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WordPress.com and the Future of Work

In The Year Without Pants, author and former Microsoft manager Scott Berkun takes readers behind the scenes of Automattic, the parent company of WordPress.com, during a pivotal moment in its growth. With remote work still a fringe idea at the time, Berkun joined Automattic to explore a radical experiment—what happens when a fast-growing tech company works without traditional management, without offices, and without pants (literally and metaphorically)?

This book is not just about WordPress or distributed teams—it’s a first-hand account of how modern work is evolving. Berkun blends journalistic observation with personal experience to reveal how creativity, autonomy, and results-driven culture can thrive without bureaucracy. He exposes the myths of traditional office culture and offers a powerful case study in trust, leadership, and how to build great work in a remote-first world.

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💡 Top 10 Key Lessons from The Year Without Pants

1. The Future of Work Is Already Here

Berkun shows that the remote-first model isn’t a futuristic concept—it’s already happening. WordPress operated globally with employees working from anywhere, showing that freedom and flexibility can drive performance when paired with strong communication.

2. Culture Trumps Structure

Despite its non-traditional setup, Automattic had a clear and intentional culture. The book proves that shared values and mutual trust are more important than formal titles, rules, or office layouts.

3. Results Matter More Than Face Time

Success was measured by output, not hours logged. This focus on results, not appearances, helped teams stay agile and accountable. It’s a reminder that what you produce matters more than how visible you are.

4. Leaders Must Let Go of Control

Berkun admits that traditional managers often struggle in remote settings. At Automattic, leadership was about facilitating, not directing—creating space for people to do their best work and trusting them to own it.

5. Meetings Are Overrated

The company thrived without excessive meetings. Communication was primarily async and text-based. This forced clarity and encouraged deep work—a valuable lesson in minimizing distractions in modern teams.

6. Transparency Builds Trust

Open communication was a cornerstone. Most internal discussions were public to the company, enabling anyone to contribute ideas. This level of transparency reduced politics and encouraged meritocracy.

7. Experimentation Is a Culture, Not a Project

From work processes to product development, the Automattic team embraced rapid experimentation. The key wasn’t perfection—it was learning through iteration.

8. Work Should Fit Life, Not the Other Way Around

The team was free to work wherever and whenever. This created a healthier work-life balance and drove home the point that happy employees build better companies.

9. Hiring for Passion Beats Experience

Automattic prioritized people who cared deeply about the mission and had the ability to learn fast—rather than just long resumes. It’s a sharp contrast to corporate hiring based solely on pedigree.

10. The Default Way of Working Is Ripe for Disruption

Perhaps the boldest message: most companies are clinging to outdated models out of fear. The Year Without Pants is a wake-up call that work can be redesigned from the ground up—and doing so may unlock unprecedented innovation.

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🎯 Final Thought

The Year Without Pants is part memoir, part management manifesto, and part future-of-work playbook. Scott Berkun doesn’t just theorize—he lives the experiment and shares the lessons that challenge every assumption we have about how great teams should function. Whether you’re a remote worker, team leader, or founder, this book will push you to rethink what productivity, leadership, and collaboration truly mean in the 21st century.