The Year Without Pants: WordPress.com and the Future of Work

von Scott Berklin

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  • They remind me of the businessman in The Little Prince by Antoine de Saint-Exupéry. In the book, the businessman has all the stars in the universe but no idea what they are good for: he just always wants more of them. Too many company founders are just collecting stars. Mullenweg is one of the few I've known who created something as powerful as WordPress yet remembers what the stars are for.

  • To be unemployed by choice meant I'd have no baggage and be free to learn a new way to be. My vague ambition was to write books, and off I went.

  • I will never stop learning. I won't just work on things that are assigned to me. I know there's no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I'll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation.

  • Making good ordered lists is the fundamental thing any effective leader does, and it's the heart of popular planning methods like Kanban and SCRUM.

  • The fundamental mistake companies that talk about innovation make is keeping barriers to entry high. They make it hard to even try out ideas, blind to how much experimentation you need to sort the good ideas from the bad.

  • Internet Explorer shipped every few months, something unheard of for software at the time (except, of course, for Netscape, the company that kicked Microsoft's ass so badly we had to ship fast to catch up).

  • What mattered was what we shipped. And he told me the only reason anything good ships is because of the programmers. They are everything. They are not factory employees; they are craftspeople, craftspeople who are the fundamental creative engine of making software.

  • The responsibility of people in power is to continually eliminate useless traditions and introduce valuable ones. An organization where nothing ever changes is not a workplace but a living museum.

  • The most striking expression of this is that management is seen as a support role.

  • Hire great people. 2. Set good priorities. 3. Remove distractions. 4. Stay out of the way.

  • To put my thoughts on the future of work another way, I'm often asked in my work as a writer what the best word processor is to use. My answer is always the same: your brain. Most people find this answer frustrating, but it's a sincere one. The hard parts cannot be mechanized. What makes a good filmmaker is not the camera he or she uses but how this person uses it, and the gear that works best for one person won't be best for someone else. This is true for all work that has any element of creativity. But people don't want to hear this. We want to believe in a singular universal solution we can buy, a faith we believe in, perhaps because most of us make livings selling other people products marketed on the false promise of those wishful thoughts. An

  • It takes more passion to choose, on your own, to build a website, a mobile application, or a company than to follow years of instructions to get a degree. A GPA is not a strong indicator of passion, except for the dubious motivation of wanting to find right answers for other people's questions.

  • Many employees at Automattic were what's called T-shaped, meaning they had one very deep skill set, and a wide range of moderate proficiencies. Although I was hired as a lead, my deep skill set in this sense was interaction design.

  • That lack of specialization made people better collaborators since there was less turf to fight over. The culture valued results more than process: people were happy to lend expertise they had or teach others what they knew.

  • Most people who work for someone else don't really want this much responsibility. If they did, they'd start their own companies or be self-employed.

  • (as Kafka wrote, “It's often safer to be in chains than to be free”

  • Everyone would be assigned an MIT (Most Important Thing) to work on.

  • But the project ran against the flow of work at the company, and some questioned if it was worth the trouble. I'm convinced it was. If we couldn't show polish for one of the few things we make every visitor to WordPress.com see, we had no right to claim that we cared about quality design at all.

  • Founder-centric companies, which most start-ups are, are a double-edged sword. The initial big ideas come from one person, which, if they are good, is fantastic for early growth. But as the company matures, the need for more people with similar courage increases.

  • they were key parts of why the meet-ups worked well. In Athens it was the quiet balcony bar with Mythos and spicy potato chips. In New York, it was our comfortable SoHo apartment, a venue we'd never replicate. In Portland it would turn out to be an out-of-the-way sports bar, the Life of Riley Tavern.

  • The transition to managing a larger team reminded me that when everything is going fine, management is easy. Thousands of managers around the world inherit healthy teams in healthy companies, do little of merit, and get great rewards for just being in the right place at the right time.

  • As a writer, I know exactly how limiting words can be to express ideas, and until Hugo's hiring, it was up to me to constantly sketch and mock up ideas others were discussing on our P2.

  • It told him it didn't matter if the sketches were “right”; what mattered was that his sketch improved the quality of the conversation, which it always did.

  • Of the many dreams I've had in my life, making great software is one. But the biggest, craziest, and most rewarding dream to chase has been the writing life.

  • For me, leaving would mean I could start working on a book about my time at Automattic, a contribution I believed would be more important than my involvement with any number of teams.

  • The last act of good leaders is to ensure things go well when they're gone. Many legendary leaders failed at this: Alexander the Great, Julius Caesar, Napoleon, and nearly every monarch in history. As much good as they did in their reigns, most of it was undone by those who followed. The same ego that drives grand leaders defeats them in the end because they can't accept the notion that someone will replace them.

  • Succession planning must be part of any long-term leader's thinking, and it has to be done now. Not all exits from leadership roles are voluntary, either due to the Brutus in your midst or the bus you forget to notice when crossing a street you've crossed a thousand times before.

  • The most dangerous tradition we hold about work is that it must be serious and meaningless. We believe that we're paid money to compensate us for work not worthwhile on its own. People who are paid the most are often the most confused, for they know in their hearts how little meaning there is in what they do, for others and for themselves. While money provides status, status doesn't guarantee meaning. They're paid well because of how poorly work compensates their souls.

  • important things are the hardest to capture in numbers. While we have a universal measure of wealth called money, there is no comparable measurement for meaning. Meaning is personal. There is no singular meaning of life; instead there are multitudes, and they're different for everyone. Emotional words like meaning, passion, and soul are scary to people who believe everything in life hinges on pure rationality. With no universal measure for meaning to compare with the seemingly solid accounting for income, we fall into the data trap.

  • We hunted and gathered in order to live. Little distinction was made between work and the rest of life.