iPad Pro Trial 2018

I really wasn’t going to buy an iPad Pro this year, I was pretty serious about that decision. But then I popped by the Apple Store, just to see what the new 2018 models look like, just to stay in the loop. I was immediately enamored. In the twenty or so minutes I spent with the new iPad Pro I wasn’t sure it would be enough to replace my MacBook Pro, but I was sure that I had to give it another shot.

I do this every year. I’ve owned every iteration of the iPad Pro since it’s inception (some not longer than the return period). I’ve tried very hard to make the switch, give up the MacBook Pro, go all in with the iPad. So far it hasn’t caught, but that’s not to say my desire has been quenched. Here are my quick thoughts from two weeks with the 2018 iPad Pro 12.9.


  • New keyboard case. It’s way more sturdy. You can pick up the iPad, keyboard deployed, without it flying off (that happened on the regular with the old design). It also is a lot easier to use on my lap, or anywhere besides a desk. I appreciate the full-ish protection it offers without having to buy another back case. The keyboard itself is the same, which I like, but the overall case is improved.
  • iOS seems to be slowly making progress. This feature was probably available before but I didn’t know about it: you can turn off the bottom auto-correcting/suggestion/copy-paste bar when typing, a huge plus. Dashlane (my password manager of choice) now sort of integrates with Safari which, though not as comprehensive a solution as in Mac OS, has been super helpful. There are also more people using iPads regularly and posting helpful tips. I wouldn’t say iOS for iPad has arrived or is even close to arriving, but it’s a little better than last year, which was better than the year before. Based on internet rumors, iOS 13 should bring more significant updates next year.
  • It runs fan-less. This is one of the first things I noticed with the iPad Pro, it’s so quiet and cool. Nothing ever whirls or heats up. The keyboard never makes my hands sweaty. It just cruises along, no hiccups, no freezes, no spinning wheels, no heat, nothing. Really impressive performance for a fan-less device.
  • Battery life and connectivity. Those two things really appeal to me, they’re two of the main reasons I keep coming back to the iPad Pro. It’s the ability to literally work anywhere, to be free from the need for an outlet or a wifi router.


  • Browser. It’s still mobile, which usually works but is infuriating when it doesn’t. One of the key components of my work is writing and editing a blog. WordPress on mobile Safari is far from ideal. Another specifically painful example: I simply can’t add a contact in Pipedrive (my CRM of choice), the ‘save’ button is located beneath the bottom of the screen and Safari won’t allow me to scroll to it while the ‘add contact’ window is open. This is close to a deal killer by itself. Sure, there’s a Pipedrive app, but it’s got about 20% of the functionality.
  • I get kind of dizzy leaning over the iPad Pro for long periods of time. I can’t lean back and look at my big external monitor like with the MacBook Pro.
  • OmniFocus, professional apps in general. I rely heavily on Omnifocus to keep my life and work organized. The iOS app is so much tougher to use than the desktop version. I’m sure it’s partly because I’m used to the desktop version, but the app is also simply less capable. The same is true for the majority of productivity tools in iOS, they lack features included in their desktop or web-based counterparts. A few that I use daily, Microsoft Office, Zoom, Files, Mail, Notes, are all missing basic features included with their Mac OS counterparts.


  • I feel uneasy using the iPad Pro for work. Do I not like it because it forces me to zoom in on things? It is definitely harder to bounce around and/or have multiple things going on, it takes more effort to be distracted which can be a good thing. But maybe iOS is just too restrictive. It almost always takes extra effort to do things that are easy in Mac OS.
  • It feels daunting to think about something like recording and uploading a video to my blog. I’m sure it’s doable, but I’m also sure it’s going to take extra work to figure it out and I’m already tired just thinking about it. Maybe that’s a personal problem, but hey, still a problem.


  • I love the form factor, the power, the lack of a fan, the battery life, the simplicity, the ease of use, the lack of loading time. There are real pros to this machine, especially on the hardware side.
  • iOS, for all that it does well, presents obstacles for my normal workflow. It’s surprisingly capable and surprisingly frustrating at the same time. I can’t save additional signatures in Mail, it takes twice as long to add and organize tasks in OmniFocus, I run into frequent website limitations with mobile Safari, the list goes on. Almost all of my issues can be ‘worked around’ in one way or another, but I find myself spending a lot of time on workarounds instead of actually working.
  • While the fact that the iPad Pro is always on and always connected is certainly a benefit, I don’t think it’s worth the trade-off for the sacrifices in the OS. In fact, because it’s so easy and fun to use, and it’s always on and always connected, I end up turning it on just to waste time. It’s fun to use but it’s hard to use for work, those two don’t make a great combination.
  • Mac OS is already great for working. All my workflows are there. It seems that the key for the iPad Pro is to recreate workflows, kind of like starting over. There could be value in that purely as an exercise, but I can recreate my workflows on my MacBook Pro too, and I’m not ready to put in all that work for the iPad Pro. Going back to my CRM: I just set my company up to use Pipedrive, and Pipedrive suffers on the iPad Pro because there’s no desktop browser. I can’t just switch the company over to something different to facilitate my desire to use an iPad as my primary work machine. I need the iPad Pro to mirror the functionality of my MacBook Pro at least a little more closely to realistically make the jump. Give me a desktop browser and windowed apps, give the developers more time and encouragement to add all the features to their iPad apps, then maybe it’s not such a compromise. For now, my MacBook Pro offers fewer compromises at a comparable price. Here’s to next year.

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