The Year Without Pants

One of the few people who can match Paul Graham as writer is Scott Berkun. They have both succeeded as technologists, Graham in Viaweb + YC, and Berkun in Microsoft and Automattic. They both write thoughtful essays on a wide range of topics, like the Cities and Ambition or Street Smarts vs Book Smarts. If anything, Berkun is a bit more personable and relatable as a writer, he’ll refer to himself a bit more than Graham and use more culturally relevant examples.

I recently finished Berkun’s book, The Year Without Pants: WordPress.com and the Future of Work, about his experience as something like a product manager for Team Social at Automattic, the parent company of WordPress.com. The title of the book refers to the fact that the company is fully distributed and so you don’t have to wear pants to work if you don’t want to. I’ve written previously about 37 Signal’s book Remote, but this book is different because it doesn’t focus so intensely on the “remote” part. In fact, large swaths of the book are about times where Team Social were working together at an in person gathering.

Berkun primarily uses his experience at Automattic as a platform to offer a variety of other interesting and unconventional ideas about work. Here are 24 of my favorite quotes from the book (which you should read) and my comments.

1. Poorly Run Meetings

“Most people doubt online meetings can work, but they somehow overlook that most in-person meetings don’t work either.”

2. Making Lists

“The first thing I tell teams of people who are struggling is ML: Make a list. Write down the list of problems to solve or issues to fix. Get it out of their brain and on paper. It’s less stressful when its written down. Then put them in order of importance”

Will be turning to lists more often myself at work.

3. Leadership and Trust

“My list of priorities looked like this: Trust is everything.”

Trust takes time to build and is based on both your competence and whether people think you’re acting in their best interest.

4. Ideas that Scale

“The inability to scale is one of the stupidest arguments against a possibly great idea: greatness rarely scales, and that’s part of what made it great in the first place.”

Or at least greatness in that exact form.

5. Traditions Block Progress

All traditions are inventions; it’s just a question of how old the invention is. … 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.

So true! As I’ve said before: creation and destruction are two sides of the same coin.

6. Private Conversations

The realization that everyone is different when you talk to them alone is a secret to success in life. … 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.

Like the private conversations I had to overcome the naysayers on my gymnastics team.

7. The Problem with Metrics

All metrics create temptations. Even with great intentions and smart minds, data runs you faster and faster into a stupid self-destructive circle. Put another way, there is no good KPI for measuring KPIs.

8. Blogging is Hard

The numbers were staggering: more than 50 percent of all [WordPress] blogs never publish a single post.

While the user interface could and would be improved, there’s always the problem of what do you blog about?

9. Fooling Yourself

To start big projects, you must have the capacity for delusion. All the rational people, despite their brilliance, are too reasonable to start crazy things.

I think back to the blog post I wrote about starting my first startup.

10. Humor Creates Trust

Humor has always been a primary part of how I lead. If I can get someone to laugh, they’re at ease. If they see me laugh at things, they’re at ease. It creates emotional space, a kind of trust, to use in a relationship.

11. Leaders Drive Organization

If ever you wonder about why a family or a company is the way it is, always look up first. The culture in any organization is shaped every day by the behavior of the most powerful person in the room.

12. Good Bosses Explain

I’ve always demanded that my bosses explain things I don’t understand. I want to be taught, not told. I don’t mind being proven wrong or trumped provided I learn something, but I did not follow decrees well.

Reminds me of one of Sarah Allen’s little rules for life: don’t ever do something just because a VP told you to.

13. Flattening the Rollercoaster

During my year at Automattic, no one ever yelled at me. I was never in a meeting that made me angry or want to storm out. … Working remotely mellowed everything out, dropping the intensity of both the highs and the lows. Depending on your previous experience, this made things better or worse.

14. How Do Things Go Without You?

The only honest test of the value of any management activity is to run projects without some of them and observe how well people perform with a lighter touch. … It’s a test few leaders have the courage to take. The worry among managers is that this test would reveal that quality improves when they do less managing.

But seriously though, how many managers do you know who would be willing to do this? Reminds of cold showers and rejection therapy. Everyone has a excuse for why they can’t.

15. The First Win

Often the first step, the first undeniable sign of progress, is the hardest to get. With the first win under your belt, everyone has a clear reminder that wins are possible.

16. The Soft Stuff is the Hard Stuff

The natural mistake engineers make is to build from the bottom up. They leave the user interface last, assuming it is the least complex technology. This is wrong. Humans are much more complex than software

17. Simple Project Planning

The easiest way to work to a schedule is a spreadsheet with three things: Each work item, listed in priority The developer assigned The developer’s work estimate.

18. The Power of a Plug-in

As of this writing, Jetpack has been downloaded over 5 million times, making it one of the most popular WordPress plug-ins in history.

19. Conflict Creates Better Products

There must be someone challenging ideas in ways their creators don’t necessarily like in order for those creators to see the blind spots in their thinking. … Many designers by their nature dislike conflict. Although they often have bold ideas, they struggle to find the courage to fight for those ideas.

It’s easy to avoid offering serious critiques of creative work because it can feel so personal, but it necessary if you want that work to improve.

20. Ideas Do Not Stand Alone

Most companies have confusing politics about who is allowed to disagree with whom and how they’re allowed to do it. … Ideas are evaluated differently depending on the mouth they come out of.

21. Tough Decisions Don’t Make Themselves

We all imagine an angel will fly down from the sky and let us know it’s time to make that change we’ve had on our minds for far too long. But that angel never comes because that angel doesn’t exist. It’s a fantasy born of our lack of faith in our own ideas.

Like the courage to have private conversations, the courage to pull the plug on a project, a relationship or a job is crucial.

22. Don’t Fear Passion

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. … Emotional words like meaning, passion, and soul are scary to people who believe everything in life hinges on pure rationality.

23. When Work Keeps You Alive

The history of work is rooted in survival. We hunted and gathered in order to live. Little distinction was made between work and the rest of life. Rather than this making life miserable, it likely made it more meaningful.

24. Teams Need Outings

Regarding the assumption that work must be serious, a critique I received on drafts of this book was how much time was spent on Team Social adventures together. … Few business books, even ones about famous projects, mention the relationships workers have, lending the pretense that they are robots.

I noticed this too – and I think he makes a really good point. Most teams that work really well together also socialize and play a lot together and those activities support each other.

Have you read A Year Without Pants? What did you enjoy most?