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24 Ideas From Scott Berkun About Tech, Leadership, and the Future of Work

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, A Year Without Pants, 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?

No Silver Bullets: Etsy’s Randy Hunt on Product Design

product-design-for-the-web-randy-hunt

While on my Peru Trip earlier this year, I read a great book  called Product Design for the Web: Principles of Designing and Releasing Products for the Web.

As one of two interaction designers who joined Etsy in 2010, Randy Hunt, now creative director, has written the book on best practices of product development for successful modern-day Internet companies. I highly recommend it.

I sat down with Randy recently to learn more about his perspective on product design. But before I jump into that conversation, here’s a brief look at some of the big ideas from the book:

Takeaways From Product Design for The Web By Randy Hunt

Note: these are not direct quotes but pretty close paraphrases

  • Great products are understandable (set expectations and live up to them) and meaningful (help people solve problems or accomplish goals) and, hopefully, delightful
  • It can be helpful to reimagine your product spec as a press release defining what the update is, who it is for and why it matters Continue reading…

How You Write 190k Words in 6 Months (While Pregnant!)

A couple years ago, I participated in National Novel Writing Month and wrote down a little over 50k words in the month of November that sort of resembled a fantasy novel. I’ve always enjoyed reading fantasy novels as a kid and it was fun (but very challenging) to write one, especially in just one month. It took a lot of discipline to find the time and energy to consistently get in the words.

So when I heard that my friend Julia Dickinson had finished a 190,000 word manuscript of her epic fantasy novel, the Evenarian, I had to talk to her about it.

The Evenarian

The book focuses on a young mage named Turo who learns of a powerful figure named the Evenarian who has been fortold in prophecy to bring the downfall of magic and bring ruin to the world. Turo joins up with a mysterious wanderer named Josh and a band of unlikely heroes to find and defeat the Evenarian. More on the story on their Kickstarter page. Continue reading…

My Biggest Takeaway on 37Signals’s New Book on Remote Work (Hint: It’s Not Technology)

REMOTE: The new book from 37signals 2013-11-08 07-41-46I just finished reading Remote: Office Not Required, by Jason Fried and David Heinemeier Hansson, partners at 37Signals.

It’s a great read and here’s the  basic premise:

  • In today’s economy, the quest for talent is so great that organizations can no longer afford to merely look at individuals co-located in their physical presence (their metro area)
  • It is easier than ever to coordinate the work of individuals from around the world with just a good internet connection and a few pieces of web-based software (including 37Signal’s own products)
  • There are many drawbacks to forcing people to work in an office and many perks to allowing them to work (even a few days a week) at home / at a cafe or coworking space that benefit both the remote worker and the organizations that employ them
  • There are simple ways to address many of the concerns people have with remote working (review the work, not time in seat; put relevant information where it can be seen by all, overlap working hours, etc)
  • There is a tipping point coming with remote work. Many organizations large and small, from across many industries, are using remote workers and it’s time you (the reader) became an early adopter.

They actually went out and interviewed a bunch of companies that do remote work as well so REMOTE is not just “the edgy opinions of Fried and DHH”. The book has useful tips for making the case for remote work to your boss (or to your team, if you are the boss). There’s a lot of value in learning how to structure a good remote work environment.

But personally, I got a bigger shift in perspective from something else.

My biggest takeaway from REMOTE:

Continue reading…

How I Published an Amazon Bestseller By Picking the Right Category

Winning Isn’t Normal has been out for a little over a week. And guess what?

It’s already become an Amazon bestseller.

If you’ve purchased the book, thank you so much for your support. If you haven’t yet, what are you waiting for? =)

Pics or it didn’t happen right? Here’s the screen shot:

Amazon Gymnastics Bestseller Book View

But here’s the thing. It’s a lot less impressive than it sounds.

When you publish a book via Kindle Direct Publishing (the way I did) you have to pick two categories for your book to fall under. Because my book is about so many things, I had trouble picking which categories.

Because many people consider The Art of Ass-Kicking a “startup blog” and because at least six of my essays in the book are directly about gymnastics or lessons that stem immediately from the sport, I ultimately settled on:

  • Sports and Outdoors -> Individual Sports -> Gymnastics
  • Business & Investing -> Small Business & Entrepreneurship -> Entrepreneurship

One category is obviously more competitive than another. Can you guess which?

A big fish in a small pond

Most of the time, I’d argue it is better to be a small fish in a big pond. Because when you are competing against the best, you learn more, you get tougher and you are forced to keep improving and never rest on your laurels.

But sometimes it is worth pursuing an area that’s more open, with fewer folks clamoring on it, so you can stand out. In this case, having this book reach number one in Gymnastics is worth the trade off of being in a more competitive category. Consider whether there are any activities in life where if you chose a less crowded approach, you could dominate the field. Might be worth trying that out.

Win Awesome Stuff from Me!

If you’ve already bough the book, consider entering my Book Review Giveaway. You could win three amazing books by Seth Godin, the Heath Brothers and Tim Ferriss, beautiful quote typography posters AND a one-on-one Skype session with me. Right now you have a really good shot of winning, so I’d get on it if I were you.

Just write a review for the book on Amazon and forward it + your receipt to winningisntnormal@gmail.com and you’re entered to win. I’m giving away TWO whole sets of prizes so don’t miss out.