To understand the intricate mechanics of our modern world, to make sense of the gig economy, to comprehend the hypocrisy of politics at the Oscars or the idiocy of the phrase “worst year ever,” readers scroll through their social media feeds and click on cultural criticism.
Her work is commonly described with traits that characterize the best of online writing: She’s funny, deeply knowledgeable about her subjects and armed with context. She finds herself drawn to stories best explained as, “Here’s a topic everybody’s mad about. Should we be?” she says with a laugh.
Forbes recently named Tolentino to its prestigious 30 Under 30 list of up-and-coming media professionals.
Such accolades arrive with an assumption: that the innovative twentysomething appeared on the scene almost from vapor, an easy narrative that discounts years of hard work and an uncanny skillset.
“I still feel very new to this,” Tolentino says in a phone interview while walking her dog in New York City. But then, a few minutes later, adds the sage advice of an old pro: “Writing succeeds when you can’t see the effort.”
Tolentino was born in Toronto and raised in Texas, where she grew into an insatiable reader and regular writer. During summers, she often read a book a day and today still regularly reads half a book before bed.
On Grounds she made a name for herself as a Jefferson Scholar and as a columnist for the Cavalier Daily. It was the first glimpse of the writer readers seek out today.
Caroline Rody (Grad ’91, ’95), a UVA English professor, describes Tolentino as one of the top literary readers she’s taught as an undergraduate. Her writing showed a maturity with “an uncommon grasp of the big picture” and displayed a “dazzling intellect,” Rody says.
But after graduation in 2009, the job market for humanities majors cratered. Tolentino served in the Peace Corps for a year, sending dispatches from Kyrgyzstan to her friends. She later earned an MFA from the University of Michigan.
She held less-than-glamorous jobs: writing college admission essays for high school students, writing grants and ghostwriting two books.
But she also tested the market as a freelance writer, which then led to a full-time gig at the Hairpin, another popular site geared toward women, before landing at Jezebel.
In August, Tolentino started writing full time for newyorker.com. Her essays have included on-the-ground reportage of the Women’s March in Washington, the dirty secret of Beauty and the Beast, and what The Boxcar Children series says about capitalism.
Tolentino hopes to keep up her indefatigable pace of reading and find room to experiment with her nuanced brand of essay writing. A Forbes 30 Under 30 mention is as much about the future as it is about the present, but for Tolentino, “It’s always been in my best interest to be as patient and chill as possible,” she says. “I never look too far forward.”