iPad Pro and commitment issues


I’ll be completely honest with you, my audience. I love my iPad Pro, it’s what I’m using to write this very post. But, in the two months I’ve been using it my commitment hasn’t been 100% unwavering. I’ve checked Apple’s refurbished website (maybe the best place to buy a laptop, full stop) for MacBook Pro options more than once. I’ve read several reviews of the new 16 inch MacBook Pro, and I questioned my friend about his with a noticeable uptick in enthusiasm. I’ve even used my iMac more than I expected, although with lackluster results (have I mentioned how distracting those things are?). The point is, working from an iPad Pro is a large adjustment, and sometimes I just want to go back to my comfortable place wasting time on a MacBook Pro. Here’s what I’ve realized, the feelings aren’t bad and it doesn’t mean I’m going to buy a MacBook Pro.

It’s normal to feel a little nostalgic for the old way of doing things. And it takes time, more than a week or two, or maybe even a month or two, to get comfortable with a new setup. But I’ll say this, after a while, it does get more comfortable. The question of whether my feelings of nostalgia are rooted in some flaw in the iPad Pro or in my own addiction to familiarity is slowly being revealed as the latter. All that stuff I wrote about the focusing power of the iPad Pro? It still rings true. All the capability and portability are still there. I still get more of my most important things done on my iPad Pro, it has forced me to work more intentionally.

So I guess this is my thought: when you commit to something, you probably have to commit to it for more than a few weeks. Change isn’t easy but it’s often better. My iPad Pro experience falls right in line with other good change initiatives, not always comfortable, but ultimately moving me in a better direction.

iPad Pro vs MacBook Pro: The Focus Question


Macs are great devices, they’re capable, they’re powerful, they’re reliable, they even look nice. A large swath of the population relies on their Macs daily to be productive. Steve Jobs famously equated desktop operating machines to trucks, full of power and function.

iPads are also great, but for different reasons and different purposes. The iPad, for most of its existence, has been seen as a consumption machine, but the release of iPad Pro and more recently, iPadOS, the understanding of the iPad has expanded to include creative and productive tasks. When Jobs equated computers with trucks he also equated mobile operating machines (iPads) with cars. As a society/economy evolves, fewer people need the power and function of a truck, or a full desktop computer, opting instead for a less power-hungry, easier to use, mobile operating machine.

This is a helpful comparison between the two types of devices, but I think the iPad vs Mac discussion goes deeper than a distinction in functionality.

iPad-as-a-computer-replacement discussions seem to generate significant traffic in online discussions and forums. I’ve read through countless articles and comment sections weighing the pro’s and con’s myself. As far as I can tell, many people would love to use the iPad as their primary productivity tool but are held back by questions of functionality. Can the iPad really handle all of my computing needs? Will the sacrifice in function be worth the trade-off in form? These were my questions as well. Previously, when I purchased an iPad Pro I thought about it as an all-or-nothing endeavor, either I would cut ties with macOS and use the iPad Pro exclusively, or I would get rid of the iPad Pro and stick with my MacBook. Either the iPad Pro could be a computer replacement or it couldn’t. More than once, I ended up frustrated with the function of the iPad Pro and went back to using a MacBook after a few weeks. I was thinking about the iPad Pro as a MacBook, and since it didn’t perform as well as a MacBook in a MacBook workflow, it felt inadequate. The question was never about the purpose of the device, it was about the raw functionality it offered. The problem with this line of thinking is that raw functionality is not the most important correlate to effectiveness. The function question isn’t the only question, maybe not even the most important question, when thinking about tools and productivity.

Productivity tools exist on a spectrum between function and focus. In order to enhance focus (and effectiveness), it can actually be helpful to give up some function. We think about tools and devices almost entirely as a form of function. Which tool is most capable of performing the tasks I need, or might need, to complete? Because of this, it makes sense that we talk about how the keyboard feels, the power of the processor, the capability of the OS, and the amount of RAM or storage that would best support our use case. Those things aren’t bad, but what we neglect almost entirely is how the tools correlate with our focus, which is arguably more important. We don’t ask how well we’re managing all of the function. Are we distracted by the multitasking capabilities? Have we spent too much time off task? Is all the function actually causing a decrease in our output? Are we burning through diesel gas driving around town? Desktop operating systems by nature offer as much function as possible, and that’s not a bad thing, sometimes we need a truck-type computer to accomplish specialized or complex tasks. But instead of only asking the function question, it’s important to also consider the focus question.

I’m really good at wasting time on a Mac. It happens automatically. All I have to do is turn on the machine, then those floating windows pop up, I see red dots in my dock, a bunch of open browser tabs catch my eye, suddenly I’m clicking links, reading stories, remembering something I wanted to check on, it’s like my mind falls into a state of hyper distraction. And then an hour has gone by, I’ve made no progress on the things that are most important to me, and I’m stressed. I’ll admit, this could be an issue unique to me, and there are ways to clamp down on the distractions of a desktop OS. If nothing else, take this as an exhortation to think about the relationship between your tool and your focus. For me, it has been helpful to use a different type of OS, one that’s not designed for multitasking, one that doesn’t encourage hypnotic attention deficit, one that leans toward the focus end of the spectrum. The iPad Pro limits multitasking, it does away with floating windows, it hides the dock automatically, and it forces the user to attend to one thing at a time. In fact, one of the most annoying things about using an iPad Pro is the friction involved with switching apps and tasks, all those taps and drags. It’s also simply harder to do some things on the iPad Pro, like manage files or build a spreadsheet. Those things may seem problematic on the surface, but when I think about the amount of time I waste task switching and managing files, and the relative unimportance of those things, the tradeoffs don’t seem quite so severe. It’s hard to quantify all of the differences between working from a Mac and working from an iPad Pro, but I know that my mind is more calm and less distracted with an iPad Pro, I know an iPad Pro encourages me to spend much more time on the more important parts of my work. The tool enhances, rather than hampers, my focus and effectiveness. The iPad Pro isn’t the most functional machine you can buy (though it’s come a long way in the last few years), but that very fact is what enables it to strike a balance between function and focus that could have vast implications for your effectiveness, and your stress level.

I’m not saying you have to buy an iPad Pro to be more effective, I’m not even saying that I’ll never buy a MacBook again, but for me, for now, the iPad Pro better accounts for my human weakness and allows me to be more effective by sacrificing some function to enhance focus. If you’re only asking the function question an iPad Pro will probably be found lacking, you can do more things faster on a Mac. But ask the focus question, that’s where the iPad Pro shines. Previously, I tried to use an iPad Pro for productivity because I wanted a better computer. But the iPad Pro is not a better computer, it’s a totally different productivity tool.

What phone do you have?


For technophiles, like yours truly, this is a really fun question. It clues me into your level of technophilia, tells me something about your priorities, and it’s a nice way to get a light conversation going on a subject about which I probably know more than you do.
But, as a confessed technophile, it’s a question I don’t only ask other people, in fact, more often it becomes a conversation I have with myself. I regularly overthink about which phone I have, why I have this phone, if I should get a different phone, if I were to get a different phone which one would it be, if I did have a different phone in mind how would I go about procuring one, and it goes on (that sounds much more disturbed as I write it out than it does when it’s happening in my brain). It doesn’t only happen with phones either. I fret about which computer to use, what configurations would be best, what size, what model, should I use a iPad instead, what if I got a desktop, if I were to get something different where would I get it, what would I do with my old one, and on, and on, and on (now I’m starting to think I may have a problem). The questions themselves aren’t bad, and the purpose, I tell myself, is worthy: I want to use tools that will help me be most effective. But, I made a discovery this morning, or maybe more like something I knew all along but pretended to not know. I determined that my effectiveness is much more affected by my endless, meandering indecision than by the tools I have or could have. So, in the interest of actual effectiveness, I’ve made a resolution: no more tech questions for one full year. I’ll allow myself the space to re-evaluate next year, conveniently right around my birthday, and decide if I want to change anything. Until then, I’m using what I’ve got, which honestly is pretty great anyways. I am a technophile after all.

iPad Pro Work: Setup


I’ve wrestled with this before, to use an iPad or to not use an iPad as a primary productivity machine. I work in financial services, specifically as an investment advisor. I don’t run any heavy-duty programs, I use Microsft’s office suite, a few communication apps, and a lot of web-based programs, so it’s not untenable. But in previous years the compromise has proved too great and my MacBook Pro too trusty.

iPadOS seems to have solved most of the most egregious of those compromises. The addition of the desktop-class browser (almost, Safari extensions are not yet available, but websites do render as desktop sites) is specifically a game-changer for my work. The improved multi-tasking abilities help too, and mouse support opens up a whole new world of possibilities (think, I could connect the iPad to the conference room display for a client meeting and run it from a Bluetooth keyboard and mouse on the table).
So I’m back, I’m giving it another honest try.

Here’s the setup:

• I bought the 12.9 inch variant over the 11 inch. The larger screen offers so much more utility. On top of simply having way more space to work with, it will also give two full-sized apps when running them in split-view instead of the phone versions of those apps. Subjectively, it’s the difference between working on a computer and an oversized phone.

• I chose silver over space gray. Space gray looks awesome, but as soon as it suffers one little nick or dent you see silver underneath. I’d rather the whole device stay one color. Also, silver looks awesome too.

• I chose the WiFi-only model over the addition of cellular. One great benefit of iPads over MacBooks is their ability to connect to cellular data and be always on and always connected. The thing is, I don’t want to be always on and always connected. I like to close my work machine and stop thinking about it for a while. Plus, I still have an iPhone, so on the rare occasion that I’m working and out of range from WiFi, hotspot is still available. The WiFi-only model is also a way to save some money, the iPad itself is cheaper and it won’t incur the extra monthly data cost. This is the one decision I can see myself waffling on in the future, but for now, I’m content.

• I went with 256gb of storage. For people who do a lot with photos and video, the higher storage tiers make sense. For me, 256gb is probably overkill. The only thing that will take up any noticeable amount of space for me is the occasional Netflix or Amazon Prime movie download for watching on the plane.

• Along with the iPad Pro, I purchased an Apple Smart Keyboard, 2nd Generation Apple Pencil, and an Apple Magic Mouse 2. I’ll comment on each of these accessories in the future.

Here goes!

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.