Author John Paul Brammer on how to rethink the ways we seek and give support.
“Are you even qualified to help me?”
This question, the first in John Paul Brammer’s book of advice essays, ¡Hola Papi!, cuts to the heart of his medium. Very quickly, the reader learns that Brammer is far from the pearl-decked, socialite woman long associated with advice columns — he’s a gay, mixed-race Mexican American from the Great Plains who jokes about his unreliable mental health. But this context arrives through his careful weighing of whether he’s a person to rely on in the first place. There’s no follow-up to that tough question, and he has to tackle it head-on: Why come to me?
People have written to columnists for guidance in newspapers and magazines since the 17th century, but rarely has the (often pseudonymous) writer had their credentials challenged. In fact, when the US saw a boom in advice columns after 1900, unwavering authority was a given. Some authors were known for delivering curt, definitive replies without elaboration: In 1912, a doubtful 20-year-old woman who asked “Mrs. Elizabeth Thompson” at the Rock Island Argus if she was too young to marry her eager boyfriend got a one-word answer: “No.”
In the past few decades, many new voices have entered the conversation, and none is quite so frosty. All the same, each tends to speak from a lofty platform; there’s the assumption that they have the keenest, most penetrating insights on humanity and the habits to sustain it. You almost can’t avoid the language of a parent telling their child how the world should be.
Brammer, however — who began writing his ¡Hola Papi! column for the gay hookup app Grindr via its online magazine, Into, in 2017 — built a following with the opposite approach. Not only does he escape the largely white, straight, domestic concerns of the advice genre by carving out space for deep thoughts on LGBTQ and racial identities, he also doubts that he or anybody else can solve your problems, or even truly get a grip on them. Instead, he refracts the anxieties of young queer readers through his own life story, from the traumas of growing up closeted in the rural town of Cache, Oklahoma, with a fragile idea of his Mexican heritage, to the search for community, love, and authentic self-expression as an adult. He remembers being tormented as an outsider in middle school, his “coming out” to the male friend in denial about their sexual relationship, and a moment when art raised him from the pit of despair.
The result is a soulful memoir, each chapter drawing on an episode of his life to glean a lesson that upends advice as you know it, inviting the reader to take hold of their personal narrative. Rather than hand down edicts and aphorisms from on high, Brammer’s writing suggests, perhaps he can help you help yourself. “Whose gaze is it, and what are you looking for,” he asks a reader who is afraid to dress gayer. “What might it be like to have a lens that is more your own?”
Brammer now publishes his column on Substack and it’s syndicated in The Cut; he receives around five letters a week, assuaging people worried about being ugly, past decisions, and meeting a soulmate; his backlog of unanswered messages is now close to 700. I spoke to him about his take on the form and why it represents a necessary change. Our conversation has been edited and condensed for length and clarity.
Miles Klee
When you began writing ¡Hola Papi!, you envisioned it as a spoof of the traditional advice column. What was it about the genre that you wanted to subvert?
John Paul Brammer
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Zack Knoll
I thought it was so funny that somebody would earnestly approach a complete stranger and say, “Here’s this weird thing I’m dealing with, what do you make of it?” Because I just don’t believe that authority like that exists. Being this long-established phenomenon — the advice column dates back to the 1600s — it’s very storied, there’s something traditional about it. And anywhere there’s tradition, you have the opportunity to run amok and turn everything on its head. It wasn’t like I had real contempt for the advice column. It was more that I saw these rules I could break.
Miles Klee
When you were flooded with letters, you quickly took on the responsibility of helping those in need. Did it seem that something crucial had been missing from the medium all along? Or that it had overlooked a significant audience?
John Paul Brammer
Certainly. People have touched on LGBTQ issues in the past with their columns, but I did exist at such a unique intersection of technology and the advice column: it was pushed out through the Grindr app. I thought it would be funny to place this “Dear Abby”-type property inside a gay leather club, basically. There’s a certain kind of person who’s on Grindr in the first place, looking for intimacy; you’re probably lonely. I think I was offering, in my own limited way, a chance at genuine connection, of reaching out to someone else and telling them something important, something real — confessing.
Miles Klee
Digital connection is a big topic. You describe a youth on AIM and Myspace. I loved the story of dating a girl you met on Myspace when you were both young teens, partly because of an emotional connection, but also to appear straight, a status you perceived as enviably “normal.” This gives way into adulthood, with apps like Twitter and Grindr — the column was named after the racialized greeting you frequently got on the app. Is the lens we bring to our struggles now inseparable from the online condition?
John Paul Brammer
The internet is bringing things into our lives that we could never have anticipated, and I don’t even mean just now — the chaos that Myspace introduced to my young life. We have this second persona that we put out on the internet, and people are interacting with that. Who I was on Myspace maybe wasn’t such a real person. But even when I was with my girlfriend at the time, obviously I wasn’t being genuinely true to myself. So those things are very symmetrical to me. You can still be a projection, a “fake” person in real life, just as much as you are on the internet. I think that chapter does the best job of conveying the chaos of the internet, but also how we bring a lot of it to our real-world interactions as well.
Miles Klee
Your style of support brings your own personal experience to the foreground. Forgoing the abstracted voice of moral certitude, you relate other people’s problems to your own, and to your evolving identity. You recount finding a job making tortillas because you felt you weren’t “Mexican enough,” and the time when a childhood bully, years later, tried to flirt with you on Grindr. What effect does this exposure have?
John Paul Brammer
Part of the funniness for the column was when someone wrote in a letter that was very serious and intimate, I would then start talking about myself. Because the character of ¡Hola Papi! was this egotistical narcissist. “Yeah, yeah, that’s your problem, let me tell you about what happened to me one time.” To an extent, he’s a cartoon character that I can write from, and he has a distinct voice that feels very separate from the way I talk and the way I write anything else. Yet, at the same time, the things I discuss are true to my life, very vulnerable. Anecdotes from my past that … there’s not much funny about it. On the internet as it exists now, it’s hard to write outside of your own experiences because people will pick it apart. What you have a right to do anymore is say how you feel specifically. Here’s how I see it. I’m afraid of overstepping, telling someone whose experience is nothing like mine how to live their life.
Miles Klee
Also in contrast to past generations of advice writers, you aren’t prescriptive. You don’t tell people what to do in extremely specific situations, but you address broader anxieties about how to be — how to live with trauma, or how to express a truer self.
John Paul Brammer
I’m so lucky that I’m running an LGBTQ advice column. Straight people are starting to write in, which I love, but that’s a recent phenomenon. A lot of those LGBTQ issues are more esoteric, have more to do with teasing things out rather than seeking a definitive answer. “How does my identity work? How can I feel more comfortable with who I am? How can I feel like I belong in this community?” When we’re talking about presentation, how you see yourself, how you make peace with yourself, that’s where I’m comfortable. And I don’t have to give these super-concrete answers, like, “You need to do this, and then do that.” I’m not operating within an established system where there are rules. I’m talking about identity, sexuality, appetites, desires. I really don’t like the ones where I’m saying, “Break up with him, sis.” I feel dumb and incapable whenever I get letters asking, “Who’s in the right here?” Like I’m at a family reunion and these people I’m not even related to are going, “Pick a side.” I don’t know, I want to go home!
Miles Klee
I was struck by your theme of reinvention. You acknowledge that we change from one moment to the next, and may hardly recognize who we were a few years ago. How does this interior, ongoing narrative shape your essays?
John Paul Brammer
I’m of this belief that we cycle through many personalities, many ways of thinking. One question I get a lot is: “What advice would you give your younger self?” That represents this non-realistic, linear way of thinking — that we accrue wisdom as we get older, and we keep all the old wisdom. But it doesn’t work that way. We lose some things. When I was a child or a teenager, I had a certain kind of wisdom that I don’t have now. Back then, I had to navigate being in the closet, violence, the idea that I could actually be hurt or physically attacked if I expressed my sexuality. There were things that kid knew back then that I don’t know now. He was tougher in a lot of ways. When I go through those different experiences and why I see them as so important, in the act of remembering them, I’m also doing some creative writing. I try to be flexible and adaptable in the way I see myself. It’s a more interesting, freeing way of seeing it than trying to pretend that I know everything.
Miles Klee
What’s a common mistake people make when giving advice to friends and loved ones?
John Paul Brammer
Sometimes we’re well-intentioned and want to give a solution. A common mistake is trying to fix it. And that sounds really counterintuitive, coming from an advice columnist, who, ostensibly, their job is to help you fix it. I get a lot of letters where it’s like, this has no solution, and they’re not looking for one. They just want to have somebody out there who’s listening to them, and to put into words what’s bugging them. That, in and of itself, is a very powerful act and can be very therapeutic, very healing for a person. I think I’m good at figuring out when that is what someone’s looking for.
Miles Klee
The book is framed by two pieces that wrestle with a tough but central concern — what, if anything, qualifies you, John Paul Brammer, to give a stranger emotional guidance. In the end, you don’t answer a gay man writing from a country where homosexuality is illegal, deciding that “my voice may do more harm than good.” Is rejecting the mantle of authority and expertise in favor of humility the most radical approach we can take to the art of advice?
John Paul Brammer
I’m going to say yes, because I love me, and I think it would be a cool idea if I was doing the most radical thing. I think we’re constantly being pushed to speak authoritatively on things we maybe don’t have the authority to speak on. This push to be an expert at everything, or the person with the smartest thing to say, is actually pretty poisonous. To write in the book about a time I was silent, and why it was good, is silly. You took a whole book to say that. But there’s a lot of wisdom in silence, a lot of virtue. Not always. But I thought of silence as this neglected altar that could use some more flowers. And I like pairing it with my job, which is “someone who’s supposed to tell other people what to do.”
Girlbosses convinced us they would change capitalism. We weren’t wrong in hoping they would.
The girlboss is one of the cruelest tricks capitalism ever perpetrated. Born in the mid-2010s, she was simultaneously a power fantasy and a utopian promise. As a female business leader — be she a CEO, an aspiring CEO, or an independent MLM superseller — the girlboss was going to unapologetically will empires from the rubble of rejection and underestimation she faced all her life. As companies grew in her image, so did her mythos; her legacy would be grand and fair, because equality was coming to work. Everyone was supposed to win when girlbosses won.
Hard work would finally pay off.
What set girlbosses apart from regular bosses was pinning feminism to hustle. Women like Facebook’s Sheryl Sandberg and former Nasty Gal CEO Sophia Amoruso — who coined the term — were finally wrangling power away from the men who had held it for so long, which was seen as a form of justice. As the concept was codified, the idea of the girlboss became about the melding of professional self and identity, capitalist aspiration, and a specific (and arguably limited) vision of empowerment.
“Literally every woman that I look up to is unrelatable,” Rachel Hollis, a very wealthy self-help guru, said in a TikTok video in April, describing how she wills herself to wake up at 4 am to conquer her day. Hollis wrote in 2016 how much she hated the term, but quotes like hers crystallize the girlboss mentality.
“If my life is relatable to most people, I’m doing it wrong,” she continued, and in the accompanying caption she compared herself to a slew of unrelatable women she looks up to, including Harriet Tubman.
If Hollis’s fetish for relentless, unstoppable work and comparison of herself to the creator of the Underground Railroad is a prime example of a girlboss gone wild, so was the swift backlash.
Hollis’s most generous critics saw her words as a moment of unchecked privilege. Her sterner critics called her out in disgust, pointing to Hollis’s casual dehumanization of her housekeeper, whom she described as the woman who “cleans her toilets,” and her Tubman comparison as examples of typical, wrongheaded girlboss attitudes. People who worked for Hollis corroborated her off-putting conduct. She was, in their view, just another white woman co-opting empowerment and feminism for profit, with no intention of lifting anyone else up.
Hollis is the latest in a recent spate of corporate women leaders — including Away CEO Steph Korey and certain founders of luxury spin classes — who create companies plagued with stories of bullying, cruelty, and overworked and underappreciated staff. It now seems as though toxic work environments were a feature of their design and not coincidental bugs. Perhaps working for a girlboss was just like working any other job.
As more and more of these stories surfaced, “girlboss” shifted culturally from a noun to a verb, one that described the sinister process of capitalist success and hollow female empowerment. On TikTok and Twitter, girlboss the verb became yoked to “gaslight” and “gatekeep” to create a kind of “live, laugh, love” of toxic, usually white feminism.
“Gaslight every moment, Gatekeep every day, Girlboss beyond words,” one image macro reads.
But it’s not that people wanted the girlboss to fail; it’s the opposite. The concept of the girlboss failed us all.
The girlboss brought to life a way to talk about real concerns and barriers in the system honestly and frankly. It also posited a solution so blazingly simple — put women in charge — that it could never work.
We wanted it to be this easy to buck the whole system. When it turned out women CEOs were just CEOs, we never let them forget it.
The girlboss succeeded because of benevolent sexism
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EyeEm via Getty Images
Girlboss’s slow march toward irony was supercharged when the neologism officially got a name seven years ago.
“In 2014, Sophia Amoruso’s memoir, called #Girlboss, comes out. This is where the word comes from,” feminist author and poet Leigh Stein explained to me. Stein is arguably the world’s foremost authority on the girlboss movement, having studied and written an entire novel about it. “That same year, Beyoncé performed at the VMAs in front of a sign that says ‘feminist’ illuminated in bright letters. As we all know, anything Beyoncé does is a huge cultural moment.”
Stein pointed out that at the time, the idea of bringing feminism, or some kind of feminism à la carte, into the corporate world was inescapable. Beyoncé and figures like Amoruso punctuated it, but it had begun brewing a year earlier, when Facebook COO Sheryl Sandberg published her lauded and controversial memoir Lean In in 2013. The book sold more than 4 million copies worldwide, and established a language to talk about women’s issues in a corporate environment. Amoruso swooped in with the shorthand soon after.
“When you look at the actual word ‘girlboss,’ there may be some internalized sexism,” Alexandra Solomon, a professor who specializes in gender and gender roles at Northwestern University, told me. “Research shows that as women get older, and as women become more powerful, they are perceived as less likable. So by using that term girlboss, there’s a desire to be powerful but a fear of losing likability.”
In some aspects, Solomon explained, the girlboss label allowed women to assert power or lean in without threatening or alienating people around them. Calling oneself a “girl” could be seen as a compromise, but it was also a way to maneuver around traditional beliefs and systems that had historically diminished women’s voices.
Riding on feminism’s increased cultural cachet (as boosted by high-performance Beyoncé octane), Sandberg, Amoruso, and the girlbosses who came after them seemed to propose (along with the press that breathlessly profiled them) that women advocating for themselves and their worth was, intrinsically, a form of justice.
In this context, power and money became measures of equality, and rising to power in a capitalist system turned into an empowering feminist victory. It was a way of framing financial success and consumerism as goodness. The implicit promise was that if consumers made these girlbosses successful, it would mean better working conditions for women, and with that, maybe empowerment for all.
“If these women could succeed while upholding feminist values and treating their employees humanely, then maybe the patriarchy was just a choice that savvy consumers could shop their way around,” Amanda Mull wrote in the Atlantic in 2020, explaining how the girlboss concept had entwined itself with justice. “Maybe people could vote for equality by buying a particular set of luggage or joining a particular co-working space.”
That cultural moment seemed to manifest itself in women-led startups such as Glossier, a direct-to-consumer cosmetics company launched in 2014; Away, a luggage retailer created in 2015; and the Wing, a coworking space for women founded in 2016.
The media narrative surrounding these very different companies’ origins was pretty similar: A woman, or a group of women, has an idea for a company that fulfills a need for young women especially; funding is difficult to find (because venture capitalists underestimate women) but is eventually secured; a unique company is created, one that is an extension of the founders’ backstories and forged by their struggles; the women succeed because they’ve leaned into their strengths as female founders, and in doing so overcome a specific stripe of sexism.
Girlboss language wasn’t just used in the C-suite stratosphere. It trickled down to lower-level workers and eventually multilevel marketing schemes. Tethering feminism to hard work and entrepreneurship with justice fit seamlessly into MLMs, which have their own predatory horror stories and are built on exploiting tight-knit, predominantly female communities with promises of financial success.
But mythologizing the girlboss didn’t last very long.
In 2015, Amoruso’s Nasty Gal became the subject of a discrimination lawsuit alleging it had illegally fired pregnant employees. After it was filed, employees came forward with stories about how Amoruso’s company was a toxic workplace. In 2016, Nasty Gal filed for bankruptcy.
In 2018, as criticism of Facebook’s handling of Russian election meddling, misinformation, and personal data abuse mounted, Sandberg’s bullying behavior and attempts to discredit the company’s critics came to light in a New York Times report.
In 2019, The Verge reported on Away employees’ allegations that co-founder and co-CEO Steph Korey bullied employees, and that the company wasn’t as inclusive or diverse as it had claimed.
In 2020, former employees of feminist oasis the Wing said the coworking and social space created was only for show, and that working there was an exercise in being undermined. They also alleged that Black and brown employees were mistreated. The Wing founder Audrey Gelman stepped down that June.
The same year, employees at Glossier alleged they faced discrimination from both their company and the customers they served. They said upper management was predominantly white women.
Similar allegations of toxic work environments and discriminatory behavior surfaced at women-led media outlets such as Refinery29, Man Repeller, Who What Wear, and Vogue, as well as women’s clothing company Reformation and the women-founded luxury exercise chain SoulCycle.
Like their origin stories, these companies’ reckonings had a similar trajectory: The businesses touted themselves as inclusive communities built by women, but behind closed doors, some employees said, was a toxic and sometimes abusive mix of, well, gaslighting and gatekeeping. Those revelations hurt these brands with their consumers.
“A huge part of the problem is if you make feminism part of your brand, then your customers are going to say, ‘Wait a second. Are you a feminist company behind the scenes? Or is [it] just optics, like optical allyship?’” Stein told me.
Girlboss-branded companies failing to live up to their own standards prompted thoughtful pieces about the way we think and frame women’s ambitions, and why these problems seemed to be ingrained into the companies’ design.
In June 2020, Stein herself wrote a viral think piece asserting the death of the girlboss. Her most convincing point was that girlboss failures weren’t some new folly or unique to women; this was, quite simply, capitalism.
“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,” Stein wrote.
The success these companies achieved in linking gender to their brand belies the idea that women are more virtuous, kind, and gentle; they weren’t supposed to succumb to greed or power, to commit the same terrible abuses male CEOs perpetuate.
“There’s a lens or mentality that a female boss will be more nurturing,” Northwestern’s Solomon told me. “It’s a setup. Her clear boundaries are then perceived as cruel boundaries or punitive. Or it goes the other way, and people perceive her gentleness as weakness.”
Girlboss downfalls, under this line of thinking, aren’t seen as just a failure of business but also as a betrayal of their gender.
The allegations of discrimination and toxic work culture at girlboss-led companies are undoubtedly serious, Stein said. But at the same time, “there’s kind of a trap” when it comes to how we talk about those business failures. She argues it’s possible to have conversations about what went wrong without losing sight of accountability or laying these failures at the feet of women writ large.
“There’s a whole exposé in the Times about the Amazon work culture and how it sounds like a nightmare to work at Amazon. But no one’s in the comment section, like, saying Jeff Bezos is bad at feminism,” Stein said. “Women are held to account for how ethical and virtuous they are as leaders in a way that men are not.”
Why girlbossing was always going to be an empty promise
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Emma McIntyre/Getty Images for Girlboss
In speaking to experts about the rise and fall of the girlboss, the one theme that keeps surfacing is that while the term ultimately flopped, the enthusiasm surrounding it was real. The barriers facing women in corporate structures, the desire to make workplaces better by making them more inclusive, the anger from being overlooked in current systems — it’s all authentic.
Lindsey Bier, a professor at USC’s Marshall School of Business who specializes in gender communication, explained that one of the reasons she thinks the term became so popular and its downfall so magnified is the lack of empowerment women face in the workplace. For more than a decade, she explained, study after study was published about how women in leadership roles were penalized for how they talked to their employees.
“Men in leadership positions are expected to be assertive and direct. Women, however, face a paradoxical situation in which they’re judged if they’re not assertive enough, but then they’re also judged if they are too assertive and direct,” Bier told me. “The data shows that both men and women judge women in leadership in this way.”
The girlboss wave of feminist-adjacent corporate empowerment offered an unapologetic promise that women would not be judged or undermined the way they would in traditional corporate settings. The hard work they put into their jobs would finally be rewarded. But the promise became emptier when basic scrutiny revealed that employees at these companies, particularly women of color, still ended up feeling overlooked, overshadowed, or even bullied.
“You’ve changed the bodies of the people who are sitting at the table, but you haven’t changed the table,” Solomon said, explaining that girlboss offered to dismantle the system but opted for cosmetic changes.
The energy and desire for something better still exists. Both Bier and Solomon told me that younger people and members of Gen Z are more aware than previous generations when it comes to companies’ and brands’ values, and they factor in those values — e.g., equality, diversity, inclusion — when deciding where to spend their money. This is a shift from previous generations, which looked for their government to enact change.
While that sentiment can be reassuring, Stein is a little more cynical when it comes to getting corporations and capitalism to bend to a consumer’s will. Pinning hopes on CEOs to dismantle structural barriers is how we got into this mess in the first place. “I actually don’t want to see more of us, like, yelling at Rachel Hollis to end racism in America. I don’t think we’re targeting our rage into the right place,” Stein told me.
Expecting Hollis or Sandberg or Amoruso to fix systemic inequality in the United States is moot when they’re not often given a chance to fix their own companies, Stein says. “I don’t think we’re actually giving them the opportunity to do better,” she told me. “These girlbosses that are 29, 30, 31, 32 when they start the first company, they’re publicly shamed in the press for their failures. Do they get to try again? Are we really saying as a culture, ‘No, they don’t get to try again’? That’s what’s unfair to me.” Fixing their own businesses isn’t as ambitious as solving America’s deep problems, but it’s at least a small step in changing the system.
If you laugh at the girlboss, she can’t hurt you
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Getty Images
In January 2021, a sentence appeared on Tumblr: “today’s agenda: gaslight gatekeep and most importantly girlboss.” Very much like how the girlboss became a cultural archetype who outgrew her original ambitions, gatekeep and gaslight are terms that, in recent years, exploded in popular usage. “Gaslight” has become the trendy synonym for lying — particularly a strain of lying where someone denies an obvious truth — and “gatekeep” has become interchangeable with discrimination.
The three Gs were linked, and the internet ran with it: TikToks, image macros, and tweets were all dedicated to these pillars of a cringe-inducing cultural moment. That “gaslight, gatekeep, girlboss” neatly traces the business practices of some of the most notorious women CEOs of the past decade may be more serendipitous than pointed. Gaslight, gatekeep, girlboss functions as more of an ironic “yeesh” at how embarrassingly enthusiastic we all were to jump on the buzzword bandwagon.
Gaslight, gatekeep, girlboss was a vibe.
Yet that hasn’t stopped the term from becoming sarcastic shorthand in interpreting pop culture, which hasn’t yet fallen out of love with girlbosses. In I Care a Lot, Rosamund Pike plays Martha Grayson, a sharp-bobbed antiheroine who scams old people out of their money via legal loopholes. Martha isn’t a bad person, she’s just going through her gaslight, gatekeep, girlboss arc.
The marketing for Disney’s new Cruella de Vil origin story, wherein Cruella is an aspiring fashion designer at odds with an even-crueler Baroness, calls to mind ads for Glossier. The phrase has even been tossed at Bethenny Frankel, who in interviews says she hates the word girlboss. Yet, in her new Apprentice-like reality competition show, The Big Shot With Bethenny, she’s portrayed as a mean and awful boss who’s also supposed to be the protagonist.
Recently, the CIA, an organization that’s known to partake in torture, created an entire ad about how it’s an inclusive place for women to thrive. It’s not torture, the internet replied, it’s just girlboss, gaslighting, and gatekeeping with some water.
#WednesdayWisdom
— CIA (@CIA) April 28, 2021
“I am unapologetically me. I want you to be unapologetically you, whoever you are. Whether you work at #CIA, or anywhere else in the world.
Command your space. Mija, you are worth it.”
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Peter Kramer/NBC/NBC Newswire/NBCUniversal via Getty Images
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