The Year Without Pants

What would your workday look like if there were no office to commute to, no formal meetings, and no boss hovering over your shoulder? In The Year Without Pants: WordPress.com and the Future of Work, Scott Berkun asks that question and answers it by immersing himself as a manager in Automattic—the company behind WordPress.com, one of the most visited websites in the world. He argues that the future of work is not a distant possibility but a reality quietly unfolding inside this unconventional, fully distributed organization. Berkun contends that freedom, trust, and results—not bureaucracy—define success in the modern workplace. But achieving this harmony means relearning what culture, leadership, and collaboration truly mean when geography disappears.

The book blends storytelling and management insight, following Berkun’s two years leading a global remote team called Team Social. He learns firsthand how work without physical offices changes everything: the meaning of teamwork, the nature of creativity, and the role of managers. The book’s central theme is cultural—the idea that culture always wins. No process, methodology, or tool can succeed in an environment with poor relationships or distrust. Automattic’s open-source ethos, transparency, and autonomy enable results that traditional companies only dream of achieving.

Freedom, Trust, and Results

At the heart of Automattic’s success lies a radical redefinition of work. Employees pick their own hours, work from anywhere, and rarely use email—all under an open philosophy derived from WordPress’s origins in open source. Instead of rigid schedules, people post updates on team blogs called P2s, engage in transparent discussions, and deploy new features live to millions of users each day. The future, Berkun says, belongs to organizations that trust their people enough to focus on results first, tradition last.

This approach exposes a tension between freedom and discipline. At Automattic, anyone can launch new projects and new ideas without seeking approval, but that openness also risks chaos. Berkun captures this paradox through humorous and candid stories of seemingly minor design decisions—like moving a “Sign Up” button—which unexpectedly led to massive improvements. Freedom without ownership, he warns, leads to drift. Freedom anchored in accountability fosters creativity.

Culture as Technology

One of Berkun’s greatest insights is that culture itself is a kind of technology. Just as software depends on architecture, human collaboration depends on values. Automattic’s founder, Matt Mullenweg, created a culture born from open-source ideals—transparency, meritocracy, and longevity. These principles act as invisible code shaping every employee’s behavior. When problems arise, people don’t look for new tools; they examine whether their actions align with the cultural code.

This theme echoes Peter Drucker’s famous phrase: “Culture eats strategy for breakfast.” Automattic proves that culture is not an accessory; it’s the operating system of the company. From new hires starting with three weeks in customer support (“Happiness Engineering”) to distributed communication across dozens of countries, everything reinforces shared purpose before hierarchy.

Lessons for the Modern Manager

Through his experience managing Team Social from afar, Berkun learns that modern leadership demands empathy over control. His humor and honesty reveal both joy and frustration—such as the absurdity of managing programmers he’s never met, or trying to inspire remote teams using only typed words. His “Year Without Pants” becomes a metaphor for stripping away outdated work norms: meetings, fixed hours, and needless bureaucracy.

By the end, Berkun synthesizes the cultural experiments of Automattic into lessons for all organizations: hire self-motivated people, design for transparency, stay patient, and empower individuals to align their passion with collective goals. If you’ve ever wondered whether work could be meaningful again—or whether technology could liberate rather than enslave—you’ll find this book’s ideas provocatively reassuring. The future of work, Berkun shows, isn’t about robots or gadgets; it’s about rediscovering humanity in how we work together.

Berkun begins by tracing the origin of WordPress and its founder Matt Mullenweg’s obsession with open-source culture. He argues that every system—whether a team or an entire company—derives its behavior from the invisible logic of its culture. The story of WordPress demonstrates how values, not techniques, drive success.

The Birth of Open-Source Values

In 2003, a young jazz saxophonist turned programmer forked an abandoned blogging tool called Cafelog and rebuilt it under a new name: WordPress. Mullenweg’s decision to use a GPL open-source license guaranteed that WordPress would remain free and transparent forever. That legal choice planted seeds of a culture grounded in three radical principles: transparency, meritocracy, and longevity. Anyone could see discussions, decisions, and code. Authority came from contributions, not titles. And the GPL ensured the software could never die.

From Philosophy to Practice

These values migrated into Automattic. Every policy—from remote work to open salary discussions—reflected faith in culture as self-governing technology. Instead of managers enforcing compliance, employees self-selected into projects they cared about. Performance was judged by results visible to all. Mullenweg, no autocrat, acted as a benevolent facilitator who protected autonomy while keeping vision aligned.

Other organizations have tried to copy cultural techniques without understanding their roots (IDEO’s famous “deep dive” method is one example). Berkun warns against this cargo cult mentality: copying visible rituals without the underlying values yields hollow results. Real transformation demands changing what people believe is important—not how they schedule meetings.

Culture vs. Technique

Berkun notes that most organizations chase trendy methods—Agile, Lean, Six Sigma—assuming procedures can replace human wisdom. But culture is emotional, not mechanical. It thrives on trust, humor, and shared stories. The leaders who understand this, he says, must nurture culture deliberately. Mullenweg’s famous creed (“I won’t just work on things assigned to me… communication is the oxygen of a distributed company…”) embodies emotional intelligence translated into action.

Key Lesson

Culture cannot be bought, copied, or installed. It must evolve from daily habits and leadership examples. When culture aligns with purpose—like Automattic’s mission to democratize publishing—techniques become amplifiers instead of replacements.

One defining feature of Automattic is its obsession with launching new work fast. Borrowing Steve Jobs’s legendary line “Real Artists Ship,” Berkun explores how the company’s philosophy of continuous deployment turns shipping into art itself. Projects are never finished in the cathedral sense—they evolve organically, like open conversations.

Continuous Deployment as Philosophy

At WordPress.com, every employee can release changes live at any hour. There are no review boards, deadlines, or multi-month schedules. Instead, features appear, break, and get fixed—sometimes within minutes. It’s chaotic but powerful. Berkun compares this to punk bands improvising together rather than orchestras following sheets of music.

Continuous deployment rewards courage. Reverting code that fails is easy; rethinking bureaucracy that prevents progress is not. Automattic believes safeguards don’t make people safe—they make them lazy. Trust makes safety real.

Shipping vs. Perfectionism

This approach collapses the old tension between perfection and progress. At Microsoft, Berkun’s former company, major versions shipped every few years. At Automattic, incremental updates arrive hourly. Perfectionism hides fear of judgment, he says; shipping reveals courage to learn publicly. Creatives who wait for flawless work risk never sharing anything at all.

Design, Simplicity, and User Happiness

Still, Berkun warns that speed can erode simplicity. WordPress’s interface accumulated clutter over time. Engineers added too many features, pleasing programmers while confusing bloggers. His analogy—the “NASCAR effect”—captures this chaos: an overloaded design plastered with competing widgets. Team Social’s later projects, like Highlander, became exercises in rebuilding elegance from accumulated mess.

Key Lesson

Shipping fast works only when guided by vision. Speed fuels innovation; clarity prevents incoherence. The best teams—whether at Apple, WordPress, or small startups—balance motion with meaning.

Innovation, Berkun argues, depends on the right amount of friction. Too little, and ideas slide aimlessly. Too much, and creativity implodes under pressure. At Automattic, hierarchy was eliminated, deadlines removed, and managers existed only to serve creators—not rule them. This low-friction environment heightened autonomy but risked stagnation when big projects demanded coordination.

Creative Abrasion

Borrowing Jerry Hirschberg’s term “creative abrasion,” Berkun shows that constructive tension sparks brilliance. During the Highlander and Jetpack projects, his team’s debates revealed how friction could refine ideas. Having too much comfort fostered mediocrity; a little discomfort forced sharper decisions.

Freedom vs. Structure

Without schedules or review cycles, developers thrived creatively but struggled strategically. Highlander aimed to unify comment systems but collided with technical chaos—hundreds of inconsistent themes required painful manual testing. Their triumph came not from freedom alone but from rallying diverse teams, experiencing what Berkun calls a “virtual barn-raising.” Collaboration replaced command.

Innovation as Coordination

Automattic proves that creativity needs bridges—between programmers, designers, and “happiness engineers.” Friction is not punishment; it’s context. Like the Beatles or Pixar (Ed Catmull’s Creativity, Inc. explores similar ideas), great teams share dissent that serves progress. Innovation blooms when debate is safe and purpose is clear.

Key Lesson

Managers must calibrate friction—protect autonomy but introduce structure when complexity demands it. Too much ease suffocates excellence; too much control kills creativity.

As a traditional project manager dropped into a hierarchy-free world, Berkun had to reinvent leadership. At Automattic, titles carried no weight; influence arose from contributions. His role as Team Social’s “lead” was to serve, guide, and remove obstacles rather than dictate.

Trust as Currency

Berkun learned quickly that managing remote creatives meant earning trust through clarity. When he couldn’t look employees in the eye, he used humor and transparency instead. He called this “management through conversation.” His monthly question to each team member—“What’s going well? What’s not? What do you want me to do more or less of?”—built psychological safety across continents.

Leading Experiments, Not Orders

His Big Talk at Seaside—where he told his team every manager is an experiment—captured Automattic’s philosophy: nothing is permanent, everything is improvable. When projects stalled, he didn’t assign blame. He made experiments out of problems: changing scope, regrouping, or even using pub games to build camaraderie. Leadership was not power—it was presence.

Managing Up and Down

At times, Berkun faced subtle challenges, like “Matt bombing”—when founder Mullenweg dropped into P2 discussions with cryptic comments that disrupted consensus. Instead of confrontation, Berkun practiced managing up, clarifying intentions privately and translating executive ambiguity into team clarity. His lesson: a leader must protect focus and communicate empathy both upward and downward.

Key Lesson

True leadership is influence earned through service and integrity—not authority bestowed by title. In distributed teams, clarity is the new charisma.

Imagine a company where no one uses email, offices don’t exist, and coworkers span every time zone. Berkun describes how this radical model of distributed work fosters autonomy, creativity, and challenge. Automattic’s global workforce lives on P2s, IRC, and Skype—blogs and chats that make every discussion transparent and searchable.

The End of Emailopathy

Berkun coins “emailopathy” for the disorder of managing overflowing inboxes. Automatticians replaced chaos with asynchronous communication. Posts on P2s created shared memory; ideas persisted beyond attention spans. Instead of inbox battles, information became communal property—an antidote to the secrecy that plagues traditional offices.

The Psychology of Remote Work

Working apart yet connected requires emotional intelligence. Berkun realized that trust is the oxygen of remote work. Without body language or hallway chatter, leaders must over-communicate. His advice mirrors Cal Newport’s Deep Work: create deliberate boundaries between focus and distraction. At Automattic, freedom is matched by responsibility—employees must self-manage motivation and morale.

Results Over Ritual

Remote work overturns industrial-era rituals. The 9–5 schedule dies; the focus shifts to measurable output. The result? Employees design lives that fit them, not vice versa. As Berkun notes, “Most people fear new ideas not because they fail—but because they change power.” Distributed work exposes how little hierarchy we truly need when collaboration is grounded in trust.

Key Lesson

Technology doesn’t change culture; culture changes how technology works. To thrive remotely, organizations must redefine management around trust and transparency, not control.

Berkun closes his story with a meditation on why work matters. He argues the most dangerous belief of modern capitalism is that work must be serious and meaningless. The future of work—seen in Automattic’s playfulness and purpose—restores meaning through autonomy, humor, and long-term vision.

Work as Play

At Team Social meet-ups—from Athens to Hawaii—games, jokes, and laughter weren’t distractions; they were cultural glue. Shuffleboard in Portland or ouzo jokes in Greece bridged creative differences more effectively than formal reviews. Play creates intimacy, Berkun writes, echoing anthropologists who observed how primal tribes bonded around fires through song and humor.

Work as Meaning

Drawing on Richard Donkin’s The History of Work and Matthew Crawford’s Shopcraft as Soulcraft, Berkun argues humans once found meaning in making things with their hands. Modern offices abstracted labor, draining its soul. Automattic’s model—crafting software to democratize expression—restores that lost satisfaction. Meaning thrives where creation connects directly to others’ lives.

Long-Term Vision as Ethical Compass

Automattic’s mission, “to democratize publishing,” embodies what philosophers call telos—a sense of lasting purpose. Mullenweg’s restraint in chasing profit echoes leaders like Tony Hsieh (Zappos) and Bob Sutton (The No Asshole Rule): culture and humanity outweigh short-term gain. Berkun’s final insight is that the future of work isn’t technological—it’s moral. We must choose meaning over compliance and trust over fear.

Key Lesson

To build the future of work, treat your organization not as a machine but as a community. Work that restores joy and autonomy restores humanity itself.