The Year Without Pants


Scott Berkun worked for a long time at Microsoft but this book goes into detail how WordPress, a free and open source blogging tool, has a very unique culture in which the small teams hardly ever work together in person, they are very informal, have little to no hierarchy, and can make updates and fix bugs daily.  This type of culture makes WordPress extremely powerful since it is so flexible and open to change.

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Key Takeaways
  1. Scott details that this book has two primary ambitions - to share what he learned as an old dog in a futuristic workplace and to capture the behind-the-scenes story of a good team at a fascinating company.
  2. WordPress' 3 core philosophies - transparency, meritocracy, longevity
  3. It is the small, daily decisions which define a company's culture
  4. "Ambiguity makes everyone tolerant of incompetence" - be extremely clear in the goals you are trying to reach and how you are going to reach them
  5. Passionate people love to feel like empowered underdogs
  6. To start big projects, you must have some capacity for delusion - or else you might not undertake such an ambitious project
What I got out of it
  1. I thought it was an Interesting book with a good message but one that could be summarized very quickly - there are hundreds of different business models and cultures that can make a business great but you need great people, clear and transparent goals and how these goals will be reached. Berkun goes into what I think is excessive detail and examples to prove the same point over and over
1 - Hotel Electra
  • Automattic, who owns Wordpress, has one of the most trafficked sites in the world. WordPress hosts over 20 million blogs and makes them easier to read and reach
  • Berkun was hired to become a team leader at WordPress even though he had no experience with software programming
  • Everyone worked remotely and wherever in the world they wanted which allowed WordPress to hire the most talented people wherever they were
2 - The First Day
  • Spent first couple days working and learning about the customer support (happiness engineers). This forces all employees to truly care and know what complaints customers are having
  • The head of systems personally walked Scott through account set up and other tedious things like that in order to get to know him and so Scott knew who he was
  • In his chats online, people were already immersing Scott in their culture by talking about going out and what they did the night before
  • On his first day Scott was granted complete editing power - able to delete or edit any blog that ran on WordPress' servers
3 - Tickets for Caturday
  • Tickets refer to issues bloggers were having with their blog that support had to help with
  • Half the battle is the ability to translate, not just knowledge of how to fix things. Knowing how to fix things doesn't help if you can't figure out what's wrong
  • Anyone who's an expert, guru, executive, or coach has likely lost any real sense of what real work is. We assume that because we can give advice on something, we are superior to those who take the advice, but that's not true
  • Scott didn't know he was being monitored on the amount of tickets he answered in a day - but everything was monitored
4 - Culture always wins
  • A great fallacy born from the failure to study culture is the assumption that you can take a practice from one culture and simply jam it into another and expect similar results.
  • Taking action without understanding the system rarely helps.
  • Matt Mullenweg is the founder of WordPress and it started in 2003 when the blog he used to post pictures on stopped sending out updates. He liked the idea of open sourcing and GPL (general public licensing) and from there started WordPress. It quickly gained momentum and was cheered on by techies everywhere
  • Everything was open source and this meant that programmers everywhere could see what Matt and others were like to work with. It encouraged cooperation and openness and attracted people from all over the world. By 2007 it was one of the most popular software products online
  • 3 essential core philosophies - transparency, meritocracy, longevity. None of these were forced but were born out of practicality and a vision/habit of what WordPress should be
  • Product creators should be head of a company. If the supporting roles, including management, dominate, the quality of products can only suffer.
  • It is the small decisions which define a culture
5 - Your Meetings Will Be Typed
  • Make a list - keeps you organized, less stressed, makes task manageable and prioritized
6 - the Bazaar at the Cathedral
  • The inability to scale is one of the stupidest arguments against a possibly great idea. Greatness rarely scales
  • Chaos requires commitment to improvisation
  • The company retreats were informal, chaotic, fun, not rehearsed. Almost exactly the opposite of what you think of when someone says company retreats
  • 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.
7 - The Big Talk
  • I kept in mind the lesson I learned from Joe Belfiore, one of the best bosses I've ever had. He told me the central way he'd evaluate me was the quality of what made it out the door. It wasn't about the ideas I had or how I managed schedules. It wasn't how I ran meetings or how well liked I was. Those were all secondary. What mattered was what we shipped.
8 - The Future of Work, Part 1
  • The advice paradox: no matter how much advice you have, you must still decide intuitively what to use and what to avoid.
  • All traditions are inventions, it's just a question of how old the invention is. There is nothing wrong with tradition until you want progress - progress demands change, and change demands a reevaluation of what the traditions are for and how they are practiced.
  • 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.
  • Automattic philosophy - 1. Hire great people. 2. Set good priorities. 3. Remove distractions. 4. Stay out of the way
  • The realization that everyone is different when you talk to them alone is a secret to success in life. In private you have their full attention. If you talk to two children in front of their mom and then each alone , you hear different things. The mystery for why some people you know succeed or fail in life is how courageous they are in pulling people aside and how effective they are in those private conversations we never see
9 - Working the Team
  • Even though Scott doesn't program, he can lead programmers by establishing trust and clarity
10 - How To Start a Fire
  • Only truly see a person's character when there is a fire
  • Little things done well can have big effects
  • Measuring metrics is good but be careful not to get lost inthem
11- Real Artists Ship
  • Steve Jobs said, "Real Artists Ship" - meaning that creative teams need to be send their "art" into the world to their customers
  • The Cathedral and the Bazaar - different ways of going about projects - one master plan that is thought out before anything begins or bazaar where you start small and immediately and revise as you go along
12 - Athens Lost and Found
  • Ambiguity makes everyone tolerant of incompetence.
13 - Double Down
  • Passionate people love to feel like empowered underdogs.
  • In project terms, if you make only small maps, of, say, the next two weeks, you never run the risk of your map being very wrong, and you learn more from the present since it has your full attention.
  • After years of leading projects, the best thing I've learned is that I have to periodically shift between thinking small (bazaar) and thinking long term (cathedral).
  • To start big projects, you must have the capacity for delusion.
14 - There Can Be Only One
  • Laughter leads to running jokes, and running jokes lead to a shared history, and a shared history is culture. What is a friend, a brother or sister, or a partner but someone you share important stories with? Families, tribes, and teams all function in similar ways, building bonds through rites of passages and shared experiences. In extreme situations, people sacrifice their lives for their culture.
15 - The Future of Work, Part 2
  • N/A
16 - Innovation and Friction
  • Believes you need the right amount of friction for good work to happen
  • Automattic had very little friction. For creatives, deadlines were the major friction and those hardly existed at Automattic
  • Scott wanted to introduce some friction to Automattic
17 - The Intense Debate
  • N/A
18 - Follow the Sun
  • N/A
19 - The Rise of Jetpack
  • For first time, created a hard deadline to release Jetback at SXSW
  • Design user interface first - most important part
20 - Show me the Money
  • Works on the freemium business model and has 4 revenue streams - upgrades, advertising, VIP services, and partnerships
  • Bureaucracies form when people's jobs are tied strictly to rules and procedures rather than the effect those things are supposed to have on the world.
  • The culture and people attracted to Automattic simply didn't care as much about financial rewards - more worried about the fact that they loved their work and could work anywhere in the world
21 - Portland and the Collective
  • If the conditions are right, a community can be much more than the sum of its parts.
22 - The Bureau of Socialization
  • N/A
23 - Exit Through Hawaii
  • A truly great leader sets up their successors for success
24 - The Future of Work, Part 3
  • Offering a results-first culture empowers people to find their own solutions for when and where to work, benefiting everyone

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