A messy slog that changed everything for me
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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.
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.
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.
Why was I hiding? A few theories:
Some of it was probably sour grapes. Like the fox who failed to reach up the grapevine and decided he wasn’t in the mood for fruit anyway, I took my foot off the gas with my strategy writing, my work naturally got less attention from tech twitter, and then perhaps subconsciously I decided I didn’t actually want their attention. I remember early in the year having brunch with my wife Sonia and crying in public as it hit me that I was grieving the loss of my writing. In retrospect it makes sense that I would probably want to avoid tech twitter after that.
But I also think something else was going on. The “middle school cafeteria” vibes of the tech community have become increasingly draining for me. The petty fights, the earth-shattering next big things that we all seem to forget about in six months, the cool kids and their simps—it’s boring. I don’t feel like I belong anymore. Sometimes I just wanna open a new tab and learn the aerodynamics of how an F1 car could drive upside down in a tunnel. Do you know what I mean?
Don’t get me wrong, I love so many people on Twitter and ultimately I never took a serious break from that website because I can’t get enough of them, and I like this little weird way that we can be in each other’s lives. But it feels like all these amazing people exist in a cultural context that is increasingly a drain on my soul.
This realization has caused me to let go of a lot of goals I set a long time ago that have little or nothing to do with the person I am today. Status within the tech community used to be a huge motivator for me, and it helped me accomplish a lot. But today, when I'm recognized at tech events or gain new Twitter followers, it doesn't mean as much to me as I thought it would. I realize the thing I actually wanted all along was just to spend my days with people I love working on stuff I am excited about. And right now I am excited to write things that hopefully feel nourishing and useful to people, and to help others do the same. For a while this year I lost sight of that. I was hiding, my work suffered, and it made me grumpy and anxious.
I don’t think I’ll ever have the same relationship to the tech community as I used to, and I think that’s a good thing. Demoting the status it holds in my brain creates more room for me to follow my curiosity and focus on making things that are useful to people. Caring less about the tech “community” will paradoxically help me focus more on the actual technologies, companies, and people that I care about.
So there’s the maker/manager thing, and the loss of motivation to chase clout within the tech world thing. Between those two, it would have already been a relatively challenging year. (Oh and also it was year two of a global pandemic, and of adjusting to living in the suburbs.) But still, if I want to be totally honest, I have to go even deeper. There’s still one more level that I have to confront. And that is my management style—my basic approach to making things happen.
This year I came to terms with some very real weaknesses I have as an entrepreneur, and I am trying to update my approach in a bigger way than I probably ever have in my career so far.
My basic style has been to come up with a big, original, creative idea, fixate on it, and then work furiously to make it happen. I like to learn how systems work and try to build a bottoms-up model of how all the pieces fit together, and then come up with new approaches that might seem weird at first but reflect this fundamental understanding. I don’t like to reason by analogy or think about ideas in a fuzzy, probabilistic way. Even if something is widely seen to not “typically” work, I still like to do it if I come up with a mechanism I think could solve the problem.
For example, when I was at Gimlet, the podcasting studio acquired by Spotify, I thought we should focus on building an email list, because RSS is a channel that offers very little control and zero data or personalization. No podcast network to my knowledge had ever really made email work or focused on it as a channel, but I thought it would be a good idea and I got fixated on making it happen.
Another example of this way of thinking is when I was at Substack. I thought we could only get big-name writers to come on board if we offered more than the 90% revshare, and expanded to providing significant upfront funding, marketing and branding resources. At the time we did not have the bandwidth to offer these things to writers, but I was fixated on it and wanted to make it work.
Same thing at Every. I wanted to create a bundle to make access to great business writing more affordable for readers, and to make access to large audiences more available to writers. I thought we could get business writers with wildly different styles, audiences, and topic focuses to all co-exist under the same brand because we could use personalization, all within the context of a bundled subscription. This is the big idea I have been fixated on for the past two years.
My approach has a lot of strengths. I am often right at a macro level. Email is a great channel, even for podcasters. Substack has succeeded in attracting big writers in large part because they’re now offering funding and support. And I think over time Every will grow into something that feels similar to the idea I have imagined.
But I get too fixated on these abstract ideas, and it hurts my ability to see what’s right in front of me with clear eyes. I push for ideas regardless of the consequences and ignoring important context that might help me make the idea happen in the way and at the time that is right.
The reason this happens, I have learned, is that our expectations shape our perception of reality, and the more tightly you cling to your expectations the more everything gets filtered and colored according to your preconceptions. If something didn’t fit with my model, it was a threat, and I either ignored it or suppressed it, or got really anxious about it. I had a lot of pet explanations.
One great example of that at Every is advertising. I didn’t think we should sell ads because I thought it would distract us from the hard work of building a great subscription business. Now we sell ads and it’s made our business better in every way, with surprisingly little distraction. Oops.
Another example is how quickly we should add writers to the bundle, and how close their work needs to be to our existing audience. Previously I thought anyone writing about business for a vaguely tech audience would be a good fit, because readers can always subscribe and unsubscribe to each newsletter separately. Now I’m learning our model works much better if we think about ourselves as pretty much just a new kind of magazine. The central “Every” editorial brand needs to stand for something more specific, because if we put the burden of pitching a value proposition to readers on each individual newsletter it creates an incoherent overall experience for readers. Oops.
The core issue is that I cling too tightly to an original vision. I’m afraid if I let go then we will get mired in mediocrity. But in fact my fear of loosening up is often what causes mediocrity to creep in. It’s not bad that I care about excellence or get excited about big ideas. The problem is when I fixate on too specific and narrow a frame of reference, creating perfection inside the frame and havoc outside of it.
I don’t know why I am this way. I have always been a questioner, and I have always liked coming up with new ways of doing things. Some types of details pop out to me as obviously important and I obsess over them. Meanwhile I am often oblivious of the macro problems caused by my micro solutions. I have always been like this. I think it must be partially genetic. I also think it’s partially because I didn’t feel listened to at school by my teachers or peers, and this created a void I am still trying to fill by pushing for my ideas to be taken seriously. (Great origin story for a writer!)
But instead of drawing up a plan that determines everything before I start, I am realizing it actually helps me move more towards excellence when I am more open and flexible. I am learning to prioritize awareness of everything that is happening at the present moment, and learning how to set my models and preconceptions to the side. I should realize sometimes when you set out on a journey you don’t know where you will end up, but you’re more likely to end up somewhere really cool if you keep your eyes open along the way.
Here was a fairly mind-bending realization for me: one of my primary drives is to build something original and innovative, but often the most innovative ideas don’t arise from some predetermined vision, they are simply a result of accurate awareness of what’s going on and why. We are building a media company in 2021, and the world is very different now than it was in the past. If we pay careful attention to the present moment, and respond to it thoughtfully, we can’t help but end up with something innovative.
Into the Fire
For 2022, my third year of working on Every, I have three goals: to spend my days making things I am proud of, to reconnect with my curiosity and write about things I care about, and to hold my models much less tightly.
What does that mean practically? Well, to start, I’m now only doing one or two meetings a day first thing in the morning, quickly taking care of any admin work that’s needed, and spending the rest of the day in focused mode working on bigger projects. I am incredibly thankful to have a business where this makes sense, and a partner in Dan that supports me and makes this possible.
What will I do with all the new space I have created for myself? I don’t know, honestly. I’m starting to read more and look at Twitter less, so that’s a good start. There are a lot of questions related to strategy and technology that still deeply interest me. They’ve been on ice for a little while but I can feel they’re starting to thaw. I also might branch out a bit into new topics.
As far as management duties, I am trying to be much more open and flexible. The key will be to notice when I am operating within a fixed, rigid frame, and remind myself that I actually can move closer toward excellence when I expand the frame and pay attention to what’s happening around me.
The thread that unites these three goals is the idea of service. When I think about spending less time on management, it makes me worried I’m being selfish. But I realized a core thing I am good at, one of my unique superpowers, is producing creative work. And I am at my best when I’m producing creative work that’s meant as a gift for other people. I want it to be genuinely helpful. It’s not about showing how smart I am or indulging myself by trying to create space to just do whatever I want, it’s about creating space to make things that could be meaningful to someone else.
This is the lesson I take from the potter who walked into the fire. His sacrifice was to make something special for others. And nothing we make can be special unless we pour ourselves into it. It is true that the process can completely consume us. But the crucible we enter when we attempt to make something special is a place that has the possibility of transforming us into something more beautiful than anything we could have imagined.
2021 kicked the shit out of me. I was burnt to a crisp. But I learned more about myself by going through it than any other year of my life, and I wouldn’t trade it for anything.
If you got this far, you might want to become a subscriber to Every so you can read some of the good stuff I wrote in 2020, which tbh holds up pretty good.
A few notables:
- Why Content is King — applying classic business strategy concepts to stories, the effects they have on us, and the communities that form around them.
- Finding Power — a deep dive on Clayton Christensen’s best and most underrated idea: the law of conservation of modularity. The name makes it sound boring but it’s actually awesome, because it explains why power tends to accrete in some parts of the value chain but not others, and why that shifts over time.
- Bundle Magic — we’ve all heard of “bundling” as a strategy, but this post explores the underlying microeconomics that make bundling a win-win for creators and consumers (and explains when it’s a bad idea to bundle).
Subscriptions come with a $1 trial that gets you access for two weeks, which should be plenty of time to read three posts. Ideally you end up deciding you like us and want to keep us, like the “temporary” dog you brought home from the shelter, but no pressure. We will find another home. 🥲
Thanks to our Sponsor: Swell
Thanks again for reading! If you've made it this far it would mean a lot to us if you check out our partner: Swell. Swell is a headless ecommerce backend for your storefront. Swell makes it easy to set up storefronts that scale: fast APIs, native storefronts, and an intuitive dashboard. Whatever your business model or shopping experience—Swell is ready to grow with you.