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The Sad Young Literary Man Is Now a Middle-Aged Dad

Keith Gessen wrote a memoir about family life. His wife, Emily Gould, is mostly okay with that.

Keith Gessen and Emily Gould with their children, Raffi and Ilya. Photo: Gillian Laub for New York Magazine
Keith Gessen and Emily Gould with their children, Raffi and Ilya. Photo: Gillian Laub for New York Magazine
Keith Gessen and Emily Gould with their children, Raffi and Ilya. Photo: Gillian Laub for New York Magazine

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Raffi Gessen-Gould, age 6, is an expert on these topics: Greek gods, international currency exchange, sharks, geology, when his father will go bald (when Raffi is a teenager), invisibility cloaks, waffles, slingshotting stretchy rubber snakes across the living room, making slime without his mom, and the benefits of getting slime stains on the couch (they feel good to touch). He is the second-tallest kid in his class. He can jump the farthest. He sleeps on the top bunk. The longest book he has ever read is 199 pages. He has not read his father’s new book, Raising Raffi: The First Five Years, which is 241 pages, and he does not seem in any hurry to do so. He did ask if he was responsible for the bad crayon drawing on the cover. (No.)

This Raffi — the real-life Raffi — will turn 7 in early June. The character Raffi in Raising Raffi will never be that mature. That Raffi is a creation of his father, Keith Gessen, a device through which Gessen explores his parental fixations: the pros and cons of teaching a child Russian or making a child play hockey, the problem of gentrifying schools, and conflicting camps of parenting advice. Raffi the literary creation is a bit of a hooligan — or, as his father puts it, a collection of “pain points.” That Raffi spends a lot of time doing stuff like punching his father in the nose and breaking down toddler gates to get into his parents’ bed at 2 a.m. That Raffi wonders what it’s like to sit on his infant brother Ilya’s head and follows through. Raffi the real person has outgrown all that now.

One recent Saturday evening, after his father opened the door to the 990-square-foot Brooklyn apartment Raffi and Keith share with the writer Emily Gould (Raffi’s mother and Keith’s wife) and Ilya, now 3, I asked Raffi how he felt about a book coming out with his name in the title.

He’s not a kid who limits his answers to areas in which he possesses expertise. “I don’t know,” he said.

Words are the family business. Gessen, 47, was a co-founder of the literary magazine n+1 and has published two novels. Thirteen years ago, Vanity Fair called him the “red-hot center to the Brooklyn literary scene,” or “at least close to it.” Gould, 40, has published two novels and a book of nonfiction, though she’s best known for her work at the media-gossip website Gawker, where her funny, confessional writing helped define the voice of the early-aughts internet. The two very publicly hooked up in 2007, not long after Gould described for Gawker’s audience Gessen bartending at an n+1 party with “tufts of black chest hair peeking from the unbuttoned collar of his American Apparel polo.”

The day I arrived, he wore a pressed blue-and-white dress shirt and dad jeans, and she stood at their kitchen counter, an Army-green apron tied around her waist, frantically whisking egg yolk and olive oil in an aluminum bowl in a second attempt at making aïoli. “I fucked it up the first time because I got cocky, and now I’m like, I don’t know, man!” she said. Her brazenness, which was once expressed in a widely circulated photo of Gould in a maillot swimsuit, middle finger aloft, was now focused on the domestic. “It’s not going the way Alison Roman promised.”

The two had tidied their Clinton Hill place to look as though theoretical kids lived there, or kids plus a nanny, but no actual kids; everybody knows you can’t really clean with 3- and 6-year-old boys around, just as you can’t really think or write. A few weeks before I showed up, Gessen, who is an assistant professor of magazine journalism at Columbia Journalism School, had traveled to Ukraine on a reporting trip for The New Yorker. Wasn’t that exhausting?

“Uhhhh, yeah,” said Gessen, staring at Gould. “I feel like it must have been much more exhausting to be here.”

Raffi and Ilya then appeared. They are adorable, truly adorable (at least to houseguests, perhaps another fiction): Gould’s glowing skin, Gessen’s soulful eyes. Also, like all young children, they are functionally insane and black holes of adult attention. Gould, still whisking, recounted for Gessen, who had spent the afternoon at a memorial service, her day with their sons: She dropped off Raffi at a birthday party, then accompanied Ilya to a playdate that turned dark after the toddlers, who were playing in a room with no adults, turned out to be decorating the walls of the host’s apartment with sticks of tempera paint. The hosts were kind but very reasonably not pleased. “They didn’t even pretend they weren’t freaking out,” Gould said. “If it were me, I’d be like, ‘Oh, who cares about a little paint all over the walls,’ but inside I’d be like, you know … So then we left. It was like, Okay, well, we’ve disgraced ourselves, bye!

After an hour of whisking, and no emulsion, we sat down at a tiny table below a bookshelf that contained David Foster Wallace, War and Peace, and an esoteric Russian literary magazine to expertly roasted chicken and an elegant platter of spring vegetables — the asparagus, radishes, carrots, and potatoes all cooked with precision and aesthetically arranged, a task that had been completed before I showed up, because it’s one thing to try to create with time and focus and another to do it amid a three-ring performance of domesticity. “Imagine what it would have been like with some garlicky aïoli,” Gould said.

The kids offered their own deranged critiques. “She picked a good chicken!” “Is that pepper?” Then Ilya left the table to put one step stool on top of another in an effort to reach cookies on a high pantry shelf, and Raffi started feeding chicken to the cat. As often happens in family life, the scene was too much, not enough, sublime, and untenable all at once.

“I couldn’t write this book. I mean I didn’t write this book,” Gould had said once the kids had retreated to their bedroom, possibly, she suggested, to murder each other. “Keith did something very different than I would have done with the material.” And yet she’s battling creative territorialism and envy. She’s also afraid of the book’s publication and a little stunned that it’s happening at all. Over the past 15 years, Gessen and Gould, but especially Gould, have mined their lives for writing material, and over those same years, readers have subjected Gessen and Gould, but especially Gould, to truly vicious comments. (Both, but again especially Gould, have dished out toxic quantities of snark.) Now their son is the title character of his father’s memoir, opening up Raffi and their parenting to public scrutiny.

I left Gessen and Gould with a huge mess, the physical one in the apartment but also the two-writer-parents problem. “Early in our relationship,” Gould said, putting away the leftover chicken, “if you had told me Keith would be the person to nonfictionally describe this part of our lives, I would have been like, What? Also, We live where? You’re not rich? A pandemic? You weigh how much?

Photo: Gillian Laub for New York Magazine

Masha Gessen, Keith’s sibling, has a theory about dad books: “There’s a particular narrative to the maturation of an American male, urban, of a certain class, who just, like, doesn’t have to take care of anybody for a really, really long time. It’s a very odd position to be in … and I think it’s also kind of extraordinary. You’re a fully formed human being by the time you have to take care of another person.” The result is you get a writer, like Keith, “who is shocked to his core by this awesome responsibility and difficulty,” and that is writing gold, an insightful character in a gripping, high-stakes, relatable drama. “Where else, in what other period, in what other country,” asked Masha, who is eight years older and also an acclaimed writer, “does a person not carry responsibility for another human until they’re completely grown up?”

When I returned in the morning, Gessen was in gym shorts, vacuuming, and Gould was in sweats, negotiating with Ilya over breakfast. (“How about if you have a pink waffle and then you can have a waffle cookie?” Ilya shook his head. “You don’t want that deal?”) Gould told me she had texted Alison Roman, whom she once profiled, about her aïoli fiasco. Roman told her the problem was the shape of the bowl; it was too wide and shallow. She needed a narrow one with tall sides.

Around 10:30 a.m., efforts mounted to go to the playground — the kids out of their pajamas, Gould into her makeup, Gessen into a long parka that looked like something Jonathan Franzen would wear birding. The day was freezing for spring. Gessen’s friend Rebecca Curtis, a longtime member of his writing group, once described Gessen in a short story as “a child of winter,” which Gould interpreted for me as “a person forged at a dark time who can do well in situations with subsistence-level resources, even sort of thrive in that environment.” He’s a little grim; she’s more interested in comfort. “He loves work,” she said. “He loves to work hard. He has made his life as difficult and complex on a professional level as possible.”

The kids rode scooters down Greene Avenue beneath the flowering Bartlett pear trees. When we arrived at what Gessen calls “the rich playground” in Raising Raffi, the place was almost entirely empty — a big bummer, especially for the adults. All books that touch on parenthood, even the literary ones, eventually get around to advice. In About Alice, Calvin Trillin relays his wife’s: “If your child is in a school play … go to every performance, including the special Thursday matinee for the fourth grade.” In I Feel Bad About My Neck, Nora Ephron’s is: “When your children are teenagers, it’s important to have a dog so that someone in the house is happy to see you.” Gessen’s is: Live as close as possible to your children’s school, playground, and day care, as the only real solution to the brain death created by young kids in a Brooklyn apartment is to meet up with kids other than your own, outside.

Also: Make more money.

That weekend, Gessen and Gould happened to be in the midst of what Gessen described as a “tricky and slightly irrelevant but maybe not entirely” housing crisis: Their landlord put their apartment on the market; they wanted to buy it but couldn’t afford to and needed to move. Shortly after we showed up at the playground, a Realtor texted about a nearby condo where, for $899,000, you could live in a basement near the Brooklyn-Queens Expressway. Might we walk over right now? The owner, a Pratt student from China who almost certainly did not buy the place with money made from words, was leaving for the day.

Gould and the boys stayed at the playground. On the way to the condo, Gessen and I talked about the dream of being a writer versus the reality and how part of the problem, for many of us, is that we form those writer dreams before we are adults. Gessen’s, in particular, were shaped by Russian Jewish parents who moved from Moscow to Massachusetts when he was 6. His mother was a translator and critic. His father was, and is, a computer programmer. In his émigré home, the writer was revered. Teenage Gessen’s understanding of the literary life was that you’d be poor and alienated from society in a romantic On the Road kind of way, and once in a while you’d come into New York and drop off a manuscript.

In high school, Gessen played hockey and football, in part because he had a lot of physical energy and his father was an amateur boxer and in part because he’s susceptible to external definitions of manliness and achievement. Through his first two years at Harvard, he believed that real writers couldn’t just hang out with other writers. A group of writers was a contradiction in terms. Nobody would have real lived experience to write about. “That’s not how literature is supposed to work,” he said.

Gessen’s views on this changed after he became friends with Chad Harbach, another ambitious Harvard student who wanted to be a writer, and saw Benjamin Kunkel read at a Harvard literary magazine. Kunkel’s work thrilled and impressed him, as did another student’s, Mark Greif. “They were actually, like, way beyond me in what they could do,” Gessen said. He quit football. (Being concussed wasn’t going to help his writing career.) After graduation — and a short first marriage to a Russian girlfriend who needed a green card, plus a few years pursuing an M.F.A. at Syracuse University under George Saunders and Mary Karr — Gessen, along with Harbach and Kunkel, landed in New York. Greif was nearby in New Haven. They worked on novels and Ph.D.’s., and, in 2004, along with Marco Roth and Allison Lorentzen, started n+1. The journal was wildly successful, both the magazine itself and the parties it threw. Gessen liked bartending, and he also liked women. Gould attended one of those parties and described Gessen as “making sure the undergraduate-looking girls got as many beers as they needed.”

Gessen tells the story of their meeting this way: “I was doing n+1, and Emily wrote mean things about me on Gawker, and then I was like, Oh, that girl’s pretty. And then Emily came to an n+1 party and wrote catty things about it. A friend of mine was like, ‘I think she likes you.’ And I was like, ‘Yeah, I’m interested.’ ”

Gessen’s first book, published in 2008.

Around this time, Gessen published his first novel, All the Sad Young Literary Men, to both fanfare and contempt. In 2008, Franzen selected Gessen for a 5 Under 35 award from the National Book Foundation, and The A.V. Club called All the Sad Young Literary Men a “vacant bildungsroman.” One of Gould’s Gawker co-workers teased Gessen so relentlessly for all the Harvard, Harvard, Harvard mentions in the novel that Gessen agreed to cross out every “Harvard” in a copy of the book and replace them with “Florida State University.”

Meanwhile, Gessen’s n+1 co-founders soared. “I was not the most educated, let’s put it that way,” Gessen said. “Do you know what a Marshall scholar is? It’s like a Rhodes scholar but for smart people.” Greif was one and is now a professor of English at Stanford. “I did a lot of editing, but it wasn’t necessarily stuff that I could do,” Gessen said. “It was over my head a little bit. A little bit.” Harbach’s novel, The Art of Fielding, drew a huge advance and became a best seller. Kunkel established himself as a left-leaning public intellectual. Gessen described him as “probably the most eloquent expositor of Marxian economics currently writing in the English language.”

The competition in his marriage Gessen can handle. If we’re honest, he’s winning, and he’s proud of his hot spouse. “If somebody’s like, ‘You’re the husband of Emily Gould,’ I’m like, ‘Yes, I am!’ That’s something I chose,” he told me. But competition with Masha? “Siblings are tricky,” he said. Masha’s status and credentials as a journalist and public intellectual, particularly regarding Russia and fascism, are unassailable.

Gessen published his second novel, A Terrible Country, in 2018. This one — narrated by a broke, bookish, lonely hockey-playing young man who spends a year in Moscow taking care of his grandmother — is far more accomplished. But it too drew praise and scorn, sometimes in the same review. In the New York Times, Dwight Garner described Gessen’s books as “ramen-packet versions of Hemingway’s A Moveable Feast” yet conceded that A Terrible Country “gets good, and then it gets very good.” On his way to Ukraine a few weeks ago, Gessen walked into a random bookstore in Poland. He found a copy of A Terrible Country on a shelf. “I’m so excited and I pick it up and I’m like, This is amazing. What a wonderful moment.” he said. “And then I look at the author bio. It says, ‘Gessen is a journalist,’ whatever. ‘He is the brother of Masha Gessen.’ ”

At the condo near the BQE, he made a video for Gould. The place was practical and unromantic — off a concrete courtyard with no landscaping, next to a loud school, zero effort spent on charm or finishes — but you could imagine some days when you wouldn’t want to stick your head in the oven. “You could do a window here so it’s not like a dungeon,” Gessen said, recording into his phone. “The ceilings are reasonable.” The worst part, or so it seemed to me, was that you’d have to walk to those Clinton Hill playgrounds and handle your jealousy. “Oh, that guy’s book came out, and it’s a best seller,” Gessen imagined his inner monologue. “But his kid … you know, his kid is having a meltdown and just peed in his pants. So I guess things aren’t going so great, Mr. Best Seller.

Before my visit, Raffi asked his father if Raising Raffi would make him famous. Gessen said, “Don’t worry, nobody reads my books.”

“Is that because they’re bad?” Raffi asked.

“No, they’re good,” Gessen said. “That’s why nobody reads them!”

Gessen hopes that if and when Raffi does read Raising Raffi, he’ll “think it’s funny and find it an interesting recounting of his early years.” (Gould jokes that Ilya might be miffed if there’s no sequel, Investigating Ilya, but that he’s also wise enough to know he’s not really missing out.) He acknowledges that it’s “an ethical minefield” to publish works about one’s children. “Everyone writes about their parents,” he said. They rationalize to themselves, “My parents made a decision to have me. Now I’m a writer, and I’m getting my revenge!” But children didn’t ask to be born, and they can’t meaningfully consent.

Gessen received a $75,000 advance for Raising Raffi. For those outside the business, $75,000, minus agent fees and taxes, broken down into the typical four installments (purchase, acceptance of manuscript, hardback publication, paperback publication), minus the loss in salary from taking a book-writing leave from teaching at Columbia Journalism School, is not a life-altering amount of money. This book does not make sense as an economic proposition. Gessen wrote it, he told me, because he loves Raffi and he loves being a parent and Raffi’s bedtime stories and skirmishes at the playground, not Sheila Fitzpatrick’s and Richard Pipes’s competing hypotheses on Bolshevism, were “the most interesting things happening in my life.” He also wanted to stop taking long reporting trips and remain close to home, for himself and for domestic peace. “I’m scared of my wife,” he said.

None of this was the plan. As a young man, Gessen writes in Raising Raffi, he “imbibed the heroic male literature of family neglect: Henry James, who skipped a family funeral because he was finishing a story … Philip Roth, who refused to have children; Tolstoy, who had many children and a long marriage but who still managed, at the very end of his life, to walk out on them.” Right up until Raffi’s birth, Gessen was still asking himself questions like, “When the baby is little, couldn’t you rock his cradle as you answer emails or write a novel?

But for all his talk, pre-fatherhood, about how he was going to stay committed to literature — of how, in William Butler Yeats’s formulation, “The intellect of man is forced to choose / perfection of the life, or of the work,” he would choose work — Gessen is an extremely engaged parent. In Raising Raffi, he tells a story about being kind of shocked to learn that his own father hadn’t gone to parent-teacher conferences; to Gessen, even in preschool, these were “major events.” His father was a product of his times. He was and remains devoted. He drove Keith to hundreds of hockey games and taught him “math, physics, how to drive, and how to throw a left hook.” But according to Masha, Keith is consumed with parenthood because he aims to be a parent like their mother, who died when Keith was in high school. “Keith grew up a boy with a mom who just unambiguously, unequivocally thought he was God’s gift to the universe,” Masha said. “If you expect that to be a really great parent you have to love unambiguously every moment of the day, that’s a really hard job.”

The need to renegotiate what this kind of all-enveloping, traditionally maternal love means for a new father who is a Russian and a Jew and a competitive person in New York who is not rich animates much of Raising Raffi. As with a lot of contemporary American fathers, part of the concept seems to be viewing child-rearing as a project at which to excel. Gessen is up six times a night, worried and Googling things. He really gets to the bottom of why The Very Hungry Caterpillar is magnificently illustrated but clunkily written. Not all his material is novel. Gould calls her husband “the Christopher Columbus of mommy blogging.” (Let that fully sink in.) The first draft of the book had a lot more about money; Gould told him to take it out. (That was a “craft note,” she says; the material got repetitive and boring.) In the book, he acknowledges that he felt fine about having no money when he also had no kids, and he would like more money now. Still, “at a certain point,” Gould told me, “it’s like, ‘Shut up or fix it.’ ”

Among the more fundamental insights in Raising Raffi is the idea that to be a happy, consistent, successful parent, you have to accept that you are the person you are, whoever that may be. You can’t engage in what Gould describes as “durational performance art.” In the book, Gessen defines himself as a “mushy, sometimes yelly Russian father” who could not make it through The Runaway Bunny, as he reads it not as a comforting tale of a steadfast mother but as a tale of parental “terror and madness.” What he does not say is the obvious: He’s a writer with a strong autobiographical impulse. So he’s going to write about his kids.

That afternoon, with the boys transferred back into Gessen’s care, I returned to the condo with Gould. She did not grow up in an émigré family. She grew up in suburban Maryland, and while she does not want that life — no Maplewood or Montclair, thank you! — neither does she want to live in an ugly, austere apartment. The desire for comfort and status, and the idiocy of that desire, has been a major theme in her work. The place was fine? “It’s very project adjacent,” she said as we walked back up Lafayette Street. “That would really be the end of my brownstone-fantasy life. Not that we are far away from that now.”

Gould’s New York Times Magazine cover story, also from 2008.

It’s so hard to figure out how to do it right. After Gould graduated from college, she worked at a New York publishing house. Then she wrote for Gawker and was so freakishly good at leveraging the power of the then-young internet — her native genius for trash talk, emotionality, and confession resulted in so much outrage and so much engagement (much of it cruel and directed at her) — that she burned too hot, too fast. The toll became unbearable. She had panic attacks and, in 2007, quit. The following year, she wrote a first-person cover story for The New York Times Magazine about her life as an oversharer. That got roundly dunked on too. Yet it landed her a $200,000 book deal, neatly reinforcing her life’s pattern of reaping humiliation and success at the same time.

By that point, Gould and Gessen were a couple. (Gould’s origin story: “Keith was sort of a nerd, and I guess I thought I was cool? And I thought, He’s a writer. He’s a real writer, and this is what it would be like if your life was just about literature. No part of me was thinking, like, Oh, this is probably the person that you’re going to spend the rest of your life with, so I wasn’t thinking about things like which of us will be the person who makes money.”) In the wake of his autofictional first novel and her public shaming, Gessen’s and Gould’s careers started to converge. With a friend, Gould founded Emily Books, a literary press that introduced readers to fantastic, “weird books by women,” including titles by Elena Ferrante and Nell Zink. After Raffi’s birth, the couple both wrote for magazines, including this one, though Gessen tended to land the fancier gigs. (He recently became a contributing writer for The New Yorker.) He also wrote Serious Journalism about Serious Topics, like Occupy Wall Street and Russia. But with regard to personal nonfiction prose, Gould is extremely good at it, arguably better. Gessen is a talented craftsman and synthesizer, a bit of an intellectualizer who inches up to vulnerability and unruly originality, then veers away. (From Raising Raffi: “Raffi did not want to kill me and marry Emily. It was more complicated and more difficult than that. What he wanted was all her attention even as he also wanted to be his own person.”) Gould is a line crosser. Her mind is like a glass-bottom boat. (From Gould’s newsletter: “Being alone for the first time basically ever while also reading a book about the last six years of my own family’s life was a mille-feuille pastry of layered mindfucks.”) She leaves readers with, yes, the sometimes prurient delight of thinking, Did she really say that?

Gould and I walked past the apartment where Gould gave birth to both their children. In Raising Raffi, Gessen wrote about choosing home birth this way: Emily “didn’t want to take a cab to the hospital and possibly give birth in it. This made sense. I imagined looking up at the taxi meter as my child was born and seeing, like, $198. I agreed to explore the option of home birth.” But as Gould now told me, the real story is: She chose home birth out of fear. There’s no controlling the narrative while naked and screaming on your hands and knees. Her years of regularly enduring reader comments like “Kill yourself” left real scars. She refused to labor in a large building filled with strangers. “I could not have some random person coming in to check my vitals or whatever and saying, ‘You look familiar!’ ” she said. “I needed everyone there to be, like, someone who I have a relationship with.”

Gould is scared about Gessen’s book coming out. Raising Raffi is tender and generous, but as every writer, and family member of a writer, knows, “it’s really violating and horrible,” as Gould put it, to be turned into a character in someone else’s story. “He’s still married to me, so he has to be like, She was so beautiful and so intelligent, but also in that one instance she was wrong.” There’s no controlling how readers will interpret the book or what critics will write. In a prepub assessment, Kirkus Reviews described Raffi as having behavioral problems. This upset Gessen. Gould was upset too, but not only at Kirkus. “You just wrote a whole book about how he has behavioral problems,” she said to her husband.

Gessen replied that he wrote a whole book about how all kids have behavioral problems.

But this book is about their son.

“A book is made out of small selfishnesses,” Claire Dederer wrote in an essay about the art of monsters in The Paris Review. “The selfishness of shutting the door against your family. The selfishness of ignoring the pram in the hall … The selfishness that comes from simply saying what you have to say.”

We kept walking through Brooklyn, past all the moms in their perfect clothes, their lives drafted, revised, tweezed, toned, colored, and edited in pursuit of looking bullet-proof before they walked out the door. “Honestly, I feel like I’ve done everything that I can to prepare myself for the psychic assault of what the actual publication of this book will be like,” Gould said. “I bumped up my Lexapro another ten milligrams. I started going to a gym. I’m really trying to take care of myself in every way that I do have control over. I no longer assume that people are going to not be horrible.”

A Harvard man writing about fatherhood is not as vulnerable as a less-pedigreed woman writing about her dating life, but you never know. “My worries are not that I’ll feel jealous. My worries are that he has made my family open to criticism in this way that I have spent the past however many years really trying hard to move away from,” she said. “I am so much more careful now. It’s like our trajectories are …” She crossed her arms. “He’s being less careful because he’s learning how to express this vulnerable part of himself. Maybe I’ll learn how to write sci-fi.”

Upstairs in the apartment, which will not be their apartment for long, Gessen and the boys ate leftover chicken and crashed out on the slime-stained couch.

Publishing is a nightmare. You pour yourself into creating something. You leave your heart exposed — often your loved ones’ hearts, too, even though they did not ask to be included in saying what you needed to say. “I’ve never associated book-publication time with parties and fun and joy,” Gould said. It’s far more elemental and painful. More like parenthood. “Everyone is like, ‘Aren’t you so happy? Isn’t this the most happy you’ve ever felt in your life?’ And you’re like” — Gould sobbed to make her own point — “ ‘Yessssss.’ ”

The Sad Young Literary Man Is Now a Middle-Aged Dad