For 30, Alana Massey looks neither haggard nor old.This was my first thought upon meeting her in a Brooklyn cafe, near the apartment she shares with her cat. It’s hard not to privately log such crass details, having read years of Massey’s strikingly frank mental notes about herself.
Since she began freelancing for digital magazines nearly three years ago, Massey has written about how online harassment made her wonder if “I was the haggard old witch on the outside that I’ve always kind of felt like on the inside”; about body dysmorphia and her resulting insecurity during sex; about a towering and abusive ex-boyfriend who threatened “all 5’2” and 108 pounds of me”; about the physical anxiety she felt working at a Manhattan strip club; about the fear of aging that led her to dye her brown hair blonde; and much more on topics many of us whisper about to confidants, if at all.
Such candor is expected in “the familiar hazing ritual that many women go through when we aren’t ushered into media through more respectable channels,” as Massey once put it. Personal essays are in vogue online, especially for aspiring journalists willing to spill about sex, dating, and body image. The former Gawker editor Emily Gould made waves in 2008 with her confessions about confessional writing. By today’s standards, though, Gould’s indiscreet blogging was rather tame. “The First-Person Industrial Complex,” Laura Bennett explained last fall in Slate, commodifies private lives for easy clicks. These pieces don’t require polished prose or much reporting; their value can derive from salaciousness, not substance. And while personal essays offer a backdoor into journalism, that often leads to a dead end. The challenge is to convert that hazing ritual into a career while maintaining some privacy and enduring the harassment that this sort of writing tends to invite, particularly toward women.
After a trying start in that space, 2015 was a breakout year for Massey. She still specializes in women’s issues, but her writing opportunities now better reflect her interests, which extend far beyond her love life. She’s a worthy exemplar of someone who didn’t just overcome the so-called “pink ghetto” of personal essay writing, but who utilized the virtues of that form to develop a dynamic, engaging style of writing. She describes her work as “writing and reporting that acknowledges the origins of a story for the journalist and the stakes involved in their writing it. It is a way of acknowledging a passion or pain point in their experience and letting that play a role in the narrative arc of a story.”
Of course, that’s not her invention, but she practices it with distinct millennial flare. Her writing voice—confessional, unpretentious, sharp-witted, and forceful—can make readers feel like they know her. She politely insists that they don’t.
Single articles are not biographies. Single articles are not histories. Single articles are not data or DNA. pic.twitter.com/LYwEJQGg1w
— Alana Massey (@AlanaMassey) January 6, 2016
Nevertheless, readers familiar with her writing across dozens of publications, who follow her delightfully eccentric social media accounts and read her blog, could give a rough sketch of Massey’s 20s. “The thing about candidness,” she notes, “is you can’t really tell how candid something is unless you know what’s being omitted.”
For example, Massey almost never writes about other people in her life (with the exception of Keith, the cat). She went to high school in San Diego, where her father was a Navy captain, then graduated from NYU in 2007. Life post-college was a struggle with alcohol, drugs, bipolar disorder, and unsatisfying jobs—PR mostly, plus stripping and fetish work to cover the bills.
“Really impulsively,” Massey, who wasn’t raised in a religious household, decided to attend Yale Divinity School at age 25. “It was an escape from New York,” she says, “but I was really scared to go any farther than Princeton, New Jersey, or New Haven, Connecticut.” She graduated with a master’s in religion in 2012. It did prompt an awakening of sorts: not to disavow aspects of her past, but to be less ashamed of them.
Seven months after graduating and returning to New York City, a friend suggested Massey write about a life experience they’d discussed for xoJane, a website that calls itself a place “where women go to be their unabashed selves.” The essay, written under the byline “Alana M.,” was headlined: “I’ve Never Had an Orgasm and I’m the Only Person That Doesn’t Care.”
It was a modest attempt at anonymity, but she failed to realize that “Alana M.” would lead Web searchers to her various online profiles. “When I dove in and people were like, You just ruined your Google results, I was like, Ok. It was kind of a manic, compulsive decision.”
Soon, she was writing under her full name. “If you are going to ruin your Google results,” she advises, “ruin them for like 20 pages.”
For many, risqué personal anecdotes are less terrifying in the hands of strangers than under the eyes of mom and dad. While some details in her early writing did come as news to her parents, like that Alana wasn’t having sex in high school but was smoking weed, “I haven’t done anything that I think would violate their concepts of morality,” she says. “I haven’t written anything that’s cruel. And I think they’d be much more upset by something that was cruel to others or myself than something embarrassing.”
Ultra-candid writing can engender devotion and resentment. Emails from readers who’ve experienced similar adversity—be it suicidal ideation, disordered eating, or abusive relationships—can be overwhelming. “It’s unsustainable” to maintain those correspondences, she explained to me. Much as she wants to help, “we’re not penpals now.”
On the other hand, anti-feminist vitriol has a chilling effect. “There are situations that have been very formative that I never want put on trial by internet commentators,” she says. “There’s some stuff going to the grave with me.”
The “training wheels” of personal essay writing, as she describes it, led to freelance gigs at a variety of outlets, with an emerging specialization in faith. In 2014, Massey applied to more than 700 jobs, she told Pacific Standard. Many applications featured ridiculously extravagant tryouts, like this one at a women’s magazine seeking a sex and relationships Web editor:
Candidates are instead asked to produce three sex tips, five “observant” listicle ideas, five news stories I would blog about, two ideas for trend pieces or “newsy reported features,” two personal essays ideas, two ideas that “lend themselves to visual treatments,” five sex or relationship experts I’d use as sources, two new franchises for the brand, three [one-to-three] paragraph blogs about news articles from that day, and a complete listicle about sex problems faced by women. I refrain from buying their print magazine to confirm with certainty that they are actually requesting that I write them a full magazine before I even interview.
She never heard back on that one, she says. But she did land a full-time job writing lists at BuzzFeed at the end of 2014, with the opportunity to contribute reported pieces and longform essays. Her breakthrough was “Being Winona in a World Made for Gwyneths,” about the relatability of Winona Ryder compared to the stiff superficiality of Gwyneth Paltrow. But the piece also became the most important time when Massey broke her rule of not writing about people in her life. She urgently needed to describe an ex, “James.”
Months earlier, when she discovered he had another girlfriend in California and was hiding Massey from her, she dumped James and alerted the woman. He responded by repeatedly threatening to kill her, and by revealing to his new girlfriend that Massey had once been a stripper. That woman grew skeptical of Massey’s motives for communicating.
“The change in tone made it clear in real time how easy it is to dress down a real woman to the vulgar trope of a delusional whore,” Massey writes.
She decided to finally announce in writing that she had worked in the sex industry. James was plotting to tell all sorts of people in her life, even the church where they’d met.
“No one is telling my secrets but me,” Massey remembers thinking. “No one is profiting off of my humiliation but me.”
When her parents read her “Winona” essay online, they learned of her experience as a stripper for the first time. She got an email from her dad: “I never knew you were so prolific,” which Massey read as code for having been through a lot. “I’m really proud you’re my daughter.”
Massey would be disappointed but unsurprised if other journalists overplayed her time as a stripper. She notes that plenty of people in pop culture have been stigmatized and pigeonholed that way. “You sort of feel bad for people who are so obtuse.”
She has blossomed into a generalist, though her commentary off the news can lose some of its liveliness. Her best writing weaves anecdotes into argument, as with a defense of porn for Pacific Standard and an explanation of being a “cultural Christian” for The Washington Post. She’s fearlessly graphic—she’s compared despicable men to “taint sweat” and a “rectal blister”—but not gratuitously vulgar. When addressing tumultuous moments in her life, she doesn’t suggest that these are novel experiences, nor does she use platitudes to belabor their universality.
In first-person writing, overexposure is not an express lane to standing out. “Alana’s earnestness really sets her apart,” says Arianna Rebolini, the editor of Massey’s list-writing team at BuzzFeed. “It’s not just the act of confessing that makes something good and worthwhile.”
Within 24 hours of the “Winona” essay being published, a literary agent offered to represent her. Massey left BuzzFeed last summer after selling a book proposal to Grand Central Publishing, a Hachette imprint.
She drafted the book in just five months. “She’s the fastest writer I’ve ever met in my entire life,” says Mark Lotto, editor in chief of Matter, where Massey began contributing last year. In April, for Matter, she wrote “Against Chill,” her most-shared piece to date. It evokes “Against Irony,” a New York Times Magazine article in 1999 about backlash in response to a perceived culture war against earnestness. Massey’s piece resonated with today’s disenchanted daters.
Chill is a sinister refashioning of “Calm down!” from an enraging and highly gendered command into an admirable attitude. Chill suggests that young love is best expressed as competitive ambivalence. Chill demands that you see a Read receipt followed by a “Hey, was asleep” text three hours later and not proceed to throw your phone into the nearest volcano. Chill asks you to be like, “LOL, what volcano?”
There is a magnetic intensity to Massey’s writing. It’s self-effacing but unapologetic. As Lotto puts it, “There’s something really dangerous about it.”
“There are a lot of writers who can get reduced to their anecdotes,” he adds. “Writers like Alana expose themselves but also try to elevate it into something much more intellectual and universal.”
When we spoke, Massey recoiled at the notion of being an intellectual. “When I hear that, I hear competitive. And I hear inaccessible knowledge as virtuous.”
She rejects highbrow/lowbrow distinctions and celebrates celebrity. Her forthcoming book, All the Lives I Want, examines women in pop culture and how their public personas relate to Massey’s self-perception. One essay will be about Amber Rose, the stripper-turned-feminist firebrand whom Massey reveres. Publication is scheduled for 2017.
@DaRealAmberRose All the ❤️ back! Can’t wait to see what you conquer next.
— Alana Massey (@AlanaMassey) October 30, 2015
While continuing to write for places like The Cut on nymag.com and The Guardian, Massey is drafting a novel and shopping a script for a TV pilot. Last fall, she wrote copy for a Gucci campaign. She writes less about sex work and “cutesy dating stuff” now, she says, because she isn’t as close to those experiences.
In whatever writing she’s doing, her goal is to “build a world.” “Women aren’t trusted to build a world or know a world beyond their own experience, and even their own experience is questioned all the time,” she tells CJR. Massey doesn’t want to be confined to first-person narratives, but she doesn’t disparage them, either. The goal at the start of her career was to underscore that writing about women’s experiences has value. It’s drawn a range of reactions, including many readers, mostly women, who comment under her essays, “thank you.”Danny Funt is a senior editor at The Week and a former CJR Delacorte Fellow. Follow him on Twitter at @dannyfunt