The Year Without Pants

Scott Berkun spent a year working as a team lead at Automattic, the company behind WordPress.com, and this book documents that experience. At the time, Automattic had around 120 employees in dozens of countries, working entirely remotely with no office, minimal email, and a culture built on trust and autonomy. Berkun gives readers an insider view of what a fully distributed company looks like in practice, writing with the same honesty and humor that defines all his work.

Why This One

Where Confessions of a Public Speaker captures Berkun at his most personal, The Year Without Pants shows him at his most observant. He embeds himself in a radically different company culture and reports back without either cheerleading or dismissing the experiment. The result is one of the best books ever written about remote work, precisely because it was written by someone who approached the experience with curiosity rather than an agenda.

The book is especially valuable for managers making the transition to distributed work. Berkun navigates questions that matter in practice: how to evaluate work when you cannot see people at their desks, how to build relationships through text, and how to maintain momentum on projects when your team is asynchronous. His background at Microsoft gives him a useful point of comparison between traditional and distributed cultures.

What to Expect

A narrative-driven book at 258 pages that reads more like a memoir than a management guide. Berkun structures it around his year at Automattic, weaving practical insights into the story of his team’s work. The writing is engaging and often funny. Expect concrete details about tools, workflows, and daily routines rather than abstract frameworks.