large bag of pain to me and not something I'm willing to agree to without first a large fight first.

With that background in mind, you might be surprised that 10 days ago, I walked away from my beloved Mac as my primary workstation. No, Bill G and Sataya N did not pay me to move to their platform; I stayed in the Apple ecosystem, but my primary computing is now iOS, specifically the iPad Pro 12.9" (second generation). This isn't a change I made lightly or without a lot of heartburn, but it was necessary and has been significantly less of a pain than I expected when contemplating this transition.

My Mac Beginnings

In 2006, my next door neighboars sold their house and the new nearly-retirees who purchased the home moved in during the winter. Come spring, when we all came out of our hibernations, I found out that the wife was a sales rep for Apple. She found out I worked in the technology industry as well, meaning we formed a very quick friendship. About a month later, she showed up on my doorstep, bringing me a Mac Mini to use.

At first, I declined, having just built a new PC in the prior months. For the prior decade+, I had been a Windows user by default, but a Linux user at heart. Microsoft's OS had never made logical sense to me, even though I knew its inner workings well. Linux was the best option for me, even though we had spent nearly a decade with Linux on the desktop being just around the corner. Maybe next year; the year after at the absolute latest.

But I'm curious; so eventually I agreed to give it a try, when I had time, but I'm busy, so it would probably be a while. She didn't need it back anytime soon, so no worries; whenever I got around to it was just fine.

One week later, I turned off the PC and never went back. The Mac made sense to me like no other computer ever did. Even with the learning curve (installing apps via DMGs were particularly confusing), within a month, I was as fluent with the Mac as it had taken me more than a decade to get with Windows. This platform made more sense to me than any computer system ever had. It was a nearly perfect match.

iOS Cometh

Just a little less than a year after my transition to a Mac, the iPhone was announced. While I found it an interesting idea, one that I thought would eventually win, it lacked many things I thought (incorrectly), that were needed to make a viable platform, namely 3G, Java, Flash and an application development layer.

Its been 11 years since the iPhone and 8 since the iPad were announced. My long-term prediction was right, but the path there was far from it. Only two of the four things I believed necessary for a viable platform were really needed, but that last one, the application development platform, was the key. Without that, much of my career over the last decade would not exist.

My first attempt to transition away from a traditional computer to an iPad came 7 years ago. My company had just launched an iPhone app, which I had lobbied very hard to get us to support on an iPad, even if only in the expanded phone mode. During the testing of the product, I came to realize that the original iPad, even in its hobbled state, was far superior to the three year old, Windows XP hobbled work laptop that I was using. The day I turned in that boat-anchor of a laptop, everyone thought I was crazy. Months went by as I used it as my primary away-from-desk computing device (I kept a desktop). My coworkers were amazed I would even bother trying, but as the months went by, and Christmas 2011 past, seeing all our executive team getting iPad 2s for the holidays, that suddenly I became a prophet of the future. Everyone wanted to know how I used it for work, because they were as frustrated with their laptops as I had been a year prior.

iOS Returneth

The following 7 years saw me flip back and forth from the iPad 3 to a 2012 MBP (home), to a 2014 MBP (work) and back to an iPad Air. The 2014 MBP won out for years... until its lease ran out.

I had been dreading this for nearly a year. My office, in a cost cutting measure, was eliminating support for Macs. This somewhat cheered me up because their Mac support was abysmal; this essentially left me unsupported but still with my chosen OS, but when the lease ran out, I was going to have a hard decision to make. Our system support team was leaning on me heavy to move to a PC, something I was entirely unwilling to do as a daily driver. I watched my coworkers complain at short battery life, random system instabilities, an OS crippled by removal of admin privileges, and I just couldn't imagine living like that. No way was I going Windows.

But the Mac wasn't much better, either. I loved the form factor of the new models, but the 12" Macbook keyboard hurt my fingers after 30 seconds of typing. The 2016 and newer Macbook Pro keyboards were failing at a rate that had me spooked, as being without my primary machine for a week while it was repaired just wasn't an option. I could get a 2015 15" rMBP, but that was essentially the same machine I had been using for 5.5 years, and while great, was overkill for email, powerpoint and web browsing, which are my primary responsibilities. I wanted a 13" device, but that just didn't exist in a reliable laptop... but it did in an iPad Pro.

Tablet Reborn

The summer of 2017 saw my wife finish her PhD and open her own practice. Her 2011 Macbook Air wasn't the right device for client work, but the 10.5" iPad Pro, with its Apple Pencil, fit the bill perfectly. She snagged one and billed it back to her new company; an instant convert. Even though I had used iPads around the house for 7 years, she had never even considered using one, but in minutes she was hooked. The old Macbook Air gathered dust for months.

Her conversion led me down the road to once again consider if the iPad could serve as a primary computing device for my job. Not just the primary mobile device, but the primary device; period. If I made the switch, my Mac laptop would not be there in case I needed it; I would need to be able to do my entire job on an iPad. It was a daunting idea, but one I could see no other viable alternative in trying.

I refused to use a PC. There was no longer a Mac that fit my needs, especially when it comes to reliability. But could an iPad, even one that had grown in capability as much as the current iOS 11 enabled version were, really do everything I needed it to do? Could I really, as the head of software development for one of the largest restaurant companies in the world, do my entire job on an iPad?

I didn't know the answer to that question... but I decided I needed to find out. My laptop's lease was up in two months and I needed to know the answer before I had to turn it back in. Now was the time to find out if it was possible or not.