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The Herald Eroded Nathaniel Rich’s Self-Doubt

Design by Michelle Vong.

Nathaniel Rich described his experience at Yale much like many of us do today—as a speck of youth. He was unsure what profession to follow, but sure that there were two types of kids: pre-professional ones and ones that are pleasant to be around. 

Rich, a boy born from parents of literary professions, an editor of his high school paper, a guy swinging through the nation’s best schools, was propelled away from the English major by insecurity in his writing. He shared, “I didn’t know I wanted to be a writer when I got to Yale. I loved writing. I loved reading.” As a literature major (the equivalent of Yale’s current comparative literature major), Rich just wanted “opportunities to write.” In high school, he had fallen into journalism not out of a passion for reporting, but as a default—journalistic writing seemed the most accessible. But he soon realized that it wasn’t for him. 

Whereas, in his eyes, the Yale Daily News was for the “self-serious pre-professional journalistic types” whom he didn’t identify with, The Herald was a haven. He described the allure of the older students within the magazine. He put it simply—to him, they were “smart and funny.” And so Rich fell into the creative and quirky weekly, and it became the essence of his literary education. 

Many assume that working with a magazine is a natural side dish, with an English major as the main course, but Rich crafted a different plate. Turns out to be a writer you don’t need to take writing classes, you just need to write. 

Rich took one writing class in his time at Yale, English 120, the equivalent of today’s English 1020 “Reading and Writing the Modern Essay.” Acknowledging that his view is controversial, he explained why the workshop model wasn’t for him. He either admired the professor and molded himself to appease them, or he didn’t and his cares floated downstream. He felt the workshop format “dilute[s] the originality of the writer’s work.” Anything sparkly and novel, he remarked, caught the attention of the editing audience, and got smoothed out, and thus, the workshop format produced a shocking uniformity. And though what he spoke of implied that he might have done poorly in his English 120 class, Rich emphasized that he worked hard, thought highly of his teacher, and did well. He both “didn’t care what other freshmen thought” and felt the workshop model erode his confidence. He knew it wouldn’t turn out well if he was a self-conscious puddle of a writer by graduation day. 

Within the freedom of The Herald though, Rich’s voice began to emerge. He describes the constellation of his writing from the magazine, offering that “the tone of each piece is inconsistent because I was trying out different personas as a writer.” He loved that The Herald offered him the liberty to do so, even when his voice got wacky and didn’t work well. But he saw those pieces as crucial development, a sort of pruning. Rich shared, “That was an important part of my development as a writer because I felt so much pressure even then to figure out what’s my voice? What’s my unique writing, what’s my style, and I had no idea what it could be. All I knew is there were writers I admired and they had very distinct styles.” So he tried each of them on: versions of Martin Amos, Joan Didion, whomever he was reading at the time. But eventually, as he said: “you become yourself because there’s no other choice.”  

Little Rich in the Big City 

The real beginning of Rich’s story starts south of Connecticut. Hailing from New York City’s midtown Manhattan, he attended The Town School (colloquially known as “Town”) through the eighth grade. He noted, with the acknowledgement that it was coming from a “Manhattan perspective” that Town felt “middle-class” to him. The kids at Town didn’t have second homes and the parents held professions like teachers, doctors, or lawyers. As Rich transitioned to Dalton—another private day school—in 9th grade, he suddenly felt like a fish out of water. He perceived himself as “the poorest person,” acknowledging that “even though it’s not like I grew up in poverty, there was a level of wealth that I’d never seen before that, and it seemed like everybody—almost everybody—had it.” 

His experience at Dalton speaks to New York as a microcosm. Despite his father being a writer for New York Magazine and a columnist for the New York Times and a mother who was an executive at Harper Collins, he still felt small next to the other Dalton families. Rich was consistently sure to step back and emphasize his awareness that he was “in a very privileged position relative to the rest of the country.” But within the New York City ecosystem, comparison transformed. 

Rich shared that the economic class that saturated his elementary and middle school is a relic of Manhattan’s past. Dalton now, he thinks, has entered a new echelon of wealth. It strikes Rich that the children of creatives or teachers can’t be a part of these Manhattan institutions, unless they’re outliers with “some angle or other” as he put it, whether that be rent control or independent wealth. And that shift matters a lot to Rich, because those kids of creatives or academics were the ones he spent weekends renting VHS tapes and grabbing pizza with.

From one pizza hub to the next, Rich did his four years in New Haven, afterwards taking a hop back to his hometown. That summer of 2002, a turning point came when editor Robert Silvers, a stern, imposing man, validated him. 

The founder of the New York Review and an editor of prolific authors, from Joan Didion to Norman Mailer to James Baldwin, Silvers interviewed Rich for his summer internship at the New York Review. Equipped with clips of his writing from The Herald, Rich entered Silvers’ office. “Do you have any editorial experience?” Silvers inquired and Rich responded with hesitation, sharing about his time at The Herald. To his shock, Silvers responded saying, “Don’t be embarrassed at all. That’s absolutely, that’s an editorial position.” So Rich went into more detail, sharing about his sophomore year as the Arts Editor. Rich spoke about that interview with fondness in his voice, recalling, “Roberts was like, that absolutely counts. And you should take pride in that.” 

With that pride, and a referral through his internship with Silvers, Rich moved to San Francisco. An advance for his book, San Francisco Noir—a guidebook exploring the city through film noir—along with sporadic freelance writing funded his frugal time on the West Coast. Rich got a taste of the lifestyle he was testing—and loved it. To him it wasn’t anything shiny nor glamorous. With a father as a writer, he “never had any illusions that it was some kind of glamorous thing.” In his mind, his era in San Francisco was a “kind of bifurcation”: a split between writing his own novel, The Mayor’s Tongue, and writing from others’ funds. He detailed the breakdown of his days: 9am writing San Francisco Noir, noon visiting locations that appeared in the movies like an alleyway or an abandoned bar, then he’d cozy up, watching a VHS tape he rented from the public library to study up for his next location visit. As the film concluded, he’d hop back into his desk chair, and from 4pm to 7pm he’d write for his own novel in “completely in secrecy.” He didn’t let anyone look at it, touch it, or read it, because he was “insecure about it” and “didn’t know if it sucked.” It turns out it didn’t suck, because at least according to Stephen King, it was “terrifying, touching, and wildly funny.” Funny how central self-doubt tends to be to the artist. 

Rich’s writing journey shook out from there. He became an editor at The Paris Review for a little while, before getting married and moving to New Orleans. Now he teaches at Tulane while he writes on his own. From his nook in The Big Easy, Rich’s words, so cushioned with that articulate diction that only comes from someone who spends all day crafting sentences, sang the value of his time spent with that small, fun-and-freedom-filled weekly, The Herald, which set him up for his life as a writer.

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