My Brief Life as a Happiness Engineer at Automattic

Automattic headquarters in San Francisco.

Part 1: Where I’m Coming From

In January of 2015, I came across an article from Matt Mullenweg, founder of Automattic, the company that produces WordPress. It said, “We’re hiring!”

I was surprised to hear this. I’d assumed Automattic was a vast company with thousands of employees, and that they hired direct from MIT, Carnegie-Mellon, and other cradles of brilliance. I appreciated this more democratic-sounding approach. It suggested that Automattic regards the entire population of Earth as its hiring pool.

I was shocked to learn, upon further reading, that Automattic had less than 400 employees. For a company that powers 25% of the internet–that’s over 90 million websites–this is impressive.

Well, I like being part of impressive things. I also needed a job. Could it be fate? I wondered.

In my experience, the most important events of my life have never simply happened to me, but have been things I’ve caused to happen. Maybe, I thought, this is a thing I need to make happen.

I decided to make it so.

I was stuck in a rocky transitional phase. For the past 15 years or so, I’d been working as a professional writer. In 1998, when I was 28 years old, I’d sold my first novel to HarperCollins Publishers for a sum that allowed me to stop working and focus exclusively on writing more fiction. I wasn’t rich, but I was independent, which is more important anyway.

But the publishing industry had been in decline for years. Although my first novel was a great success, the ones that followed were not as commercially viable, even though the critics seemed to like them well enough. My income from royalties and advances had been growing smaller every year, and I’d had to look further and further afield to supplement it. By the time I saw that ad from Automattic, I was doing what many people do these days to make ends meet: working in three or four seemingly disparate areas at once, generating small amounts of income in each one, lying awake at night worrying about how I would pay the bills, and hoping something would turn up soon that would allow me a modicum of both stability and satisfaction.

About ten years earlier, I’d started teaching myself how to build websites for fun. Using WordPress was a natural outgrowth of this pastime. By the time I came across that job ad, I’d been using the platform for a couple of years, and I loved it. From watching dozens of hours of YouTube videos, poring over the Codex, examining how other sites were built, and picking the brains of developers and designers in online conversations, I’d taught myself the rudiments of theme development, PHP, general web design, and a few other skills. Although I cannot by any stretch of the imagination be considered a programmer, or even much of a developer, I love web-related stuff in general, and WordPress in particular. It’s never ceased to amaze me that a person can build a website with no resources other than a computer and his own brain, and that this website can, theoretically, reach a worldwide audience. At 45, I’m old enough to remember a time when there was no internet. The ways in which it has permeated our daily lives still astonishes me, and probably always will.

There were three or four types of jobs available at Automattic. The only one for which I was even remotely qualified was “Happiness Engineer,” which sounded suspiciously Disney-esque, but was a sobriquet I was willing to live with.

This image of a little girl in Bhutan twirling a stick is the best image I could find on Flickr while searching for "happiness engineer." It works, kinda.
This image of a little girl in Bhutan twirling a stick is what comes up on Flickr under “happiness engineer.” It works, kinda.

As a Happiness Engineer, you got to set your own hours, and you could work from home. I live in rural Nova Scotia, and high-paying professional jobs are scarce around here, so that was appealing.

I seemed to possess all the required skills. You had to be familiar with HTML and CSS; you had to have good writing skills; you had to like helping people, especially people who really didn’t understand much about computers; and you had to have a decent understanding of how WordPress itself worked. I could check off all those boxes without stretching the truth. Based on the description, it seemed like a natural fit.

I sent off my application letter in January, 2015. I heard nothing back beyond a brief automated confirmation email. Then, in February, I got a temporary job with a large company in Halifax, and I began to work full-time.

It was my first office job. It involved work I enjoyed, though it also meant a two-hour commute. That, and the fact that I was a contract employee, were the only downsides. I missed being able to write whenever I felt like it, but the relief of a steady paycheck more than made up for it.

Part 2: It Begins

In June, after having forgotten all about my application, I heard back from Automattic. They contacted me to schedule a preliminary interview. It was to take place over Slack, a chat application I hadn’t used before. This felt like a novelty–a job interview in a chat room! How futuristic and internetty! Let me park my hoverboard, and I’ll beam myself in!

This is totally a hoverboard.
This is totally a hoverboard.
The interview was with two people, a man and a woman. They came across as friendly and professional, or as much as its possible to do so through the medium of characters on a screen. They asked me general questions, including my experience with WordPress and my philosophy of customer service.

Our conversation went well enough for them to move me on to the next phase, which was a test that involved some basic website work. In the interests of fairness to new applicants, as well as to Automattic, I won’t get into the details of that here, but I will say that it posed a challenge, and I was pleased when I was informed that I’d passed that hurdle, too.

A second chat interview followed, after which I was offered a chance to work as an HE for $25.00 per hour, part-time, on a week-by-week basis, until I was either hired permanently or informed that it wasn’t working out. This is known as the trial period, and the people going through it are referred to as ‘trials’.

Just like that, I had super-admin powers over nearly 90 million websites.

Let’s try not to delete 25% of the internet by mistake, I told myself.

I was delighted. But I was also apprehensive, because I knew I had some very long days ahead of me. I was going to have to continue working full-time while doing my trial work in the evenings.

Many trials find themselves in this situation, and many can’t hack it, especially those with young children. It’s… grueling. Automattic doesn’t demand this of you, of course; you demand it of yourself. But you can’t quit your day job until you’ve passed your trial.

I was fortunate in that my own day job offered flexible hours, meaning I could go in whenever I wanted, within reason. My new schedule went like this:

  • 5:00 am – Get ass out of bed.
  • 5:00 to 5:30 am – Eat a banana, drink coffee, shower and dress.
  • 5:30 am – Leave for work.
  • 6:30 am – Arrive at work.
  • 6:30 am to 2:30 pm – Do work.
  • 2:30 pm – Leave for home.
  • 3:30 pm – Arrive home, lie down for a few minutes, cram food in my gob, stare blankly at the wall.
  • 4:00 pm – Sit down at my home computer and log into my super-secret Automattic identity.
  • 4:00 to 8:00pm – Do Automattic work, which often required some very rapid-fire brain processes, lots of learning, and short, fast doses of intense fear, coupled with a creeping sense of inadequacy.
  • 9:30 pm – Bedtime.

On weekends, I crammed a further eight hours in. I’d been told that I probably wouldn’t succeed unless I devoted at least 20 hours per week to my trial experience; 30 would be a better number. Including my 10 hours of commuting each week, that meant I would be putting in 75- to 80-hour weeks for as many as six weeks… maybe eight. I know some people like working that much all the time, but frankly I think those people are nuts.  I need a better work-life balance than that.

But, when you’re a dad, you put your own needs to the side and do what’s required of you. This is the very thing dads are for: providing in times of need. So I said hi to my wife once in a while, and saw my kids in passing. Whenever I felt like complaining, I reminded myself: I was really doing this for them.

At the beginning of my trial period, there was a short training session that lasted a couple of days, during which I realized almost immediately that all my preconceived notions about this job were completely wrong, and that I probably wasn’t going to like it very much. Naively, I’d thought I would be spending most of my time helping people build websites, like the ones I had built for myself and a few clients. In retrospect, I have no idea why I thought that. I didn’t really know very much at all about, the free version of the WP platform. I’d never used it, in fact. All my experience had been with, the self-hosted version. Of course there was a great deal of crossover–I couldn’t have passed my first tests if there hadn’t been–but they were, as I was quickly to learn, two different worlds. And it was, the world I didn’t know as well, that I would be dealing with.

An example: somehow, it had never occurred to me that a significant portion of my time as a Happiness Engineer would be spent doing the online equivalent of retail sales. Although much of the purchasing experience for Automattic customers is… well, automatic, there are still a number of transactions involving various products that HEs end up putting through themselves. I had to deal with credit cards, receipts, complaints, refunds, and all the other things that go along with a retail business, none of which I have any patience for or interest in.

Another significant portion of time seemed to involve repeating the same thing to different support clients, many, many times per day: No, you can’t install plugins on free-hosted sites. Here is a link that explains the difference between and Your DNS changes may take several hours, so you can’t expect your new custom domain to show up right away. Et cetera, et cetera. I kept stock responses on a text document, and just pasted them into my chats. That part was wearing, too. WordPress has tens of millions of users. I could see myself repeating those phrases for eternity.

There were many things I liked about it, though. For one thing, I was able to help people with site-related problems they couldn’t solve themselves. This has always brought me satisfaction. There’s nothing complicated about it. I just like helping people with their challenges.

Automattic believes in “democratizing the web,” or making it accessible to everyone, which is something I firmly believe in, too; it was a major reason I wanted to work for them. To illustrate this, my favorite interaction was probably the one in which I chatted for some twenty minutes with a preacher about how to get one of his new blog posts up. An elderly man, he lived in a small village somewhere in Africa–I can’t remember which country–and he’d recently begun to post his sermons on his website, so that the world could be enlightened by them. He was not evangelical so much as he was motivated by a simple desire to share. I’m not religious in the slightest, but I found myself moved by our conversation, and I was really impressed by his desire to embrace technology. At such moments, I’m keenly aware that I am peeking into another dimension of the human experience, having the sort of conversation I never would have been able to have before the existence of the internet: me in Nova Scotia, he in Africa, each of us peering into glowing portals that formed a temporary tunnel to each other’s homes.

Then a very strange thing happened. On my second day of support chat, against astronomical odds, in wandered a person who’d been a classmate of mine at Emerson College, a school in Boston I attended for one year more than half my life ago. He lives in London, England, and I hadn’t seen him since about 1989, but I recognized him instantly, both by his username and his avatar, which was his actual portrait. I was too weirded out to say anything to him at the time, but after I had finished answering his questions, I emailed to ask if that was actually him. It was. If I was more into signs and omens, I would have taken it to mean something, but as it was, I just thought it was really cool.

The experience got stranger, but in different ways. Automattic prides itself on being a fully distributed company. In fact, it has to be distributed. What this means is that its employees work in no central office; there are no set hours of business; everyone is scattered all around the world; and all interaction between employees, as well as between employees and customers, takes place in chat rooms. This all sounds very groovy and futuristic, but the novelty of it wore off quickly for me. Something like 90% of all human interaction is non-verbal. You never get to see the people you work with, except maybe once a year during annual company-wide meetups. In a chat room, you can’t take in any facial expressions, body language, vocal tones and inflections, pheromones, or any of the other factors that form such a huge part of how we talk to each other.

To compensate for this, Automatticians use plenty of emoticons, and hundreds of exclamation points per day!!! This is so that you understand they are really enthusiastic about what they do, and that they really mean it! 🙂

At least, I think that’s why. I found it difficult to tell what someone was actually thinking or feeling when I was talking to them, and frankly, I found this an insurmountable obstacle. I felt quite lonely, here in my little shed/studio in Nova Scotia (about which I have written in this blog post), talking to people in California, France, New York, the Dominican Republic, Ireland, various parts of Africa, Europe, and practically anywhere else you can think of.

My wee writing studio, a.k.a. "the shed."
My shed, generally referred to as”the shed.”

The biggest surprise for me was that being a Happiness Engineer really turned out to be a tech support job. Granted, it’s a better tech support job than most others out there, the quality of the company is far higher, and it offers far more potential to its employees. You are working for one of the most exciting and interesting companies in the world, and because WordPress is the platform on which tens of millions of sites are run, the rotational projects you work on have the potential to change the entire internet.

But this was not where I had seen myself.

Nor, frankly, was it where I belonged.

Part 3: It Ends

There were a few points at which I wanted to give up on my trial period. By the end of my first 80-hour week, I was exhausted. Only the promise of a return to autonomy kept me going forward; for at Automattic, in theory anyway, you could work whenever you wanted to, as long as you put in your allotted hours per week. That was the way I had spent the past 15 years, and I liked the idea of returning to it–though, truth be told, I was also intimately familiar with the drawbacks of total independence as well, like the part where I never got out of my pajamas or left the house. (That may sound great, but trust me, you really do forget how to socialize after a while.) My wife and I made vague plans to move to Mexico if I got hired, just because we could. I looked forward to a time when I wasn’t permanently exhausted. Mostly, though, I just tried to survive.

Salary, oddly, was never discussed. I knew from asking around that salaries are not fixed; you will be paid very decently, but it will be based on the economy in which you live, and not based on, say, the San Francisco economy, where Automattic has its headquarters. I assumed that whatever I made would be greater than the $25.00 per hour I was being paid as a trial, but how much greater, I never found out.

At the end of the month, I was told in no uncertain terms that it wasn’t working out, and that my time as a trial was over. I was welcome to reapply in six months if I wanted to, but Automattic had decided that for now, I wasn’t what they were looking for. No more specific information was offered.


In my first interview, I had asked if it was true, as I’d read on other posts, that Automattic never told people why they were let go, but simply issued a curt “It’s not working out.” My training leader, a woman I had come to respect, told me that wasn’t actually what happened. At the end of every trial week, there was a feedback session, and the trainee was told precisely in which areas they needed to improve. If and when they were let go, it would be because they hadn’t improved enough in those very areas. There would be no mystery about it, but they weren’t going to spend a lot of time making sure you understood, either. I got the impression Automattic likes to tell you things once.

My feedback for the first three weeks had been pretty good. My numbers were rising, and I’d been told repeatedly they were in a good range. My satisfaction rating was good, too. In fact, during my first three feedback sessions, I received practically no negative comments at all. I was told repeatedly that I was doing everything right, and that I should just keep on doing them.

At the beginning of the fourth week, I was told that they would be subjecting me to a far greater degree of scrutiny, because this was when they really began the winnowing process. It was at the end of this week when I learned I wouldn’t be getting the job.

I was confused. What, specifically, had I done wrong? I asked this question during my exit interview, and it was deliberately ignored. I knew this was based on some sort of policy, but it’s a policy I don’t agree with. It felt childish and secretive, even if it’s a question I should theoretically already know the answer to.

But this was a minor annoyance. I felt disappointment, but I also felt relief. I won’t lie–I was frustrated, and my ego was stung. It’s never a good feeling to put a huge amount of energy into something that fails. I’d already been told by my “training buddy” that the mere fact I’d made it so far in the process was something to be very proud of. Three years earlier, I’d never even heard of WordPress, yet for the past month I’d occupied a position with the company that many others had vied for and failed to get, all based on my own independent learning. That was something to be proud of, for sure. Having come that far, naturally, I wanted to move on to the next level, so I could be proud of that, too.

But that was the wrong reason to want to be hired. Casting my mind back to my third feedback session, I remembered being told that I needed to do better about documenting things; Automattic contains massive knowledge bases that are constantly being added to and linked to, and for some reason I just couldn’t get used to writing everything down. It’s quite likely that was one reason I wasn’t hired.

Or maybe I was just too slow to pick up on new skills. We were expected to learn an awful lot of stuff very quickly, and because of my initial misunderstanding of what the job entailed, I felt behind the curve. I had no tech support background at all, whereas many other new HEs had lots of experience with other companies. I asked a lot of questions, and although that was officially encouraged, I had the distinct impression that it actually caused certain people to regard me with annoyance. People paid a lot of lip service to the notion of open dialogue and continuous learning, but as in all organizations, there are those standards that are publicly praised, and those standards that are actually adhered to.

Many other senior HEs were wonderful, of course, and they went out of their way to help me find answers to tough questions. These conversations went much like the dialogue called “Meno”, in which Socrates proves that even an ignorant slave boy naturally possesses the ability to derive the principles of geometry out of nothing, as long as he is drawn out properly by a skilled philosopher. More than once, a very knowledgeable Automattician showed me, through a series of strategic questions, that I actually already knew the answers to the problem I was trying to solve. This is the best way to teach, and the best way to learn. (Socrates also apparently believed that the soul gained this knowledge during past incarnations, but that’s a bit beyond the purview of this blog post.)

I learned a great deal in that month. If nothing else, it taught me, once again, that I can do practically anything I want to do, if I want to do it badly enough. That’s always a good thing to be reminded of.

Yet in the end, it was the shitcan for me. Though my feelings were bruised, I was relieved. I went back to a more normal schedule. I got to see my family again. Having just one full-time job felt like being on vacation. And I felt quite certain that as much as I hated to admit it, the correct decision had been made. I would have felt no happiness as a Happiness Engineer.

For a few days, I sulked. I wondered if I would ever use again. I felt like a jilted lover, pointedly avoiding the places he knows his ex still haunts. I guess I was a little more bitter than I was willing to admit.

But I couldn’t stay away from it; the platform is just too rich and powerful, and the things I can do with it just too amazing. Matt Mullenweg, I wish I knew how to quit you.

Matt Mullenweg, having fun without me.
Matt Mullenweg, having fun without me.

I came away, too, with a huge amount of respect for full-time Automattic employees. Everyone I “met”, virtually speaking, was extremely bright, hard-working, and motivated. The people at Automattic are all working on projects that are going to have far-reaching effects on huge portions of the internet. They are far more than tech support personnel. It was an honor to be one of them, for a brief time. If you ever find yourself talking to an Automattician, you should know you are talking to someone who is very intelligent, very capable, and has worked his or her proverbial ass off to get that job, beating out many, many other almost-as-qualified applicants.

My situation has improved a great deal since then. I’ve been made a permanent employee at my day job, which means benefits and stability. Although I’m stuck in an office all day, it forces me to get out of the house, which is a good thing. The people I work with are every bit as smart and hard-working as my fellow Automatticians had been, and I’ve formed a bond with them that could never have formed in a chat room. I still get to do cool computery stuff, too. While the effects of it are not as far-ranging as what’s happening on WordPress, the work we do is important to a lot of people, and I take pride in doing it well. Things are good. I am content. I don’t have to get up at 5 am any more, but I often do, so that I can put in an hour or so on the new novel I’m writing. In many ways, I’m back to where I was twenty years ago, when I was working full time and trying to write my first book. Full circle moments like these contain important lessons.

Another great outcome of this experience was that I gained much of the knowledge I needed to run my own WordPress multisite network. It’s called My Writing Network, and it functions exactly the way does, because it’s based on the same open-source software. My Writing Network exists to provide free websites and social networking opportunities to anyone in the writing and publishing community. If that’s you, come check it out.

During my final conversation as a trial HE, as I was being fired, they told me that less than half of all trial Automatticians are hired the first time around. Many of them have to go through two trial periods or more before they get hired on. Personally, I can’t imagine going through that again. I don’t want it bad enough; actually, I don’t want it at all. But I’m still proud of myself for having made it as far as I did in a complicated technical environment–me, a non-programmer, a middle-aged novelist, a self-taught web designer. It was a great adventure. I’m glad I did it. I’m glad it’s over.

Oh, and by the way–Automattic is still hiring.

Automattic featured image credit: Scott Beale/Laughing Squid. Used under CC BY-SA 2.0
Make It So gif file: author unknown.
Little girl in Bhutan photo credit: Flickr user Nagarjun Kandukuru. Used under CC BY-SA 2.0
Hoverboard photo credit: Flickr user Lee Jordan. Used under CC BY-SA 2.0

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