In 2014, an ecommerce entrepreneur named Sophia Amoruso published #Girlboss, a mixture of memoir and career advice for women. While judging a book by its cover is frowned upon, the #Girlboss dust jacket—Millennial pink, aggressively hashtagged, its subject front and center with a little black dress and a triumphant smirk—reveals the whole plot. It’s about a woman who gets rich by selling a fast-fashion vision of what a woman on her way to getting rich should be like. It was a bestseller.
By 2017, Amoruso had expanded her #Girlboss universe to include a digital media company of the same name. “Girlboss is a feeling, a philosophy,” she said at its launch party. Like Sheryl Sandberg’s “Lean In,” the slogan yoked careerism to feminism. Never mind that Amoruso's business ventures weren't wildly successful. (Her online store Nasty Gal filed for bankruptcy in 2016.) While she struggled in the retail world, Amoruso found longer-lasting success publicizing this new archetype. Her potent personal branding? That was scalable. The Girlboss was everywhere in the 2010s. She was hawking luggage (Stephanie Korey, founder of Away) or makeup (Emily Weiss, founder of Glossier) or workout gear (Tyler Haney, founder of Outdoor Voices). She was almost always white, thin, and charming. She was always Instagrammable. She understood what the modern woman wanted, and how to sell it to her. She would break the glass ceiling, and the shards would fly into the eyes of her haters.
If anyone was most likely to out-girlboss them all, it was Audrey Gelman, a gamine public relations whiz who’d already reached a certain tier of New York–centric fame for her friendship with Lena Dunham. In 2016, she founded The Wing, a meticulously chic women’s social club with devoted members and carefully cultivated celebrity endorsements. (Representative Alexandria Ocasio-Cortez’s praise was splashed on its website; fellow niche celebrities like Tavi Gevinson and Hari Nef were members.) Perhaps more than any other woman in the startup world, Gelman excelled at commodifying feminism as a lifestyle. She expertly sold the idea that joining an upscale coworking community was a progressive, empowering political choice. Media coverage of The Wing was largely positive and frequently glowing, and Gelman hustled to win over her detractors.
For several years, it worked beautifully. The 2016 election imbued Gelman’s fledgling company with resistance-tinted patina. “The Wing was conceived amid great expectations for the Hillary Clinton presidency, but it was her defeat that sharpened the company’s sense of mission,” cultural critic and reporter Amanda Hess wrote in a New York Times Magazine story from earlier this year. What had originally been pitched as a resting place for ladies on the go became recast as membership-as-direct-action. “Gelman began to speak about a Wing membership as analogous to political agitation,” Hess continued. The Wing raised over $100 million in funding. It expanded from its original Flatiron location to a handful of equally lavish spots in Manhattan and Brooklyn, then nationally and internationally, opening spaces from Los Angeles to Paris, taking its bougie womb aesthetic global. Gelman was the first visibly pregnant CEO to appear on the cover of a business magazine. Girlboss 2.0 had arrived.
Leigh Stein, a writer who herself cofounded an online community and event series for women during the 2010s, has written a delightfully tart literary satire of the Girlboss with her new book, Self Care. The novel, out this week, arrives at an opportune moment, as the world Stein skewers is going through the same kind of upheaval she creates within her fictional universe, so much so that some of the passages appear nearly clairvoyant.
The novel switches perspectives between three characters—founders Maren Gelb and Devin Avery, and their first hire, Khadijah Walker—who run Richual, an online wellness-focused community for women. They favor some distinctly Nasty Gal-core accessories, like Devin’s “Namaslay” T-shirt or Maren’s “MALE TEARS” mug, and Stein riffs on the Goop-y world of wellness influencers in her characterization of CEO Devin, who never met a fancy serum she didn’t want to endorse. But its fictional trappings and trajectory most closely resemble that of The Wing. Here’s Devin’s description of the way Richual’s launch is received: “Cover story in Fast Company, profile in the Styles section, slideshow on Vogue dot com: ‘Workplace as Vulva—And Why Not?’” Just like The Wing, Richual’s origin story is molded by Trump’s 2016 victory. “The election was a gift to us,” COO Maren thinks. So was the cover story in Fast Company: “Paltrow, Meet Steinem: How Millennials Devin Avery and Maren Gelb Are Making Wellness Woke.”
A spate of recent novels by women have featured female protagonists with preoccupations with wellness and beauty, including Alexandra Kleeman’s You Too Can Have a Body Like Mine and Ottessa Moshfegh’s My Year of Rest and Relaxation. In those books, the central characters are defined by their disaffection. The women in Self Care have shades of this passivity—like the unnamed protagonist of My Year of Rest and Relaxation, Devin has her own habit of fetishizing sleeping, and Maren’s reliance on downers becomes a major plot point—but they are defined by their attempts to belong in the world rather than to escape from it. Instead of opting out, they are leaning in actively—and cynically.
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Self Care kicks off with Maren drinking Chardonnay at night in the office after facing backlash for a bad joke she’d tweeted. It’s the beginning of a rocky stretch for Richual, which is also hampered by revelations that its board member (and primary funding source) has been accused of sexual misconduct. Oh, and he’s sleeping with Devin. Oh, and Khadijah, who actually does most of the work, is pregnant, but too nervous to ask her bosses for maternity leave. (In a particularly accurate startup-world detail, there’s no HR department.) Devin and Maren are both, for lack of a nicer turn of phrase, profoundly corny dingbats, while Khadijah always reads more like a plot device than a person, and the contempt that the book has for its characters gives it a brisk, brusque verve.
Some of the book’s most lacerating moments come when Stein lays out exactly how nihilistic the women are beneath their Audre Lorde–quoting public personas. Maren’s advice for an influencer receiving criticism, for example, is bracingly manipulative—“I told her she had two choices: She could capitulate, admit she was wrong, apologize, promise to never again post selfies she took with the orphans she cared for in Mombasa because now she understood the meaning of white saviorism. Or she and I could go back to her questionnaire, find something from her past that showed that she, too, had suffered, and with a single post we could turn the tides of sympathy in her direction.” Maren sees giving women space to bare the darkest corners of their souls in exchange for digital validation as the core business model. Devin would like to keep things light and easily monetizable, but is also interested in building Richual’s audience through deliberate emotional manipulation. “The only thing women love more than being angry is being angry at those who are angry about the wrong things. And if there was a way to monetize that anger? Why shouldn’t Richual be the first to capitalize on that,” Devin thinks after deciding to greenlight a digital video series called Stay Woke Y’all.
Two weeks before the release of Self Care, Audrey Gelman resigned from The Wing. (And one week before its release, Sophia Amoruso also stepped down from Girlboss.) Gelman had attempted to address some criticisms of her leadership style last February with a confessional essay in Fast Company headlined “Where I Got It Wrong.” But the next month, Hess’ Times Magazine report highlighted how unhappy many former and current Wing employees still were with the way the company operated. Late this spring, employees went on a virtual strike to protest her leadership and the way Black and brown employees had been treated, and continued to call for sweeping change. And so Gelman exited. Self Care ends with a founder ouster, too. Maren attempts to test her own advice about using vulnerability as a way to win people over—not totally unlike Gelman’s essay—but her plan backfires.
Self Care is a comedy of boardroom manners, and succeeds as such. But it did leave me wishing that it would scratch at its characters’ psychologies with as much precision as it skewered their sensibilities. Seeing the girlbosses of yore knocked off their pale dogwood pedestals this June has underlined just how shaky their claims to power and influence were all along. Self Care ends with the fall from grace. But the most interesting part will be what comes next.
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