Is Substack the Media Future We Want?


Haley Nahman was having a weird time. She had spent most of the pandemic inside, shuttling around the one-bedroom apartment she shares with her partner, Avi. “Not to paint too bleak a picture, but I’ve started sitting down in the shower,” she wrote, in September, in an e-mail. “I’ve noticed that when you hug your knees to your chest and watch the water pitter-patter against your toes, drips sliding down your nose and into your mouth, it feels almost like getting caught in a warm rainstorm.” She recommended reading Ross Gay’s poem “A Small Needful Fact,” a Jacobin essay about socialism, and a profile of Miranda July in New York magazine. In October, she reflected on the long-term consequences of “collective, inexhaustible despair”; in November, she clarified that, despite sounding depressed, she was doing fine, before segueing into a two-thousand-word meditation on anxiety, which she illustrated with a photograph of her cat, Bug, a sleepy Persian. Three weeks later, she took a small dose of psychedelic mushrooms and walked around a lake. “I then proceeded to make the most colorful stoner drawing of my life, which I’m convinced healed something inside of me,” she reported, attaching a photo of herself bundled up in winter clothes, looking peaceful.

Nahman, who is thirty-one and lives in Brooklyn, sends out missives like these every Sunday, to some thirty thousand subscribers. They are the core offering of “Maybe Baby,” a weekly e-mail newsletter, of which she is the sole writer and editor. (The name, she has written, was inspired by her appreciation of uncertainty.) Just before the pandemic arrived in New York City, Nahman left her job as the features director of Man Repeller, a women’s media site, with a long-held plan to go freelance; in late March, she announced the launch of “Maybe Baby” on Instagram, where she has ninety thousand followers. “It will be a place for me to write more freely than I’ve been able, explore ideas (and feelings) I think deserve more attention, and generally connect with you all via the amazing technology of e-mail™️,” Nahman wrote, beneath a photograph of herself sitting on her bed in a red sweater, the word “Announcement” superimposed over her head, like a crown.

Nahman publishes “Maybe Baby” on Substack, a service that enables writers to draft, edit, and send e-mail newsletters to subscribers. Writers can choose whether subscriptions are free or paid; the minimum charge for paid subscriptions is five dollars a month or thirty dollars a year, and Substack takes ten per cent of all revenue. Nahman’s Sunday newsletter is free, but a paid subscription to “Maybe Baby,” which costs the minimum fee, includes access to a weekly podcast and a monthly advice column. Nahman’s writing is warm, candid, thoughtful, and gently political; she cites theorists such as Karl Marx, Jean Baudrillard, and Marshall McLuhan, offering an accessible leftist lens on everything from celebrity culture to the changing seasons. On her newsletter’s About page, Nahman explains that her goal is to make subscribers feel like they’ve just had “a long talk with a friend”—“slightly less anxious or confused about the alien hellscape that is the modern world.”

For a couple of months in 2020, “Maybe Baby” was among Substack’s top twenty-five paid publications, which the company ranked on a public leaderboard, like in a spin class. (In December, Substack introduced multiple leaderboards, split into categories such as Culture, Health, Faith, and Food & Drink.) To date, there are thousands of newsletters on Substack, and more than two hundred and fifty thousand paid subscribers. Lately, the most popular publications have included “Petition,” which offers “curated distressed investing, restructuring, and bankruptcy news/analysis” (forty-nine dollars per month); “The Corners by Nadia Bolz-Weber,” a collection of unconventional prayers, meditations, and spiritual inquiries (five dollars per month); and “ParentData,” by Emily Oster, a roughly biweekly parenting dispatch that takes a scientific, data-driven approach to topics like prenatal alcohol exposure, breast-milk freezing, and microplastics (free). “Letters from an American,” a newsletter that draws parallels between the current political situation and historical events, written by Heather Cox Richardson, a professor of history at Boston College, consistently tops the Politics leaderboard (five dollars per month); in Business, the No. 1 newsletter is “The Bitcoin Forecast by Willy Woo”—Woo is an independent cryptocurrency researcher—which promises “a solid forecast of Bitcoin’s next price move using blockchain data” (fifty dollars per month).

People working in and around Silicon Valley tend to be early adopters of new consumer products, and so there is a glut of newsletters written by venture capitalists and entrepreneurs, about venture capital and entrepreneurship. There are also newsletters dedicated to sexism in sports, witchcraft, design, cricket, bread baking, Bob Dylan concerts throughout history, “The Hudsucker Proxy,” and human-animal relationships. “David” is a bracing series on family, literature, and sexuality, ostensibly structured around historic Davids: Bowie, Foster Wallace, Hyde Pierce, Lynch, Wojnarowicz (five dollars per month). “Beauty IRL” contains essays and reporting on beauty, politics, and pop culture (seven dollars per month); “I Know a Spot” offers pithy commentary on unusual and dreamy properties listed on Zillow (free); “Foreign Bodies” focusses on immigrant and refugee communities, and the destigmatization of mental illness (five dollars per month); “Unsnackable” wanders between reviews of idiosyncratic snacks and diaristic reflections (free); “Deep Voices” is a regular, hour-long playlist accompanied by digital liner notes (free); and “Books on Cities” reviews books on cities (five dollars per month).

In its variety, the Substack corpus resembles the blogosphere. It is produced by a mix of career journalists, bloggers, specialists, novelists, hobbyists, dabblers, and white-collar professionals looking to plump up their personal brands. The company has tried to recruit high-profile writers, offering (to a select few) health-care stipends, design help, and money to hire freelance editors. In certain instances, Substack has also paid advances, often in the generous six figures, incentivizing writers to produce work without employing them. Substack writers can apply for access to a legal-defense fund, which covers up to a million dollars in legal fees on a case-by-case basis. Casey Newton, a tech journalist who has written about Silicon Valley for a decade, left the Verge in September to launch the Substack newsletter “Platformer,” a solo venture, where he analyzes news about social networks and democracy (ten dollars per month). Newton, who is a friend of mine, declined an advance but took a health-care stipend; he joked to me that his life has now been twice disrupted by the Internet—first when he was a newspaper journalist, “and the Web came along and devoured print,” and then a decade later, when “social networks came along and devoured the Web.” Substack has also recruited the former BuzzFeed culture writer Anne Helen Petersen and the Vox co-founder Matthew Yglesias, who left his staff job to write a newsletter; both were given substantial advances. Other well-known writers have started Substack newsletters without brokering deals with the company, including the rock critic Robert Christgau, whose “And It Don’t Stop” is a trove of winding essays on music, television, and science fiction (five dollars per month). After going on leave from the Times this spring, the food writer Alison Roman started “A Newsletter,” which contains recipes and breezy, bossy, self-deprecating anecdotes (five dollars per month).

When Substack launched, in 2017, the founders posted a mission statement of sorts to “Substack Blog” (free). After beginning with an anecdote about how, in 1883, the New York Sun incorporated advertisements, the post went on to detail the current state of journalism:

The great journalistic totems of the last century are dying. News organizations—and other entities that masquerade as them—are turning to increasingly desperate measures for survival. And so we have content farms, clickbait, listicles, inane but viral debates over optical illusions, and a “fake news” epidemic. Just as damaging is that, in the eyes of consumers, journalistic content has lost much of its perceived value—especially as measured in dollars.It’s easy to feel discouraged by these dire developments, but in every crisis there is opportunity. We believe that journalistic content has intrinsic value and that it doesn’t have to be given away for free. We believe that what you read matters. And we believe that there has never been a better time to bolster and protect those ideals.

The subscription-based news industry, the founders speculated, could someday “be much larger than the newspaper business ever was, much like the ride-hailing industry in San Francisco is bigger than the taxi industry was before Lyft and Uber.” These days, Substack’s founders, investors, and marketing materials all have different ways of describing the startup’s mission. Depending on which source you consult, Substack might be “reinventing publishing,” “pioneering a new ‘business model for culture,’ ” or “attempting to build an alternative media economy that gives journalists autonomy.” It is “writers firing their old business model” or “a better future for news.” Substack’s C.E.O., Chris Best, has said that the company’s intention is “to make it so that you could type into this box, and if the things you type are good, you’re going to get rich.” Hamish McKenzie, one of Substack’s co-founders, told me that he sees the company as an alternative to social-media platforms like Facebook and Twitter. “We started Substack because we were fed up about the effects of the social-media diet,” McKenzie said. Substack’s home page now reads, “Take back your mind.”

“I have to go—it’s time to feed the cat.”Cartoon by Kaamran Hafeez


Substack, like Facebook, insists that it is not a media company; it is, instead, “a platform that enables writers and readers.” But other newsletter platforms, such as Revue, Lede, or TinyLetter (a service owned by Mailchimp, the e-mail-marketing company), have never offered incentives to attract writers. By piloting programs, like the legal-defense fund, that “re-create some of the value provided by newsrooms,” as McKenzie put it, Substack has made itself difficult to categorize: it’s a software company with the trappings of a digital-media concern. The company, which currently has twenty employees, has a lightweight content-moderation policy, which prohibits harassment, threats, spam, pornography, and calls for violence; moderation decisions are made by the founders, and, McKenzie told me, the company does not comment on them. Best has suggested that Substack contains a built-in moderation mechanism in the form of the Unsubscribe button.

It’s an interesting time for such a hands-off, free-market approach. The Internet is flooded with disinformation and conspiracy theories. Amazon’s self-publishing arm has become a haven for extremist content. The flattening effect of digital platforms has led to confusion among readers about what is reporting and what is opinion. Newsrooms at the Times and the Wall Street Journal have taken pains to distinguish their work from that found in the op-ed sections. Substack has advertised itself as a friendly home for journalism, but few of its newsletters publish original reporting; the majority offer personal writing, opinion pieces, research, and analysis.

A Substack newsletter is both a product and a portfolio: a way to make money, but also a venue for displaying personality, intelligence, and taste. Read enough of them and certain patterns begin to emerge. Newsletters in the business and tech categories tend to adopt para-LinkedIn tics. They are often studded with Twitter screenshots and lists of links. Single-sentence paragraphs appear frequently, as do uplifting rhetorical devices. (“Imagine a world where you had a personal board of advisors—the people you most admire and respect—and you gave them upside in your future earnings in exchange for helping you. . . . Imagine if you could diversify by pooling 1% of your future income with your ten smartest friends.”) Just as there is “podcast voice”—that inquisitive, staccato bedtime-story cadence—there is Substack tone, a semi-professional quality suited to mass e-mail. Some newsletters convey intimacy, in the language of psychotherapy and self-help, but their style is more polished and structured than that of the looser, rangier blogs of the early two-thousands. “Maybe Baby,” for all its vulnerability, is also aware of itself as a commodity, dialled in to its audience. Still, it’s nice, from time to time, to receive a chatty, engaging, personable e-mail from someone who doesn’t expect a response.

Newsletters have existed since time immemorial. As Silicon Valley came into being, newsletters were among the earliest trade publications. In 1983, Esther Dyson, a former business reporter and Wall Street securities analyst in her thirties, purchased a nine-year-old newsletter about semiconductors and personal computing, the “Rosen Electronics Letter,” from her boss, Ben Rosen, who was selling it to focus on his work at a venture-capital firm. Dyson, who wrote for the newsletter and had a reputation as a confident, quotable technology expert, renamed the publication “Release 1.0.” The design was unadorned, formatted in a single column, and printed on white paper; an early issue, published that November, offered twenty-nine pages of her research and opinions on hot topics of the day, from end-user training to newly public tech companies. “Normally we don’t like to be nasty: we’d rather simply be silent,” she wrote, in a section on vaporware. “But the current rash of purported revolutions, breakthroughs and new generations requires some comment.” The subscriber base included two thousand people, most of whom paid three hundred and ninety-five dollars a year to receive the newsletter monthly, through the mail. This readership was modest by mass-media standards, but it included an enviable A-list of Silicon Valley entrepreneurs and executives, bolstering Dyson’s nascent image as one of the most powerful women in computing.

In 1985, Aldus, a small startup in Seattle, began working on a software program called PageMaker, to design and organize newspaper layouts. (Paul Brainerd, an Aldus co-founder, who coined the term “desktop publishing,” had previously worked as a journalist.) The company caught the attention of Steve Jobs, who encouraged the founders to adapt the software for a broader business environment. That year, Apple released its first mass-market laser printer, the LaserWriter—a seven-thousand-dollar beige machine that produced professional-grade text and images—and promoted it alongside PageMaker, an early desktop-publishing program for Macintosh. A corporate office or a carpeted den could now become a bespoke printshop. PageMaker’s layout elements mimicked those of a newspaper. The software, with its suggestive columns, seemed to say: Circulate!

Almost immediately, newsletters—on personal finance, high-end travel, U.F.O.s, carnivorous plants, surfing, bluegrass, numismatics, farming, and, of course, computing—proliferated. Independent publications had long circulated in the finance and technology sectors, offering data and analysis not easily found elsewhere. (Charles Schwab, the financial-services company, began as “Investment Indicator,” a newsletter first published in 1963.) But, for the most part, newsletters had been the province of civic groups, religious congregations, cultural and educational institutions, and corporations—as well as some restaurant enthusiasts, including Tim and Nina Zagat, who began printing “The Zagat Survey,” a collection of crowdsourced restaurant reviews, in 1979. “Desktop Publishing,” a guidebook released in 1986, included a chapter on newsletters’ “golden opportunity,” and emphasized the value of a unique, voice-driven editorial style. A small galaxy of adjacent companies, such as digital-font foundries and clip-art production outfits, emerged to satisfy the desire for customization. “One of the unfortunate side effects of the desktop publishing craze is that we are being flooded with publications that look as if they had been created by a drunken committee under a full moon,” a 1987 Times article read. “The ease of cutting, pasting and assembling a publication in no way guarantees the merit of the end product in either content or visual appeal.”

“Maybe make this one a little less true to life.”Cartoon by Suerynn Lee


In the nineties, as desktop computers and printers became more affordable, some subscription newsletters began serving groups whose needs were unmet by larger media outlets, in a sort of professionalized parallel to zine culture. “Out & About,” a newsletter founded in 1992, rated hotel chains and travel agencies on their “gay-friendliness,” and recommended companies such as Eco-Explorations, a lesbian-owned scuba-and-sea-kayak concern, and Gay’n’Gray Partners in Travel, for men over forty. “Bully Pulpit,” launched in 1998 by the Welfare Reform Network, published rebuttals to misinformation in the media about poverty and government assistance. Newsletters also provided a forum for fringe political views: the medium was popular among violent anti-abortion activists and members of militias. At the height of the nineties culture wars, figures like Rush Limbaugh (“The Limbaugh Letter”) and Paul Weyrich (“The Weyrich Report”) also found an additional revenue stream in newsletters.

The rise of the commercial Internet upended newsletters, along with everything else. Publications offering restaurant listings or information about frequent-flier deals were usurped by message boards, forums, search engines, and free public databases. Communities found blogs, and bloggers found new sources of income in advertisements, sponsors, and affiliate links. Some newsletters went digital, or folded; others morphed into more traditional enterprises. “The Hideaway Report,” a luxury-vacation newsletter launched in 1979, became a boutique travel agency; “Dr. Andrew Weil’s Self Healing Newsletter,” first published in 1995, spawned a small empire. (The newsletter was later purchased, together with Body & Soul Magazine, by Martha Stewart Living Omnimedia, for six million dollars.) “In many ways, I see the example of how I work as representative of the way things are going for creators,” Dyson told the Times in 1996, in an article about PC Forum, a conference held for “Release 1.0” subscribers, which brought in $1.5 million a year. “The money-making part of my business is really an offshoot of the content production. Also, I do other things: consulting, speeches, which come to me because of my writing. In other words, I get paid for my activity rather than my products.”

Dyson was once again prescient: today’s “creators” often split their activity across a range of platforms. They use multiple social-media accounts to craft and maintain their personal brands; to monetize them, they offer exclusive content or privileges. In recent years, companies like Patreon and OnlyFans have made it easier for people to support, via subscriptions and micropayments, writers, artists, podcasters, comedians, fitness instructors, photographers, musicians, singers, sex workers, gamers, dancers, educators, and influencers. Substack allows writers to collect subscription income without leaving the Web site, through an integration with the payment processor Stripe. (Stripe takes about three per cent of every subscription charge, as well as thirty cents per transaction; this comes out of the writer’s revenue share.)

In 2018, Substack raised fifteen million dollars in funding, primarily from the venture-capital firm Andreessen Horowitz, whose portfolio companies also include Lyft, Caviar, and Instacart. Substack operates in what Andreessen Horowitz has taken to calling the “creator economy” or the “passion economy.” In 2019, in a blog post titled “The Passion Economy and the Future of Work,” Li Jin, a partner at the time, discussed the opportunity for “monetizing individuality.” Drawing on the example of the gig-work economy, Jin suggested that everyone could be an independent contractor. She pointed to Outschool—a Web site where teachers and coaches offer instruction on topics like playwriting, mindfulness, and English as a second language—and to Cameo, the surreal online marketplace where celebrities can be hired to record customized video messages. “Gig work isn’t going anywhere—but there are now more ways to capitalize on creativity,” she wrote. “This has huge implications for entrepreneurship and what we’ll think of as a ‘job’ in the future.” When I spoke to Dyson recently, she told me that she was intrigued by applications like OnlyFans, in which she saw a new business model for celebrities and influencers, one that did not depend on advertising: “People who receive attention, kind of for free, then give attention back to people and charge for it—the attention they’ve garnered has become a genuine commodity that they can sell.”

Nahman’s income from “Maybe Baby” well exceeds the full-time salary she made at Man Repeller; Yglesias’s newsletter, “Slow Boring,” has a readership that includes more than six thousand paid subscribers, and he is making twenty-seven thousand dollars a month. (Yglesias opted to receive a two-hundred-and-fifty-thousand-dollar advance from Substack, which, in return, will take eighty-five per cent of the subscription revenue from his first year. In his second year, Substack’s commission will revert to ten per cent.) But Substack’s founders have acknowledged that, for the majority of writers, a newsletter will be a side hustle. In most cases, subscription fees will generate not a salary but something closer to tips. In a recent blog post on Medium, Hunter Walk, a venture capitalist, compared a newsletter to a stock-keeping unit, or SKU, a term of art in inventory management. “The biggest impact of someone like Casey [Newton] unbundling himself” from the Verge, Walk wrote, “is that he is now an entrepreneur with a product called Casey. His beachhead may very well be a paid newsletter . . . but the newsletter is just one SKU. . . . There could be a podcast SKU. A speaking fee SKU. A book deal SKU. A consulting SKU. A guest columnist SKU. And so on.” Lisa Gitelman, a media historian and professor at New York University, said, of Substack, “They obviously want to call it a democratizing gesture, which I find a little bit specious. It’s the democracy of neoliberal self-empowerment. The message to users is that you can empower yourself by creating.”

The “passion economy” thesis assumes that an audience will want everything a creator brings to market, the way viewers of the “Rachael Ray” show will often buy Rachael Ray cookbooks and cookware. But starting a newsletter does not immediately lead to speaking engagements, and not all writers can generate multiple distinct products. Yglesias told me that he considered Twitter to be “an incredible acquisition funnel for customers,” but said that “the interplay between Twitter, which is obviously free, and the newsletter, which is mostly paid, is the trickiest thing to get right in the business.”

Substack has some social features, like comments sections and discussion threads, but the newsletter ecosystem seems to lack the camaraderie that animated blogging communities. Unlike blogs, which link to other blogs almost as an ontological condition, most newsletters are impossible to find without an external referral or recommendation. Non-subscribers can read free newsletters online, but there isn’t much of a discovery mechanism—just the leaderboards. Reggie James, the founder of Eternal, a social network in development, and the author of “Product Lost,” a newsletter that takes an artistic, humanist approach to technology (free), was skeptical of the idea that Substack was an antidote to social media; about half his readers come through social networks. As long as writers were beholden to the logic of social-media algorithms, he said, Substack was still “playing the game of the platforms.”

Readers of magazines, newspapers, and many Web sites, which publish established writers alongside emerging ones, automatically encounter new voices; on Substack, the most successful newsletters are almost always written by people who have already cultivated an audience at traditional publications or built up a following elsewhere. (I learned about “Maybe Baby” via the Instagram Explore algorithm.) Many of these writers, like Yglesias, consolidated their reputations in the previous two decades, as bloggers, before leveraging that work into book deals or columns at traditional outlets; now, having built large followings, they are working as free agents. Substack is a natural fit for the influencer, the pundit, the personality, and the political contrarian. It’s debatable whether this represents “a better future for news.” But it’s great business for Substack.

The durability and sustainability of the digital-newsletter model remain to be seen. Carving out new ways for writers to make money from their work is surely a good thing: the United States lost sixteen thousand newsroom jobs this year, and many mainstream publications have struggled to overcome issues like discrimination, clubbiness, and prohibitively low compensation. But whether Substack is good for writers is one question; another is whether a world in which subscription newsletters rival magazines and newspapers is a world that people want. A robust press is essential to a functioning democracy, and a cultural turn toward journalistic individualism might not be in the collective interest. It is expensive and laborious to hold powerful people and institutions to account, and, at many media organizations, any given article is the result of collaboration between writers, editors, copy editors, fact checkers, and producers. McKenzie, the Substack co-founder, assured me that the platform should be considered only “one of the models alongside others,” pointing to the potential for worker-owned coöperatives, nonprofit newsrooms, and state-funded media. (There are also other models for newsletters; one Substack competitor, Ghost, is a nonprofit, and its technology is open-source.) McKenzie went on, “The more ‘generalized newspaper’ world has been diminishing anyway, a trend that started before Substack, and I don’t think there’s any turning back on that. The genie is out of the bottle.”

“Don’t worry, everything is going to be O.K.”Cartoon by Julia Leigh and Phillip Day


In the past year, Substack’s political newsletters have gained traction. The most popular is “The Dispatch,” a conservative publication run by former writers and editors of The Weekly Standard and National Review. (“The Dispatch” costs ten dollars a month, and, like a more traditional media startup, it has also raised six million dollars from investors.) In July, the former New York columnist Andrew Sullivan, expressing a desire for editorial freedom after readers and colleagues criticized his politics as retrograde and noxious, launched “The Weekly Dish” (five dollars per month); the newsletter ranks fifth on the Politics leaderboard. Moving to Substack has become a statement of protest or independence. Dana Loesch, the former N.R.A. spokesperson, recently moved her newsletter from Mailchimp to Substack; she has claimed that the former “deplatforms conservatives.” Her newsletter, “Chapter and Verse” (free), which offers link roundups and brief commentary on other people’s tweets—primarily to reiterate right-wing talking points—quickly rose to the Culture leaderboard’s top five. Substack has, intentionally or not, become a player in the culture wars. Reggie James suggested that the next QAnon could easily find a home there. “When you don’t do editorial but you do power the individual identity—and that individual identity has the engine of a viral mechanism like Twitter—you can get into some really interesting and weird corners,” he said. In November, an anonymous Substack account published a newsletter titled “vote_pattern_analysis,” with a single, elaborate post claiming election fraud. On Twitter, the link was tagged with a fact-check label. For a time in December, the newsletter became one of the top free publications on Substack.

Substack recently launched a feature called Substack Reader, which gathers readers’ newsletter and podcast subscriptions in one place, on the company’s Web site. The product is the digital equivalent of a three-ring binder: a way to manage newsletter overload. Reader also has an option for integrating outside RSS feeds. It seems to have taken its cue from Google Reader, an aggregator that, until it shut down, in 2013, had an ardent user base. It also resembles Tumblr’s dashboard, Twitter’s timeline, and Facebook’s News Feed, and looks less like a reaction against social media than like its evolution. Substack, like these social networks, allows readers to create an information ecosystem populated by individuals of their choosing.

For many readers and writers, the personal, intimate quality of newsletters is their appeal. “You assume certain levels of familiarity,” Yglesias told me, explaining that, vying for attention on the “algorithm-driven Internet,” he’d never quite known for whom he was writing. He was working on a story about train-station design on the Green Line Extension in Boston, and, although he didn’t expect it to go viral, he knew that his readers would appreciate it. “I think people who have been following me for years have developed an ongoing interest in mass-transit construction in the United States,” he said. “They know why I’m writing about this kind of weird thing.”

In November, Nahman sent her paid subscribers a new edition of her advice column, “Dear Baby.” A reader had inquired about Nahman’s life as a freelance writer, and whether it had matched up with her expectations. Nahman wrote that her first day as a freelancer had also been the first day many New Yorkers went into quarantine. Her vision of pitching editors, working in cafés, and meeting with other writers had been replaced by a new reality. The newsletter, she wrote, was never meant to be the thing she spent most of her time on. This surprised me: the newsletter seemed so deliberate. I hit Reply and wrote back.

She responded immediately. “Maybe Baby,” she told me, had initially been an experiment. After the launch announcement on Instagram, ten thousand people signed up. Nahman soon decided to go all in. Writing the newsletter had been a welcome change of pace. After four years of writing and editing multiple posts a day, each with a search-engine-optimized headline, and working hours she described as “insane and untenable,” she was taking pleasure in spending several days on each installment. The newsletter had made her reflect on how she measured success. “For a while, I had a fear that this wasn’t real writing and that I wasn’t going to gain respect by putting out a newsletter,” she said. She had been “unlearning those ideas.” She went on, “I’m working less, and I get to write whatever I want. Isn’t that kind of the dream?” But the business model had novel challenges. One week in October, she was feeling low and like she had “absolutely nothing to say.” She wrote a newsletter in which she described fifteen things she had thought of writing but which she “could not manage to cohere into a single worthwhile idea.” The post had not been her most popular, and she was haunted by it. “If business is down, or people are unsubscribing, it’s definitely a very direct referendum on me,” she said. “Or it feels like it.”

Readers regularly replied to her e-mails, and she had begun setting aside a day each week to respond to them. She had managed to shake her Man Repeller voice—“spunky, making jokes that aren’t really that funny”—and was settling into running her own small media business. In addition to the newsletter, she hoped to try her hand at screenwriting. She had recently signed with a literary agent, and was thinking about her first book, an essay collection about “self-mythology and how that guides decisions.” She imagined it as being similar to “Maybe Baby”—“cultural commentary, maybe a little philosophical,” she said. “But, well, hopefully more professional.” ♦