The Standard Substack Fallacy

And a lesson from Chris Paul

This post is about the Substack world, but I hope it has some broader applicability. Because, the Substack experience has taught me, generally, that we sometimes have more agency than seems obvious. In life, it’s easy to fall into certain negative patterns, a miserable Möbius strip. I’ve been there. I jumped to this website because of it. The promise of this medium is that you can break a pattern or two.

And I’m not saying that because Substack is offering me a bonus, though I am accepting of all gifts around the holiday season. I’m saying it because I mean it, even with the understanding that I got lucky here and that most newsletters economically fail. That’s the nature of not just writing, but of business in general. It’s why I was consumed with anxious thoughts the night before I launched. But the appeal of this isn’t guaranteed success; it’s guaranteed autonomy. And it’s harder to get the former if you forget about the latter.

Latest HoS podcast guest Matt Taibbi critiqued a recent Vanity Fair article on a phenomenon some are calling “Substack burnout.” The basic premise is that this medium, having once promised freedom, ends up feeling like a trap. It includes quotes like:

And so the internet’s latest shining promise of creative autonomy denatures into another burnout-inducing hamster-wheel game of keep up, as Gimlet executive Reyhan Harmanci noted recently. The realities and pressures of the digital economy have made subscription newslettering just as much of a grind as the nine-to-five job you quit to do this in the first place.

The article references Charlie Warzel of the “Galaxy Brain” newsletter, who announced he was leaving Substack in a nuanced post that included some grim takes, such as:

I was reasonably surprised at some of the emails I received from people telling me that, because they were paying for me, they expected x/y/z. I very much understand wanting value in return for your money. But I thought it really interesting how a very small minority of paid subscribers lorded this over me. I tweeted once about feeling burned out and producing less and somebody emailed me to say they’d cancelled their subscription as a result (which…fine!). Anyhow, I came away with even more appreciation for creators. There’s a lot of people who think they own you because they pay the equivalent of one craft beer a month to access your work.

That’s candid, but I can’t relate, even if the occasional reader communicates similarly. I can’t relate because I don’t necessarily internalize the message. When responders complain, I don’t shit on them. People, especially customers, are entitled to their criticisms. But HoS is what it is. It’s run how it’s run. And frankly, business is good. I only feel guilty about output if I’m not working hard, consistently, or meeting self-imposed standards. Simple lunkhead that I am, I assume that, so long as you work hard at this, you will, on balance, serve the interests of customers. Gotta trust the process.

I can sympathize with how new Substackers, hailing from publications of prestige, experience a lot of angst over their subscription numbers. Those can bounce around, somewhat unpredictably, taking your self-esteem along for a ride. The sub game is a different dynamic from when I worked at ESPN, where I was a little more protected from knowledge of market forces. There, you wrote something and unconsciously judged its success based on retweets, which is a skewed metric that favors the preferences of media colleagues. Obligatory tweets from media friends gave you a higher floor, even if you knew when an article fell flat. But, when an article fell flat, there wasn’t a sense of real failure like you get when no subs roll in.

In this Substack saga, I am incredibly fortunate to have spent three years writing at The Athletic, where I and every other staffer I knew over there went through subscription angst. The Athletic was a grand experiment in sports journalism, revolutionary in the way it aligned incentives with productivity. Writers could all see how many people subscribed after clicking on your story, which was a powerful motivator. The flip side was that you’d start to feel sick in a dry spell, like you were the salesman whose prize wasn’t going to be the Cadillac El Dorado or the set of steak knives. Ultimately, you had to grow a sense of stoicism about the whole setup. Don’t get too high in feast, don’t get too low in famine. It’s easier said than done, but in reading some of these Substack confessionals, it occurs to me that emotional resilience is often developed over time. I have The Athletic to thank for a head start on building the emotional resilience necessary for being one’s own business.

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Standard Substack Fallacy

In the past, I’d read descriptions of what Substack is like because I was searching for guidance. Now, I read these articles more with idle curiosity, as I never end up relating. Casey Newton’s one-year retrospective on his tech newsletter is one such example. I really appreciated his honest thoughts on the business and they were well-considered. I also just didn’t find them relevant to the HoS experience. For instance, from Newton:

I converted a smaller percentage of subscribers to paid than I thought I would. Guidance I had gotten from Substack suggested I might expect 10 percent or so of my free subscribers to go paid. Given that 24,000 people had been reading me four days a week when I launched — some for three years — I thought that 10 percent would be a slam dunk. Instead, it was closer to 5 percent. That number has grown a bit over the past year, but it’s still well under 10.

The HoS conversion rate is well over 10 percent, trending towards 20. That’s not a brag. Casey Newton is a bigger deal than I am, with far more subscribers, especially on his “free” list. I’ve also been advised that I should court more readers of free content, and that this is the key to long-term success. Maybe so, but I’m noting the conversion difference because it reveals a difference in kind in terms of business model and approach.

Newton’s Substack is rich in late-breaking information, as it’s an up-to-the-minute analysis of the tech world. Basically, it’s a much different thing than my thing, which is almost like a running first-person nonfiction book on sports and culture, written with a bent towards taboo topics. Many people likely subscribe to Newton’s free list because they want to keep abreast of the fast-moving tech scene. These aren’t necessarily content addicts, or loyal readers; these are people who don’t want to miss out on what just happened, sometimes out of professional obligation. Reaching that base of customers means that your content has its own shape and its own fit. My people like content that’s slower, and less rooted in pure information, and more grounded in a particular perspective. Newton’s reach is broader and his content is faster. So, some of his rules for success don’t apply to whatever the hell I’m doing.

Newton likely gets that approaches on Substack are individualized but a few culture critics don’t seem to. Instead, they fall into what I’m calling the “Standard Substack Fallacy.” Because this medium is new, observers are attempting to divine broad truths from discrete experiences.

So yes, you can have a story on how one or a dozen writers does this job, but Substacking is as dependent on individual approach as book writing is. Are there some broad similarities between creators in a medium? Sure, just like how a cookbook writer and Stephen King both type words and send them off to a publisher. Obviously, one author’s process probably doesn’t explain much about the other’s, scenes of savage butchery perhaps excepted. What I’m saying is, Substack is more of a tool than a process. It’s one that, for better or for worse, you are in control of. 

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On Not Getting Sped Up

Having rejected the eternal truths of newsletter analysts, I prefer to grab bits of applicable insights from other places, such as NBA star Chris Paul’s annual summer basketball camp. And by the way, I have a particular affinity for Chris Paul’s basketball camp speeches. There are quite a few of them on YouTube and nearly every one contains deep kōans. 

Paul isn’t the most-loved player in the league, even if he was the longtime player’s union president. He can be a Machiavellian shit behind the scenes and an overbearing dick to teammates when the lights are bright. But nobody can deny his love of the game or his work ethic. There is inspiration and wisdom in that man’s story.

You see, Paul, who’s listed at 6′0″ but who is likely shorter in socks, had no business pulling off a lengthy, successful NBA career. He’s too short and beyond that, not a top-tier athlete. So what’s his secret? 

Among others, he refuses to let the defender speed him up. A larger defensive player will often come after Paul, with a sort of frantic, disruptive energy and Paul just pounds the ball steadily, like a metronome, while keeping it away from prying hands. He explains, to an aspiring college player:

If a guy want to get all up into you and play aggressive, let him. But don’t let that speed you up. Duke, they real good at that, at defending guys. They put a lot of pressure on you. And they make you start going a lot faster than you want to go. But good players don’t get sped up.

Chris Paul has put in an incredible amount of work into becoming a good player, especially in how he dribbles, and it’s the source of his confidence. After you do the work, and develop your internal sense of control, you must trust those abilities in the outside world, even as it gets frenzied around you.

I’ve come to think of this venture similarly. I have a certain pace at HoS and I work according to it. Most weeks (Thanksgiving excepted, btw), I’m shooting for two written posts and maybe a podcast. Some readers want more content, but I believe that following such a route would be penny wise and pound foolish. Also, I’m just wary of putting out lower-quality posts. Over the weekend, I did a lot of research and interviews on the gambling industry in sports. I’ll probably use what I learned down the road, but for now, the knowledge lacks the necessary connective tissue for an article or essay. And so I drop it, until a later date, leaving my site a bit lighter in the interim.

I don’t insult the readers who want more or get my feelings hurt if a few move on for this reason. I appreciate my customers, and greatly enjoy the Weekend Discussion thread where they sound off. In many ways, I feel a responsibility to those customers and I badly want to do well for them. But I won’t let the occasional reader, or the surrounding world, speed me up. The pace is the pace. The work is the work. And the product? Ultimately, it’s my product.

That last part isn’t just about my own pique, by the way. This site is only differentiated because it’s a vision, implemented by a person. If it becomes something else, it starts to be like so much else. So, I try to keep my own pace, not just because this is my product, but because it is yours as well. Does that process work? All I can say is that it seems to be working. Not only does it seem to be working, but all the hours spent on it haven’t felt so much like work.

Burnout? Maybe it’ll happen one day, but for now, this site and these readers have saved and galvanized me. It’s difficult to forge one’s own path, to be sure. I’d just advise those trying it to remember that it is, indeed, in the end, your path. Walk it the way you want and see what happens.