Year Two

Early in my career I heard a story that stuck with me. It was about an entrepreneur of sorts, or perhaps more of an artist, who gave his life to develop the perfect glaze for his porcelain vases. Every day he lit up his kiln, experimenting with different precise combinations of temperature, time, and chemistry. But no matter how many variations he tried he could not achieve the perfection he imagined. So he decided his meaningful life was over and walked into the white hot kiln along with his pottery. The next morning, his assistant came to the studio and discovered inside the kiln a collection of vases with the most perfect glaze anyone had ever seen.

The story stuck with me partially because it’s gruesome, but also because the moral upshot is ambiguous: is the point that I have to pour my whole self into my work if I want to achieve excellence? Or is it actually a cautionary tale, warning me that I could die in a fire if I don’t keep my perfectionism in check?

I am recalling this story now because 2021, my second year of working on Every, was a hard year for me. I suspect I am not the only entrepreneur who gets their ass kicked in year two of their business. Like the potter, I feel a bit burned. Unlike the potter, I don’t feel like I have a beautiful glaze to show for it. But I am excited for 2022, year three, because I think I’ve figured out what happened, I’ve done something about it, and I can feel that it is working.

I am writing this to nail it down, and because I know there are a lot of you who are going through your own crucibles. If this feels like you, hopefully you find something useful here. (If not, congrats! 😉) 

In some ways, the stakes couldn’t be lower: I’m healthy, I have a nice place to live, I don’t worry too much about money, I’ve found the love of my life, and we’re expecting our first child soon. But I think it would be a mistake to tell ourselves to “suck it up” when we struggle at work. It only makes things worse. In my experience, the human spirit stubbornly refuses to submit to even our best laid plans if we ignore it. We are forced to reckon with it.

So here I am.

In reflecting on what happened this year, I realized I ran into three demons: Burnout, Disillusionment, and Perfectionism. Here is what I have learned about them.

Burnout

My first problem is simple: when I look back on everything I did last year, there’s not much creative work I’m proud of. I spent far less time writing than I did the year before, and what I did write was mostly rushed. This was not an accident—it was a strategic decision my co-founder and I made. My focus this year was to build Every into an organization that could publish a lot of writers. This meant big changes in how I spent my time. A lot more meetings and small tasks; a lot less wide open days with time to read and write, design and code.

I’m proud of what Every accomplished this year. We’re growing and making money and I know my work was indispensable in getting us there. But I miss those wide open days. I love waking up in the morning and having all day to do one big thing. I love the feeling of finishing that big thing and seeing it produce results. It’s so immediate and tangible. Managing is important, but it does not give me the same satisfaction. Giving away my space to create burned me out.

This is a classic challenge: organizations need people to coordinate activity and act as the glue that holds everything together, but for the people who volunteer as tribute to the machine, it can be difficult. Managers create extraordinary value for organizations—for which they are rewarded with increases in pay and power—but management is often emotionally unfulfilling, especially at first. This is not universally true, but talk to anyone who’s made the transition and they will tell you it’s a real thing almost everyone contends with. It can get better, but it will never feel the same as directly creating. Ultimately you have to decide what you want your impact to be, and how you want to spend your days.

The challenge is to set aside our ideas about what we “should” do, which are often lies. We think we need to do things that we don’t actually want to do, and don’t even bring us closer to our goals. These rules we create for ourselves come from a place of fearfulness and conformity. It takes a surprising amount of courage to admit to yourself what you actually want, I learned this year.

Here is what I got: I like to spend my days mostly making. A little management here and there isn’t so bad, but when it prevents me from making for too many days in a row, I get sad. This is who I am. 

The problem is, I want to build Every into something bigger than myself. Pro-socially, I want it to become a platform that can help other makers realize their dreams and do their best work. Selfishly, I want it to become a company that has significant enterprise value—a fancy way of saying “makes money while I sleep.” Balancing these goals with my drive to spend time making was something I mostly failed at this year.

I thought I had to be involved in every decision and project and meeting. I thought I had so much on my plate I didn’t have time to do anything right. For example I probably spent 100 afternoons editing drafts with the same types of problems, and it was only very recently when I made the time to write with Dan a general-purpose document that we can send writers anytime they run into that particular issue. Go slow to go fast, and all that. It’s a real thing!

Anyway, it is tempting for me to accept a narrative where my problems begin and end with a lack of focused work time. All I’d have to do is just cancel a few recurring meetings and I’d be good! But if I’m being honest, I know that’s not all there is to it. Something deeper also happened.

Disillusionment

Every year since around 2010, when I first got interested in technology startups and the tech community, I’ve been more or less obsessed with it and cared about little else. This year, for some reason, that changed. Of course it wasn’t all or nothing. Maybe I used to occupy 80% of my waking hours with tech and now it’s closer to 60%, if we want to quantify it. But the point is, there was a real change in how I allocated my brainspace.

What did I turn towards instead of tech? Such topics as: formula 1 racing, baking, DIY home improvement / interior design, espresso, central Texas style brisket, and health and fitness topics like zone 2 cardio, glucose monitoring, lifting, etc.

It used to be the case that whatever I got obsessed with was likely something that I could write about in Divinations, because it probably had something to do with media, technology, or business. But in 2021 my interests increasingly diverged. I stopped looking at Twitter as much or being as interested in what everyone else in tech seemed to be interested in. It was easier for me to show up and put in an honest day’s work with management tasks than it was for me to write about the topics I used to love. For me, management was a way of hiding.