From The Cut:
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.”are u coming?Late-night dispatches from a city ready to party.
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.)
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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. X OUT OF TEN PEOPLE ARE GOING TO SHOW UP AND READ THAT AND JUST BE LIKE, ‘THIS IS IMPENETRABLE, I’M OUT,’
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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.*
Link to the rest at The Cut