Not a week on this still somewhat habitable Earth goes by when I don’t think about this 2017 Evan Williams profile, wherein Biz Stone, his fellow Twitter cofounder, perfectly roasts Williams’s ambition to make publishing profitable: “I was like, ‘Yeah, so does everyone else.’ How far along are we? Somewhere between zero and half a percent.” In the long arc of human civilization’s grapple with arts patronage, the internet-sized problem of monetizing digital content that Williams–type believers still cutely attempt to crack with various Rumpelstiltskinian turns of code remains the most fascinating chapter yet, only because every few years, it seems like some newfangled holy grail—native advertising! short-form video! “engagement metrics!”—appears on the scene, promising to finally link good writing with money forever.

Subscription newsletters are no exception. In the wake of the Summer of Substack, the novelty of launching a newsletter where readers pay directly for your work has given way to the reality of, well, keeping that newsletter up. And keeping those readers happy. And finding new ones when, inevitably, some of those readers decide they’re kind of over you (nicely termed as “churn”). Inevitably, a writer freed from the constraints of pesky editors and SEO dictates must become a writer and a one-person P.R./circulation/audience-development strategist all at once. (Turns out, media companies had those things for a reason?)

Layer in the ongoing Great Resignation energy (and like, a worldwide pandemic), and it’s no wonder that newsletter-writer fatigue has set in as writers begin navigating the logistical implications of signing themselves up as a one-person subscription product: How do you keep up with your publishing cadence? How do you make sure your readers are continuously getting their money’s “worth”? Does it feel fair to take a few weeks off for the holidays when people pay a monthly subscription?

And, if for whatever reason you need to quit, how do you get off this ride?

Last week’s news about The Atlantic’s new stable of newsletter writers could be read as one potential answer to this last question, or at least as a sign toward mainstream media’s acknowledgement of (Oscar Isaac voice) newsletter power and the inevitable bundling to come. Charlie Warzel, who originally left The New York Times to write the tech newsletter “Galaxy Brain,” was one of the writers bringing an existing newsletter into The Atlantic fold. His announcement of the move took time to explain some of the sobering realities of Substacking solo: namely, that it was all less lucrative than he’d hoped, and it involved a weird dynamic where some subscribers felt entitled to hold their $6 per month “hostage” unless Warzel’s work aligned with their expectations.

There was also the issue of refunds: Because “Galaxy Brain” would now be a subscriber-only product at The Atlantic, readers who already paid up front for a year of the newsletter would receive prorated refunds, which Warzel said he’d issue personally. I asked Warzel how much money those refunds would entail, and he estimated it as “likely tens of thousands of dollars.”

For anyone looking to get out of the game without an Atlantic–sized landing pad—or who hasn’t quite budgeted for the possibility of issuing subscription refunds—the cost of quitting might well be prohibitive. Casey Lewis, who writes the youth culture newsletter “After School,” told me she once looked into putting her paid newsletter on hold during a bout of freelance busyness and calculated the potential amount she’d refund. “You’re talking about $5,000 to $7,000, and you’re talking about writers who are living paycheck to paycheck,” she told me. “I ended up talking myself off that cliff.”

(Alternately, of course, we agreed you could also just be a dick and like, not pay people back. As a Substack spokesperson told me, “Readers are considered the writer’s customers, not ours, so the writer gets to decide how they want to handle a breakup.”)

In my view—both meta and biased as it will be for a former Substack poster child who never actually dabbled in matters of paid subscription herself—the cleanest newsletter exit by far is the one executed by Nick Quah, who sold his podcast trade newsletter “Hot Pod” to The Verge this summer and joined the Vox Mediaverse himself as Vulture’s podcast critic. (Disclosure: Warzel, Quah, and I were part of the Sidechannel newsletter Discord together.) Quah got the best of both worlds: the big full-time media job and the ability to see his newsletter brand live on—without any of the messy business of having to issue prorated refunds, as Warzel did, because The Verge simply took the “Hot Pod” subscription over (they did not have an existing paid product to merge it with).

When I called Quah up to ask how, exactly, he figured out how to get off the newsletter ride, Quah laughed and told me, “it’s harder to stay on.” Early this year, he’d been writing “Hot Pod” for almost seven years and felt incredibly burned out. Writing directly for subscribers—“Hot Pod” was priced at $7 a month, a figure Quah based purely off of Ben Thompson’s then $10-per-month rate at “Stratechery” (now $12)—began feeling like a “psychological trap” that only worsened with the expectations of some overly-entitled subscribers and the dark email magic of being able to look up who, exactly, was actually reading and paying.

“I try to be a professional person and not have ill feelings about people who’ve disabled the auto renews,” he added—this is where I started to sweat, thinking of all the ones I’ve chosen not to renew in the past year. “But I remember every single one.”

The height of Substack mania made Quah fantasize about quitting before his next birthday. “My thinking was, Fuck all of this if you think this shit is easy,” Quah said. “Like, wouldn’t it be funny if I just lit ‘Hot Pod’ on fire and walked away?” He’d already talked to his accountant and a lawyer, made a spreadsheet to keep track of who he’d have to refund, and made sure his business bank account could clear those debts. Then The Verge came calling. But, Quah notes, “I had the matches in my hand. I was going to burn it into the ground.” (When reached for a comment, The Verge editor in chief Nilay Patel said, “We had the perfect reporter in Ashley Carman to take it over, and we're happy Nick trusted us with it instead of burning it down.”)

Barring that kind of deus ex Vox Media twist, though, most subscription newsletter exits will likely follow a far less elegant trajectory involving a good deal of manual refunding—or at least, good faith offers to do so. Substack automatically cancels monthly subscriptions when you end a newsletter but paying readers back for buying an annual package is up to you . And while most of the newsletter writers I’ve talked to, like Quah, emphasize the fact that the majority of readers are happy to support independent writers and aren’t obsessively nickeling-and-diming their subscription value, there is an underlying awareness of the contract inherent to a paid subscription.

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. Obviously, it isn’t the newsletter format, or even the general Substackification at fault here: I maintain that mainstreamed mechanisms for directly supporting work on the internet is still a net good. Still, it’s clear that basic ideas about digital publishing, both old and new (the default weekly-ness of newsletter publishing, the industry standard $5-per-month subscription floor) deserve to be questioned alongside more general modern premises like “productivity” and the “work day.” Because of course this isn’t just an issue of how hard it is to be, essentially, a one-person publication that has to continuously produce.

When I asked Quah if full-time employment had reduced the sense of burnout, he allowed that it did feel more liberating to be on a team, though it brought its own kind of pressure. “Now it’s like, Am I a good enough writer? Am I matching up to my peers and colleagues? That’s a different kind of anxiety.” And then, of course, there are other brands of angst. “We’re employees now,” Quah reminds me. “If they need to cut the rope and let you fall because they need to save themselves, they’ll do it.” The ride, it seems, never really stops.

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