Rediscovering infatuation.

Every summer, I seem to go through familiar cycles, examining how I do things, and breaking down well-worn workflows to experiment with new ones. I feel that this serves two goals: on one hand, there’s a cadence to this process, as a new iOS release looms in the near distance, but at the same time, something about this time of year leads me to question how and why I do things.

I’ll chalk it up to summer being one of my favorite times of year, where the warmth of the sun energizes me physically and mentally, and I find myself stirred into new modes of activity and thinking. Whatever it is, I’ve decided not to fight it, and I almost look forward to it each year, knowing it’s on the way, quietly wondering what I’ll decide to strip down to parts and rebuild.

Last year it was task management: the psychic overhead, the bifurcation of worlds, and the sheer tactical action required to make my world keep turning. This year, I’m focused on a vector into that and many other aspects of life. This year, I’m taking a different look at the iPad.


I’ve been a fan of the iPad since day one. I got the very first model as soon as it was available and adored it from the start. I always saw potential and shades of the future in it, despite its initial limitations, its basic pedigree as an older sibling to the iPhone, and the seemingly unending stream of naysayers ready and willing to knock it down for not being all things to all people.

The core argument, of course, is that it’s not a “real computer”. It can’t do all the same things a laptop can do, so it’s not worth anything. As though every tool needs to do all the same things every other tool does.

There are two fundamental tenets to my position on this that are worth remembering:

  • computing is not a zero-sum game; there are many users, many needs, and many ways to engage with technology successfully
  • value, like beauty, is in the eye of the beholder

I’m not going to waste my time (or anyone else’s) retreading these arguments. It’s beyond uninteresting, and crosses into eye-rolling so severe that it risks permanent ocular damage. What I would like to do is explore a few things I’m truly excited about as the iPad continues its slow evolution into what I’d consider a worthy independent computing platform.


I’ve been using two iPad Pros since last fall: a 12.9″ model that I bought in the beginning of 2016, and a 9.7″ that I bought in October. I’ve explained some of the thinking behind this on our show, so I’ll cut to the chase. I decided that having a big iPad at home and a smaller one to travel with to and from the office and on trips was the right choice for me. It’s been a nice way to use the devices, and I’ve enjoyed always having the right device for the right context.

Lately I’ve been gravitating toward the 9.7 though, for a few reasons. I still like the giant iPad because it’s just so nice to have that extra room, but what I’ve been exploring lately just makes the 9.7 the better overall target for this type of use.

As such, the majority of these points I’ll make directly refer to the smaller of the two iPads. I’ll likely make reference to this in certain areas, but it’s worth keeping in mind as a frame of reference, so that you aren’t constantly wondering, or—more probably—saying “that would be ridiculous on the big iPad”. Much of this would. But hey, maybe it wouldn’t for some folks.

That’s what’s cool about everyone living their own lives. You don’t have to do what everyone else does, or listen to everyone else’s opinions as though they’re fact.

Also worth keeping in mind.


Anyway, here’s what I’ve been thinking about lately.


  • The Smart Keyboard
  • Using the iPad by itself
  • Using the Pencil, replacing paper
  • Portrait orientation
  • iOS 11 and next steps

The first four have been overlapping and working in tandem. The last one is obviously pertinent for this summer.

The Smart Keyboard

I’ve long been a fan of using keyboards with the iPad. I’m not a fan of bulky cases.

I would search to find what I considered the best option that mixed a standalone, iOS-ready (when possible) keyboard with an easy way to detach, because I always like to decouple the two and use the device on its own if I’m not doing heavy text entry. I’ve always been ok with a slightly smaller keyboard size anyway, as my hands aren’t that large and I get used to them fairly quickly.

I started this quest with the Logitech Ultrathin Keyboard cover for the original iPad Air. It was a great solution for having a decent hardware keyboard while keeping weight fairly low. When I upgraded to the Air 2, I couldn’t bring myself to buy the same exact thing again, so I switched to this Microsoft keyboard because it was small, but with very good battery life and what I consider comfortable keys. It also allowed me to keep the Smart Cover attached and sit with it easily while using the keyboard. It didn’t attach the same way that the Logitech did, but it allowed me to use the iPad by itself as well.

When I bought the 12.9, I decided to take the plunge and try the Smart Keyboard. Yes, it looks a bit odd. Yes, the keys are a little weird at first. In truth, I despised them. Tried it in the store and was physically repelled by it. After 24 hours, I was a convert.

The Smart Keyboard may not be the best keyboard, but I believe it’s the best companion to the iPad Pro.

The Smart Keyboard will have its detractors, but when you get right down to it, it is the best compact solution to minimize bulk and still provide the functionality of hard keys. If you don’t mind extra heft, or need backlight, or want additional iOS-specific function keys, then move along.

I bought the Logitech Create for the 9.7 initially. I wanted something that was more like a notebook, and since I was carrying the Pencil with that device, the built-in loop was a big benefit. I used it dutifully for about six months, when it began to feel bulky. I started to think about the Smart Keyboard, but was struck with the idea that the Pencil wouldn’t have a nice little home anymore. To this day I’m shocked that Apple itself doesn’t have a better solution for this.

And no, this is not a solution.

But what I’ve come to realize is that the Pencil, the iPad, and the Smart Keyboard don’t need to be connected to one another all the time. They simply need to be in each other’s immediate orbit in order to deliver the value they can provide. The Smart Keyboard (especially at the smaller size) makes the 9.7 highly functional and barely adds any bulk.

I’ve been enjoying it way more than I anticipated.

Using the iPad by itself

One of the defining factors of all of those keyboards I mentioned was the ease with which I could pull them off and use the iPad on its own. That’s been paramount to my use case for the device for as long as I can remember.

As the iPad got thinner and more powerful, I found myself simply marveling at the hardware and the way it felt to hold it on its own. With the 9.7 Pro, this has actually shifted from “isn’t this really something” to a sea change in how I use the device.

I was thinking one day about how I was more inclined to grab my phone to do something as opposed to the iPad. I stopped and really thought about why that was the case. Broke the action down to its most elemental level.

Pick up a device, unlock, use… right? Not that complicated.

But with the iPad, there was often a keyboard of some kind, or at least a Smart Cover attached. One extra tiny action that created imperceptible friction; that on a subconscious level resulted in me going for my phone because it would “be faster” somehow.

Then I watched my wife’s dad one weekend with his iPad. He leaves it around on the counter, ready to pick up and use, no cover, no keyboard. He has an iPhone too. He almost always goes for the iPad first, likely because it has a larger screen and is more comfortable. But then it dawned on me.

If both screens are available in the same capacity and without any extra steps, apart from an app not appearing in one place or the other, why wouldn’t I use the iPad first?

So I tried it. One day at work, I was walking around my office, Smart Keyboard on the desk, iPad and Pencil in hand. It was so light, so effortless, and so enjoyable, that it began to feel like I’d discovered something new. A way of using a device—of which I thought I knew every angle—that I’d simply never considered. Put it down, go do something else, grab it and unlock, it’s ready.

It sounds positively stupid, but this simple change has made a big difference not only in the amount of time I’m spending with the device, but also in the ways in which I’m using it.

Using the Pencil, replacing paper

One of the big benefits of the iPad Pro is of course the ability to use the Apple Pencil along with it. Unlike the Smart Keyboard, I was sold on this accessory from the instant I held it and used it. I’ve tried a ton of different stylus options, and the Pencil is the best around, full stop.

I also tried a bunch of different apps for handwriting. The one that feels the most like it matches my handwriting mechanics is Notes Plus. I’ve made a conscious shift in the way I capture and process information now on a daily basis. Revisiting handwriting as a way to gather information has forced me to slow my thinking and listen more, which has led to other creative benefits as well. With my mind engaged in this way, it is freed up to do other things as I work with colleagues, and quite honestly, I find writing by hand to be a relaxing activity.

I also frequently sketch concepts, diagrams, small bits of UI that I’m describing to others, and all manner of other things. Just having the ability to do this quickly–and then immediately follow it with a digital action (saving it, sharing it, etc.) is hugely beneficial to my workflows.

I carried paper notebooks for a long time. Getting myself into the habit of reaching for the Pencil has been a lot of fun and very cool. That’s worth calling out as well: making work fun can’t be underestimated. If I’m enjoying the tools I use, it makes whatever I’m doing more pleasurable, leading to a positive feedback loop. Increasing the utility of what I’m doing (because I’m a nerd this way) is also fun, which also funnels back into that loop.

Making the ways you do your work more enjoyable is a great way to improve your daily quality of life, trust me.

Portrait orientation

The last discovery was a complete shock to me.

From the moment I got my very first iPad, I defaulted to using it in landscape orientation. I’d watched Steve Jobs demo the device onstage, sitting in that iconic Eames chair, reading and relaxing, and I thought “well that’s nice” but it never felt right to me. I guess somewhere in my mind, I always saw screens as horizontal appliances–using it in a vertical capacity just felt odd. I’d occasionally read a magazine that way, or some other very targeted activity… but it never lasted.

That’s where this whole “isn’t it fun to try new things that I ordinarily wouldn’t” thing starts to pay off. I always use Notes Plus in portrait, because I like the layout and spacing of the page in that orientation far more than in landscape. I’m using the Pencil more and more… and I’m detaching the iPad and walking around with it. So one day I just turned it and held it in portrait while I was discussing some things with people. I was taking some notes, but I also was popping around and doing a few other things. I responded to a message and realized I could type fairly easily in portrait on the 9.7, especially with nothing else attached to it because it is so lightweight, and the balance of the device when held in this way is incredible.

The balance of the device when held in portrait, with no cover or other accoutrements, is incredible.

I literally had never considered this, ever, in all the years I’d used it. It was an epiphany. But Steve knew it. It was suddenly so obvious. The device was designed to be this way.

It can’t change computing if we’re always looking at it like it’s a computer.

All this time, and it felt like I was suddenly holding an entirely different device. Again, like the notion of using it without a cover because it’s easier to unlock, this was a moment in which I considered the fact that I was a total moron. But it was undeniable. I’d stumbled onto something a whole lot of people probably knew already, but it was brand new to me.

I’ve been carrying the iPad, bare, with the Pencil, like a single sheet of digital paper, and it’s changing the way I work, and the way I do just about everything on it.

iOS 11 and next steps

This year marks the most radical shift in the iPad’s software capabilities we’ve seen. iOS 11 is poised to enable new levels of functionality in the device, unlocking increased flexibility and moving the platform forward to a level of maturity fans have been clamoring for.

I’ve been a beta person in the past, and I’ve lived with the battery-cooking, display-busting, data-losing bugs. I threw developer beta 1 on the 12.9 when it dropped because I was really curious to see it in motion after watching the WWDC keynote. I played with it for a few days, but restored back down to iOS 10 because I’d rather be using the device in a stable capacity for the time being, and because I’ve come to realize the big release in the fall just isn’t as exciting if I’ve had it for months prior.

What I saw is a wonderful but complicated step forward. iOS 11 brings incredible new things to the platform, but it also ratchets up UX complexity in ways a lot of users may not be ready for. One thing iOS has traditionally done well is to add new features and functionality but not make it necessary to engage with it. This allows most users to keep doing things pretty much the way they always have, and gets power users happy about new stuff. iOS 11 makes some big modifications–for everyone–and it’ll be interesting to see how that affects things overall.

I’m certainly not hinting at some kind of backlash (although we all know the tech press will latch onto just about anything it can find that would indicate one). It’s just that we’re about to see a big shift in the UI that means another learning curve. Anyone who loves iOS as a productivity platform is ready and willing to accept and keep running with this change, and it’s been a long time coming. But the typical year-to-year balance afforded to mainstream users is about to change too.

Evolution is hard, and not without trade-offs. But it’s what’s necessary to keep moving forward.


The iPad has traveled a long, strange road to get to where it is today. I’m honestly thrilled that after all this time I can still find new things to love about it, and change how I interact with my world. This next chapter will be one of the most interesting in its lifecycle to date. I’m ready for this device to cross over into a new class of utility.

With the introduction of the 10.5 Pro, and my increasing love of the smaller of my two current sizes, I may also move to a single-iPad life again when I decide to upgrade. Won’t be any time soon because my current stuff more than meets my needs and I’ve never once felt like it’s lacking in any way, but it’s on my mind. The 10.5 looks to be a fantastic device, and a great compromise for someone like me who’s experienced both sizes and wants to simplify.

I’ve said it before, and I think it bears repeating: this is not a zero-sum game. I still love the Mac, and use it every single day. It’s the best tool for many jobs. But the gaps are shrinking–not entirely, but markedly, for many use cases–and it’s interesting to watch this process. I use the Mac because it’s a great platform that allows me to do work in the way I prefer. I love iOS because it feels like the future in a way that the Mac once did, and (let’s be honest) probably won’t again.

To the point of all these personal observations, however: the fact that I can still find these small bits of discovery and everything continues to feel new to me is testament to how interesting a device this really is. We’re on the verge of some very big changes, and it’s one of those rare times in which I am unabashedly excited about what’s around the corner.

They seem to be harder to come by as I get older, so I have to revel in these moments when they show up.

Things I like this week, volume 34.

Bojack Horseman

Netflix has a lot of original content these days. A lot. And some of it is incredible. And some of it is just there. I’d seen Bojack Horseman come up a lot in the carousels the service shows you when you’re using it. My match rating was high. A ton of people whose work I enjoy contribute voices to it. Everything was pointing me in the right direction. But I just never watched.

What finally nudged me in was an episode of Imaginary Worlds, a previous TILTW that’s a terrific exploration on its own. Through the podcast’s descriptions of the show, and the style, and the characters, and the tone, and right through the interview segments with Lisa Hanawalt (the show’s designer), it just seemed like something I had waited too long to look at.

So I finally sat down and watched episode one. And was immediately drawn into this quirky, hilarious, and poignant world that had been created. I was amazed at how utterly silly and heartbreaking the show could be in almost the same breath, which I consider a huge achievement.

If you’re an animation fan and looking for a new obsession, there’s almost certainly something here for you.

Bojack Horseman