Chapitre 1
When Work Becomes Pantless: A Revolution in Remote Collaboration
In 2010, Scott Berkun did something most management experts never do - he put his own advice to the test. After writing four successful books on management and innovation, he accepted an offer from WordPress founder Matt Mullenweg to join Automattic (the company behind WordPress.com) as a team leader. What made this move remarkable wasn't just Berkun's willingness to practice what he preached, but the revolutionary workplace he was entering. WordPress.com, the fifteenth most trafficked website in the world, operated with no offices, no email, and employees scattered across the globe who rarely met in person.
The experiment would last eighteen months, during which Berkun would lead "Team Social" through the development of major features used by millions of people worldwide. His experience, chronicled in "The Year Without Pants," offers a fascinating glimpse into a company that was pioneering remote work long before the pandemic made it mainstream. With its irreverent title (referencing the joke that remote workers could technically work without pants), the book has become required reading for forward-thinking companies reimagining workplace structures. Even tech giants like Microsoft and Google have incorporated lessons from Automattic's distributed work model, making this book's insights more relevant than ever in our hybrid work world.
Chapitre 2
The Birth of a Digital Democracy
WordPress began in 2003 when Matt Mullenweg, a 19-year-old college student from Houston, found himself frustrated with the abandoned blogging software called Cafelog (also known as b2). After its original developer disappeared, leaving thousands of users stranded, Mullenweg wrote a fateful blog post titled "The Blogging Software Dilemma." Though his post initially received no attention, programmer Mike Little from the UK offered to help the next day, marking the beginning of an unprecedented collaboration that would reshape the internet's future.
Working remotely across continents-Little from England and Mullenweg from Texas-they rapidly built WordPress as a fork of the original Cafelog codebase. By June 2003, their creation had already surpassed its predecessor in functionality and reliability. In a remarkable turn of events, the original Cafelog developer Michel Valdrighi eventually emerged and joined their effort, providing both technical expertise and moral validation to their project. This early validation helped establish WordPress's legitimacy in the open-source community.
The project's culture evolved organically around three fundamental principles that would later become cornerstones of the WordPress philosophy. First, transparency became paramount-all discussions, decisions, and development happened in public forums where anyone could participate. Second, a true meritocracy emerged where respect and influence were earned through meaningful contributions rather than titles or seniority. Third, they emphasized longevity by ensuring the project would survive indefinitely through careful open source licensing and community governance. These principles weren't formally documented at first but emerged naturally from the founders' working style and values.
Scott Berkun's personal journey with WordPress began in September 2003, shortly after leaving his position at Microsoft. His perspective as an early adopter provides an interesting contrast: while Mullenweg was deeply committed to open source principles and digital democracy, Berkun was simply drawn to WordPress's elegant simplicity and practical functionality. This dichotomy highlights a crucial lesson about successful products: while developers may be motivated by philosophical ideals, users primarily care about solving their immediate problems effectively.
As WordPress's popularity exploded, Mullenweg faced a critical decision. The project's growing complexity and user base demanded more consistent attention than a volunteer community could provide. This realization led to the formation of Automattic in 2005, a company designed to support WordPress's development while maintaining its open-source ethos. The company introduced innovative business models, including WordPress.com hosting services and enterprise solutions, while keeping the core WordPress software free and open source. This delicate balance between commercial interests and community values became a model for other open-source projects, though few have managed to replicate its success at such scale.
The early years also saw the establishment of crucial community practices that endure today, including the famous "Five for the Future" initiative encouraging companies to contribute 5% of their resources back to WordPress development, and the introduction of WordCamps-local community conferences that would eventually spread to six continents.
Chapitre 3
A Workplace Without Walls
Berkun's first day at Automattic was unlike any traditional onboarding experience. His commute was fifteen seconds from bed to desk, with only his dog Griz blocking the hallway. Rather than orientation sessions and paperwork, he began with three days of customer support training-all new employees work with the support team before starting their primary job. At WordPress.com, they call support "Happiness" and support staff are "Happiness Engineers."
This practice reveals a fundamental company value-making everyone work in support forces all employees to take customers seriously. Unlike Microsoft's approach of merely having employees listen in on support calls, Automattic's approach puts employees directly in the position of solving customer problems. Despite his initial distaste for support work, Berkun recognized this practice as fantastic for building customer empathy.
Communication at Automattic primarily happened through text rather than voice, even when using tools like Skype that offered both options. His first interaction with his trainer Hanni Ross was through a casual Skype chat where she confessed to having gone out for sake and karaoke with Matt the night before, setting the tone for the company's informal culture.
Most surprising was the level of trust immediately extended to new employees. On his first day, Berkun was granted full administrative access to the WordPress.com system-he could edit, delete, or change anything on any blog. Rather than giving him a limited training version, he was trusted with complete access from day one. This felt surreal-like having access to a supervillain's world-controlling device, except it was real.
The company's communication infrastructure was equally unconventional. While most organizations rely heavily on email, Automattic's communication happened primarily through P2 blogs (75%), with IRC chat (14%), Skype (5%), and email (1%) making up the rest. P2s functioned as searchable, categorized conversation spaces that inverted traditional email assumptions: readers chose what to read and when, content remained searchable forever, and knowledge stayed accessible to all employees.
Chapitre 4
Results Trump Traditions
What makes Automattic's approach revolutionary is its relentless questioning of workplace traditions that have persisted for generations. Why must work start at 9am and end at 5pm when global teams operate across time zones? Why are meetings arbitrarily set to 60 minutes when some topics need 15 and others need 90? Why enforce specific dress codes in an era of video calls and digital collaboration? These practices persist not because they produce better work but because they're familiar traditions that organizations cling to out of habit and fear of change.
Automattic's culture prioritized results above all conventional metrics. Nobody cared when you worked or where-even if pantless in your living room at 3am or swinging in a hammock with a martini at noon. What mattered was output quality, measured through concrete deliverables and impact. Working distributedly eliminated numerous status-based traditions: the political theater of who arrives earliest or stays latest, who gets the corner office or reserved parking, who lunches with executives. Instead, colleagues were judged solely by their tangible contributions: their code quality, design innovations, number of resolved tickets, or thoughtful written comments in discussions.
Some Automattic employees gravitated toward coworking spaces, which provided a middle ground between isolation and traditional offices. The company offered generous stipends for these spaces, supporting employees in discovering their optimal work environment through experimentation. This approach recognized that productivity is deeply personal-some developers need absolute quiet for deep coding sessions, others thrive on coffee shop background noise, and many benefit from a mix of focused solitude and occasional social interaction. Employees could even switch environments based on the type of work they were doing that day.
Matt Mullenweg's leadership style exemplified letting unimportant things slide while maintaining laser focus on results. His personal experience defying conventions (dropping out of college, building free software, championing remote work before it was mainstream) reinforced his confidence that the best way to learn is through action rather than theory. He consistently chose experimentation over lengthy debates or elaborate strategic planning sessions, understanding that while many experiments would fail, each attempt generated valuable data and insights. This approach created a culture where employees felt empowered to challenge any tradition that didn't directly contribute to better outcomes.
The company's success demonstrated that when you strip away artificial constraints and focus purely on results, people often exceed expectations. Teams developed their own rhythms and practices, creating innovative solutions to collaboration challenges that traditional offices never even considered. This results-first mindset attracted self-motivated individuals who thrived on autonomy and measured their success through impact rather than hours logged or meetings attended.
Chapitre 5
Hiring Self-Sufficient, Passionate People
At Automattic, Berkun discovered that hiring self-sufficient, passionate people was fundamental to their success. While some workplace issues would be problematic at traditional companies, Automatticians' talents and passion compensated for these challenges. As Tracy Kidder observed in "The Soul of a New Machine," when people are internally motivated, "Labor was no longer coerced. Labor volunteered." This intrinsic motivation proved essential in a remote environment where direct supervision was impossible.
The WordPress mission of democratizing publishing naturally attracts passionate people who believe in the transformative power of open-source software. However, Berkun learned that traditional indicators like resumes and degrees poorly predict passion and capability. Many successful Automatticians didn't formally study design or development but instead mastered their craft through hands-on experience as freelancers, consultants, or passionate hobbyists. Most exhibited "T-shaped" skill profiles-having one deep area of expertise (like PHP development or UI design) combined with a wide range of moderate proficiencies in related areas. This versatility made them self-sufficient problem-solvers who were unafraid to learn whatever skills were needed to complete projects, from basic server administration to customer support.
Automattic's hiring process deliberately breaks from conventional corporate practices. Instead of formal interviews filled with algorithmic puzzles or behavioral questions, they employ a practical trial system where candidates complete real projects using the actual tools and systems they would use if hired. This approach eliminates the artificiality of inflated resumes and rehearsed interview answers, allowing candidates to demonstrate their true abilities through tangible work. The trial projects typically last 2-4 weeks and involve actual tasks the company needs completed. Since everything can be done remotely, candidates don't need to travel for interviews, and those who can't find time for the trial project naturally self-select out of consideration.
This emphasis on self-sufficiency eliminated the need for traditional hierarchical management structures. Automatticians regularly tackle tasks that would span multiple job titles in conventional companies, reducing territorial disputes and encouraging organic collaboration. The culture valued practical results over rigid processes, with employees freely sharing expertise across traditional role boundaries. For example, developers might contribute to marketing initiatives, while support specialists could suggest product improvements based on customer feedback.
Remote work demands exceptional psychological self-management-the discipline to avoid home distractions, maintain productive work routines, and build meaningful social connections outside of work. Automattic's hire-by-trial approach naturally filtered out those unsuited for this level of independence, as the trial period revealed candidates' ability to manage their time, communicate effectively in writing, and maintain productivity without direct supervision. This careful selection process resulted in a workforce particularly well-suited to the unique challenges of distributed work, with employees demonstrating high levels of autonomy, initiative, and personal accountability.
Chapitre 6
Real Artists Ship
In September 1983, the Apple Macintosh project was behind schedule with a burned-out team. Steve Jobs wrote "Real Artists Ship" on an easel to motivate them to finish. Today this quote serves as a rallying cry for creatives, though Jobs was emphasizing shipping over artistry. The truth is no one starts a project planning not to ship-everyone who makes things wants to see their work used by others.
At WordPress.com something shipped every day. By August 2010, there had been twenty-five thousand releases, growing to over fifty thousand by 2012. Toni Schneider called this "continuous deployment"-endless small changes where customers always used the latest version. Programmers could ship whenever they finished, with no testing queue or review board. In the worst case, changes could be reverted, but this was rare. Instead, programmers fixed problems with new changes and stayed online for hours after launching to ensure things went smoothly.
This approach eliminated the fear of falling behind schedule, replacing it with small but frequent payoffs. Work felt like Spanish tapas-small plates of deliciousness arriving continuously. Sometimes twenty-five changes would go live in a single day, a stark contrast to Berkun's experience at Microsoft where Windows shipped every few years.
The adjustment was surprisingly easy. At Microsoft's Internet Explorer team, they had a similar "daily build" process, though only internally available. WordPress.com's philosophy was that safeguards don't make you safe; they make you lazy. Without railings, like climbing a dangerous tower in Delhi, employees paid more attention. By keeping things a little dangerous and treating employees like adults, things were actually safer.
The real challenge wasn't safety but coherence. Despite WordPress's continuous deployment culture, its interface had become complicated like Microsoft's products. As WordPress and WordPress.com grew larger, Matt Mullenweg had less time to provide product vision, and the system accumulated hundreds of competing features-the classic consequence of continuous deployment where programmers think only about their own ideas rather than the whole product.
Chapitre 7
Team Building Across Time Zones
Team Social became the most distributed team in the company when Beau moved to Perth, Australia in late December 2010. With team members spaced eight hours apart around the globe-Mike and Scott on Pacific time, Andy in Ireland (+8), and Beau in Australia (+16)-they hit the natural limits of space and time. For simultaneous meetings, someone had to be miserable, and Beau volunteered to wake up at 2:00 a.m. each week.
Despite the team's playful banter about their global distribution, this extreme time difference created drag on team morale. The work wasn't divided in a way that made "Follow The Sun" collaboration effective. Berkun regretted not redividing the work to take advantage of their distribution. December became Team Social's least productive month ever as they slogged through a difficult project with little progress and low excitement.
To boost morale, Berkun mixed in small "snack projects" that gave the team quick wins and breaks from the main project. This strategy proved effective, as small victories reminded everyone that progress was possible, inspiring new effort.
What made the distributed team work despite these challenges was the periodic in-person meet-ups. When Team Social gathered in Athens, Greece, they experienced the transformative energy of being physically together. Though they appeared to be just young travelers playing with laptops in the Hotel Electra lobby, they could launch features affecting millions with a single click.
These meet-ups became crucial for team bonding and productivity. Berkun established three feedback traditions: first-night dinners to reconnect personally without an agenda, project decisions on the first night (though he usually knew what they'd work on), and one-on-ones with each team member focused on four questions: What's going well? What's not? What do you want me to do more of? What do you want me to do less of?
The meet-ups weren't just about work-they included adventures that built team identity. In Athens, after a long day of coding, the team went out with Matt Mullenweg until 2:00 a.m., walking through cobbled streets where Beau, emboldened by Mythos beer, attempted to jump between bollards (short posts protecting sidewalks). His failed attempt and tuck-and-roll landing became a shared story that bonded the team. These shared experiences created a team culture that transcended their digital collaboration.
Chapitre 8
Making Big Bets: The Jetpack and Highlander Projects
During their Athens meet-up, Team Social made two significant decisions that would define their work for the next year. The first was "Highlander," a project to unify WordPress.com's commenting system with IntenseDebate, a commenting plug-in Automattic had acquired in 2009. The name referenced the classic sci-fi film where "there can be only one"-they would create a single unified commenting system rather than maintaining two separate codebases.
The second and more ambitious project was "Jetpack," which would realize Mullenweg's vision for ".org connect"-a bridge allowing self-hosted WordPress blogs to access WordPress.com features. This brilliant concept could potentially connect all 60 million WordPress blogs worldwide to enhanced features, benefiting bloggers, WordPress, and WordPress.com alike.
Taking on both projects simultaneously was risky-"doubling down" as the team called it, borrowing from blackjack terminology. The commitment to build Jetpack was the biggest bet any team could make, requiring a capacity for delusion that rational people often lack. Their day walking in the footsteps of ancient Greek philosophers had inspired grand dreams.
For Jetpack, Berkun identified five major challenges: the need for a different work culture with deadlines, programmers who'd never done estimates before, insufficient team size, the necessity for a simple user interface despite complex technology, and the requirement for rigorous testing across different hosting environments.
Mullenweg backed up the project's importance by providing resources-Berkun borrowed designer Joen Asmussen from Denmark and veteran programmer Andy Skelton from Texas to join Team Social. The team adopted new practices, including voice meetings instead of IRC, detailed task lists, and a spreadsheet with prioritized work items, assigned developers, and time estimates to create a real schedule with accountability.
The SXSW launch went smoothly, though with fewer first-day downloads than expected. Jetpack continued to evolve with new features every few weeks, eventually becoming one of WordPress's most popular plugins with over 5 million downloads. The team, now calling themselves the "Bureau of Socialization," had successfully bridged WordPress.com's servers with WordPress, providing valuable features to bloggers worldwide.
Chapitre 9
Show Me the Money: WordPress.com's Business Model
WordPress.com's business model is simple and transparent: it's freemium, with four revenue streams. First, upgrades-users can pay small subscription fees for storage, premium themes, or domain names. Second, advertising-WordPress.com is the fifteenth most trafficked website globally, with ads on less than 1% of pages. Third, VIP services-premier companies like CNN and Time magazine host on WordPress.com servers for premium prices and special engineering support. Fourth, partnerships with other services.
Despite these revenue streams, WordPress.com's store remains surprisingly hidden-just a small text button tucked inside the dashboard. The Money P2 was quiet, as no team was dedicated specifically to revenue. This reflected a deliberate choice in organizational design-teams create territories, which helps focus but leaves gaps for projects falling between teams.
Mullenweg showed remarkable restraint about profit-chasing, avoiding the common founder mistake of pursuing revenue too early. Despite Berkun's alarm at leaving easy revenue on the table, he respected Mullenweg's conviction and patience for long-term prospects.
The explanation for this relaxed approach to business was WordPress.com's amazing growth-its traffic charts were entrepreneurial fantasies, consistently ranking in the world's top twenty websites with steady annual growth. Even with slowing growth, it remained one of the web's most valuable properties, having turned down a $200 million acquisition offer back in 2007.
Most Automatticians were extremely happy at the company-working for something they loved, without having to relocate. Financial compensation rarely came up in conversation, unlike most companies where raises and bonuses dominate thinking. Automattic paid at or above-market salaries, but employees recognized their freedom over time was perhaps the most important compensation. The company's attrition rate was remarkably low-fewer than six people left during Berkun's eighteen months there, a testament to the quality of life Automattic offered.
Chapitre 10
The Future of Work Is Already Here
The most dangerous tradition we hold about work is that it must be serious and meaningless. Modern high-paying jobs often leave souls empty, while historically, work was more integrated with life and provided deeper meaning. Unlike our data-driven culture that measures wealth but not meaning, Automattic returns work to its roots where purpose matters.
Modern companies mock cubicle culture through Dilbert and The Office, forgetting that for centuries prior, crafts and skills gave us pride. Humor, play and joy are central elements of quality work-not distractions. Automattic's success stems from its long-term vision and open source roots that make meaning easy to find.
What makes Automattic's approach revolutionary isn't specific practices like P2 blogs or IRC chat rooms, but its willingness to question fundamental assumptions about work. The fundamental question for any organization becomes: What assumptions about your workplace might be hurting you, and what experiments are you conducting to discover better ways to work?
Berkun's eighteen-month experiment ended in May 2012, after stepping down as team lead in January and working briefly as an individual contributor. The Highlander project achieved moderate success with nearly 800 million comments posted to date. Jetpack became one of the most popular WordPress plugins in history. Most team members mentioned in the book remained at Automattic-Mike Adams led Team Social for over a year before being succeeded by Beau Lebens, Andy Peatling became leader of Team Titan, and Tim Moore led the Jetpack team.
By May 2013, Automattic had grown to 170 employees, with two new WordPress.com blogs started every second and 400 million monthly visitors reading nearly 40 million new blog posts. The company moved to a new headquarters on Hawthorne Street in San Francisco, though like the previous office, it remained mostly empty-a physical reminder that the future of work isn't about where you sit, but what you create and how you collaborate with others who share your passion.
