The End of the Girlboss Is Here

The girlboss didn’t change the system; she thrived within it. Now that system is cracking, and so is this icon of millennial hustle.

Leigh Stein
Jun 22 · 11 min read

Seven years ago, if you were an ambitious young white woman seeking to break through the glass ceiling at work, Sheryl Sandberg was your mentor. Her bestselling 2013 book Lean In: Women, Work, and the Will to Lead was your guide to overcoming the type-A personality defects — perfectionism, people-pleasing, fear of criticism, self-doubt — holding you back from the C-suite.

Lean In offered a game plan for success in the corporate workplace through the lens of self-improvement. Sandberg never set out to dismantle the system, but to excel inside it. (Which she has: As the COO of Facebook, her net worth is estimated to be $1.7 billion.) If women just leaned in, could we change the system through our own self-motivated behavioral choices? Institutional barriers versus internal barriers is the “ultimate chicken-and-egg situation,” she writes. But “rather than engage in philosophical arguments over which comes first, let’s agree to wage battles on both fronts.”

By presenting gender disparities in the workplace as a war to be fought on a personal level, Sandberg allowed women to feel like they were activists whenever they advocated for themselves. It’s inspiring to feel like you’re on the right side of a good cause, like you’re a part of history in the making. Sandberg invited readers to ask themselves “How can I make the system work better for me?” instead of “Who is the system designed to work for?” She gave women permission to define feminism on their own terms, ushering in the cotton-candy pink epoch of the girlboss, c. 2013–2020.

The girlboss was the millennial embodiment of unapologetic ambition. Her greatest pleasure was success; being underestimated only motivated her to trounce her doubters. She’s Election’s Tracy Flick at 30 with nicer clothes. (“Some people say I’m an overachiever, but I think they’re just jealous.”) She’s Emily Weiss getting 11 nos from male venture capitalists before her first yes to launch Glossier. To the girlboss, Yahoo exec Marissa Mayer’s 130-hour work week was an aspirational metric. #Riseandgrind workaholism was part of a girlboss’s DNA.

The rise and fall of the girlboss is about how comfortable we’ve become mixing capitalism with social justice. We looked to corporations to implement social changes because we lost faith in our public institutions to do so.

The girlboss was a disruptor; where others saw a problem, she saw an opportunity. Millennials weren’t buying $18 lipsticks at department store beauty counters? Sell them $18 lipsticks on Instagram. The ascendancy of the girlboss entrepreneur coincided with the growth of direct-to-consumer brands, which spent a gazillion dollars on targeted social advertising to meet their customers where they’re at — scrolling.

The original girlboss was too cool for politics. In her memoir #Girlboss, Sophia Amoruso, CEO of fashion site Nasty Gal, writes, “Is 2014 a new era of feminism where we don’t have to talk about it? I don’t know, but I want to pretend that it is.” In retrospect, I almost appreciate the candor. When I weigh the 36-year-old Amoruso’s successes and failures — the rise and fall and rise of a girlboss — I think of her as an entrepreneur first, not as the figurehead of a movement. Amoruso was crowned the “Cinderella of tech” for her shoplifter rags-to-riches story and made the Business Insider list of “sexiest CEOs alive.” But Amoruso never branded herself as a feminist. In 2015, four former employees sued Amoruso and Nasty Gal, claiming they were terminated when they became pregnant. The following year, the company filed for bankruptcy. On June 22, Amoruso announced on Instagram that she, “along with the majority of our team, are no longer with Girlboss,” and that the downturn from Covid-19 had “decimated” her business.

“The feminist scammer rarely sets out to scam anyone,” Jia Tolentino writes in her essay “The Story of a Generation in Seven Scams.” “She just wants to be successful, to gain the agency that men claim so easily, to have the sort of life she wants. She should be able to have that, shouldn’t she?”

The gap between everything that successful men took for granted and everything that ambitious women wanted became outrageous tinder for the girlboss’s fire. Hillary Clinton’s 2016 presidential run was the match that lit the flame — it was a total girlboss move to run again after losing the primary to Obama in 2008. The white girlboss, and so many of them were white, sat at the unique intersection of oppression and privilege. She saw gender inequity everywhere she looked; this gave her something to wage war against. Racial inequity was never really on her radar. That was someone else’s problem to solve.


I’ve never set foot in The Wing, but each time I type the name of the co-working space my brain returns image search results of pink velvet sofas and brass lighting fixtures. Girlboss wasn’t just a mindset — it was an aesthetic. Audrey Gelman and Lauren Kassan founded The Wing in October 2016; they had a speaker series prepared to celebrate the first 90 days of the Clinton administration. Their timing was impeccable, until it wasn’t. And their branding was immaculate, until feminism itself became the company’s kryptonite.

Originally, Gelman was going to call her co-working space Refresh, envisioning a place where she could freshen up between meetings for her job at a political consulting firm. The Flatiron flagship launched with a beauty room, showers, and Chanel products. It was a sanctuary for a certain class of New Yorkers, and yet early criticisms of the co-working space called the membership fees prohibitively expensive. (In 2016, membership was $185 a month; WeWork was $350 for a similar shared workspace but it didn’t face the same criticism for lack of accessibility.)

Gelman and Kassan’s “social club” wasn’t a riot grrrl meetup in your parents’ basement. This was for-profit feminism, the Lean In dream to make a difference and make money at the same time. The membership fee bought you access to a network of other women who could afford to be there. The setting provided sumptuous backdrops for Instagram posts. The Wing’s revenue projections were high enough to garner $100 million in funding over the next three years.


The importance of making feminism marketable was made clear to me when I co-founded Out of the Binders, a feminist 501(c)(3) in 2014, right around when Sophia Amoruso was in her prime. We organized bicoastal writing conferences called BinderCon and one of our major donors was a philanthropic organization dedicated to improving the lives of women and girls. It provided us with necessary funding; in return, we gave them brand placement on our livestream and signage.

When the organization’s consultant on contemporary feminism asked me who in Hollywood I’d like an introduction to, if she could make it happen, I said Shonda Rhimes. We hoped to invite her as a keynote speaker. The consultant said our website wasn’t attractive enough to email to Rhimes, so we redesigned it. Then I stopped hearing back from the consultant, because she was busy with everything the organization was doing at Sundance. (The consultant went on to start a lifestyle brand and venture capital firm that “invests in women” via an e-commerce site where you can buy products made by other girlbosses.)

As Jessa Crispin writes in her 2017 manifesto Why I’m Not a Feminist, when you make feminism so accessible and palatable it can be universally adopted, you put the “focus on labels and identity, rather than on the philosophical and political content of the movement, [and] what becomes most important are the things on the surface.” Things like Chanel products, velvet chairs, and pretty websites.

The modes of diversity that can be visually represented by race and ethnicity, gender, or size play a big role in the girlboss aesthetic, which is targeted at millennial consumers. If you visited The Wing’s website today without knowing anything about the company, you might assume 75% of their members are women of color. This not only invites more women of color to join — it also signals to white women that The Wing is woke.

She saw gender inequity everywhere she looked; this gave her something to wage war against. Racial inequity was never really on her radar. That was someone else’s problem to solve.

While Gelman and Kassan raised millions, I was trying to fundraise enough money to put on two conferences a year and pay a single staff person, me, a $40,000 salary. (The most I would make in a year as the executive director of the organization was $12,500.) The Washington Post named me a “leading feminist.” A marketing consultant encouraged me to work on my personal brand so I could get on the paid speaking circuit. I was told to update my LinkedIn profile to say I was a millennial thought leader. “Why are you guys a 501(c)(3) and not a B-corp?” someone asked me. I’d never heard of a B-corp. What she was really asking was: Why aren’t you trying to make money off this? Why aren’t you a girlboss?

There was no money in what I wanted to do, which was feminist organizing, building an inclusive and accessible event that would provide networking opportunities to a diverse community of writers. I couldn’t find any organization that would pay me to do this. (I even applied for a community manager position at The Wing but didn’t get an interview.) Demoralized, burnt out, on antidepressants, and $8,000 in debt, I resigned in 2017.

During the fall of 2017, as the #MeToo movement gained momentum, the spotlight was off powerful women and back on powerful men. Reports of sexual assault and harassment at work — not just from celebrities but from everyone you knew on social media — were all anyone could talk about. Men were very bad and bad men were everywhere. It seemed like every lunch conversation I had that fall was about trauma. In the stories I heard, the perpetrators were always men and the victims always women.

An obvious solution to men abusing their power in the workplace was to put more women in charge. But the women who leaned into their ambition and founded their own companies were not necessarily any more virtuous, ethical, or respectful than their male counterparts. Though unlikely to be serial sexual predators like Harvey Weinstein, girlbosses could abuse their power in the workplace, too.

It was during this time that I started writing my satirical novel Self Care, about female founders of a wellness startup and how feminist values can be distorted by those in power. For research I collected the stories of abusive girlbosses: Miki Agrawal, self-proclaimed She-E-O of the underwear brand Thinx, was accused of sexual harassment in the workplace, including touching an employee’s breasts. At the end of last year, The Verge reported on the toxic workplace culture at Away, a direct-to-consumer luggage brand founded by Stephanie Korey and Jen Rubio. In addition to requiring 16-hour days from the customer experience team members and holding holiday vacation days hostage, employees were not allowed to email each other, which “created a culture of intimidation and constant surveillance.”

“I went to work for Outdoor Voices because it was my dream company and Ty [Heaney] was my dream CEO. A young female founder who was so inspiring, and I believed so much in what her company stood for,” one former employee told BuzzFeed News. But Heaney “spoke to me like I was in an abusive relationship.”

The problem with making girlboss feminism a part of your brand in order to appeal to customers was that those customers were going to expect you to put your values into practice.

On March 17, the New York Times published an exposé about workplace culture at The Wing. The hourly employees who worked the front desk, washed dishes, and scrubbed toilets described being treated like “the help” by members, and at the same time were scouted by management to model “THE JOY OF SISTERHOOD” T-shirts on the company website. (In my novel, a Black employee checks the company blog to make sure it meets her white boss’s standard “of two stock photos with women of color for every one stock photo of all white women.”) The same day the Times piece came out, Mayor de Blasio told New Yorkers to prepare for a stay-at-home order. Seemingly overnight, America changed in response to the virus. A women-only co-working space already seems like a relic from another era.

In recent weeks, nationwide protests for Black lives and against police corruption and brutality have coincided with a racial reckoning in media and corporate culture that is playing out live, on social media. Brands “are listening” and have quickly come around to the fact that feminism is out, anti-racism is in.

Journalist Phoebe Maltz Bovy observes that the culture pivoted from championing a self-empowerment mode of feminism that’s all about assertiveness and persistence, to deriding Karen, a meme that can stand in for a racist white woman, an entitled white woman, or really any “woman who makes too much of a fuss, or makes a fuss for an inappropriate reason.”

On June 1, The Wing announced a $200,000 donation to three racial justice organizations. That same day, as reported by the New York Times, the company told staff members that it had run out of funds in its Employee Relief Fund and couldn’t offer any more one-time assistance grants of $500. The response online was variations on a theme: performative AF.

In two weeks, support for Black Lives Matter increased almost as much as it had over the previous two years. Now that racism is on her radar, the girlboss is on an apology tour, donating to bail funds and sharing the mic. So why do I find myself bracing to find out how anti-racism becomes the branding for her next for-profit venture?

Robin DiAngelo’s White Fragility is number one on the New York Times bestseller list and it’s poised to become the Lean In of the 2020s, a book by a white woman, for white women, that says: See this big systemic problem? Start by working on yourself. White Fragility is social justice through the lens of self-improvement and, as is always the case with self-improvement programs marketed to white women, there’s money to be made here. DiAngelo is available to speak to your organization for a $30,000 to $40,000 fee. If you want anti-racist education in the comfort of your own home, Saira Rao and Regina Jackson will come to your dinner party for $2,500. The Wing may never recover as a luxurious in-person hub for ambitious go-getters, but working on your white privilege is fast becoming the next elite social club.

The end of the girlboss does not represent the failure of women to make corporate America more diverse, inclusive, and equitable in 10 years or less. That would be asking a lot of her (and nothing from the men at the top). The rise and fall of the girlboss says more about how comfortable we’ve become mixing capitalism with social justice, as we look to corporations to implement social changes because we’ve lost faith in our public institutions to do so. As Americans become less religious, and our distrust in politicians grows, we increasingly turn to corporations and influencers for moral leadership.

Woke capitalism lets the elites maintain the status quo while paying lip service to the demands of activists, and, as ethical consumers, millennials get to feel like they’re making a difference every time they go shopping. Until this country is willing to reckon with its extraordinary wealth inequality, and our government requires corporations to pay their fair share in taxes, we will continue to see reincarnations of the girlboss because she’s a manifestation of the American myth that says if you’re not succeeding, it must be because you’re not trying hard enough.

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What matters now. A Medium publication about politics, power, and culture.

Leigh Stein

Written by

Author of SELF CARE, a satire about the wellness industry and girlboss feminism, out June 30 and available for preorder now. www.leighstein.com

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GEN

What matters now. A Medium publication about politics, power, and culture.

Leigh Stein

Written by

Author of SELF CARE, a satire about the wellness industry and girlboss feminism, out June 30 and available for preorder now. www.leighstein.com

GEN

GEN

What matters now. A Medium publication about politics, power, and culture.

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