For most of July and August 2017 I’ve used an iPad Pro as my primary work computer. Here are my thoughts as I wrap up the experiment.
I chose a 9.7-inch iPad Pro with the Apple Pencil and Smart Keyboard.
Why do this? Two reasons. First, as an empathy challenge to look for quality issues in the products I work on for Automattic. To truly feel the pain of working from a mobile device, that’s more common than a laptop or desktop computer for many of our customers. Second, to try it as a viable alternative for normal work. As Matt told us in a work chat, the iPad Pro is “always on, super fast, split screen, always connected [with available SIM option and a paid mobile broadband account], long battery life, fantastic screen, works on desk or lean back.”
For other perspectives, see Beau Lebens’s recap Working on an iPad from late 2016, and Paolo Belcastro’s iPad-only experiment in 2014. I also recommend this review on Quartz: The new iPad Pro is pretty great—if you accept it for what it is.
Below are my notes in journal form. I used the iOS Simplenote app to document my findings as I went along.
July 1, 2017
Which apps support Pencil? How can I use it to draw? What about annotating screenshots? Keyboard doesn’t appear so can’t use TextExpander; unless I can configure a shortcut key instead. Using iOS text replacement works instead.
July 8, 2017
Tried out Penultimate based on Beau’s recommendation. Sweet app, just need to work on my penmanship. Could help me be more visual in my communication, Maeda style. Note up things and not just in text. Mark up images, highlight things, share graphics.
Right away I miss things from TextExpander like ttime
to put in the current time stamp.
This keyboard will also take getting used to; it’s tiny! I wonder if I could connect my bigger Mac keyboard to it temporarily. It’s a bit harder to type, so might lead to wrist or hand strain versus the iMac keyboard which takes almost no effort to push down the keys.
I miss in-page or in-app search. Say I’m editing a Dropbox text file, and want to see if I already mentioned a word. On desktop I’d Cmd-F but on iOS I can’t seem to have the same function, so might duplicate some things, and lose time scrolling around. Simplenote search is nice, though.
Might be a time-waster to not have Cmd-F for websites — I use that a ton on P2s and stuff. Note, I discovered that both Chrome and Safari apps support it, but not all iOS apps do.
Notes on Simplenote or Dropbox for text editing: bigger text size in Simplenote is nicer to read. Simplenote saves immediately, Dropbox I could forget to click Save.
What are other amazing notes apps? I might switch back to Simplenote for everything — tags instead of folders. And archive things in Dropbox folders if not an “active” project or team. Alister recommends Bear, but it’s iOS only and I have an Android phone.
I really like the Penultimate app. Lined or plain paper, grid layout; easy to erase and highlight. The only thing to learn is a smoother sharing flow. Currently trying Evernote to sync the images back to my other computer.
Now trying with my Logitech K811 keyboard, the action is super nice but the whole thing feels huge (the keyboard). Could work. Wouldn’t travel with it, though, so getting used to the small one is probably smarter.
July 8, 2017
I miss accessing the internal employee directory to look up people and teams at work, and other internal tools. Might need to set up VPN for some things, but turns out on iOS using our internal proxy requires a jailbreak.
Annoying quirk of iOS that start of sentences require capitalization; even in text documents where I want to say iOS it fixes it. Also my personal todo format with lowercase O is hard to do. 🙂 Hack: type two letters, then backspace to remove the uppercase one. IiPad
then delete first I, to leave iPad
.
I love the iOS text replacement for quick-and-easy TextExpander replacement. Also like touching the suggested spellings in the tablet’s bottom bar. I imagine this is what the Touch Bar on the new MacBooks is like, but haven’t used one yet.
July 10, 2017
Booked a flight, bought a jacket on REI, read P2s, posted to Delta P2, answered emails, and edited some Google documents. Not bad. Tried out Zoom and Skype — the camera angle might be less than ideal. Also can’t use my Sennheiser headset because it’s USB only.
For using this while traveling will want to set up a SIM card for broadband. Or try an MacBook Air or MacBook instead. The touch screen is super cool, though — and I’d mostly just need something on a plane once in awhile.
July 11, 2017
It’s naturally quite hard to open links in Chrome. The launcher in the Share menu only gives the option to use “Add bookmark” or “Add to reading list” — when I simply need “Open this link in Chrome” as the action. Exception to this are Google apps; Gmail gives the option to launch in Chrome or Safari, with the ability to save the preference for all links. Kind of like the Choosy app on OS X used to work.
Using the native app in iOS actually feels… behind Calypso (WordPress.com) in Chrome webview. I was surprised by that. Aesthetically, and also when using WordPress.com Reader for internal P2s and comments, the functionality feels clunky in the app. Seeing comment replies together with the post body feels more natural.
I miss RescueTime and other timing apps. They don’t work on iOS apparently due to security and privacy for apps and usage.
Split screen is super nice. Simplenote is so smooth — such a beautiful experience on iPad.
I keep running into the first letter capitalization default setting with iOS. Trying to type “w00t” is a challenge.
Screenshot from a P2 theme comment form:

Settings change in iOS:

Doesn’t seem to stick for first letter auto-capitalization. Hmm. Still using the first two letter hack I mentioned before.
July 13–21, 2017
Using the sketching apps with Pencil fun and inspiring in a way I didn’t expect. Sync via Evernote is nice, sometimes exporting to Dropbox for reference in situ. The freehand drawing makes me miss type setting, though, since that always looks great. My attempts to liven up a blank white page with a digital pen are sort of terrible so far.
Here are two examples from Penultimate:
I’m loving the autocorrect on this OS. It’s pretty slick. When you mistype something, you just keep going and it works. The only thing I’m noticing is my thumb on the space bar is getting a bit tired, just today.
July 21, 2017
Quick notes today about using the iPad Pro as a main machine. Harder than I expected to move text around, though OK on iPad (really bad on my Nexus 6P phone when trying to move a flight itinerary by copy-paste from a web page to Simplenote). Annoying quirk with first letter capitalization in iOS is still bugging me. Oh well.
July 27, 2017
Loving the Cmd keyboard shortcuts much like on desktop: Cmd-tab to switch apps, Cmd-space to search like Spotlight, Cmd-Shift-3 to take a screenshot, Cmd-h to go to home screen directly. Tip: hold down Cmd to see the available shortcuts for the current app.
July 28, 2017
Publishing a blog post to simpledream.net was a bit slow, trying to grab a YouTube video and link to slides. I ended up with a lost post content (was able to copy the HTML first). Frozen editor pane, couldn’t save or recover it.
I use keyboard controls a lot, and certain ones don’t work on the iPad: Cmd-d to delete from start of a line, when using Cmd-L for address bar, choices come down in a menu — can’t use arrow and Enter like on desktop (Chrome, Safari).
August 1, 2017
Biggest issue after one month is ergonomic: my neck and shoulders hurt because of the angle; typing on the small keyboard is harder on my wrists. I love the laser focus with 1-2 apps at once, portability and battery life, drawing with Pencil, and the beautiful screen. I didn’t purchase a mobile broadband plan for the available SIM option — just used WiFi everywhere.
Because of the ergonomics I wouldn’t consider using this full-time as a main computer. Besides the neck and wrist discomfort, there’s the issue of the camera angle. It’s hard to get it right — straight at my face, slightly down.
Aug 8, 2017
My coworker Marek mentioned the 10.5″ iPad Pro has a wider keyboard; could be a better fit. I might just get another laptop next time, though — to continue coding when needed, as well as access to internal tools.
As I mentioned before, I love discovering new keyboard shortcuts by holding down the Cmd key. With Chrome for example, you see all the options and don’t have to memorize them. Just remember holding down the Cmd key.
Screenshot from the GitHub website, using Chrome:

Aug 9, 2017
Used the iPad on the flight from Europe back to the USA. Plugged into power, so didn’t test the battery life. Went well with Zoom, was able to join a team meeting even with the inflight GoGo wireless. The form factor is nice and compact, making it ideal for small plane seats.
Nice fit on a small plane seat, allows lots of reading and writing when you need the focus. I think at home, or with a nice office setup, it’d feel restrictive. For my coworkers that travel a lot, though, could compete with a lightweight laptop for primary travel machine — especially if a slightly bigger version. But, a touchscreen laptop like Surface Pro could be the best of both worlds. Next version of the Touch Bar? iPad and MacBook merging someday?

For developers and designers it’ll probably never be powerful enough. For writers, it probably would be perfect if the ergonomics were better: screen at eye height, comfortable hand position for keyboard. Screen resolution and brightness is superb, however. Using Simplenote and Google Drive for document editing is a pleasure.
August 13, 2017
To wrap it up, I’ll probably use the iPad often, just not as a primary machine. Supplement my visual sketch work, reading, newspapers and magazines; great for travel and tight spaces; ideal for writing and reading when focus is at a premium. Overall, it’s not a full replacement for a laptop because of the bad ergonomics over long periods, and the lack of full access to necessary work tools.
Interesting to read about the progression. I’m glad you touched on the ergonomics aspect, which has always been my biggest problem with trying to use the Surface Pro as a primary work machine. I also agree on the webcam problem, it’s kind of hard to get the right angle.
I’m curious if you found yourself using touch, type, or tap (with stylus) more often than others and whether that came down to “this is the most obvious way” vs “this is the most convenient way”? Even with my Surface Pro, I found over time that trying to mix touch, type, and/or tap often slowed me down, which meant once I found the most efficient way I pretty much stuck with it. Interested in your insight, cool post!
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Have you tried any iPad stands? I had huge posture problems a while ago and getting a laptop stand (Roost) and external keyboard solved them nicely for me. I wonder if there are any great stands that work well for such a setup (and are ideally portable).
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Nope, didn’t try any iPad stands. Good idea, though; as you said, portability for travel would be a concern — and maybe defeat the purpose of the tiny machine.
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Thanks Drew, good question on the mix of touch, type, stylus. I’d say my preference is for 100% keyboard, which isn’t the case on iOS, and may never be possible. I found the convenience of a quick finger tap usually just fine (and have touched my laptop screen a few times by accident since!). I didn’t use the stylus to navigate much — besides a few cases where it was in my hand anyway for sketching.
I think if apps like Chrome supported just 10-15% more keyboard conventions from macOS it’d make it feel much more natural and easy to switch back and forth for me.
How do you like the Surface Pro overall? I’ve thought of trying one both to test IE / Windows and to do the same type of empathy experiment since so many more people use Windows than Mac.
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My webcam trick was to put my iPhone behind the iPad between it and the triangle part of the smart keyboard case. That angles it a bit closer to 90° and I can usually find something to put it on to get it a bit taller. I also prefer that angle for watching movies / etc.
I’m certain there will be a Bluetooth headset at some point that has the same quality as the USB Sennheiser we currently like, it’s just a matter of time and the bandwidth / lag getting better.
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Smart trick on a wedge to tilt the tablet forward. ⭐️
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I am planning to buy this iPad Pro.
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