Amidst the upheaval of last summer, one thing was for sure: The girlboss—that dewy-faced, planner-toting, serum-slinging embodiment of 21st-century hucksterism insisting that we, too, could be she-EOs of our lives if only we hustled a little harder—was over. Highly public comeuppance had already come for a few buzzy female start-up founders, unmasking the likes of Elizabeth Holmes and Miki Agrawal.

But the summer of 2020, and the great societal reevaluation that came with it, shifted into high gear: In a matter of weeks, Leandra Medine stepped away from her near-eponymous blog turned mini media empire, Man Repeller; the Wing’s Audrey Gelman resigned as CEO of the coworking space; and even the original #Girlboss herself, Sophia Amoruso, left Girlboss Media. The pandemic hurt business, sure, but all three founders had long faced criticism for creating corporate environments that failed to live up to the utopian feminist ideals they’d so espoused. The girlboss had left the building, headlines pronounced. Good riddance, we agreed, to one of the cruelest tricks 21st-century capitalism had perpetrated.

In the year since, we’ve witnessed the girlboss’s final paroxysms sputter out along familiar lines. Upon reading the room, female founders and girlboss adjacents promised to take a step back, mix up the grid a bit, and do some hard listening. Now they’re testing the waters for their public comebacks. Take the widely jeered interview of Leandra Medine on the Cutting Room Floor podcast, which has lit up group texts legion since its release nearly a month ago on July 7 and incited a full-out dunkstorm: first in response to Medine’s slow-motion train wreck of glibness—“Upper East Sider Realizes She’s Privileged,” The Cut proclaimed—then in criticism over comments made by designer and host Recho Omondi that listeners found to be anti-Semitic, prompting an edited rerelease of the episode days later. The promised part two of the interview was then delayed twice; on August 17, Omondi definitively announced on the podcast’s Patreon page that the second part would not air. “It’s a lot of headache for something that I don’t even think is worth it at this point,” she explained in a 10-minute audio recording, alluding to the backlash the podcast itself received for anti-Semitic remarks.

The whole ordeal proves how fraught the road is for those girlbosses who are attempting second acts via their requisite apologies. Medine, who last summer faced criticism along with her media company, Man Repeller, for her alleged performative solidarity with Black lives, stepped down in June 2020; the outlet briefly rebranded as Repeller without her and eventually shuttered that October. Ostensibly, Medine was on the fashion podcast to discuss what she’d learned since her “cancellation rite of passage.” Over 87 minutes—the final of three interview attempts, we were told by Omondi, who also caveated right off the bat, “I don’t like this episode”—Medine attempted to embark on a journey of redemptive self-castigation.

“I’m not surprised that people have had bad experiences at Man Repeller, but I don’t think this is because I’m a racist,” Medine said early in the interview, adding, “I’m an equal opportunity asshole. I sucked as a leader.”

As far as the old girlboss maxims go—admitting you’re not perfect, insisting on personal growth—it was an admission that read almost admirably frank. And there were points where Medine offered up her vulnerability so directly that it was not hard to be sympathetic: On the cancellation, she described having a trauma response and alluded to thoughts of self-harm; on the burden of being an influencer-cum-CEO with a “super-codependent relationship” with her 10-year-old company, she sounded genuinely miserable. (How codependent? Medine admitted that she only got back together with her now husband after she started the site, as he suddenly saw her “as this, like, attractive, independent woman.”)

On their own these admissions could be worth further excavation within the larger contexts of influencer burnout, the realities of the media industry, or our tendency as a society to equate work to worth. But the interview sidestepped a bigger question: What has Leandra Medine learned? The closest we got to an answer came via an earful about her rich-but-not-mega-rich childhood demarcated by feeling othered via her Iranian-Turkish heritage and Jewish identity on the Upper East Side, which admittedly does wrinkle the white-villain template often applied to the #Girlboss downfall story.

That isn’t to say Medine’s issues don’t matter; she talked about the guilt she has wrestling with these questions, wondering if she’s allowed “any version of adversity” amidst a time of societal upheaval and systemic inequality. At the end of the day, it’s both clear that Medine was ill-equipped to run a media company purporting to elevate “all voices”—and that Medine is still unaware of the depths of her privilege. Is it possible that Medine was truly that oblivious and tone-deaf, to have had three chances to explain herself on this podcast and instead fumble her way into self-pity over being unable to befriend former employees and that “I thought I was poor” pull quote for the ages? Or was this all a calculated positioning statement from a savvy influencer in the vein of a job candidate who, when asked about her greatest weakness, thinks pulling the perfectionist card is still the move? (Medine’s claim that she was obsessed with having employee satisfaction be 100% is textbook girlbossian.)

That Omondi and the podcast received backlash for the anti-Semitic remarks proves the thorniness of privilege as a casual podcast topic (in the original version of the episode, Omondi called Medine a “Jewish American Princess,” adding, “At the end of the day, you guys are going to get your nose jobs and your keratin treatments and change your last name from Ralph Lifshitz to Ralph Lauren and you will be fine”; these lines have since been removed along with a comment about Jewish slave owners. Omandi posted a six-minute apology to Jewish communities on July 20). The meta-meta commentary dizzies the mind, hearkening back to the whole Reply All “Test Kitchen” fiasco and reminding us that none of these conversations exist in a vacuum—the backlash to the backlash to the thing that’s just begun.

Since the first interview’s release, Medine does not appear to have acknowledged its existence on her social media. In a July 20 interview with Business of Fashion, Omondi said she sent an edit of the episode to Medine ahead of publication, but that Medine chose not to comment to her at the time or since. (Apropos of nothing, the day after the original episode aired, Medine’s book club on Substack announced it had chosen Elif Batuman’s The Idiot to read.) The much-hyped part two of the episode, which was originally set to be released via The Cutting Room Floor’s Patreon on July 21, was rescheduled to July 28 and then delayed again via a last-minute announcement posted to Patreon.

Let that be a lesson to us all about how the interrogation of privilege proves itself unwieldy work that isn’t easily tidied into the usual volley of a podcast episode—much less a single press release, heartfelt Instagram post, or tweet. Even if this mystery follow-up episode finally offers Medine the absolution she seeks (fourth time’s the charm?), the whole ordeal doesn’t exactly inspire confidence in true girlboss genuflection.

You’d think that the COVID-enabled era of celebrity misbehavior and Twitter cancellations would engender a golden age for the high-profile apology, but it’s clear that not even the girlbosses (or even their own critics) can get it immediately right. Turns out there’s no one-and-done optics move, no press-friendly pirouette that, at the end of the day, doesn’t still involve doubling down on the ego-centric narrative that undergirds the original girlboss mythos. Maybe you go on Ziwe’s show and try to embarrass yourself into amnesty. You could pay $2,500 to host an intimate dinner party and have your and seven friends’ white privilege deconstructed from the safety of your own home. A $10 million commitment to bolster inclusion in the industry is impressive, but then aren’t we in the same trap again, a never-ending cycle of brand-building exercises? The girlboss of yore insisted her ascent up the business rungs was our ascent; the girlboss 2.0 insists she can keep climbing and tackle her white fragility on the side too. She isn’t gone; she’s just found a new project.

UPDATE (August 17, 2021): This post has been updated to reflect Omondi’s ultimate decision against posting the interview’s second part.   

— Behind the Scenes of Anthony Bourdain’s Iconic Nude Portrait
— Will TikTok Save the Olympics?
— King Edward VIII, King George VI, and the Rift That Changed History
— New Summer Books for Every Mood
— Jeff Bezos and the Life-Changing Magic of Going to Space
— The Best Next-Gen Face Toners for Balanced Skin
— Jared and Ivanka Have Reportedly Closed on Billionaire Bunker Mansion 2.0
— The Rehabilitation of Prince Edward and Sophie
— From the Archive: How John Kennedy Gracefully Took His Place in History
— Sign up for The Buyline to receive a curated list of fashion, books, and beauty buys in one weekly newsletter.