It was 8:15 a.m., and I was crying on the L train. The proximate cause was the most recent issue of Helena Fitzgerald’s Griefbacon, an email newsletter she sends out regularly to subscribers who pay, slightly less regularly to subscribers who don’t. I had broken up with my partner the day before, and stayed out half the night in a very 20-something attempt to keep reality at arm’s length. Now Fitzgerald had the nerve to go long on, of all things, love, right there in my inbox: “Happy was one out of handfuls of possible endings and every single other one was painful, a tree branch through a house and long months of picking up pieces, rewiring the lights and making emergency plans in the wreckage,” she wrote of her own relationship. “Most love is more lessons than happiness, more damage than joy. The thing that lasts, that works, that wakes up one more day and doesn’t break your heart, is the luck just before your car goes off the bridge.”
She had survived the bridge. I had crashed. Still there was something comforting in reading her thoughts about love, the doubts that crept into her own togetherness. Here was a writer I admired finally coming up for air after slamming her heart repeatedly against a wall, just as I was. And here she was telling me about it in what felt like a one-on-one format, a diary entry with her as the pen and me as the page.
As an editor, my newsletter metabolism is somewhat higher than average. My morning diet consists of CNN’s Reliable Sources; Politico’s Playbook; Axios AM; Nuzzel news digest; the New York Times DealBook Briefing; Quartz Daily Brief. At around 4 P.M., the evening versions begin to roll in: Axios PM; Intelligencer’s top stories. And that’s not counting various email alerts from the Washington Post, the Times, and other outlets, should news break. They carry the familiar, obligatory headlines: “New Tech Clampdowns Could Threaten a U.S.-China Trade Deal.” “Trump Puts New Sanctions on Iran.” Like maxing out on your daily serving of vegetables, these emails give me everything I need to stay on top of the day’s events.
Then there’s the delightful crush of personal newsletters that hit my inbox more sporadically—the ones that feel like hearing from a friend. Some, like Alison Griswold’s Oversharing, are industry-oriented. Some are themed: Brette Warshaw’s What’s the Difference? breaks down the distinction between things like “biodegradable” and “compostable.” Delia Cai’s Deez Links is media-industry chatter and good hate-reads. Marian Bull’s Mess Hall is a meditation on cooking and “all the things that fly around it.” Kara Cutruzzula’s Brass Ring Daily is like a life coach in your inbox. There are others whose only unifying principle is the format and author: Fitzgerald’s; Ann Friedman’s Ann Friedman Weekly; Daniel Mallory Ortberg’s The Shatner Chatner; Heather Havrilesky’s Ask Molly; Jamelle Bouie’s The Newsletter™, since absorbed by the New York Times. All are uniquely delightful, and many have the uncanny tendency to arrive when I need them most. “I like to think of my own meaning-making as a kind of arts and crafts project of the soul, for idiots.” Havrilesky wrote in a recent issue. “Whatever I happen to need to believe on any given day, I just tell myself it’s true.”
It’s tough to pinpoint the birth of the personal newsletter. “Peak newsletter has been happening continuously since like 1986,” said Rusty Foster, purveyor of the once beloved, now defunct Today in Tabs, which he told me had somewhere in the ballpark of 12,000 subscribers at its zenith. “It’s sort of always been there...it’s like the one perpetual form of media.” Foster launched Tabs in 2013, which happens to be the year a number of other notable newsletters were conceived. (It’s also around the time that the personal-blogging boom hit a dead end, in part due to the movement’s failure to monetize. Starting a newsletter, Friedman said, was “fully recognized as what you do, because you don’t blog anymore.”) That’s when Ben Thompson launched Stratechery, one of the earliest examples of the genre that happened to be financially viable. It’s when Friedman started sending her weekly dispatch, which pioneered its own system for monetization—a combination of subscriber-only content and classifieds ads—and it’s a year before Charlotte Shane began to write Prostitute Laundry, a TinyLetter that helped redefine what a TinyLetter could be. (Brooklyn Magazine described it as “a novel in serial form.”) But the roots of that wave run deep, too. “I distinctly remember having the attitude of, everyone has a TinyLetter,” Friedman said. “I guess I’ll get on this bandwagon.”
Still, in recent years, there’s been an unquestionable uptick in the volume of email newsletters—particularly the sort that aspire to the literary quality of Fitzgerald’s and Havrilesky’s, or that, like Bouie’s, fold bits of the writer’s personal life between in-line links. The boom has been driven in part by Substack, a platform founded by developers Chris Best and Jairaj Sethi, and journalist Hamish McKenzie in 2017. Substack was created with the ostensible goal of helping writers earn money, making tiered subscription services for personal newsletters easy and accessible. It debuted with MarketWatch cofounder Bill Bishop’s Sinocism, and has since added people like Nicole Cliffe and Ortberg to its ranks. Griswold’s Oversharing is on Substack, as is Fitzgerald’s Griefbacon and Cai’s Deez Links. By July 2018, Substack had just over 11,000 paid subscribers who shelled out on average nearly $80 a year. Now, McKenzie tells me, they’re at “(comfortably) more than 50,000 paying subscribers across the network.”
“What people are making from [Substack] subscriptions, it’s slightly mind-blowing,” said Foster, who was paid a syndication fee by Newsweek and then Fast Company. (When I asked whether he’d consider reviving Tabs, now that a platform like Substack exists, he replied, “Is there a possibility I will find myself someday being like, I don’t have a tech job anymore and still need money; what can I do? Maybe I will. That might happen. So I don’t know. Stay tuned.” For now he writes “really good” work emails. “But the audience is obviously a lot smaller.”)
Best has described Substack as “diametrically opposed to the broader internet news model.” Which is essentially true. Personal newsletters are largely immune to the churn of Twitter and exist in a separate sphere from the content mines of an online publication. They retain some of the intimacy of the early digital-media days, when online writing felt less polished, more vital, the cornerstone of connection for people like me, then a lame-ish teen fumbling her way through junior high in a wealthy suburban Texas bubble. As someone who entered the New York media scene just after that era, I’m forever chasing it down, enthralled—perhaps misguidedly—by what it represented, and what it got away with.
To me, part of that ethos is retained in the newsletter ecosystem. “The magic of newsletters, I think, is how they cut through the noise of social media and establish this consistent, pretty intimate connection,” said Cai, who in 2015 spun her habit of DM’ing links to coworkers into Deez Links, and who now has 1,200 subscribers. “You end up building a relationship with people in a format that isn’t completely obsessive about the scale of your audience or monetization, so it can kind of float under the radar and feel like a big inside joke or a fun club.” As Warshaw put it, “in this age of the attention economy, newsletters let you be intentional about who you give your attention to.”
Foster agreed. “I always compared newsletters to podcasts. Podcasts sound like somebody’s talking directly into your ears. Newsletters are like somebody’s sending you an email...I was just trying to tell what I thought was the truth about what was going on that day,” he added, noting that Tabs was essentially his “first draft,” with minimal editing. “But I think people responded to that.”
Of course any trendlet is bound to have its detractors. “No one needs more shit to read,” wrote Erica Buist in a widely circulated Medium post entitled “The Personal Newsletter Fad Needs to End,” citing Twitter, print magazines, and her nightstand book stack as competing entities. It’s true that my Pocket app, Chrome tabs, bookshelves, and feeds are all crammed with reading material. Yet somehow I never begrudge a new newsletter landing in my inbox. In part that’s due to the emotional connection Cai referenced—the feeling of a one-on-one interaction, even one I know is false. In part it’s because I have an inordinate amount of control over whose newsletters I get, and when. These are people whose work I have explicitly solicited, and who deliver it to me in (mostly) predictable dispatches. If I decide I don’t want it, I can unsubscribe. “If I’m super busy, I’m very quick to just delete,” said Friedman, who sent me an “incomplete list” of 68 newsletters she subscribes to herself. “I don’t feel an obligation to read every single one, nor do I expect my subscribers to read every single one.”
Mostly, though, I do want it. (I actually, physically laughed out loud reading an edition of Ask Molly titled “How to Stay Married Forever,” a risky move in an open office.) And the fact that I want it is good for the writers too. “You have a list of people who want your work,” Friedman explained. Who are willing to pay for it even. That’s valuable to potential employers, but more importantly, it’s valuable to individual writers, who are often forced to string together economic safety nets in order to stay financially afloat. Friedman estimates her newsletter brings in about 20% of her income. Distribution companies do take a cut, but as Friedman puts it, “horrible people in Silicon Valley are not getting rich off of our desire to talk to one another.”
Which isn’t to say the world of personal newsletters is totally divorced from Silicon Valley. Sure, writers like the New York Times’s Mike Isaac have described feeling less dependent on social media thanks to their newsletters, a shift toward private models of sharing that are increasingly appealing to a perpetually overexposed demographic. (“It’s really allowed me to fully emotionally divest from Twitter,” Friedman said.) Still Twitter remains a popular venue for announcing the launch of a new newsletter, or for promoting an existing one. Some writers successfully convert followers into subscribers. Some newsletters deliberately engage with the internet discourse. Many, including mine, derive their offerings from the endless swirl of content that circulates primarily online.
As a result newsletters are vulnerable to the same structural flaws that characterize the rest of the digital world. “Directly singing for your supper to readers is always going to prioritize people who already have an audience, who already have a certain amount of privilege, or who are speaking to an audience that has a certain amount of money,” Friedman said. The same questions arise about who gets paid for what, and why. While writers like Friedman have worked out a sustainable model, others are just beginning to weigh the question. “It would be odd to me to charge for a newsletter that predominantly highlights other people’s work,” Cai said. “But maybe I’m not thinking like a white dude named Josh who’s probably monetizing the shit out of [his newsletter] and taking himself to a monthly omakase as a result.” Warshaw is working on a book proposal around What’s the Difference, and has some licensing deals with publishers in the works. Ultimately newsletters are just like any other type of writing: salable. The illusion that they exist in a rarefied bubble, away from the melee of the rest of the internet, just makes them a better product.
Not that there’s necessarily anything wrong with that—especially if middlemen and advertisers aren’t part of the equation. As Foster put it, “When you find that person you want to tell you what’s going on”—or, say, to short-circuit your emotions during your morning commute, prompting strangers to stare in concern—“it’s worth a little bit of money every month to do that.”
This article has been updated.
