Do What You’re Bad At [Video]

This video accompanies a blog post of the same title. The content is basically the same – if you prefer videos, watch this video. If you prefer blog posts, go read the blog post. If you’re a superfan, try both and spot the differences. You weirdo.

Also available on YouTube or on Facebook.

Do What You’re Bad At

This blog post is also available as a video. Would you prefer to watch/listen to me tell you about how I’ve learned to enjoy doing what I’m bad at?

There are a great number of things that I’m bad at. One thing I’m bad at (but that I’m trying to get better at) is being more-accepting of the fact that there are things that I am bad at.

Against a pale background, Dan, deep in thought and with a finger to his lips, staring into space. A stylised thought bubble above him shows that he is thinking about himself thinking about himself thinking about himself, and so on (implied to infinity).
I’ve also been thinking about how I’m bad at thinking about how I’m bad at thinking about how I’m bad at thinking about…

I’m pretty bad in a pub quiz. I’m bad at operating my pizza oven without destroying cookware. I’m especially bad at learning languages. I’m appallingly bad at surfing. Every time my work periodically leans in that direction I remember how bad I am at React. And I’ve repeatedly shown that I’m bad at keeping on top of blogging, to the extent that I’ve periodically declared bankruptcy on my drafts folder.

So yeah, pretty bad at things.

But hang on: that assessment isn’t entirely true.

Photograph showing a yellow banana on a pink background. The banana has a silver chain wrapped around it three times. Photo courtesy Deon Black.
I’m also particularly bad at choosing suitable stock photos for use in blog posts.

Being Bad

As a young kid, I was a smart cookie. I benefited from being an only child and getting lots of attention from a pair of clever parents, but I was also pretty bright and a quick learner with an interest in just about anything I tried. This made me appear naturally talented at a great many things, and – pushed-on by the praise of teachers, peers, and others – I discovered that I could “coast” pretty easily.

But a flair for things will only carry you so far, and a problem with not having to work hard at your education means that you don’t learn how to learn. I got bitten by this when I was in higher education, when I found that I actually had to work at getting new information to stick in my head (of course, being older makes learning harder too, as became especially obvious to me during my most-recent qualification)!

Dan, aged around 4, dressed in a duffel coat, bobble hat and gloves, kneeling on a red plastic sledge in a snow-filled garden. The garden is bordered by a wire fence, and in the background a man can be seen scraping icee off a car.
Ignore the fact that you’ve now seen me trying to sledge uphill and just accept that I was a clever kid (except at photography), okay?

A side-effect of these formative experiences is that I grew into an adult who strongly differentiated between two distinct classes of activities:

  1. Things I was good at, either because of talent or because I’d thoroughly studied them already. I experienced people’s admiration and respect when I practised these things, and it took little effort to stay “on top” of these fields, and
  2. Things I was bad at, because I didn’t have a natural aptitude and hadn’t yet put the time in to learning them. We don’t often give adults external reinforcement for “trying hard”, and I’d become somewhat addicted to being seen as awesome… so I shied away from things I was “bad at”.

The net result: I missed out on opportunities to learn new things, simply because I didn’t want to be seen as going through the “amateur” phase. In hindsight, that’s really disappointing! And this “I’m bad at (new) things” attitude definitely fed into the imposter syndrome I felt when I first started at Automattic.

Being Better

Leaving the Bodleian after 8½ years might have helped stimulate a change in me. I’d carved out a role for myself defined by the fields I knew best; advancing my career would require that I could learn new things. But beyond that, I benefited from my new employer whose “creed culture” strongly promotes continuous learning (I’ve vlogged about this before), and from my coach who’s been great at encouraging me towards a growth mindset.

A cake with icing printed with a picture of Dan in a library. Beneath are iced the words "Good Luck Dan".
“Good Luck Dan”, my Bodleian buddies said. But perhaps they should’ve said “Keep Learning Dan”.

But perhaps the biggest stimulus to remind me to keep actively learning, even (especially?) when it’s hard, might have been the pandemic. Going slightly crazy with cabin fever during the second lockdown, I decided to try and teach myself how to play the piano. Turns out I wasn’t alone, as I’ve mentioned before: the pandemic did strange things to us all.

I have no real experience of music; I didn’t even get to play recorder in primary school. And I’ve certainly got no talent for it (I can hear well enough to tell how awful my singing is, but that’s more a curse than a blessing). Also, every single beginners’ book and video course I looked at starts from the assumption that you’re going to want to “feel” your way into it, and that just didn’t sit well with the way my brain works.

Animation showing Dan, wearing a black t-shirt and tracksuit bottoms, playing an upright piano.
90% of what I do in front of a piano might be described as “Dan Mucks About (in B Minor)”, but that’s fine by me.

I wanted a theoretical background before I even sat down at a keyboard, so I took a free online course in music theory. Then I started working through a “beginners’ piano” book we got for the kids. Then I graduated to “first 50 Disney songs”, because I know how virtually all of them sound well enough that I’d be able to hear where I was going wrong. Since then, I’ve started gradually making my way through a transcription of Einaudi’s Islands. Feeling like I’d got a good handle on what I was supposed to be doing, I then took inspiration from a book JTA gave me and started trying to improvise.

Most days, I get no more than about 10 minutes on the piano. But little by little, day by day, that’s enough to learn. Nowadays even my inner critic perfectionist can tolerate hearing myself play. And while I know that I’ll probably never be as good as, say, the average 8-year-old on YouTube, I’m content in my limited capacity.

Three books on a blue-and-white tablecloth: John Thompson's Easiest Piano Course (Part One), First 50 Disney Songs, and Essential Einaudi - Islands. Beneath them sits a simplified diagram showing the circle of fifths.
Let’s start at the very beginning. (A very good place to start.)

If I’m trying to cultivate my wonder syndrome, I need to stay alert for “things I’m bad at” that I could conceivably be better at if I were just brave enough to try to learn. I’m now proudly an “embarrassingly amateur” pianist, which I’m at-long-last growing to see as better than a being non-pianist.

Off the back of that experience, I’m going to try to spend more time doing things that I’m bad at. And I’d encourage you to do the same.

Automattic International

(This is yet another post about Automattic. Seee more posts about my experience of working at Automattic.)

Off the back of my recent post about privileges I enjoy as a result of my location and first language, even at my highly-multinational employer, and inspired by my colleague Atanas‘ data-mining into where Automatticians are located, I decided to do another treemap, this time about which countries Automatticians call home:

Where are the Automatticians?

Treemap showing countries of Automatticians. North America and specifically the USA dominates, the UK has the most in Europe, etc.
If raw data’s your thing (or if you’re just struggling to make out the names of the countries with fewer Automatticians), here’s a CSV file for you.

To get a better picture of that, let’s plot a couple of cartograms. This animation cycles between showing countries at (a) their actual (landmass) size and (b) approximately proportional to the number of Automatticians based in each country:

Animation showing countries "actual size" changing to proportional-to-Automattician-presence.
This animation alternates between showing countries at “actual size” and proportional to the number of Automatticians based there. North America and Europe dominate the map, but there are other quirks too: look at e.g. how South Africa, New Zealand and India balloon.

Another way to consider the data would be be comparing (a) the population of each country to (b) the number of Automatticians there. Let’s try that:

Animation showing countries proportional to population changing to proportional-to-Automattician-presence.
Here we see countries proportional to their relative population change shape to show number of Automatticians, as seen before. Notice how countries with larger populations like China shrink away to nothing while those with comparatively lower population density like Australia blow up.

There’s definitely something to learn from these maps about the cultural impact of our employee diversity, but I can’t say more about that right now… primarily because I’m not smart enough, but also at least in part because I’ve watched the map animations for too long and made myself seasick.

A note on methodology

A few quick notes on methodology, for the nerds out there who’ll want to argue with me:

  1. Country data was extracted directly from Automattic’s internal staff directory today and is based on self-declaration by employees (this is relevant because we employ a relatively high number of “digital nomads”, some of whom might not consider any one country their home).
  2. Countries were mapped to continents using this dataset.
  3. Maps are scaled using Robinson projection. Take your arguments about this over here.
  4. The treemaps were made using Excel. The cartographs were produced based on work by Gastner MT, Seguy V, More P. [Fast flow-based algorithm for creating density-equalizing map projections. Proc Natl Acad Sci USA 115(10):E2156–E2164 (2018)].
  5. Some countries have multiple names or varied name spellings and I tried to detect these and line-up the data right but apologies if I made a mess of it and missed yours.

Automattic Privilege

I’ve been thinking recently about three kinds of geographic privilege I enjoy in my work at Automattic. (See more posts about my experience of working at Automattic.)

1. Timezone Privilege

Take a look at the map below. I’m the pink pin here in Oxfordshire. The green pins are my immediate team – the people I work with on a day-to-day basis – and the blue pins are people outside of my immediate team but in its parent team (Automattic’s org chart is a bit like a fractal).

World map showing the locations of Dan, his immediate team, and its parent team. There's a cluster of nine pins Europe, a few pins further East in Russia and Indonesia, one in Cape Town, two in North America, and one in Central America.
I’m the pink pin; my immediate team are the green pins. People elsewhere in our parent team are the blue pins. Some pins represent multiple people.

Thinking about timezones, there are two big benefits to being where I am:

  1. I’m in the median timezone, which makes times that are suitable-for-everybody pretty convenient for me (I have a lot of lunchtime/early-afternoon meetings where I get to watch the sun rise and set, simultaneously, through my teammates’ windows).
  2. I’m West of the mean timezone, which means that most of my immediate coworkers start their day before me so I’m unlikely to start my day blocked by anything I’m waiting on.

(Of course, this privilege is in itself a side-effect of living close to the meridian, whose arbitrary location owes a lot to British naval and political clout in the 19th century: had France and Latin American countries gotten their way the prime median would have probably cut through the Atlantic or Pacific oceans.)

2. Language Privilege

English is Automattic’s first language (followed perhaps by PHP and Javascript!), not one of the 120 other languages spoken by Automatticians. That’s somewhat a consequence of the first language of its founders and the language in which the keywords of most programming languages occur.

It’s also a side-effect of how widely English is spoken, which in comes from (a) British colonialism and (b) the USA using Hollywood etc. to try to score a cultural victory.

Treemap showing languages spoken by Automatticians: English dominates, followed by Spanish, French, German, Italian, Hindi, Portugese, Mandarin, Russian, Japanese, Polish, Afrikaans, Dutch, Green, Catalan, Cantonese, Romanian, and many others.
Languages self-reportedly spoken by Automatticians, sized proportional to the number of speakers. No interpretation/filtering has been done, so you’ll see multiple dialects of the same root language.

I’ve long been a fan of the concept of an international axillary language but I appreciate that’s an idealistic dream whose war has probably already been lost.

For now, then, I benefit from being able to think, speak, and write in my first language all day, every day, and not have the experience of e.g. my two Indonesian colleagues who routinely speak English to one another rather than their shared tongue, just for the benefit of the rest of us in the room!

3. Passport Privilege

Despite the efforts of my government these last few years to isolate us from the world stage, a British passport holds an incredible amount of power, ranking fifth or sixth in the world depending on whose passport index you follow. Compared to many of my colleagues, I can enjoy visa-free and/or low-effort travel to a wider diversity of destinations.

Normally I might show you a map here, but everything’s a bit screwed by COVID-19, which still bars me from travelling to many places around the globe, but as restrictions start to lift my team have begun talking about our next in-person meetup, something we haven’t done since I first started when I met up with my colleagues in Cape Town and got assaulted by a penguin.

But even looking back to that trip, I recall the difficulties faced by colleagues who e.g. had to travel to a different country in order tom find an embassy just to apply for the visa they’d eventually need to travel to the meetup destination. If you’re not a holder of a privileged passport, international travel can be a lot harder, and I’ve definitely taken that for granted in the past.

I’m going to try to be more conscious of these privileges in my industry.

Automattic Growth

It just passed two years since I started working at Automattic, and I just made a startling discovery: I’ve now been with the company for longer than 50% of the staff.

When you hear that from a 2-year employee at a tech company, it’s easy to assume that they have a high staff turnover, but Automattic’s churn rate is relatively low, especially for our sector: 86% of developers stay longer than 5 years. So what’s happening? Let’s visualise it:

Graph showing all 1.802 current Automatticians as coloured squares, ordered by their start date. Dan Q's square is squarely (LOL) in the middle.
Everything in this graph, in which each current Automattician is a square, explains how I feel right now: still sometimes like a new fish, but in an increasingly big sea.

All that “red” at the bottom of the graph? That’s recent growth. Automattic’s expanding really rapidly right now, taking on new talent at a never-before-seen speed.

Since before I joined it’s been the case that our goals have demanded an influx of new engineers at a faster rate than we’ve been able to recruit, but it looks like things are improving. Recent refinements to our recruitment process (of which I’ve written about my experience) have helped, but I wonder how much we’ve also been aided by pandemic-related changes to working patterns? Many people, and especially in tech fields, have now discovered that working-from-home works for them, and a company like Automattic that’s been built for the last decade and a half on a “distributed” model is an ideal place to see that approach work at it’s best.

We’re rolling out new induction programmes to support this growth. Because I care about our corporate culture, I’ve volunteered myself as a Culture Buddy, so I’m going to spend some of this winter helping Newmatticians integrate into our (sometimes quirky, often chaotic) ways of working. I’m quite excited to be at a point where I’m in the “older 50%” of the organisation and so have a responsibility for supporting the “younger 50%”, even though I’m surprised that it came around so quickly.

Screenshot from officetoday.wordpress.com, where Automatticians share photos of their current work environment.
Automattic… culture? Can’t we just show them Office Today and be done with it?

I wonder how that graph will look in another two years.

Creed Cult-ure

My employer, Automattic, has a creed. Right now it reads:

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

Lots of companies have something like this, even if it falls short of a “creed”. It could be a “vision”, or a set of “values”, or something in that line.

Of course, sometimes that just means they’ve strung three clichéd words together because they think it looks good under their company logo, and they might as well have picked any equally-meaningless words.

Future logo and values of of Any Company, Anywhere.

But while most companies (and their staff) might pay lip service to their beliefs, Automattic’s one of few that seems to actually live it. And not in an awkward, shoehorned-in way: people here actually believe this stuff.

By way of example:

A woman in a wheelchair waves to a colleague via her laptop screen; she's smiling and has a cup of coffee by her side. Photo by Marcus Aurelius from Pexels.
Coffee: check. Webcam: check. Let’s touch bases, random colleague!

We’ve got a bot that, among other things, pairs up people from across the company for virtual “watercooler chat”/”coffee dates”/etc. It’s cool: I pair-up with random colleagues in my division, or the whole company, or fellow queermatticians… and collectively these provide me a half-hour hangout about once a week. It’s a great way to experience the diversity of culture, background and interests of your colleagues, as well as being a useful way to foster idea-sharing and “watercooler effect” serendipity.

For the last six months or so, I’ve been bringing a particular question to almost every random-chat I’ve been paired into:

What part of the Automattic creed resonates most-strongly for you right now?

Two women in black dresses sit in a graveyard by candlelight and hold up the Automattic logo. Edited image based on original photo by Valeria Boltneva from Pexels (used with permission) and the Automattic logo (used under the assumption that they won't mind, given the context).
On a good day, I’m at least 90% certain I’m a senior software engineer and not a cult member.

I volunteer my own answer first. It’s varied over time. Often I’m most-attached to “I will never stop learning.” Other times I connect best to “I will communicate as much as possible…” or “I am in a marathon, not a sprint…”. Lately I’ve felt a particular engagement with “I will never pass up the opportunity to help a colleague…”.

It varies for other people too. But every single person I’ve asked this question has been able to answer it. And they’ve been able to answer it confidently and with justifications for or examples of their choice.

Have you ever worked anywhere before where seemingly all your coworkers profess a genuine belief in the corporate creed? Like, enough that some of them get it tattooed onto their bodies. Unless you’ve been brainwashed by a cult, the answer is probably no.

Dan sits in his office; behind him, four separate monitors show the Automattic logo.
If Automattic is a cult, then it might be too late for me.

Why are Automatticians like that?

For some folks, of course, the creed is descriptive rather than prescriptive. Regarding its initial creation, Matt says that “as a hack to introduce new folks to our culture, we put a beta Automattic Creed, basically a statement of things important to us, written in the first person.”

But this alone isn’t an explanation, because back then there were only around a hundred people in the company: nowadays there are over 1,500. So how can the creed continue to be such a pervasive influence? Or to put it another way: why are Automatticians… like that?

  • Do we simply attract like-minded individuals? The creed is highly visible and cross-referenced by our recruitment pages, so it wouldn’t be entirely surprising.
  • Maybe we filter for people who are ideologically-compatible with the creed? Insofar as the qualities it describes are essential to integrating into our corporate culture, yes: our recruitment process does a great job of testing for those qualities.
  • Perhaps we converge on these values as a result of our experience as Automatticians? Once you’re in, you’re indoctrinated into the tenets of the creed and internalise its ideas.
  • Or perhaps it’s a combination of the three, in some ratio or another. (What’s the ratio?)

I’ve been here 1⅔ years and don’t know the answer yet. But I’ll tell you this: it’s inspiring to be part of a team that really seem to believe in what they do.

The Automattic Creed presented as an infographic with icons accompanying each tenet.
People keep making infographics of the creed, just for fun. Even if they’re not Automatticians (any longer). That’s not creepy, right?

Incidentally: if the creed speaks to you too, you might like to look at some of the many open positions! I promise we’re not actually a cult.

Plus we’ve been doing “work anywhere” for longer than almost anybody else and we’re really, really good at it.

If you enjoyed this, you might also like other blog posts about my time with Automattic: the recruitment process, accepting an offer, my induction, and the experience of lockdown in a distributed company, among others.

Automattic Retrospective (days 207 to 334)

Last year, I accepted a job offer with Automattic and I’ve been writing about it every 128 days. I’ve talked about my recruitment, induction, and experience of lockdown (which in turn inspired a post about the future of work). I’ve even helped enthuse other new Automatticians! Since my last post I’ve moved house so my home office has changed shape, but I’m still plodding along as always… and fast-approaching my first “Automattic birthday”! (This post ran a little late; the 128-day block was three weeks ago!)

Dan in his home office (links to an interactive 360° panoramic photo with info points).
If you missed it the first time around, click through to explore an interactive panoramic view of my workspace. It’s slightly more “unpacked” now.

As I approach my first full year as an Automattician, I find myself looking back on everything I’ve learned… but also looking around at all the things I still don’t understand! I’m not learning something new every day any more… but I’m still learning something new most weeks.

This summer I’ve been getting up-close and personal with Gutenberg components. I’d mostly managed to avoid learning the React (eww; JSX, bad documentation, and an elephantine payload…) necessary to hack Gutenberg, but in helping to implement new tools for WooCommerce.com I’ve discovered that it’s… not quite as painful as I’d thought. There are even some bits I quite like. But I don’t expect to fall in love with React any time soon. This autumn I’ve been mostly working on search and personalisation, integrating customer analytics data with our marketplace to help understand what people look for on our sites and using that to guide their future experience (and that of others “like” them). There’s always something new.

Alpha project planning meeting via Zoom.
I suppose that by now everybody‘s used to meetings that look like this, but when I first started at Automattic a year ago they were less-commonplace.

My team continues to grow, with two newmatticians this month and a third starting in January. In fact, my team’s planning to fork into two closely-linked subteams; one with a focus on customers and vendors, the other geared towards infrastructure. It’s exciting to see my role grow and change, but I worry about the risk of gradually pigeon-holing myself into an increasingly narrow specialisation. Which wouldn’t suit me: I like to keep a finger in all the pies. Still; my manager’s reassuring that this isn’t likely to be the case and our plans are going in the “right” direction.

Kudos to Dan "for resolving a weeks worth of project issues in one day".
Our “Kudos” system can be used to acknowledge other Automatticians going above and beyond. I was particularly proud of this one.

On the side of my various project work, I’ve occasionally found the opportunity for more-creative things. Last month, I did some data-mining over the company’s “kudos” history of the last five years and ran it through vis.js to try to find a new angle on understanding how Automattic’s staff, teams, and divisions interact with one another. It lead to some interesting results: panning through time, for example, you can see the separate island of Tumblr staff who joined us during the acquisition gradually become more-interconnected with the rest of the organisation over the course of the last year.

Automattic Kudos social graph for September 2020
Automattic as a social graph of kudos given/received during September 2020, colour-coded by team. Were you one of us, you’d be able to zoom in and find yourself. The large “branch” in the bottom right is mostly comprised of Tumblr staff.

The biggest disappointment of my time at Automattic so far was that I’ve not managed to go to a GM! The 2019 one – which looked awesome – took place only a couple of weeks before my contract started (despite my best efforts to wrangle my contract dates with the Bodleian and Automattic to try to work around that), but people reassured me that it was okay because I’d make it to the next one. Well.. 2020 makes fools of us all, I guess, because of course there’s no in-person GM this year. Maybe, hopefully, if and when the world goes back to normal I’ll get to spend time in-person with my colleagues once in a while… but for now, we’re having to suffice with Internet-based socialisation only, just like the rest of the world.

Buying Another House

Seven years ago, I wrote a six-part blog series (1, 2, 3, 4, 5, 6) about our Ruth, JTA and I’s experience of buying our first house. Now, though, we’re moving again, and it’s brought up all the same kinds of challenges and stresses as last time, plus a whole lot of bonus ones to boot.

Our house in Kidlington
Our old house – seen here in 2013 – has served its purpose. It’s time for us to move on.

In particular, new challenges this time around have included:

  • As owners, rather than renters, we’ve had both directions on the ladder to deal with. Not only did we have to find somewhere to move to that we can afford but we needed to find somebody who’d buy our current house (for enough money that we can afford the new place).
  • The first letting agents we appointed were pretty useless, somehow managing to get us no viewings whatsoever. Incidentally their local branch got closed soon after we ditched them and the last time I checked, the building was still up for sale: it doesn’t bode well for them that they can’t even sell their own building, does it?
  • The replacement letting agents (who sold us this house in the first place) were much better, but it still took a long time before we started getting offers we could act on.
  • We finally selected some buyers, accepting a lower offer because they were cash buyers and it would allow us to act quickly on the property we wanted to buy, only for the coronavirus lockdown to completely scupper our plans of a speedy move. And make any move a logistical nightmare.
  • Plus: we’re now doing this with lots more stuff (this won’t be a “rally some friends and rent a van” job like last time!), with two kids (who’re under our feet a lot on account of the lockdown), and so on.
Dan with his solar panels.
We added significant value to our old house during the time we owned it, for example by installing solar panels which continue to generate income as well as “free” energy. As well as being now conveniently close to a train line to London which I suppose would be good for commuters even though we’ve mostly used it for fun.

But it’s finally all coming together. We’ve got a house full of boxes, mind, and we can’t find anything, and somehow it still doesn’t feel like we’re prepared for when the removals lorry comes later this week. But we’re getting there. After a half-hour period between handing over the keys to the old place and picking up the keys to the new place (during which I guess we’ll technically be very-briefly homeless) we’ll this weekend be resident in our new home.

The Green, our new home
Our new home’s pretty delightful. I’ll vlog you a tour or something once we’re moved in, under the assumption that a housewarming party is still likely to be rendered impossible by coronavirus.

Our new house will:

  • Be out in the fabulous West Oxfordshire countryside.
  • Have sufficient rooms to retain an office and a “spare” bedroom while still giving the kids each their own bedroom.
  • Boast a fabulously-sized garden (we might have already promised the kids a climbing frame).
  • Have an incredible amount of storage space plus the potential for further expansion/conversion should the need ever arise. (On our second-to-last visit to the place with discovered an entire room, albeit an unfinished one, that we hadn’t known about before!)
  • Get ludicrously fast Internet access.

We lose some convenient public transport links, but you can’t have everything. And with me working from home all the time, Ruth – like many software geeks – likely working from home for the foreseeable future (except when she cycles into work), and JTA working from home for now but probably returning to what was always a driving commute “down the line”, those links aren’t as essential to us as they once were.

Sure: we’re going to be paying for it for the rest of our lives. But right now, at least, it feels like what we’re buying is a house we could well live in for the rest of our lives, too.

I certainly hope so. Moving house is hard.

Future Challenges for Remote Working

When the COVID-19 lockdown forced many offices to close and their staff to work remotely, some of us saw what was unfolding as an… opportunity in disguise. Instead of the slow-but-steady decentralisation of work that’s very slowly become possible (technically, administratively, and politically) over the last 50 years, suddenly a torrent of people were discovering that remote working can work.

Man in sci-fi jumpsuit and futuristic AR goggles.
Unfulfilled promises of the world of tomorrow include flying cars, viable fusion power, accessible space travel, post-scarcity economies, and – until recently – widespread teleworking. Still waiting on my holodeck too.

The Future is Now

As much as I hate to be part of the “where’s my flying car?” brigade, I wrote ten years ago about my dissatisfaction that remote working wasn’t yet commonplace, let alone mainstream. I recalled a book I’d read as a child in the 1980s that promised a then-future 2020 of:

  1. near-universal automation of manual labour as machines become capable of an increasing diversity of human endeavours (we’re getting there, but slowly),
  2. a three- or four-day work week becoming typical as efficiency improvements are reinvested in the interests of humans rather than of corporations (we might have lost sight of that goal along the way, although there’s been some fresh interest in it lately), and
  3. widespread “teleworking”/”telecommuting”, as white-collar sectors grow and improvements in computing and telecommunications facilitate the “anywhere office”

Of those three dreams, the third soon seemed like it would become the most-immediate. Revolutionary advances in mobile telephony, miniaturisation of computers, and broadband networking ran way ahead of the developments in AI that might precipitate the first dream… or the sociological shift required for the second. But still… progress was slow.

At eight years old, I genuinely believed that most of my working life would be spent… wherever I happened to be. So far, most of my working life has been spent in an office, despite personally working quite hard for that not to be the case!

Driver's temperature being checked at the roadside by somebody in full protective equipment.
Apply directly to the head! Commuting looks different today than it did last year, but at least the roads are quieter.

I started at Automattic six months ago, an entirely distributed company. And so when friends and colleagues found themselves required to work remotely by the lockdown they came in droves to me for advice about how to do it! I was, of course, happy to help where I could: questions often covered running meetings and projects, maintaining morale, measuring output, and facilitating communication… and usually I think I gave good answers. Sometimes, though, the answer was “If you’re going to make that change, you’re going to need a cultural shift and some infrastructure investment first.” Y’know: “Don’t start from here.” If you received that advice from me: sorry!

(Incidentally, if you have a question I haven’t answered yet, try these clever people first for even better answers!)

More-recently, I was excited to see that many companies have adopted this “new normal” not as a temporary measure, but as a possible shape of things to come. Facebook, Twitter, Shopify, Square, and Spotify have all announced that they’re going to permit or encourage remote work as standard, even after the crisis is over.

Obviously tech companies are leading the way, here: not only are they most-likely to have the infrastructure and culture already in place to support this kind of shift. Also, they’re often competing for the same pool of talent and need to be seen as at-least as progressive as their direct rivals. Matt Mullenweg observes that:

What’s going to be newsworthy by the end of the year is not technology companies saying they’re embracing distributed work, but those that aren’t.

…some employers trapped in the past will force people to go to offices, but the illusion that the office was about work will be shattered forever, and companies that hold on to that legacy will be replaced by companies who embrace the antifragile nature of distributed organizations.

Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.
I’ve shared this before, I know, but it exudes Matt’s enthusiasm for distributed work so well that I’m sharing it again. Plus, some of the challenges I describe below map nicely to the borders between some of

Tomorrow’s Challenges

We’re all acutely familiar with the challenges companies are faced with today as they adapt to a remote-first environment. I’m more interested in the challenges that they might face in the future, as they attempt to continue to use a distributed workforce as the pandemic recedes. It’s easy to make the mistake of assuming that what many people are doing today is a rehearsal for the future of work, but the future will look different.

Some people, of course, prefer to spend some or all of their work hours in an office environment. Of the companies that went remote-first during the lockdown and now plan to stay that way indefinitely, some will lose employees who preferred the “old way”. For this and other reasons, some companies will retain their offices and go remote-optional, allowing flexible teleworking, and this has it’s own pitfalls:

  • Some remote-optional offices have an inherent bias towards in-person staff. In some companies with a mixture of in-person and remote staff, remote workers don’t get included in ad-hoc discussions, or don’t become part of the in-person social circles. They get overlooked for projects or promotions, or treated as second-class citizens. It’s easy to do this completely by accident and create a two-tiered system, which can lead to a cascade effect that eventually collapses the “optional” aspect of remote-optional; nowhere was this more visible that in Yahoo!’s backslide against remote-optional working in 2013.
  • Some remote-optional offices retain an archaic view on presenteeism and “core hours”. Does the routine you keep really matter? Remote-first working demands that productivity is measured by output, not by attendance, but management-by-attendance is (sadly) easier to implement, and some high-profile organisations favour this lazy but less-effective approach. It’s easy, but ineffective, for a remote-optional company to simply extend hours-counting performance metrics to their remote staff. Instead, allowing your staff (insofar as is possible) to work the hours that suit them as individuals opens up your hiring pool to a huge number of groups whom you might not otherwise reach (like single parents, carers, digital nomads, and international applicants) and helps you to get the best out of every one of them, whether they’re an early bird, a night owl, or somebody who’s most-productive after their siesta!
  • Pastoral care doesn’t stop being important after the crisis is over. Many companies that went remote-first for the coronavirus crisis have done an excellent job of being supportive and caring towards their employees (who, of course, are also victims of the crisis: by now, is there anybody whose life hasn’t been impacted?). But when these companies later go remote-optional, it’ll be easy for them to regress to their old patterns. They’ll start monitoring the wellbeing only of those right in front of them. Remote working is already challenging, but it can be made much harder if your company culture makes it hard to take a sick day, seek support on a HR issue, or make small-talk with a colleague.
Teleworker dressed from the waist up.
On the Internet, nobody knows that you’re only properly-dressed from the waist up. No, wait: as of 2020, everybody knows that. Let’s just all collectively own it, ‘k.

These are challenges specifically for companies that go permanently remote-optional following a period of remote-first during the coronavirus crisis.

Towards a Post-Lockdown Remote-Optional Workplace

How you face those challenges will vary for every company and industry, but it seems to me that there are five lessons a company can learn as it adapts to remote-optional work in a post-lockdown world:

  1. Measure impact, not input. You can’t effectively manage a remote team by headcount or closely tracking hours; you need to track outputs (what is produced), not inputs (person-hours). If your outputs aren’t measurable, make them measurable, to paraphrase probably-not-Galileo. Find metrics you can work with and rely on, keep them transparent and open, and re-evaluate often. Use the same metrics for in-office and remote workers.
  2. Level the playing field. Learn to spot the biases you create. Do the in-person attendees do all the talking at your semi-remote meetings? Do your remote workers have to “call in” to access information only stored on-site (including in individual’s heads)? When they’re small, these biases have a huge impact on productivity and morale. If they get big, they collapse your remote-optional environment.
  3. Always think bigger. You’re already committing to a shakeup, dragging your company from the 2020 of the real world into the 2020 we once dreamed of. Can you go further? Can you let your staff pick their own hours? Or workdays? Can your staff work in other countries? Can you switch some of your synchronous communications channels (e.g. meetings) into asynchronous information streams (chat, blogs, etc.)? Which of your telecommunications tools serve you, and which do you serve?
  4. Remember the human. Your remote workers aren’t faceless (pantsless) interchangeable components in your corporate machine. Foster interpersonal relationships and don’t let technology sever the interpersonal links between your staff. Encourage and facilitate (optional, but awesome) opportunities for networking and connection. Don’t forget to get together in-person sometimes: we’re a pack animal, and we form tribes more-easily when we can see one another.
  5. Support people through the change. Remote working requires a particular skillset; provide tools to help your staff adapt to it. Make training and development options available to in-office staff too: encourage as flexible a working environment as your industry permits. Succeed, and your best staff will pay you back in productivity and loyalty. Fail, and your best staff will leave you for your competitors.

I’m less-optimistic than Matt that effective distributed working is the inexorable future of work. But out of the ashes of the coronavirus crisis will come its best chance yet, and I know that there’ll be companies who get left behind in the dust. What are you doing to make sure your company isn’t one of them?

Automattic Lockdown (days 79 to 206)

Since I accepted a job offer with Automattic last summer I’ve been writing about my experience on a nice, round 128-day schedule. My first post described my application and recruitment process; my second post covered my induction, my initial two weeks working alongside the Happiness team (tech support), and my first month in my role. This is the third post, running through to the end of six and a half months as an Automattician.

Always Be Deploying

One of the things that’s quite striking about working on many of Automattic’s products, compared to places I’ve worked before, is the velocity. Their continuous integration game is pretty spectacular. We’re not talking “move fast and break things” iteration speeds (thank heavens), but we’re still talking fast.

Graph showing Automattic deployments for a typical week. Two of the 144 deployments on Monday were by Dan.
Deployments-per-day in a reasonably typical week. A minor bug slipped through in the first of the deployments I pushed on the Monday shown, so it was swiftly followed by a second deployment (no external end-users were affected: phew!).

My team tackles a constant stream of improvements in two-week sprints, with every third sprint being a cool-down period to focus on refactoring, technical debt, quick wins, and the like. Periodic HACK weeks – where HACK is (since 2018) a backronym for Helpful Acts in Customer Kindness – facilitate focussed efforts on improving our ecosystem and user experiences.

I’m working in a larger immediate team than I had for most of my pre-Automattic career. I’m working alongside nine other developers, typically in groups of two to four depending on the needs of whatever project I’m on. There’s a great deal of individual autonomy: we’re all part of a greater whole and we’re all pushing in the same direction, but outside of the requirements of the strategic goals of our division, the team’s tactical operations are very-much devolved and consensus-driven. We work out as a team how to solve the gnarly (and fun!) problems, how to make best use of our skills, how to share our knowledge, and how to schedule our priorities.

Dan in front of three monitors and a laptop.
My usual workspace looks pretty much exactly like you’re thinking that it does.

This team-level experience echoes the experience of being an individual at Automattic, too. The level of individual responsibility and autonomy we enjoy is similar to that I’ve seen only after accruing a couple of years of experience and authority at most other places I’ve worked. It’s amazing to see that you can give a large group of people so much self-controlled direction… and somehow get order out of the chaos. More than elsewhere, management is more to do with shepherding people into moving in the same direction than it is about dictating how the ultimate strategic goals might be achieved.

Na na na na na na na na VAT MAN!

Somewhere along the way, I somehow became my team’s live-in expert on tax. You know how it is: you solve a bug with VAT calculation in Europe… then you help roll out changes to support registration with the GST in Australia… and then one day you find yourself reading Mexican digital services tax legislation and you can’t remember where the transition was from being a general full-stack developer to having a specialisation in tax.

An Oxford coworking space.
Before the coronavirus lockdown, though, I’d sometimes find a coworking space (or cafe, or pub!) to chill in while I worked. This one was quiet on the day I took the photo.

Tax isn’t a major part of my work. But it’s definitely reached a point at which I’m a go-to figure. A week or so ago when somebody had a question about the application of sales taxes to purchases on the WooCommerce.com extensions store, their first thought was “I’ll ask Dan!” There’s something I wouldn’t have anticipated, six month ago.

Automattic’s culture lends itself to this kind of selective micro-specialisation. The company actively encourages staff to keep learning new things but mostly without providing a specific direction, and this – along with their tendency to attract folks who, like me, could foster an interest in almost any new topic so long as they’re learning something – means that my colleagues and I always seem to be developing some new skill or other.

Batman, with his costume's logo adapted to be "VAT man".
I ended up posting this picture to my team’s internal workspace, this week, as I looked a VAT-related calculation.

I know off the top of my head who I’d talk to about if I had a question about headless browser automation, or database index performance, or email marketing impact assessment, or queer representation, or getting the best airline fares, or whatever else. And if I didn’t, I could probably find them. None of their job descriptions mention that aspect of their work. They’re just the kind of people who, when they see a problem, try to deepen their understanding of it as a whole rather than just solving it for today.

A lack of pigeonholing, coupled with the kind of information management that comes out of being an entirely-distributed company, means that the specialisation of individuals becomes a Search-Don’t-Sort problem. You don’t necessarily find an internal specialist by their job title: you’re more-likely to find them by looking for previous work on particular topics. That feels pretty dynamic and exciting… although it does necessarily lead to occasional moments of temporary panic when you discover that something important (but short of mission-critical) doesn’t actually have anybody directly responsible for it.

Crisis response

No examination of somebody’s first 6+ months at a new company, covering Spring 2020, would be complete without mention of that company’s response to the coronavirus crisis. Because, let’s face it, that’s what everybody’s talking about everywhere right now.

Dan in a video meeting, in a hammock.
All workplace meetings should be done this way.

In many ways, Automattic is better-placed than most companies to weather the situation. What, we have to work from home now? Hold my beer. Got to shift your hours around childcare and other obligations? Sit down, let us show you how it’s done. Need time off for COVID-related reasons? We already have an open leave policy in place and it’s great, thanks.

As the UK’s lockdown (eventually) took hold I found myself treated within my social circle like some kind of expert on remote working. My inboxes filled up with queries from friends… How do I measure  output? How do I run a productive meeting? How do I maintain morale? I tried to help, but unfortunately some of my answers relied slightly on already having a distributed culture: having the information and resource management and teleworking infrastructure in-place before the crisis. Still, I’m optimistic that companies will come out of the other side of this situation with a better idea about how to plan for and execute remote working strategies.

Laptop screen showing five people videoconferencing.
Social distancing is much easier when you’re almost never in the same room as your colleagues anyway.

I’ve been quite impressed that even though Automattic’s all sorted for how work carries on through this crisis, we’ve gone a step further and tried to organise (remote) events for people who might be feeling more-isolated as a result of the various lockdowns around the world. I’ve seen mention of wine tasting events, toddler groups, guided meditation sessions, yoga clubs, and even a virtual dog park (?), all of which try to leverage the company’s existing distributed infrastructure to support employees who’re affected by the pandemic. That’s pretty cute.

(It might also have provided some inspiration for the murder mystery party I plan to run a week on Saturday…)

Distributed Work's Five Levels of Autonomy, by Matt Mullenweg.
Matt shared this diagram last month, and its strata seem increasingly visible as many companies adapt (with varying levels of success) to remote work.

In summary: Automattic’s still proving to be an adventure, I’m still loving their quirky and chaotic culture and the opportunity to learn something new every week, and while their response to the coronavirus crisis has been as solid as you’d expect from a fully-distributed company I’ve also been impressed by the company’s efforts to support staff (in a huge diversity of situations across many different countries) through it.

Getting Hired at Automattic

This article is a repost promoting content originally published elsewhere. See more things Dan's reposted.

I started at Automattic on November 20, 2019, and it’s an incredible place to work. I’m constantly impressed by my coworkers kindness, intelligence, and compassion. If you’re looking for a rewarding remote job that you can work from anywhere in the world, definitely apply.

I’m still overjoyed and amazed I was hired. While going through the hiring process, I devoured the blog posts from people describing their journeys. Here’s my contribution to the catalog. I hope it helps someone.

I’ve written about my own experience of Automattic’s hiring process and how awesome it is, but if you’re looking for a more-concise summary of what to expect from applying to and interviewing for a position, this is pretty great.