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 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

The Wave, Ivan Aivazovsky

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.

Bob Dylan and The Band — 1974 by Jim Summaria

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.

The power of social pressures on behaviour


Here’s Don Norman in The Design of Everyday Things on fighting the incredible power of social pressures on behaviour. What kind of social pressures? The social forces that cause “otherwise sensible people to do things they know are wrong and possibly dangerous.”

When I was in training to do underwater (scuba) diving, our instructor was so concerned about this that he said he would reward anyone who stopped a dive early in favour of safety. People are normally buoyant, so they need weights to get them beneath the surface. When the water is cold, the problem is intensified because divers must then wear either wet or dry suits to keep warm, and these suits add buoyancy. Adjusting buoyancy is an important part of the dive, so along with the weights, divers also wear air vests into which they continually add or remove air so that the body is close to neutral buoyancy. (As divers go deeper, increased water pressure compresses the air in their protective suits and lungs, so they become heavier: the divers need to add air to their vests to compensate.)

When divers have gotten into difficulties and needed to get to the surface quickly, or when they were at the surface close to the shore but being tossed around by waves, some drowned because they were still being encumbered by their heavy weights. Because the weights are expensive, the divers didn’t want to release them. In addition, if the divers released the wights and then made it back safely, they could never prove that the release of the weights was necessary, so they would feel embarrassed, creating self-induced social pressure. Our instructor was very aware of the resulting reluctance of people to take the critical step of releasing their weights when they weren’t entirely positive it was necessary. To counteract this tendency, he announced that if anyone dropped the weights for safety reasons, he would publicly praise the diver and replace the weights at no cost to the person. This was a very persuasive attempt to overcome social pressures.


Normal, regular people — just like you and me — are out there every day risking drowning over a set of diving weights. Don Norman’s instructor is a genius and probably a hero. I hope you’re not going to get into life-threatening situations every day but you’re going to get into potentially life-worsening ones pretty often. It’s probably worth asking what potentially life-worsening or bettering behaviours you’re rewarding in your life.