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Jia Tolentino has been dubbed the ‘voice of a generation’, a blogger turned New Yorker writer whose journalistic musings traverse everything from vaping to religion. She talks about the art of literary exploration and her much-anticipated debut book, Trick Mirror. “One of the reasons I write so much is that I’m not so good at thinking about things as they’re happening. Unless I’m writing about something, it’s not often that I’m analytically clear about my own present reality. I tend to just wander through it and hope that I will make sense of it later.” By Wendy Syfret.

The cultural insights of Jia Tolentino

Writer Jia Tolentino.
Credit: ELENA MUDD

The hype surrounding Jia Tolentino’s first book was so thick that its arrival on The New York Times bestseller list felt almost inevitable. In the weeks since its release it has been nearly impossible to open Twitter or glance into a stranger’s bag without spotting the distinctive cover. Trick Mirror: Reflections on Self-delusion has had the kind of impact that books – especially debuts – rarely enjoy. “Especially not a book of essays that are dense and combative and don’t really have a point,” adds Tolentino.

The book’s cover reads like a young writer’s dream journal. Zadie Smith says Tolentino’s style is “enviable”; Rebecca Solnit calls her “the best young essayist at work in the United States”. Tolentino, a staff writer at The New Yorker, admits all the attention has begun to feel surreal. “I go to websites I read and see my face and am like, ‘Goddammit!’ ” she says. It’s a complicated position for a writer who has always been “careful to not let myself be packaged into something that is kind of shiny and brandable”. When asked how it feels to be embedded in the zeitgeist that she usually deconstructs, Tolentino pauses. “You know when you’re feeling vulnerable, like when you’re about to cry and someone is really nice to you and it feels devastating?” she says. “It felt like that. This is just not an experience that most people get to have.”

The endless comparisons to Joan Didion and liberal nominations for “the voice of a generation” would draw eye-rolls, if they didn’t feel so apt for 30-year-old Tolentino. And while the media has roundly embraced her book as a sudden and blinding cultural flashpoint, a cult has been slowly massing around her for years.

Back in 2012, Tolentino was an unpaid contributor at The Hairpin, a much-loved and much-missed women’s website that served as a prolific early incubator for some of the web’s brightest and most eclectic cultural commentators. Within a year, editor Emma Carmichael brought her on as contributing editor at the site and Tolentino began churning out the abundance of content familiar to any blogger. But her weekend round-ups, song premieres, aggregated news and viral animal stories were shot through with her signature style – a mesh of breezy intellectualism and chatty internet speak that somehow didn’t agonise. A short feature about actress Blake Lively’s – now abandoned – lifestyle site, Preserve, was funny and weird, with a casual subplot about female performance online. For a column interviewing adult virgins, she pushed the conversation to questions of family, books, female medical care and God.

When Tolentino was growing up, religion was central to her life. Born in Canada to Filipino parents, she spent her early years in the community surrounding a Southern Baptist megachurch in Houston. The $US34 million campus, spread across 17 hectares, was known by students as “the Repentagon”. At 16, Tolentino persuaded her conservative school to let her join the cast of the early 2000s reality show Girls v. Boys: Puerto Rico by arguing she would “be a light for Jesus, but on television”.

In the Trick Mirror essay “Reality TV Me”, she reflects on what motivated her to take such a surreal break from her own life. For years she told herself and others that she applied for the show on a dare. But, working on the piece, Tolentino realised it was an experience she pursued – and coveted – as proof that she was, as she suspected, exceptional.

There were practical stakes tied to her turn on reality TV, too. In her final year of high school, she was offered early admission to Yale, but her parents couldn’t afford the tuition. Tolentino hoped to make enough money on Girls v. Boys to pay her own way. When the plan didn’t work, rather than burden her family with financial pressure, she accepted a scholarship from the University of Virginia. Once there, she immersed herself fully – joining a sorority and even an a cappella group named The Virginia Belles.

After college she entered the Peace Corps and was sent to Kyrgyzstan, an experience that was both confronting and transformative. Returning to the US she found herself choked by the comparative wealth and excess surrounding her and turned to writing. “[It’s] the thing that brings me the most meaning, that I care about the most, and will do forever,” Tolentino admits. “One of the reasons I write so much is that I’m not so good at thinking about things as they’re happening. Unless I’m writing about something, it’s not often that I’m analytically clear about my own present reality. I tend to just wander through it and hope that I will make sense of it later.” Following this instinct, though still sceptical it could ever be a career, she moved to Ann Arbor to complete a master’s of fine arts at the University of Michigan and began sending cold pitches to The Hairpin.

In 2014, when Emma Carmichael left The Hairpin to become editor-in-chief of Jezebel, a women’s site owned by the now-fallen digital media monolith Gawker, she took Tolentino with her. It was there Tolentino’s skill for shaping impossibly complex feelings into precise words became apparent. During her two-year tenure as deputy editor, she maintained an exhausting output – several pieces every day – but coupled her elevated internet commentary with exploration of knottier subjects. Trick Mirror’s essays on children’s literature, sexual assault on college campuses and the dangers of a convenience economy have roots in work Tolentino began at Jezebel.

But her experience in women’s media, though formative, also led her to interrogate her growing frustrations with writing for the internet. “I got so sick of the self-explanatory, firm resolution, the movement at the end of the essay where it’s like, ‘Here’s why I was right all along’ or ‘Here’s why I’m actually good and here’s why it wraps up like this.’ I just don’t trust it,” she now says.

For Tolentino, the challenge became to “take a question and push it as far down into the ground as possible… [to] write arguments without conclusions and see how long you can go doing that”. Satisfaction came from “having moved as far away from my original place that I could”. As a result, Tolentino’s writing still feels unsealed. Her essays and articles are finished but not finite. She is not constricted by the pressure to make the definitive point; confident in the knowledge that it is a pleasure to simply bear witness to her arguing with herself.

This increasingly singular approach to reporting brought her to the attention of The New Yorker. She accepted a job offer from the magazine in 2016, the same day Gawker announced it was filing for bankruptcy after losing a $US140 million invasion of privacy suit brought against the site over the publishing of a sex tape by wrestler Hulk Hogan. Tolentino insists her decision was made independently of the news.

Despite her upstart blog origins, The New Yorker’s editor, David Remnick, clearly had no intention of trying to straighten Tolentino’s eclectic instincts when he hired her into the literary institution. Her most talked-about pieces for the magazine glide between vape culture, the rise of athleisure wear, Borat jokes, house plants and the cultural impact of the Me Too movement.

Frequently she blurs autobiography and cultural criticism, displaying her ability to digest huge amounts of information and report it back as simply as ordering a sandwich.

By her own admission, Tolentino doesn’t have one subject that consumes her. Rather she’s “attracted to writing about things that contain poles within them … that can be true and false at the same time. Things that are magnetic but also repulsive, that are full of promise but also punishing.” She believes “our best qualities are entangled with our worst. The most productive impulses that we have can also be the most devastating.” Reflecting on that dichotomy in her own life, she says: “I think one of my best qualities is that on a personal level I’m pretty carefree, and I think one of my worst qualities on a personal level is that I’m pretty careless, and those things will always be related.”

Trick Mirror’s focus is disparate; its essays span reality TV, marriage, the commercialisation of feminism, scams and religion. But they are linked by a curiosity about how visible and invisible, internal and global, systems shape our lives.

The confluence of experience that brought Tolentino to write Trick Mirror allows her to thread the book with personal reflections on seismic topics. In “The I in the Internet” and “The Story of a Generation in Seven Scams” she looks at how the pieces of ourselves that feel unique and pure are constructs of engineered trends designed to keep us engaging in a world that treats us as consumers and products. “The Cult of the Difficult Woman” argues that our good intentions in changing the way women are judged in the media have created a toxic slipstream where legitimately deplorable behaviour is shaded from criticism or, if called out, that criticism is misread as sexist. “Always Be Optimizing”, meanwhile, points to the hamster wheel of brutalising work–life balance that leaves us exhausted and reliant on expensive comforts that tie us back to our exhausting jobs.

Among all the systems she dissects, religion stands out as the most personally fortifying. “Ecstasy” is Trick Mirror’s most luminous essay – wherein she draws parallels between the ecstasy she experienced in church with her later love of music and the drug MDMA. It also offers the clearest impression of how systems influence not only what she writes but also the way she thinks. “A lot of what I find the most transcendently pleasurable and important is still related to religion,” she reflects.

In her late teens, Tolentino’s connection to the church began to wane as she struggled with the completeness of religious narratives – right and wrong, heaven and hell, good and bad. “That might have been an early inkling that I wasn’t inclined towards neat stories,” she says. The doctrine “that the real kingdom is in heaven” was a point of particular frustration – Tolentino remembers how it often “allowed people to interact with the world [in a way] I found super-repulsive. I think there is a conservative Christian who really believes that the Earth is ours to plunder.”

Revisiting this time in the church when writing Trick Mirror, Tolentino was surprised by the elasticity of her memory. “I was very religious for longer than I thought,” she admits. She worked through notes and diaries with her friend and freelance editor Carrie Frye, who remarked, “I feel like there might have been more tension there that you don’t remember.” When Tolentino re-read old journals, she saw Frye was right. There were years of “really intense overlap between wanting to trust my questions and instincts and desires for ecstasy of a different kind and really feeling that I was put on this Earth to be a child of God”. Like many raised within a religious faith they no longer hold, Tolentino filled the space left with “a wealth of substitutes”. But, she notes, “There are parts of it, in terms of a moral self-searching, that writing has provided.”

Her lifetime of journals comes up frequently in her book, and in conversation. Reading back over these tomes she was “super-aware [that] as a kid I was persuasive to myself most of all ... that even in narrating my day I would be trying to bend it into a shape that made me come out well”.

Tolentino never wanted to “condescend to the reader” by twisting reality to give Trick Mirror an “obvious and aesthetically unbearable end” that promises all is not lost. But it should be said, for a book that deals so intimately with the parts of our lives that make us feel the most lost and confused, it’s not a depressing read. Rather, the rejection of final answers creates a sense of sunny nihilism, in which Tolentino suggests any illusion of meaning is misleading.

“I think all writers should be suspicious of being persuasive,” she says. “We’re really good at bullshitting ourselves.”

This article was first published in the print edition of The Saturday Paper on Oct 19, 2019 as "Jia metrics". Subscribe here.

Wendy Syfret
is a Melbourne-based writer and editor who formerly served as managing editor of VICE Asia and Australian editor of pioneering fashion publication i-D.