What I read (and what I didn’t read) in 2018

This is a long one! In this post we’ve got all my short reviews of the books I read in 2018, some very brief notes on the books I put down in 2018 without completing, notes on coming back to Twitter, and finally some notes on leaving Facebook. (The last one made my life much better, I think.)

Here’s what I read and didn’t read in 2018. (All book title links are affiliate-free links to Goodreads.)

What I read

Principles: Life and Work by Ray Dalio

Recommended for anyone interested in the continual design of the life or organization they find themselves in. Best seen as Dalio seems to suggest as a catalyst for abstracting out your own principles by facing down the hard truths of reality and demanding feedback on the truths you might be blinded to. In other words, chew the book up, digest as much as you can, and use it as fuel to create your own version of this book. It’s got me tweaking some items in my own routines so it seems to have clicked with me. I would have given the book five stars if the back half wasn’t such a slog. It’s more like an open reference manual for Bridgewater employees and Dalio claims it was not intended to be read straight through.

Macbeth by William Shakespeare

Things go downhill fast for Macbeth and the play moves just as quickly. The world comes undone alongside his actions and reactions to them. Reality can’t stand a king that won’t act kingly and Macbeth finally curses life itself. Also, there are gory-locked ghosts. It’s not exactly a fun read but that’s not exactly why you read it, and you should read it, it’s great — but not the Amazon Classics Edition I read. I was surprised at the lack of footnotes. Pay some money for a decent edition.

Warbreaker by Brandon Sanderson

Brandon Sanderson is probably my favourite “page turner” author but this book really pales in comparison next to his first Mistborn trilogy and the Stormlight series. I only really read it because characters in this book appear in the Stormlight books and it was that alone that pushed me on to the end. It really dragged for me until the middle of the book but then the pace picked up and it was at least diverting.

Leadership and Self-Deception: Getting Out of the Box by The Arbinger Institute

An extended business-oriented parable on what happens when you ignore the instinctual feeling to help those around you. You either honor that feeling or you betray it. What happens when you betray it? It isn’t good according to the book. It’s self-betrayal that sets off a chain of events that leaves you feeling justified and others looking contemptible. You wind up calling that your character and living in a warped version of reality with warped results in all your actions. Worse still you’re probably doing this all the time. It has a dated Sunday School feel to it for a book published in 2002 but I won’t knock points for that. It all rang true. Highly recommended.

The Anatomy of Peace: Resolving the Heart of Conflict by the Arbinger Institute

A sequel (and narrative prequel) to Leadership and Self-Deception again written in the style of a “Church Movie Night” drama. You’ll know it if you’ve seen one: It’s teachable moment after teachable moment piled on in dialogue after dialogue. Again excellent despite that. Mostly a reiteration and expansion of the previous book though this one draws out more of the stoicism implicit in the ideas here. The key idea is again something like: “You and everyone on the planet are going to feel a desire to treat people as persons and help them when they’re in need. You’re either going to honor that desire in your behaviors towards them — which may or may not help them — or betray that desire and dehumanize yourself and them. That won’t work out well for either of you.” There’s no real argument or proof for the inciting incident (the instant and unconscious, or maybe even biological, desire to help) but it feels right enough. Well worth anyone’s time. (It’s very short.)

Design is Storytelling by Ellen Lupton

A pleasant introduction to a wide variety of psychological and storytelling ideas that can be and are successfully applied to the thinking and problem solving involved in the practice of designing things. Again, it’s just “pleasant” or a good primer.

Jung: A Very Short Introduction by Anthony Stevens

Definitely worth reading if the title is what you’d like. I feel like Jung and the origins of analysis are less of a mystery now. I was surprised to find out that there is some scientific evidence now for some of Jung’s conjecture about consciousness, how much actually was conjecture, and how against the grain it was when he was developing it.

The Courage to be Disliked by Ichiro Kishimi and Fumitake Koga

Something like an introduction to psychologist Alfred Adler, a contemporary of Freud and Jung who I, and apparently many other people, had previously known little about. If you’ve read any Dale Carnegie or Stephen Covey you’ve already had your own little introduction. It seems Adler was an influence on them.

With my own background reading I was reminded of Stoicism’s rejection of “things you can’t change” in understanding the world and Adlerian Psychology often felt to my mind like a more systematic and expansive restating of that idea. It often sounded pretty radical. Which is why the format of the book is so great. Presented as a dialogue between a philosopher steeped in Adler and a youth who thinks Adler sounds nuts you can come alongside the youth.

Recommended if you’re interested in practical life philosophies or how one might live better type stuff.

Uprooted by Naomi Novik

Given that I read this over one 24 hour period that must be a sure sign I think it’s good. It’s wizards and witches fighting back a corrupt and evil Wood with a capital W in a fantasy world that draws on Eastern Europe for inspiration. It’s also an emotionally real story about friendship, loss, honesty, and finding home. With cool action scenes, awesome magic, and gross monsters. I really liked it. It reminded me a lot of Jonathan Strange & Mr Norrel.

I’m super-excited to see that Novik has another fantasy book out. It’s near the top of my to-read list.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Malone Scott

On my required reading list for people who are a “boss”. (The other being Managing Humans.) Do people report to you in any way? You’re a “boss”. I really appreciated the fundamental core first step to starting on the path of being a “kickass boss”: ask for people to provide you with radical candor and work to make sure they provide you with it. Everything starts there and you work out from that virtue and individual oriented position. Don’t think you’ve got this Radical Candor thing down with the medium post summary version. There’s good advice here on running a team and communicating effectively. As in, communicating in order to get things done.

I wish I’d read this book years ago.

Unsafe Thinking: How to be Nimble and Bold When You Need it Most by Jonah Sachs

Pretty decent summary on what it feels like to take risks, how to lean into that anxiety, making space for creative thinking, and protecting it. A little too surface level for me. I was looking for a deep dive and not something as broad. The best parts were the stories and anecdotes but I didn’t find enough of that either. Still pretty decent though.

Product Management in Practice: A Real-World Guide to the Key Connective Role of the 21st Century by Matt Lemay

Do you lead or manage teams of people who make things? This belongs on your shelf next to Managing Humans and Radical Candor. It’s written in a conversational style that focuses on where the theory of getting things done breaks down in real life — and then it tells you how to push through. Highly recommended. This book was a 10x confidence booster, corrective, and guide for me. Might have been the best book I read all year.

Strategize: Product Strategy and Product Roadmap Practices for the Digital Age by Roman Pichler

A great reference book on forming a product strategy, getting it into a roadmap, and implementing it milestone by milestone. My limited experience with full-blown “official” Agile development made some parts a little cloudier for me but if I made it through anyone can.

Little Bets: How Breakthrough Ideas Emerge from Small Discoveries by Peter Sims

Lively, short book on creativity, risk-taking, feedback, and making successful products. Loved it. Really encouraging.

The Compound Effect: Jumpstart Your Income, Your Life, Your Success by Darren Hardy

Read on the suggestion of an executive coach and surprised myself by liking this as much as I did. I think if you went into it with the attitude that the book is much like a coach in written form you might like it too. Another book about the power of habit and routine but with its own flavor of attitude, inspirational anecdata, and good advice. The book comes with a set of templates for analyzing ones life as well. Which I used, and to my surprise, also enjoyed. Almost perfect but for a hard sell that surrounds the book and the get-rich quick dressing that surrounds it all. It’s a hard-work over time with the right direction produces compound investment curves type book.

I love giving people books on how to form good habits and I wound up giving this one as a Christmas gift to someone.

The 12 Week Year by Brian P. Moran

Another recommendation from an executive coach. I was pretty skeptical of this one — just shorten the year and you’re done! — but it’s really good. The branding of the title is a bit much but think of it as a total system for approaching rapid advancement of goals in the short term towards a longer term vision while eliminating distractions through practical management of your time and, well, that’s the book in a nutshell from my point of view. Lots to learn here.

User Experience Management: Essential Skills for Leading Effective UX Teams by Arnie Lund

Almost too much to read. A compendium of literally everything one would want to know about leading a UX team from hiring, to building a lab, including finding room in a budget, to leadership skills, and evangelizing work internally/externally. It’s peppered with real stories from real managers and leaders through the UX field. Kind of an incredible effort though a slog at many points. I might have hit a record number of highlights here. There’s just so much practical and useful stuff in here.

A Higher Standard: Leadership Strategies from America’s First Female Four-Star General by Ann Dunwoody

I mined this book for insight into leadership skills and management anecdotes but what I especially enjoyed in the end was a newfound respect for military life. And most especially the sense of multi-generational teamwork along with the sense of dedicating ones life to something bigger than themselves. But back to leadership skills: I wound up highlighting almost an entire chapter on what it means to have a vision, develop it, share it, and drive towards it. Probably the best no nonsense explanation of that task out there.

Design Thinking: Integrating Innovation, Customer Experience, and Brand Value by Thomas Lockwood

Great series of essays on what makes Design Thinking. Most interesting for me turned out to be the essays on Service Design and Brand Design. A little dry at times so don’t go in expecting an easy read. But this is the book on Design Thinking.

Tribe of Mentors: Short Life Advice from the Best in the World by Timothy Ferriss

What a great book. It’s more like a collection of short interviews all following the same short set of questions posed to a diverse group of accomplished people. And it’s fascinating. Interesting routine ideas, battle-tested advice, inspirational quotes, and a resulting shot of empathy when you realize how “the same” everyone is. I even loved the experience of reading it and talking about the people I was learning about or learning new things about.

The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt and Jeff Cox

6 stars out of 5. This page-turner business novel about identifying constraints in manufacturing, really in systems, and removing them was incredible. Highly recommended. I want posters in my office with the five focusing steps, and three key questions, and “what is the goal?” question from this book. I wish I read this decades ago.

The Rime of the Ancient Mariner by Samuel Taylor Coleridge

Like a rotting, slimy, nightmare about sin, confession, and maybe responsibility. Does that sound like a good time? If so, read this poem. I recommend reading it out loud.

What I didn’t read

Notable books I started and put down for various reasons, skimmed and read at only a surface-level, or where I only read select parts …

A note on Twitter

I started using Twitter again this year after a two-year absence that is really more like four or five years if you count me being really engaged with it. I wanted to make a note here about the three types of thing I avoided reading.

  1. Negative tweets in general from people I follow. How? I did a mass unfollowing of accounts that were generally negative. I’m super-suspicious of what I like to call “black box algorithmic media”. That’s content delivered to me by an algorithm I have no insight into highly likely to be trained on prioritizing “it’s a train wreck and I can’t look away” content that will make me angry or upset. I don’t need that in my life in general and I especially don’t need to train a bot to make it worse so I don’t follow people who are likely to deliver that content to me.
  2. Negative content from the people I do follow that I don’t really want to read. For the first time in about ten years of using Twitter I’m muting select terms to clean up my feed. It’s mostly political and current events type things that tend to skew towards polarization and general negativity. Things that an algorithm is going to love to surface to me in the worst kind of feedback loop.
  3. Replies from people who don’t really want to have a conversation but instead want to have an argument. I just ignore these types of tweets now. This is the type of content that made me stop using Twitter in the first place. I recommend just avoiding it.

A note on Facebook

In a few weeks my Facebook account will have been deactivated for about a year. I think I’m better off for not having read anything on Facebook in that time. See my thoughts above on “black box algorithmic media” and consider that it wasn’t until about a month ago that I finally realized that I’d lost the compulsion to want to check in on Facebook. So, about nine or ten months to break that habit.


It’s Dangerous to Go Alone

Some thoughts on how to push back against the gravity of “going it alone” when working remote or in an all-distributed company.


I have several friends at work who love the Zelda game series from Nintendo. And I played the first few games growing up so the video-game-famous quote from the first game, “It’s dangerous to go alone! Take this.” has been stuck in my head for years now. So maybe it’s no surprise that the other day while thinking about what it’s like to work in an 800+ person fully-distributed company where everyone is working “remote” I realized that there’s a high chance that this sort of sums up what I think is one of the most important survival mechanisms or truisms for that kind of work.

Here’s the idea broke down into two principles.

1. Remember that it’s dangerous to go alone.
2. Gear up when you go it alone.

Be careful about letting people go it alone and make sure you’re armed to the teeth whenever it looks like you might be.

Remember that it’s dangerous to go alone

This first principle should be pretty obvious but I find it surprising how often we (as in humans in general) tend to forget it. Going it alone kind of sucks. You wind up bearing the burden of what will likely wind up being more and more increasingly complex decisions. It’s all on you. Sometimes it means you can move faster but remember, it’s dangerous.

Here’s an example from outside of the world of Zelda.

“… pairs of people working together can make better decisions than the better member of the pair working alone.”
Neuroscientists Uta and Chris Frith

Let’s reverse that, let’s say you’re a pretty smart person and make great decisions on your own. You’re missing out on making even better decisions when you’re not pairing up with someone. (Also, there’s a high chance you’re not as smart as you think you are — or maybe you’re even smarter than you think! Self-awareness can be tricky and your smarts are situational.)

Recently at work we’ve been experimenting with pairing up design leads with tech leads, or business leads with tech leads, to run projects. And experimenting with small groups of three designers leading design teams for products. We’ve found this to work extremely well.

As I look back on the first fruits of these experiments it’s seemed like unusually rapid progress has been made on complex problems with work that stretches across multiple teams, divisions, and even products. I like to think that this pairing has helped with that.

Inside our distributed design team for WordPress.com we try and work similarly. We take advantage of video calls to bring people together in the same way. A weekly “show and tell”, bi-weekly “team times” where we talk about how we work or share knowledge, pairing during video-based “working sessions” (remote control with Zoom is especially cool), and in general, just trying not to let anyone get stuck out there on their own on important projects.

Gear up when you go it alone

Note that in the Zelda game the intrepid hero Link is going it alone. He’s getting that sword because it’s dangerous out there. What’s the sword you’re going to bring with you when you go it alone? Like Dr. Seuss says, “Whether you like it or not, alone will be something you’ll be quite a lot.”

The short answer is, I don’t really know yet, but it’s something I’m always trying to figure out. I think it looks a lot like just taking care of yourself.

  • Journal
  • Meditate
  • Exercise
  • Eat right
  • Get outside
  • Take real breaks away from work

The truth is that we need partners, we need guides, and we need friends. Lean on your relationships and networks at work. Ask for some help once in a while. Take care of yourself.

And be creative. I love this tweet from my colleague Alison Rand.

Distributed work is a different kind of work. That means taking the time to think creatively about new rituals and new ways of communicating with people.

I know that things like this can seem obvious but it also seems like they’re surprisingly easy to forget. I see people forgetting it all the time. Working in an all-distributed team means I can sit in my home office in the middle of Canada and work with people from all around the world. It also means I have a responsibility to make that work as well as it can for myself and my colleagues.

In other words, it’s worthwhile to be conscious about it.

Also, I’d love to hear about how you make your situation work for you if you work remotely or in an all-distributed company! Send me an email or leave a comment below.


We’re nominating Design for Best Supporting Actor and Actress


We’ve started using Design as “best supporting actor/actress” as a metaphorical goal for our centralized Design teams at Automattic. It’s an interesting metaphor, right? It’s got to feel good to be up on stage clutching a golden trophy. But why not nominate Design for the starring role? Here’s how I’ve started to think about it.

Imagine it’s Oscar night at your company. Best picture? Those are the projects and goals that led to success for the business and our users this past year. We went out to see that story come to life. Best actor or actress? The product and platform teams that drove those projects to completion. The teams that gave all they had to realize the stories we came to see.

But now it’s the envelope for best supporting actor or actress being opened. Who’s going to win? If we’re doing our job right that’s our Design team. We had a big role to fill. We were there supporting the organization, our business metrics, our teams, and the experience our users are trying to tell us they need.

Think of Heath Ledger as the Joker in The Dark Knight or Whoopi Goldberg in Ghost. They weren’t the stars of the film. But it was their roles that helped to make the picture a complete and memorable work. And so Design will be there helping to bring it all together.

Recognizing a supporting role is really about recognizing teamwork. Recognizing the effort in supporting everyone’s effort and needs in order to make something greater than what any of us could do alone.

When the Academy of Motion Picture Arts and Sciences started handing out awards in this category with their ninth go at the Oscars in 1936 they were recognizing that a motion picture is made up of many parts. A holistic enterprise where everyone supports a larger effort. That’s an award I look forward to our design teams winning.


Self-Inflicted Chaos

An interesting analysis from John Cutler on Self-inflicted Chaos in organizations. What’s self-inflicted chaos?

Self-inflicted chaos

– Trying to do too much at once, and ending up doing nothing particularly well.
– Misjudging the blast radius of task or project, and the non-linear impacts that misjudgment will have on the whole organization.


– When a startup team is “killing it”, there tends to be an almost eery sense of focus.
– Fewer meetings, that produce “good ideas” or “wouldn’t it be cool ifs” and more “done, done, next thing on-deck, no blockers.”

Good to remember. Are you headed in the direction of eerie focus? And done, done, done? Or in the opposite direction in your work? And how can you make certain it’s the former day by day? Those are the questions I asked myself this morning. Workin’ on answering them in the processes I control.

Via my always-on-process colleague Brie.



The wisdom of duplication

I love this passage from Arnie Lund’s tome on User Experience Management. I think it’s really important to consider. Especially if you lead in a distributed organization.

We perceive information via three channels:
– Visual (60%)
– Audio (30%)
– and Semantic (10%).

When we share information via e-mail or any other sharing tool, it is perceived only via semantic channel which is usually not sufficient.

That is why it is wise to duplicate orally at least some data that have been shared in written form, and to provide visual support for audio information. Distant communication is less vivid than live, so we have to be more careful with jokes, avoid using slang, and so forth.

It is also more difficult to jump from one topic to another, therefore it is recommended to discuss issues and summarize after each of them.

(Passage lightly edited by me to up the visual support.)

Working in a 100% distributed organization I’m pretty sure I’ve seen a lack of duplication hurt communication. I’m come that conclusion because I’m pretty sure because I’ve seen it happen with myself in the past! It’s something I try and work on improving in my role as a leader.

What could this look like if we really pushed it? I tried to take this out a bit further when thinking about it with an extreme example of what that duplication could look like. A religious organization. Consider a church.

How many sermons or homilies are delivered every week around the world? Backed by how many books? Letters? Essays? Paintings and iconography? That level of duplication and variation on a theme is something you want in your toolkit if you’re going to maintain an idea and a community for millennia. (It sounds a bit like a science-fiction story when I think of it that way.)

Bringing that back to my day to day it makes me wonder: what could alignment look like for a year-level project if we applied a millennia-level alignment tool to it? If you made a practice of ensuring a concept or a plan was understood, example by example, week by week, month by month, channel by channel?

I’m not suggesting we go out and start practicing iconography and toiling at an illuminated manuscript. But consider the value in visual aids, support for ideas via a quick video demonstration, a regular review of important “whys” via a voice or video call, and, most importantly, a willingness to duplicate a message.


Closing the gap


I like to think we all know of someone we admire. Someone who possesses a character or set of skills we’d like to see in ourselves. It’s certainly true of me and has been my whole life. What to do about it? We can’t go back in time and relive our lives and I’m sure we wouldn’t want to but there is something we can do.

We can close the gap.

We can start on something small pointed in the same direction as that person or persons. Starting small can really work. Starting with one push-up a day and growing from there led me into a 276-day streak of daily exercise. We can found new habits and move the biggest levers that we know of that will propel us on that journey of closing the gap between ourselves and the people we admire.

Here’s one lever: reach out to those people and talk to them. Send a friendly message along and ask for some advice. You might be surprised at who’s willing to help you. Think creatively of forcing functions like that. Look for things that will propel you along. Sometimes you have to trick yourself into doing what you know is right.

No matter how far away we are from where we want to be we can always work on closing the gap.



Worse is Better

I came across the software design philosophy of “Worse is Better” via a post from John Maeda titled Perfection vs Just Ship It. The idea is that software which follows the “worse-is-better” approach has “better survival characteristics than the-right-thing.” You can read all about it in the original essay —  The Rise of “Worse is Better” — but I made a table here for easier side-by-side comparison.



The Wave

For a while now I’ve been using my iPhone wallpaper and lock screen to get some more art in my life. (I do the same thing on my Desktop with a rotating custom gallery in Momentum.) The current iPhone art is The Wave by 19th Century Russian artist, Ivan Aivazovsky. It’s apparently one of his most bleak works of sailors lost at sea but I just see people trying their hardest to work make the impossible work. Sometimes I think what I’m working on is impossible or at least extremely difficult. It’s nowhere near as difficult as that. It’s a good reminder.


Ray Dalio and Bob Dylan on challenging the unconcious mind

What does Ray Dalio, super-investor and author of Principles for Life and Work think your greatest challenge is? It’s mastering the part of you that won’t be mastered.

Your greatest challenge will be having your thoughtful higher-level you manage your emotional lower-level you. The best way to do that is to consciously develop habits that will make doing the things that are good for you habitual.
— Ray Dalio in Principles for Life and Work

I’ve been thinking of this as more like a struggle. The struggle for your (somewhat) free will — your conscious thought — to control and tame your (mostly) chained will — or unconscious mind. If you’ve ever tried to break a bad habit, a really, really ingrained one — for Ray Dalio it’s close-mindedness or something like narcissistic conversation — you can probably relate to the metaphor of a struggle. It’s not easy.

That struggle is well-expressed in a thread from one of my favourite Bob Dylan songs: Where Are You Tonight? (Journey Through Dark Heat).

The truth was obscure, too profound and too pure
To live it you have to explode
In that last hour of need, we entirely agreed
Sacrifice was the code of the road

I fought with my twin, that enemy within
’Til both of us fell by the way
Horseplay and disease is killing me by degrees
While the law looks the other way

There’s a white diamond gloom on the dark side of this room
And a pathway that leads up to the stars
If you don’t believe there’s a price for this sweet paradise
Remind me to show you the scars

There’s a new day at dawn and I’ve finally arrived
If I’m there in the morning, baby, you’ll know I’ve survived
I can’t believe it, I can’t believe I’m alive

Your greatest challenge:

You have to do things that seem too hard and face much discomfort. (It’s uncomfortable developing good habits and breaking bad ones.) The discomfort is in doing things that the “lower-level you” doesn’t want to do. You have to explode an old way of doing things. There will be sacrifice. The struggle between you and your twin (the “lower-level you” or enemy within that’s easily misled by horseplay and dis-ease) will lead to both combatants falling. There are going to be scars but you’ll arrive at your destination even though you might find you can’t believe it.



Improving focus by removing the web browser from my phone

road-nature-hand-path (1).jpg

Five days ago I used the restrictions settings on my iPhone to block access to my web browser. I did it on a whim wondering what it would be like and since that time I’ve turned it on once for only a few minutes. I was in Home Depot and wanted to know what kind of tape I needed for insulation vapour barrier. (It’s Tuck Tape.)

It’s been an interesting experiment.

Why? It was immediately apparent that it was destroying my focus in an incredible way. Or at least, having access to it was. I do most of my personal reading on my phone using the Kindle app and it was only by removing access to my browser that I was able to see how often I was jumping away to some distraction instead of making progress in a book. There was a sad first hour where I’d continually jump out looking for the Safari app every minute or so. I felt embarrassed that I couldn’t keep my attention on the book.

I’ve experimented with some other attempts to improve focus in a world where smart phones are the norm. I routinely delete apps from my phone that distract me. I use the Freedom app to block sites that deliver content to me through algorithms designed to “hook” me. Just like removing the browser all together they’re all easily disabled. I can delete an app or change settings. But I find that putting a simple barrier between me and distractions helps. I’m just lazy enough that I don’t want to have to update a setting in order to read something that I don’t really need to read.

You may have realized, like I did later, that I didn’t need to turn on access to my browser in Home Depot. I could have just asked someone in the store. When I’ve wanted to look something up this week I’ve instead decided to wait. Or walk to my office in the house to check something out on the laptop. Ironically making me more mobile.

That may not seem pretty radical — unless you’re like me and always have a smart phone on your hip. (“I might have to talk to someone?! Or wait?!”) You might want to give it a shot. I’m going to keep it up. My initial impression is that it’s smart to make your phone dumber.