Things I like this week, volume 21.

Leuchtturm1917 Pen Loop

I caught wind of this little thing from my friend Myke Hurley, who is a bona fide writing implement enthusiast, but who took this and applied a serious hashtag life hack, and adopted it as a holster for the Apple Pencil with the iPad Pro.

I carry the Pencil with me in my bag every day, but I often don’t use it because I have to go get it (heaven forbid) and get it out. Mostly I just forget about it, but I’d like to use it more, because it’s totally awesome, and I think having it easily available at all times will definitely make me reach for it.

I’ve mounted mine on the center of the part of the back of the Smart Keyboard that folds and remains exposed while the keyboard is deployed in position. I thought about mounting it to the iPad itself, but I like separating it occasionally and using it on its own, and I didn’t want anything hanging off of it. The back of the Smart Keyboard feels like a reasonable place to apply it, and it doesn’t look too bad. It’s there when I want it (if the cover is closed) and hidden away in the back if I’m typing–but always around.

It’s a very nice, not-too-expensive add-on to my setup that continues to make the iPad Pro the ultimate notebook/computer for me right now.

Leuchtturm1917 Pen Loop

Reversing orbit.

For the past few months, I’ve become increasingly iPad-centric in my use of iOS. This had been happening since iOS 9 came out, certainly, but the scales tipped inexplicably about two months ago, and the momentum was only accelerated by the adoption of the 12.9″ Pro. I now spend the majority of my time on the iPad, doing everything I had been doing and a lot more.

My iPhone 6s, meanwhile, has been relegated to a different role. I still use it quite a bit, but if we’re being honest, it’s definitely my second choice if I want to do something. Sometimes it’s the only choice, in a scenario where I don’t have the iPad, but given the choice, at this point, it’s number two.

This got me thinking. I take my iPad to the office each day, and bring it home. It’s my anchor. My iPhone is the smaller device I always have with me: my camera, my hotspot, my payment token. If I’m going to carry two devices (almost) everywhere, why not lighten the load a little bit?

Then this happened.

And I went, “wow, cool, a tiny phone with big phone guts” like a lot of other people. I’ve always liked the iPhone 5/5s style. In fact, I actually still prefer it to the iPhone 6/6s style. I like the new style, but it just never felt as natural to me. And while some folks saw the SE as a step backward in terms of looks, I agree with Apple:

we started with a beloved design…

But I held onto my 6s. Then I was pushing one of my kids in the stroller around the neighborhood while trying to text with the other hand, and it started to dawn on me: my specific use cases for my phone have changed. It used to be my do-literally-everything device, and it has become my do-a-handful-of-things-well device. Which I am absolutely fine with. As such, the thought that kept gnawing at me since then has been clear.

I think I’m going back to a(n even) smaller phone.

Right now, my phone needs to be able to do exactly four things well:

  • camera
  • communication
  • payments
  • capture small bits of information

Prior to the SE announcement, there was no way a 5s was going to close out that list. It’d get there on #2 and #4, but #1 after seeing the 6s photos? Nope. And no Apple Pay–I’d be lying if I said I don’t use it every chance I get.

The SE does those. In a tiny, powerful package. With a design I always liked, without (much) compromise.

Yes, I’ll have to live without 3D Touch. In all honesty, while I do use it, I often forget it’s there. It’s never stuck with me all that much, and I’ve really tried. I always press everything to see what happens, but it’s inconsistently applied, and in some cases, just not worth the time. Maybe someday, but not now.

Yes, there’s going to be a lot less onscreen at once. This is probably the biggest trade off I’ll need to make, and the toughest to come to terms with. It’s nice having a bit of extra room to read and interact with things. But you know what? I interacted with this smaller size for freaking years in the absence of a larger phone, and my world kept turning. I do a lot of reading on my phone, but I’m prepared to make a change in how I use it to see if the difference makes sense.

Yes, there will likely be a new phone in the fall, that does amazing things. See that list up there that I mentioned? Those four things are truly all my phone needs to do these days.

But what it does do well, is plenty. The camera and internals are 6s-quality. Apple Pay is in. Touch ID, while not as fast as the 6s, is there. The things that are integral to the “portable communicator” table stakes are there.

There’s something else though.

I’ve written about my time away from Twitter and the web at large and how it changed me. Part of that was spending less time looking at my tiny screen(s) in general. I’ve set upon an internal logic for this new thought technology:

  1. If I have the iPad, I will use the iPad, because it is better.
  2. If I don’t have the iPad, chances are I am somewhere where it is either not necessary to be looking at a screen, or not appropriate.
  3. If this is the case, the only things I probably need to do are take a photo, pay for something, or communicate quickly.

Which basically means the time I spend looking at screens is better spent, and the time when I am not looking at screens is even better spent. I will be (or at least try to be, I mean, this is an experiment, after all) more present, more attentive, and more in the moment. I feel like this is a natural extension of my thought process for the past few months, and even though there’s a part of my brain that’s like “you are seriously drunk, man”… I’m thinking it’s at least worth a try.

Worst case scenario: I freak out, return it or sell it, and go back to a bigger phone. Best case scenario: I was right, a new pattern emerges, and the things I care about come into focus a little more.

Hey, if this is my biggest challenge right now, I’m thankful as hell. In the meantime, I’m off to buy a tiny phone.

Things I like this week, volume 20.

The Esquire Classic Podcast

Last summer I began exploring different kinds of podcasts, having grown somewhat tired of tech-focused shows. I’ve continued to do this, adding a show here and there to my list of favorites I can’t miss.

The Esquire Classic podcast has quickly become one I really look forward to each time it’s released. It is a show in which some of the magazine’s most famous non-fiction articles are reviewed, dissected, and discussed, either with the author or in many cases the editor at the time. Portions of the piece are read alongside the discussion, which adds a bit of dramatic narrative and storytelling to the analytical parts of the conversation, and overall, it’s a great mix.

As compelling as the pieces themselves are, the stories behind them are often absolutely incredible and full of rich detail about the surrounding situation, the process by which the article was written, or about the author’s feelings and approach. It’s a terrific look at a type of journalism we often don’t get in quite the same way these days, viewed in a modern context, and bridging the stories of the past with a critical look through the lens of hindsight.

If you like great stories and hearing about how they came to pass, it’s a pretty sure bet you’ll dig this.

The Esquire Classic Podcast (iTunes)
More at

Vacation, all I ever wanted.

As I’ve said before, I’m a little late to most nerd parties these days, and this is no different. I’ve been hearing a lot about 2Do for a while now, spurred primarily by Federico’s exhaustive review a few months back. I had first purchased the app back when it was released many years ago, and had peeked at it from time to time since. What started as an opinionated UI with some seemingly odd UX conventions has shifted into a more attractive, highly customizable, and totally flexible app to manage every kind of actionable item you can throw at it.

So when everyone started talking about it, as is my way, I dismissed it as “this is what everyone’s talking about now” and didn’t really bother to dig in. Something about the way the app looked and worked didn’t mesh with the way I thought about my task management. As I’ve mentioned many times before, I’m primarily psychically invested in the OmniFocus way of life, and have been using the app for years. I’ve also used Todoist in a similar way with great success and I’m in there now, for a lot of reasons. And I’m always looking for ways to change things up and increase efficiencies, and just generally make things work better for me. To my detriment, I didn’t explore what 2Do had become, and I wasn’t prepared to integrate it into my workflow.

Last week, after much of the recent fervor had subsided, I had an hour of free time (unheard of these days) and something compelled me to install it and poke at it for more than a few seconds. I can probably attribute that to friends who incessantly discuss its benefits and how it’s totally blown their worlds up in a good way. Whatever it was, I pulled the trigger and spent the hour with the app.

What I discovered was that while I’ve allowed myself to gain comfort and speed in other apps, learning 2Do isn’t like learning another todo system. It’s essentially Drafts for task management–if you want it, you can probably do it. At first, this seemed off-putting to me: like, make some choices, and don’t give the user free reign to do, well, anything, right? Have some boundaries, and fence in your property. That’s just how most things work. Once I surrendered that preconception, I found myself in awe of how utterly malleable the app becomes once you spend time learning and understanding its syntax and its abilities.

I’m honestly shocked at how much I was missing by not taking the time to really dig in. I shouldn’t be, but I guess I’m still whittling away at my own habits in certain areas of my life. I’m glad I allowed myself the time to do it.

I’m not going to write about what the app does. There are many other places to read all that. What I will say is that in my week’s worth of exploration, I’ve discovered ways of managing what I considered to be a completely solidified mental model that I didn’t realize were possible for myself.

No single app (nor switching to an app) is going to physically make you do more stuff. That continues to be on you, and always will be. But being able to visualize different angles around the things you have to do in your life is never a bad thing. There’s something utterly comforting about embracing a system that works for you and never changing and I’ve definitely been there. But there’s also something to be said for making leaps of faith occasionally and trying new things, even if you come running back to your safe place, because it’s allowed you to step outside of the confines of your environment and gain a little distance. It’s why we take vacations, why we like traveling away from home. Seeing things that are similar, but in different ways. Sometimes seeing things that we could not have expected, or that we expected we’d even like. Sometimes those vacations lead us right back to where we belong, but occasionally we end up finding that we’d rather be somewhere else, and we stay.

I’m not sure, after a week of being away, that I’m ready to call the moving company, but I’m sure glad I booked the flight. I’m going to continue exploring the app and really dig in to see how else it can work for me. It’s a bit of an onion, this one, and I’ve only begun peeling.

Things I like this week, volume 19.

iPad Pro 12.9″ and Smart Keyboard

As I mentioned earlier this week, I took the plunge and finally talked myself into getting the big iPad. I’d convinced myself that it was too big, that it wouldn’t be comfortable for the things I do the most, and that the 9.7″ size was right for me. I was in love with my Air 2, and planned on keeping it for another year.

Well, as I often do, I let my mind wander, and a few good friends goaded me (not really) into giving it a go. I went to the Apple Store last Friday afternoon, and got a 12.9″, 128GB Space Gray monolith. I also got the Smart Keyboard, which I had tried previously, and detested each time. No, seriously. I couldn’t stand it. It felt like an abomination. I think I literally think shook my head in disgust after the first time I tried typing on it. People nearby probably thought I walked through a cloud of farts or something, the way I must have looked.

Turns out I love the giant screen and adore the keyboard after only 24 hours of solid use. Is it my favorite keyboard ever? No, not by a long shot. But it’s very sleek, adds almost nothing in terms of bulk/weight, and works well.

I’d listened to people talk about the Pro when it came out and had really decided it wasn’t the right device for me, but I’m glad I changed my mind. As I start to move as much of my daily personal computing to iOS as possible, I’ve discovered that while I might not want or need the big phone (I bought a 6s Plus last year but went down to a 6s), having the big iPad makes a lot of sense for me. I haven’t even begun to push it to the limits yet (still just exploring and trying stuff), but I like knowing that it’s got the goods under the hood. My plan is to make this my only computer for the next year at least, and see where I land. For now, it’s the slim, powerful, pixel-filled window I always wanted and I couldn’t be happier.

iPad Pro
Smart Keyboard

Where the action is.

I’ve been steadily moving toward an iOS-only computing shift in my personal life, aided by certain bits here and there. This past weekend, after just extolling the virtues of my Air 2 and its new keyboard companion, I buckled, took the plunge, indulged my inner child, and bought myself a 12.9″ iPad Pro and Smart Keyboard. I know I’m a few months late to this party, but just allow me to say… wow.

iOS 9 is a terrific update, especially on the iPad. Paired with a keyboard, it’s as close to the hybrid device I’ve always wanted as we’ve gotten yet (although the Surface could win on a technicality, but that’s another discussion). Sure, there are things that you still can’t do (or do well) but that gap is smaller than it’s ever been. And it’s closing. And for most normal, non-edge-case stuff people do with computers, it’s tiny.

I still do some stuff on my Mac: podcasting, heavy audio recording/production tasks, certain massive file management/admin tasks. But the fact of the matter is that I don’t even open my MacBook Air most days… most weeks. Right now, it’s got a local copy of my iCloud Photo Library content, and I occasionally open up Transmit there to move giant amounts of files between destinations. But even before I got this behemoth, I was doing way more on the iPad than I ever had. Having a little more room to do it (ok, a lot more room) has been transformative.

I use a Mac every day at work. I know it inside and out. I’ve been using Macs every day since the early 90s. But that’s not where my interest is anymore. iOS is far more interesting than OS X, and that trajectory has never been clearer. The past me would have bemoaned the lack of file system access, but the me of today is grateful that security is handled by design. The lack of interoperability has been addressed, and while there’s tons of room for improvement, moving data between apps on iOS is good, and getting better. Conveniences like Touch ID and Apple Pay, solid battery life/performance, extreme portability, and fast wireless radios afford these devices a place in our lives that laptops can never take. We’ve reached a point where the thought of even carrying a second camera for most people is nonsense. Your iPhone takes incredible pictures, and things like Live Photos capture moments in ways we didn’t even realize we wanted. (Admittedly, I totally thought they were a gimmick when they were announced, and all I do now is shoot my kids for a few seconds at a time and grin like an idiot; they are absolutely one of my favorite parts of iOS.)

I have immense respect for the history of computing. I’ve grown up through what I would consider the breadth of its most important developments and most rapid advancements to date. But the thing about technology is that it never stands still, it’s always moving, evolving.

There will always be trucks, and some of us (myself included) will want and need them for certain things. But what we really all want is new bicycles. iOS and the devices that run it capture our imaginations and interest more every day. Sometimes I get anxious at the very thought of keeping up with just how quickly things are changing. But I can’t help but marvel at the incomprehensibly thin slabs of glass I carry around and smile, because we are truly living in an incredible time.