The Year Without Pants

Scott Berkun, a veteran of Microsoft’s early days, spent a year working as a team lead at Automattic, the company behind WordPress.com. At the time, Automattic had around 120 employees scattered across dozens of countries, working entirely remotely with no office, minimal email, and a culture built on trust and autonomy. Berkun documents this experience with the honesty and humor that define his writing, giving readers an insider view of what a fully distributed company actually looks like in practice.

Why This One

Where Remote makes the philosophical argument, The Year Without Pants provides the case study. Berkun does not idealize the experience. He writes openly about the challenges of managing people across time zones, the difficulty of building relationships through text, and the moments when the lack of physical presence created real problems. This balance makes the book more credible than a pure advocacy piece.

The book is especially valuable for managers. Berkun navigates questions that matter in practice: how to run effective remote meetings, how to evaluate work when you cannot see people at their desks, 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 office culture and Automattic’s radical experiment.

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. A good complement to Remote, offering the messy, real-world details that a shorter, more polished book necessarily leaves out.