The Year Without Pants

This summer, I attended a really good local conference called CodeStock at which I also sat in on what turned out to be a really bad session on being a remote worker. The original speaker for the session wound up not showing, so someone representing one of the conference sponsors stepped in to lead the session, since there was interest. So it was understandable that he didn’t have a bunch of information prepared. But he had worked mostly from a home office for a while, and he managed a remote team, so he felt equipped to lead a chat on the topic.

The problem was that he didn’t have a real understanding of how remote work ought to function. His advice seemed mostly to include ways of trying to shoehorn in-office work into a remote-office scenario. His approach, in other words, was to try to make working remotely mirror as closely as possible the experience of working from an office. I disagreed vociferously with nearly everything the man said, and it was all I could do to avoid rolling around on the ground in despair. I’ve worked from a home office for nearly a decade with companies that really embrace remote work as a new type of work rather than as a mere perk for workers, and so I figured that my experience probably wasn’t terribly relevant for the others in the session, who would likely be in just the type of environment the leader gleefully perpetrated and who gobbled up his well-meaning advice. I kept mum and swallowed my despair.

I’ve worked at Automattic for approaching three years now. We’re a fully distributed company, with employees happily working from at least a couple of dozen countries. It’s the best place I’ve ever worked, and I’ve been really happy at a couple of my other jobs. For a few months of my first year at Automattic, I worked with Scott Berkun, who has recently published an account of his time there in the form of a book titled The Year Without Pants.

I should go ahead and confess that this isn’t generally my sort of book. I like to read fiction, usually the more ponderous and confusing the better, and business books just don’t interest me a whole lot. I don’t have mental bandwidth for them. Still, it’s a book about my company and a book that — since I worked with Scott a little on a project to encourage people to blog daily — it was infinitesimally possible I might get a brief mention in (I don’t). So, tailor your reception of my brief review with this confession about my qualification for reading the genre in mind. My view of the book is that of an insider and not of a particular expert on business books.

Of course, being an insider makes the book hard to judge in a meaningful way. I know the people discussed in the book. I spent a few days last week actually hanging out with them at a company meetup, in fact (I’m famous by proxy!). And just as you hardly recognize your recorded voice as your own, it’s hard to know whether what someone writes about your company squares with 100% faithfulness to the company as you know it. Does the book have it wrong or do I?

Some of what Scott writes does seen genuinely wrong, or at least betrays a net cast too wide. For example, in writing about development process, he makes the unqualified statement that our method is to write a launch post prior to beginning feature development. This isn’t something I’ve ever done, though doubtless other teams within the company have.

Scott writes largely about the team he led while at Automattic, and I feel at times as if he assumes that team’s method of working represented that of the company as a whole. Whether he does so out of editorial expediency or out of myopia it’s hard to say. If it’s a defect, it’s a small one.

I don’t feel as if the book ultimately lives up to the promise of its subtitle (“WordPress.com and the future of work”). As a reader of a business book (if not an expert such reader), I expect something of a payoff or prescription for how the sort of work done at WordPress.com is leaching into the larger occupational consciousness, or of how other companies might emulate the Automattic work experience. The book does include three chapters that purport to make a sort of prescription, but the prescription is pretty squishy (necessarily — it’s the nature of the beast), and the chapters seem tucked into a book that mostly stands well enough on its own as a document describing Scott’s experience at Automattic. In other words, the book feels a bit like a memoir that got hammered sort of halfway into something that could be sold as a business book. I think I would have preferred straight memoir.

As semi-memoir, it’s a nice read. The affection Scott had for his team shines through, and the book shows enough of the work process to be instructive and thus not dismissed as pure personal fluff. You get a sense of the friendships that form at Automattic, which are unlike any I’ve had at past jobs (however much I genuinely like many of my past coworkers).

Put enough smart, compassionate, passionate people together in a company and great things happen. This is why Automattic is a great place to work. Scott touches on the fact and illustrates it in his portrayal of how his team was built and how they bonded and grew. I don’t think there’s a recipe for making a great distributed company, or if there is, it’s something vague like “use great ingredients,” which doesn’t make for a highly marketable business book.

If I weren’t an Automattic insider, I don’t know honestly whether I would have enjoyed Scott’s book or not. Chances are that I would have found it fairly interesting to read some of the stories he tells about individuals and gatherings. Chances are that I would have found some of the few prescriptions (e.g. “hire great people” and “set good priorities”) pretty disappointing, if inevitable and actually correct.

Read the book if you’re curious about Automattic and how we work, and I imagine you’ll find it interesting. If you’re looking for a cure-all for how to build a company, you’re probably doing it wrong to begin with, though maybe there’s something useful in Scott’s book at least in its portrayal of how one company has had great success with the distributed model. I don’t have enough distance from the subject matter to say much else, other than that Automattic is hiring.

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