iPad Pro as Primary Work Computer

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:

2 lowercase-first
Can’t seem to w00t, just W00t.

Settings change in iOS:

3 settings
iOS settings screen for keyboard settings.

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:

4 cmd-shortcuts
Chrome browser’s Cmd key shortcuts for iPad Pro.

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?


2017-08-09 16.06.23
Using the iPad Pro on a Delta flight over the Atlantic, on a team call with Zoom app.

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.

Pragmatic Thinking & Learning

Pragmatic Thinking & Learning, Refactor Your Wetware by Andy Hunt (2008) is sensible and matter-of-fact, a gem of a book that works well both as reference and as inspiration. A science-based lifehacker manual that serves as the ultimate guide to personal productivity.


Full of tips, tricks, philosophies, and science behind how our brains function best for learning and thinking, the book covers topics such as reading and study habits, control over context and environment, trusting intuition while questioning everything, discovery and capture of ideas, and how to pay better attention. All tied to harnessing the power of opposite sides of the brain, creative versus practical, reactive versus thoughtful. Seeing both the forest and the trees.

Since the book is too full of useful information to summarize in one blog post, I’d like to share a few of my favorite parts.

Intuition and pattern matching replace explicit knowledge.

This echoes my philosophy of The Investigative Mindset where rules are not a substitute for clear thinking while considering the context. You can trust your intuition, yet you would do well to verify it by asking questions and digging deeper and keeping in mind your expectations and cognitive biases.

If you don’t keep track of great ideas, you will stop noticing you have them. Everyone has good ideas, fewer go further to keep track, act on them, and pull it off.

So true. Keep a journal, review it often, and take action on the best ideas. Share them with others for accountability, they can improve with feedback, or someone else can run with it if you don’t have time or energy to do so.

Rewire your brain with belief and constant practice; thinking makes it so.

This idea of mastery through constant, focused effort echoes what I’ve learned elsewhere, including a new book I’m excited about, Peak: Secrets from the New Science of Expertise (review to come soon).

A random approach, without goals and feedback, tends to give random results.

“You got to be careful if you don’t know where you’re going, because you might not get there.” —Yogi Berra

The best efforts need a plan, because if you work on a team like mine at Automattic you’ll know from experience that starting on things without a clear goal in mind, nor a plan on how to get there, without specific metrics to track it — means it’ll be almost impossible to measure the results.

I love the concept of SMART goals: specific, measurable, achievable, relevant, and time-boxed. Reminds me of Google’s Objectives and Key Results.

Read deliberately with SQ3R (scan, question, read, recite, review), which I find similar and complementary to Adler’s ideas on how to read books, as described by Ian Stewart.

You are who you hang out with: attitudes, behaviors, beliefs, and emotions are all contagious.

What does it take to stay sharp? Awareness. Learn to quiet your mind’s endless chatter, keep track of your ideas by working on and adding to your thoughts in progress, and avoid context switching.

Pragmatic Thinking & Learning is a must-read for all thinkers and learners. Hat tip: Nikolay Bachiyski.

GTD Quadrant Flowchart

From time to time I take a close look at my workflow to see if I can improve it in any way. Incorporate new tools, processes, or ideas—or remove things that don’t work or cause more noise than signal.

I’d like to share a productivity hack that’s worked well for me recently when trying to decide what to work on each day. Faced with a full plate of tasks, requests, emails, and interruptions—which should I tackle first?

I apply a few simple questions to each email, task, or incoming ping—things I might need to work on next. The questions are:

  1. Do I have to do it?
  2. Do I want to do it?
  3. Is it urgent for today?
  4. Can someone else do it?

Here’s my version of a decision tree that combines the questions and answers.

GTD Quadrant Flowchart by Lance Willett

I’m inspired by similar grids and charts that you might have seen. There are several variations of these “getting things done” (GTD) decision trees and quadrant matrices.

1. David Allen’s GTD philosophies, illustrated in this flowchart:

Screen Shot 2015-10-06 at 14.35.31

2. The Eisenhower Matrix (see also this Todoist implementation):

Screen Shot 2015-10-06 at 14.38.15

3. Stephen Covey’s “time management matrix” which uses quadrants to rank task in a two-by-two matrix based on importance and urgency.

4. A “want to do/have to do” prioritization method using a two-by-two matrix. (I don’t know where this comes from; anyone know the source?)

Processed with VSCOcam with b3 preset

A few notes about my flowchart graphic [direct download in PNG format, 224 KB].

  • I use @ notation for email labels to determine both status and type of action needed: @action, @reply, and @read/review, etc.
  • The “Soon / Later” items at the bottom right—those logged for later—do become things to start with again once they come up in review. In my workflow, I repeat the flowchart decisions for each item during weekly and monthly review.
  • “Quick wins” aren’t mapped here; they are tasks that don’t take much time and are easy to complete. You can shortcut the flowchart from “Not urgent for today” to “Do it now” for these quick ones.

Sweet! Now I can mark as done posting this to my blog.

SSH Config for Slow Connections

Via Andy Skelton in 2010, proving once again that great advice is timeless.

With these lines in your SSH config file—usually in .ssh directory in your user home directory—you’ll enjoy a more reliable remote shell session.

# Do not kill connection if route is down temporarily.
TCPKeepAlive no

# Allow ten minutes down time before giving up the connection.
ServerAliveCountMax 30
ServerAliveInterval 20

# Conserve bandwith. (Compression is off by default.)
Compression yes

Automatic WordPress Updates with SVN

Want to keep your WordPress install up to date automatically? Follow these steps to add a cron job to update your WordPress install every 6 hours.

Set up the install

The WordPress install must be a Subversion checkout. You can grab the bleeding edge source with a command like this:

svn co http://core.svn.wordpress.org/trunk/ .

If you aren’t familiar with Subversion, start here:

Schedule the updates

Add the cron job from the command line.

  1. Edit the cron job list.
    crontab -e
  2. Add the cron job (edit the path to your WordPress install).
    # Update WordPress install every six hours
    * */6 * * * svn up -q ~/path/to/your/wp-install
  3. Save and close.

To learn more about editing cron jobs from the command line search Google for man cron and man crontab.

You can also use a GUI tool like CronniX on Mac OS X to manage the cron jobs.


  • The -q parameter tells the svn update command to run silently so that you don’t have to worry about any output from the cron job. But, you should add the MAILTO definition if you want to completely silence output.
  • Some systems don’t recognize the */6 syntax for hourly notation. If you get an error when trying to save the cron job you might have to change it to comma-separated values instead: 0,6,12 or similar.