The Sound of My Inbox

The financial promise of email newsletters has launched countless micropublications — and created a new literary genre.

Photo-Illustration: Party of One
Photo-Illustration: Party of One
Photo-Illustration: Party of One

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Christine Smallwood’s recent novel The Life of the Mind — a bleak, funny tour of academia’s outer fringe — offers a lament for the state of email. Dorothy, the book’s grad-student heroine, “used to love email, used to have long, meaningful, occasionally thrilling email correspondences that involved the testing of ideas and the exchange of videos and music links.” Emails had been the way Dorothy and her friends “crafted personas, narrated events, made sense of their lives,” Smallwood writes. “That way of life, alas, had ended.” Now the emails they exchange are perfunctory, businesslike, “and if you wanted to know what someone was doing, you could usually find out on social media.” Still, the craving for digital connection persists. “Dorothy had not stopped checking, expecting, or wishing that a good message might be out there, waiting in the ether just for her.”

Would it be a consolation to Dorothy to know that long emails aren’t quite dead? I now get emails that are longer than ever, in fact. They strain against the confines of Gmail, these emails; they demand to be opened in new tabs. The videos and links are still there, and often ideas, too. In no sense, however, are these emails “just for me.” These are emails composed for an audience not of one friend but of many fans. These emails are newsletters.

Personas are still crafted, events exhaustively narrated, just now at industrial scale. The newsletters of today can be professional editorial operations, like Politico’s Playbook (which casts its readers as fellow Beltway insiders) or The Skimm (which casts them as brunch-drunk sorority sisters). They can also be scrappier, more idiosyncratic missives akin to personal blogs. Newsletters can be like newspaper columns, cut loose from institutional authority. They can be like podcasts that you cannot absorb while running errands, like zines without the photocopy static, like Instagram with the lifestyle recommendations rendered as text instead of subtext. Many newsletters partake in the limitlessly available navel-gazing of online media commentary. Newsletter writers describe the process of writing a newsletter; creators who monetize their personalities through their newsletters report on the ways that other creators are monetizing theirs.

Newsletters vary in subject as widely as, for example, books do, and their authors may be cryptocurrency investors or indie musicians. What they share is the direct personal appeal of special delivery. They require the self-confidence involved in making this appeal to dozens, if not hundreds or thousands, of strangers. A newsletter reshapes a writer’s relationship to their readers. The first-person informality that has been present since the earliest days of web writing achieves its business apotheosis in the newsletter: from personal essay to personal brand. “Subscribe directly to writers you trust,” urges Substack. In a newsletter, the reader is welcomed as a supporter, an ally — or perhaps even a friend. Addressing an audience of fellow Substack writers last year, Delia Cai (who started the media newsletter Deez Links) explained that “growing your subscriber base is like making friends.” The comparison may sound “cheesy,” she admitted, “but I do think that it speaks to this very personal nature of newsletters. You’re sliding into their inbox every morning or every week, and your subscribers can just hit RESPOND and tell you what they think. It’s worth investing in those relationships because once you become friends with these people, they’re there for you forever.”

The contemporary email newsletter is not a novel form; often it amounts to a new delivery system for the same sorts of content — essays, explainers, Q&As, news roundups, advice, and lists — that have long been staples of online media. (Subscribe to enough newsletters and sort them the right way, and it’s possible to re-create something like an RSS-feed reader.) Indeed, ready access to what one already knows and likes tends to be a selling point. But spurred in part by services like Mailchimp and TinyLetter, which made it easy to send mass emails, newsletters gained traction as a business tool for both media organizations and independent writers — a way for publications to reach readers more insistently and a way for writers to circumvent existing publications altogether. Substack, crucially, made it easy to charge subscribers, then attracted further scrutiny by offering a handful of established writers six-figure advances. In late June, Facebook entered the fray with a newsletter service called Bulletin. Consumers of digital media now find themselves in a newsletter deluge.

Early on, circa 2015, there was a while when every first-person writer who might once have written a Tumblr began writing a TinyLetter. At the time, the writer Lyz Lenz observed that newsletters seemed to create a new kind of safe space. A newsletter’s self-selecting audience was part of its appeal, especially for women writers who had experienced harassment elsewhere online. Whatever its perils, “online life is unavoidable, and it can also be a valuable source of support for women who might otherwise be isolated,” Lenz wrote for the Cut. “So where can they seek community? For some, the answer is your inbox.” (I should note, as a former editor at the Cut and a writer, I’ve crossed paths with many of the newsletter writers mentioned here. Start talking with anyone who works in media about newsletters and things get tangly fast.)

This era now feels somewhat distant. The stereotype that Substack often conjures today is of the writer who scorns a safe space — indeed, the perception that the platform had become a home for anti-trans views inspired a fresh round of Substack debate this spring. But what newsletters offer readers is still the sense of access to a social sphere limited by design — a project that can take many forms. The newsletter may be marked by intimacy, or it may hold out the promise of exclusive intelligence on such matters as places to go and things to buy. Its author may be a guru who is also a friend or a dissident purveyor of samizdat. Its audience may be a community of people who imagine themselves holed up in the same bunker or who all get the same inside jokes.

Hunter Harris (a former New York staffer and current contributor) was recruited by Substack, where she now writes a newsletter called Hung Up about pop culture. It is an open-ended category, and in February she devoted one installment to the clothing brand Reformation’s marketing emails. The subject lines on these emails, Harris wrote, “read like one-off missives from that girl you met in line for the bathroom at that concert that one time.” They raise the question “What if, after you and that girl exchanged numbers and swore to get drinks sometime, she just kept texting you?” The results are things like “DO YOU EVEN GO OUT” and “DOING NOTHING IN A HOT TUB,” among other surreal and aggressive overtures. “I have so many ideas about this character,” Harris wrote of the imaginary woman in whose voice the brand speaks. (Still, “as a rule, I hate brand emails, mostly because I hate emails.”) In her own subject lines (“Happy Bennifer to All Who Celebrate”), Harris brings the confident charm of a natural performer to the stage of strangers’ inboxes; she sounds chatty but not unhinged. The most skilled newsletter writers seem conscious of the delicate balance they must strike. “Your friend” is the desired voice of many newsletters — one long-running weekly link roundup is called Links I Would GChat You If We Were Friends — just as it is the desired voice of many brands.

People want an email because they want company, and, like listening to a podcast, subscribing to a newsletter can provide the parasocial pleasure of having a slightly famous imaginary friend. In the reader testimonials Ann Friedman includes with her newsletter, one longtime subscriber attested to “five years of Friday evenings spent reading her links with a glass of wine.” Another wrote that the newsletter “makes me wish we lived in the same town so we could hang out!”

Signing up for a newsletter means subscribing to a person, and it can also mean joining a club. Often the ability to participate in comment threads and discussions is a bonus for readers who pay. Earlier this year, a group of writers with popular tech and culture newsletters expanded upon this premise; they joined together to launch a Discord server called Sidechannel where all their subscribers could meet and chat. (“So it’s just people paying for internet friends?” asked one woman I know when this arrangement was described to her. Yes, and currently Sidechannel has some 5,000 members, several hundred of whom may be active at a given time.)

In its combination of work and social grace, writing a newsletter can be a bit like hosting a party. This is the approach taken by Rachel Seville Tashjian, a writer at GQ, in her energetic, eccentric, and totally delightful fashion newsletter, Opulent Tips. Fielding a volley of questions from fans identified as “Reader and Friend to Me,” or RAFTM (as in “RAFTM Nicole Eisenman is searching for a TERRY CLOTH ROBE”), she cultivates the sense that her Sunday missives are a weekly gathering of familiar names one need only email her to join. (Opulent Tips bills itself as “the internet’s first invitation-only Natural Style-Email newsletter,” which seems to mean it comes from Tashjian’s personal account.) Even if you don’t share Tashjian’s taste for, say, straw boaters, her flair for hospitality makes her good company.

The writers of newsletters inevitably offer up a character, whether it be Tashjian’s Latter-Day Diana Vreeland, Cheryl Strayed’s Twinkle-Eyed Sage (“Keep on walking, dear hearts. There’s light ahead”), or the countless writers who have taken up the mantle of Concerned Citizen Willing to Say What No One Else Will. Perhaps most often, the character presents as an uncensored version of the writer herself — though few are willing to commit to this intimacy quite as fully as Samantha Irby, who, this spring, published in her newsletter a harrowing account of contracting E. coli (subject line: “i ate shit”; subhead: “don’t open this if u are squeamish or u will die”). Blackbird Spyplane, a men’s-style newsletter by journalist Jonah Weiner and design scout Erin Wylie, represents another extreme: newsletter as alternate identity. “Rogen built his comedic persona around the prerogatives of adolescence in real time,” wrote Weiner in a profile of Seth Rogen for The New York Times Magazine. “I couldn’t help but notice that Seth’s taste in jawns & design is … quietly Mach 3+??” he followed up in Blackbird Spyplane. “Not every NYT reader has eagle-eyed jawn-perceptual faculties, but those who do noticed that Seth was rocking an understatedly popping fit in the opening paragraphs.” The baroque goofiness of Blackbird Spyplane’s house style can be something of a test for readers of the newsletter (the “sletter,” in Blackbird Spyplane parlance). “X out of ten people are going to show up and read that and just be like, This is impenetrable, I’m out,” Weiner told one interviewer. “But for the people who stick around, I think that it adds to a sense of, Oh, this is like an in-joke that I’m in on.” And better (at least to this reader) that clubbiness take a niche form — it is less claustrophobia-inducing than the many newsletters that seem to insist we are all wearily following the same disputes on Twitter, all inevitably watching the same shows on Netflix. Such newsletters wind up feeling like crowded rooms with too few windows on the world beyond.

Subscribe to a person and it’s up to that person to decide what you’re going to get. Some writers treat their newsletters as outlets for particular projects. The novelist Brandon Taylor uses his for literary and art criticism, and the novelist Jami Attenberg uses hers to run an annual two-week-long writing challenge (as well as give craft advice year round). Tressie McMillan Cottom — the sociologist, author, and MacArthur genius — maintains a newsletter alongside her academic writing, popular writing, podcasting, and tweeting; in an interview with Ezra Klein, she described the ongoing challenge of deciding what form a given idea should take. “I sit down and I go, Okay, what is the right speed for this? What’s the right genre? When will I know that this argument is done?” McMillan Cottom explained. “I like a complete argument. I like to walk away from something and say I left it all on the court. And sometimes that’s 240 characters, sometimes it’s 20,000 words.” She treats the newsletter as a complement to her work elsewhere — a place for discussions with people who aren’t her students, for personal meditations, for essays untethered from the news. Earlier this year, McMillan Cottom chatted with readers about the podcast Dolly Parton’s America; the podcast came out in 2019, but Parton was a perfect case study for her interests in class, race, status, and beauty, so why not? The newsletter isn’t the centerpiece of McMillan Cottom’s output, which would seem to diminish the pressures of timeliness and volume, as well as the incentive to weigh in at length on every microcontroversy.

In other cases, though, newsletter subscribers who also follow a writer’s Twitter may find themselves receiving newsletter-length expansions of ideas that began their lives as tweets and might comfortably have remained as such. For writers who have made a newsletter central to their livelihood, the very structure of the transaction — the self offered up as another content service — probably argues against restraint. Besides, with a subscription model, the quality of any piece of writing may matter less than the sense of the writer as a cause to be supported. This is part of the appeal of paying to subscribe in the first place: the chance to consume conscientiously and, in so doing, to become part of a like-minded community. Writers often strike a pledge-drive note (Bari Weiss: “We are working hard to tell the stories others are ignoring”), and for readers, a $5 monthly payment joins GoFundMe donations and gift certificates to local businesses in the category of virtuous spending. Glenn Greenwald, who left the Intercept for Substack late last year, has voiced the idea that newsletter subscriptions are “more a cause than transaction.”

Understanding one’s self as a cause to be championed risks a certain unappetizing self-regard. One newsletter from Greenwald promoting his new book began with an account of a bygone evening with Carl Bernstein: Bernstein, he wrote, had congratulated Greenwald on his NSA reporting and noted wistfully that such a journalistic triumph was likely to be “a once-in-a-lifetime experience.” But, Greenwald now proclaimed, his subsequent career had “proved [Bernstein’s] prediction quite wrong.” He underscored the point, some 26 paragraphs later, with a 14-second video clip of himself standing before a crowd of Brazilians as they cheered. Helen Lewis, writing in The Atlantic, compared the outsize personalities of Substack to characters in a soap opera, their convoluted feuds tracked eagerly by fans. (“Glenn Greenwald may have quit the Intercept, but he can’t quit the feud,” read the headline of a May Washington Post story detailing Greenwald’s public acrimony for his former colleagues. Greenwald took issue with the Post story in a subsequent newsletter.) Professional sports — which give fans the feeling of participation through their allegiance — may be another analogy.

Yet for all the ways newsletters encourage a sense of belonging, there can be a loneliness to their prose — a palpable lack of anyone else behind the scenes saying, Hmmm, maybe not. While Substack has made efforts to provide editing services, and some writers do take advantage of them, the fundamental fact of the form remains. Generally speaking, one person is the brand, the main attraction; one person worries their preoccupations ad infinitum. And when, for example, a writer spends two paragraphs referring to “Burkini Faso” instead of Burkina Faso, he does not inspire confidence. “Which topics need more coverage?” Matt Taibbi asked his subscribers in April. Since they were “now functionally my editor,” he was seeking their advice on potential reporting projects. One suggestion — that he write about Ibram X. Kendi and Robin DiAngelo — swiftly gave way to a long debate among readers over whether race was biological.

Ideally, a writer and editor’s work together is an actual collaboration. An editor may be protective at times and productively adversarial at others, but either way, the relationship works best when it’s founded on mutual trust and shared power. An editor is, among other things, a surrogate for the reader. How can writers bridge the gap between what they want to say and what someone else understands? Eleven months later, a line from Anne Helen Petersen’s announcement of her Substack newsletter haunts me still: Writing a newsletter, Petersen wrote, meant she could publish “pieces that take ten paragraphs to get to the nut graf, if there’s one at all.” This came in the context of weighing what she stood to gain and lose in leaving a staff job at BuzzFeed. She knew the worth of what editors, fact-checkers, designers, and other colleagues brought to a piece of writing. At the same time, she was tired of working around the “imperatives of social media sharing.” Clarity and concision are not metrics imposed by the Facebook algorithm, of course — but perhaps such concerns lose some of their urgency when readers have already pledged their support.

The newsletter is the ultimate form for a moment in which writers feel pressure to produce a steady stream of advertisements for themselves. “The dominant literary style in America is careerism,” the critic Christian Lorentzen wrote this spring. (“This is neither a judgment nor a slur,” he added, not quite credibly.) Lorentzen was referring to “novelists, story writers, even poets,” who in recent decades have been expected to devote themselves as much to courting an audience as to writing their books. I would hazard that among essayists, memoirists, and reporters, the situation is, if anything, more extreme. The distance between a tweet thread and an op-ed is narrower than that between an Instagram post and a novel, which makes it easier for writer and reader alike to lose track of where the promotion of the work ends and the work itself begins. In a newsletter, the two are virtually indistinguishable. “Substack is longform media Twitter, for good and for ill,” wrote Ashley Feinberg in the first installment of her Substack. To complain that newsletters are self-promotional would be absurd; selves and promotion are the point. Their creators acknowledge this reality from time to time, whether with fretful disclaimers (“Hey, folks, a few quick housekeeping notes …”) or a wink. The writer Kyle Chayka calls his Substack newsletter Kyle Chayka Industries.

The newsletters I open with the greatest interest appear only occasionally, approximately whenever the writer feels like it. Meaghan Garvey’s Substack, SCARY COOL SAD GOODBYE, arrives maybe once a month, maybe three times, and whenever it does, it surfaces such unforeseen rich subjects as Overdrive, a magazine for American truckers. This is hardly a formula for anything that will save the media business from its woes. But it does stave off the sense that what I’m reading is marketing copy — prose generated to sustain a relationship that amounts to brand loyalty.

When I set out to write about newsletters, I was hopeful. I like having a lot to read and having the reading count as work. Twitter — that conveyor belt of distractions — didn’t count as work, but, flush with subscriptions, my email inbox now did. For novelty and volume, it felt nearly on par with social media: a bottomless hole of scroll. Put something new on my eyes, I’d think, opening up the old inbox to see what I saw. What morsels of entertainment would await? My brain would relax into a state of receptive passivity: Everything was coming to me. I absorbed link roundups, news roundups, and personal essays. I’d treat myself to a little newsletter dive at lunch and linger reading after I ate. Interviews and news analysis washed over me. Sometimes the news analysis was cultural analysis, and sometimes it was about influencers, and sometimes it was about cancel culture. Often the analysis concerned someone else’s mood about the news. No week in 2020, or 2021, or maybe human history, was without both its highs and its lows. The writers of weekly newsletters were continually obliged to grapple with this. The newsletters discussed articles I’d read and articles I hadn’t, tweets I’d seen and tweets I hadn’t, other newsletters. The newsletters urged me to contact their authors for a free subscription if I was a student, precariously employed, or otherwise in need. That was nice, I supposed.

What motivated my newsletter reading habits normally? In large part, affection and light voyeurism. I subscribed to the newsletters of people I knew, who treated the form the way they had once treated personal blogs. I skimmed the dadlike suggestions of Sam Sifton in the New York Times’ Cooking newsletter (skillet chicken and Lana Del Rey’s “Chemtrails Over the Country Club” — sure, okay). I subscribed briefly to Alison Roman’s recipe newsletter before deciding that the ratio of Alison Roman to recipes was much too high. On a colleague’s recommendation, I subscribed to Emily Atkin’s climate newsletter and soon felt guilty because it was so long and came so often that I let it pile up unread.

But in order to write about newsletters, I binged. I went about subscribing in a way no sentient reader was likely to do — omnivorously, promiscuously, heedless of redundancy, completely open to hate-reading. I had not expected to like everything I received. Still, as the flood continued, I experienced a response I did not expect. I was bored.

I did not care to open Heather Cox Richardson’s summary of national politics. (Her top-ranked Substack Letters From an American is like a daily visit from a mild-mannered history professor.) I did not wish to see the words critical race theory used in any context whatsoever, nor to hear about anyone’s latest appearance on a podcast. I did not want advice. I did not want to see a list of things anybody had bought, considered buying, or proposed I might buy. I did not want to peruse a list of links to articles someone had read in the past week — at least half the time, they were the same ones I had read, or else had elected not to read, when everyone on Twitter was recommending them.

I had, I realized, transformed my inbox into the rest of the internet. The great hope of newsletter writers seems to be some escape from the internet as it exists now — escape into nostalgia for a bygone era of blogs or into a past when liberalism reigned. Escape to the refuge of a safe space or escape from the cancel-culture mob. Escape from an online landscape shaped by the imperatives of big tech. Escape was what I wanted too — I saw this now. I want to read a newsletter that feels like a dispatch from another planet, and I haven’t found it yet.

The Sound of My Inbox