Essays

This week, I handed Holloway's CEO reins over to my co-founder, Josh Levy. As we built Holloway over the last four years, I got the chance to explore the depths of my love for research, writing, and sharing stories. My belief in the purpose and mission of this company hasn’t wavered, but over the last six months I found myself wishing I could be a full-time independent creator. And at the end of July Josh and I came up with a way for me to do that. 

A few weeks ago, a Good Work reader asked if I’d write about recovering from failure. At Holloway, we have a policy of keeping Good Work to four paragraphs and a set of links. But I felt like this subject was worth making an exception for. I was grateful to have been given the opportunity to think about this one.

Over the last year, I’ve spent a lot of time thinking about how we get the word out about Holloway. I’ve read more than I ever thought I would about the field of marketing, but the thing that surprised me the most is how important it is to understand, and master, what I call “having a good ground game.”

I loved video games in middle school. So when the Xbox came out, I made an appeal to my parents to purchase this glorious machine. My dad, forever the teacher, told me I could have one if I figured out a way to pay for it. I came up with a scheme to use all the assorted machinery in the garage—lawnmower, leaf blower, that kind of thing—to see if I could sell my services to the neighbors.

Work, as we often think about it, is a place to get things done, to put food on the table, to make that bread. But for me, work has also been the place I’ve met my closest friends.Kurt Vonnegut wrote that when couples tend to fight, “what they’re really saying is, ‘you’re not enough people.’”

At Mattermark, the company I helped start before Holloway, we were in the business of collecting data on private companies so investors could determine which ones might make good investment targets. To measure this and convey it to our customers, we began thinking about companies in terms of physics equations. For example, we built a “momentum score” (momentum = mass * velocity) that took into account how big the company was and how fast it was either growing or shrinking.

Have you ever noticed that learning to swim feels a lot like drowning? At least at first. How can we tell when all that flailing around is actually exactly what we’re supposed to do on our way to mastery? Founders have to start from scratch a lot. When you’re hiring someone new to lead a function, for instance, you have to master enough of the material to assess someone else’s ability to actually take action in that domain. Design, marketing, or engineering—how do you know when you’ve learned enough?

Yoda said, “Do or do not,” but do I did not. This week’s Good Work is one week late and about procrastination. Procrastination starts when a task is added to one of our many plates, and we don’t decide and communicate that it isn’t urgent, that we can’t consume that much right now. Sometimes we record the task in a to-do list. In other moments we tell ourselves a cute story, “I’ll remember it in the morning.”

In my century-old house, the hinges on every door are covered in layers of paint. For a hundred years, the people painting this house refused to find a screwdriver or to tape around the hinges, dooming me to stare at this mess. On Holloway’s Work-From-Home Wednesday this week, around 5 o’clock PM, some part of me snapped. I had to go nuclear on those suckers, strip them down to the brass I knew lay below the strata of practical beiges, “Careful Whisper” blues, and a hundred other bad decisions and attempts to mask them.

When I sat down to write this week’s Good Work, I stumbled on a note I’d taken of something executive coach Khalid Halim told me in July of 2016: “Trust is made up of three things: sincerity, reliability, and competence. And trust crumbles at anything less than having all three.”

In the first few years I was managing people it felt like everyone had something to complain about. The grievances poured into a sad swimming pool of injustice. I did my best to address the issues, but it doesn’t take many complaints at once to overwhelm even the most well-intentioned managers. I quickly came to dread complaints, becoming fast friends with phrases like, “Here we go again.”

When work is a choice, why the hell do some people choose to do it? Why would someone with $2M, $50M, or $800M in the bank choose to do the kinds of daily tasks most people think of as chores, or necessary evils?

It’s hard to make the case that studying someone who mastered a craft by reading their biography would be a waste of time. Likewise, reading popular non-fiction that aims to explain how some part of the world works can hardly be spun as a waste of time. But it’s a hell of a lot less clear how fiction fits into the picture of self-directed professional growth. After all, how could something made up be related to a career? But isn’t that exactly what a career is—something made up?

When I was nineteen, a friend and I started brewing beer. I headed to Barnes & Noble and asked the gentleman at the counter if there were any books about brewing beer. Without a worry over being complicit in an underage brewing ring (😬), he ultimately helped me find Brewing Up a Business by Dogfish Head Brewing Company founder Sam Calagione. So began my career as an entrepreneur. Since then I’ve bought books on how to write, sell, market a product, manage people, lead a team, understand design, build a product, and more.

Julian Weisser introduced me to a phrase I fell in love with this week: “putting people in play.” Over my career, I’ve repeatedly felt like a threadbare piece of discount clothing, not much good in the first place, stretched thin, and useful to nobody. Growing up, it felt like so many of the adults I knew had sold their souls for rafts of stability. Being an optimist, believing there’s big, bold, and beautiful opportunities in life, turned me into this angry sort of Holden Caulfield who just thought everyone else kind of sucked. It’s hard to look back on the person I was, clawing for an opportunity to find some depth to life.

There’s this perverted idea that taking time to rest is an indulgence, like catching our breath over the weekend is the equivalent of eating a swimming pool of Ben & Jerry’s Cherry Garcia. For many of us, our work takes on the personality of a jealous and territorial lover. One day you wake up, hungover from a fight with work the night before, power cords flung around the room, fingers stained with the dregs of coffee we sucked through the filters in the trash, realizing you’ve missed any depth of life outside your codependent relationship with work.

There’s this Jim Beam commercial I love. It’s called Bold Choices. It’s the best commercial I’ve ever seen. Yes, it’s a commercial advertising an alcoholic beverage, but it’s also a beautiful reminder that our lives are not on a strict path from birth, and the bigger the risks you take, the farther you could end up from where you started. No matter how many people we talk with, no matter how many alternatives we consider, our decisions are ultimately ours. We have to live with how we made them and who else they affected Figuring out why we make the choices we do can be the hardest work of all.

In Where Good Ideas Come From, Steven Johnson writes about what he calls “the slow hunch.” Charles Darwin didn’t wake up one day with the entire theory of natural selection worked out, for instance. It took him months to work out what his findings in the Galapagos meant, but first he had to write them down.

A few weeks back, a friend of mine asked me a question over text. “Now that you are where you are in your career, fairly established, how do you think about building your network and furthering those relationships? Or is it mostly a byproduct of what Holloway needs?” What a lovely question to ask and what a delightful one to answer.

Tyler Lyman, a new Good Work subscriber, wrote us on Monday asking if we had plans any time soon to explore the relationship between startup founder and executive coach. I hadn’t decided what to write about for this week’s Good Work yet and thought tackling the subject would be a breeze-my co-founder, Josh, and I happened to be headed in to see our coach the next day.

In editions four and five of Good Work, I wrote about the importance of asking ourselves what we’re optimizing for. It’s painfully easy to stumble around in life without pausing to reflect on whether we’re pointed in the right direction, and there’s endless pressure to point ourselves off The Cliffs of Workaholism and The Pits of “Oh My God This is Not Where I Thought I’d Be By Now.” Tools for figuring out what we’re optimizing for and whether that’s what we want are about as abundant as tools for physical fitness, but this week I’d like to explore one close to my heart: journaling.

Last week, we wrote about the importance of looking within to answer the question, “What are you optimizing for?” In a delightful turn—and reason #2,573 why I love the internet—Medium featured a piece on its homepage this week, “We’re Optimizing Ourselves to Death” by Zander Nethercutt.Here’s what I love about Nethercutt’s piece. When read alongside Neil postman’s Amusing Ourselves to Death (cartoon version by Stuart McMillen here), a new theory takes shape that neither George Orwell nor Aldous Huxley predicted. We don’t live in Orwell’s dystopia of banned books and thought crimes. And we don’t live in Huxley’s hedonopia (it’s not a word, but maybe it should be) where everybody is so addicted to Netflix and Fortnite that nobody bothers to work or participate in society.

In their book, Designing Your Life, Bill Burnett and Dave Evans talk about the importance of finding your “north star.” The phrase is a bit too Disney for me, but I like the distinction that a north star is something you optimize for over decades whereas goals are stepping stones towards your north star. We’re never optimizing for one thing, and these layers of wants, goals, and north stars interact with each other. Knowing what we’re optimizing for can be the real challenge, and the most rewarding one to figure out.

My favorite people are irrationally passionate. They’re the ones who get to work getting things done and forego the temptation to stick to talk. These people don’t spectate, they participate. Whether they’re writers on fire about writing, dancers stoked about dancing, chefs who can’t stop cooking, teachers teaching even when they aren’t teaching, whatevers whatevering so strong you stop talking about the weather—these are my people.

I doubt myself a lot. Everyone is totally just winging it, all the time is one of my favorite articles ever. It makes me feel far less alone with my fears. Will my company be successful? Am I nuts? Are all my friends avoiding the trouble of telling me I’m working on bullshit?

A 2015 post exploring the role of COOs in startups based on my experience as the COO of Mattermark at the time.