Taffy Brodesser-Akner Talks About Her Debut Novel

There are celebrity profiles, and then there are celebrity profiles written by Taffy Brodesser-Akner.

The New York Times Magazine staff writer has earned a reputation as one of the best in the business for her highly insightful, keenly observant long-form stories on some of the most culturally relevant and influential people in the celebrity ecosystem, from Gwyneth Paltrow to Bradley Cooper to Jonathan Franzen to Nicki Minaj. Those profiles have earned her a kind of viral following, but she also succeeds at in-depth reporting, such as her piece on Weight Watchers and diet culture, and a feature on sexual discrimination and harassment at one of the country’s largest retail jewelry chains.

Her knack for weaving a personal essay-style voice into profiles where she so astutely observes her subjects makes her work uniquely thought-provoking, taking her readers beyond the surface and beyond the superficial. She asks the tough questions and goes deeper than her subjects sometimes want her to go, but she does it with empathy, and the payoff is huge.

Ms. Brodesser-Akner brought those skills to bear in her debut novel, “Fleishman Is In Trouble,” which was released by Random House in June. Since then, it has become a New York Times best-seller, and has been hailed as one of the must-read books of the summer. The author recently took time out of her busy press tour to talk to the Southampton Press about her novel and the philosophies and thought processes that inform her work, both as an author and journalist.

Ms. Brodesser-Akner has said that “Fleishman Is In Trouble” was born out of her desire to examine the world of modern dating, where men and women who, in their younger years, had been forced to, as she’s said in other interviews, “show up in their disgusting human form” on in-person dates and were now, divorced and in their 40s, engaging in an entirely new way of meeting people and forming relationships, thanks to the proliferation of dating apps. When her efforts to pitch it as a long-form magazine story did not work, for various reasons, she decided to write a work of fiction. What started as an effort to examine modern dating became more of a book about divorce. In an interview with Jennifer Lipman of the Jewish Chronicle, she described the book as “the piddling thoughts of somebody one summer who had a question about whether marriage is really a viable institution if it keeps failing us, and how women are supposed to survive if the rules keep changing on us.”

She explores these questions through a cast of fictional characters, including Toby and Rachel Fleishman, who are going through a divorce. Toby Fleishman is a liver doctor in Manhattan, making more than $200,000 per year, which sounds great, except it’s not when you are surrounded by “finance bros,” as she terms them in her novel, and, more importantly, when your wife is making significantly more than you running her own high-powered talent agency and is essentially the primary breadwinner, leaving her husband to assume primary caregiver duties for their two children.

The story is narrated by Libby, a college friend of Toby’s who is experiencing her own midlife crisis of sorts, after giving up her career as a staff writer for a men’s magazine and trying to adjust to life as a suburban mom. Libby’s character arc takes shape in the middle and latter portions of the book. The initial focus is on Toby, who is enjoying his newly single life, thanks to his popularity on dating apps. But his new world is thrown into disarray when Rachel drops the kids off early for his weekend time with them, and then disappears for weeks, leaving Toby to deal with the fallout. Toby’s perspective is the earlier focus of the novel, and the points of view of Rachel and Libby come later.

Ms. Brodesser-Akner has freely admitted in the many interviews she’s done on her book tour that her borderline obsession with interrogating and thinking about marriage and divorce probably springs, at least in part, from her own lived experience as a child of divorce. She wrote the first draft of the novel in roughly six months, mostly, she said, while she was on airplanes or waiting for someone to show up for an interview. Immersing herself in those big-picture questions didn’t really change her thoughts on marriage or divorce, and she said she didn’t expect it to. That’s not really the point anyway. She says she is “marked by ambivalence on every topic you can think of,”—although she is quick to point out that that doesn’t mean she doesn’t have opinions; she does. The inclination toward ambivalence is what she says has made her successful as both a fiction writer and journalist.

“I really think that I’m able to see both sides of things in a way I used to feel was a weakness, but that has worked out for me,” she said. “I sold that book two years ago, which means I was writing it three years ago, and I think sometimes, oh my god, I must have been really trying to work through something at that time; oh you poor dear. That’s the tenor of how I look at it now. Which means that everything I write, from writing about my flat feet to conversations about whether my job is legitimate, it’s not the writing that works them out, it’s the writing and see the reaction to the writing that works it out.

“There really is something powerful with people agreeing with you,” she added. “With people coming out in numbers and saying, I feel this too. Finding that you’ve moved people is nice, because that’s what a writer wants to do. Finding that you’ve spoken for people means you weren’t alone this whole time, in the category of things that would’ve been weird to bring up at lunch.”

From that perspective—from the feedback she’s received from people telling her how deeply they related to the characters and their struggles and motivations and humanity--Ms. Brodesser-Akner feels that she has achieved what she set out to achieve when she wrote the novel.

People have said Fleishman Is In Trouble is a novel about marriage; about divorce; about the particular struggles of people in mid-life, with all its attendant crises. That is all true. But it is also about the particular struggles women face, especially as they try to balance motherhood and careers. Libby addresses this early on in the novel: When I told people what I did, they’d say “Being a mother is the hardest job there is.” But it wasn’t. The hardest job there was was being a mother and having an actual job, with pants and a commuter train pass and pens and lipstick. Back when I had a job, no one ever said to me, “Having an actual job and being a mother is the hardest job there is.”

In speaking about the challenges of working motherhood, Ms. Brodesser-Akner expresses something that doubtless has had that demographic of readers nodding in agreement.

“I think there’s no way to have something called marriage, a heterosexual marriage, in which women don’t get screwed a little bit. Either for staying at home or going to work. Either for taking care of kids or for outsourcing it. I don’t see a balance coming toward us. I think the institutional memory of men is too strong. It used to be that the man would come home from work and his wife would hand him a martini. Those things are hard not to want. But women now require this too. The women have had long, confusing days at the office or with their children, and they feel they have the right to speak now. And it’s tough. I have the comfort of community around all that. It’s comforting when people reach out. It must mean there’s a way to exorcise the suffering around a complaint without actually resolving the complaint.”

Ms. Brodesser-Akner’s fashion of invoking her own humanity in her journalistic work is a move most writers cannot pull off without seeming self-absorbed. Ms. Brodesser-Akner not only possesses the skill to make it effective, but does it in a way that elevates the art of that style of writing. She is willing to do it because she believes that it is not only important, but it’s at the essence of what she does. In a profile of the actor Bradley Cooper, where he was unwilling to engage with certain questions about his personal life, she reminds him that “people want to know the artists behind the art,” and reminds him that her job “hinges on that notion.”

She spoke of another experience interviewing a female celebrity for a profile in a popular women’s magazine, where her subject was not interested in answering certain questions, and felt that Ms. Brodesser-Akner’s line of questioning was perhaps sexist; that she was asking questions she would not ask a man. She reminded the woman that she was a “famous person that people loved,” and that by refusing to engage in talking about certain issues, and declining a chance to make herself relatable, she was alienating women seeking the comfort of community.

It’s something she thinks about a lot, Ms. Brodesser-Akner said, and going on a book tour, where she has experienced the role reversal of being the interviewee rather than the interviewer has given her a new perspective on that topic.

“I never related that to my work,” she said. “I related that to the answers of the interviews. In this, I kind of see that I love that people find what they need. That’s the purpose of art.”

Ms. Brodesser-Akner certainly fulfills that purpose in her novel, which surely would have been enough—more than enough—but she also adds the bonus of making the reader laugh out loud almost as frequently as they feel seen and understood in a way that pierces the soul. Year-round East End residents will surely take pure delight—as this lifelong year-round reporter did—in her devastatingly accurate description of the Hamptons, where Toby and Rachel own a second home:It was all such an insult, the Hamptons. It was an insult to economic disparity. It was an insult to leading a good life and asking hard questions about what one should sacrifice in the name of decency. It was an insult to having enough—to knowing there was such a thing as enough. Inside those houses weren’t altruistic, good people whom fortune had smiled down on in exchange for their kind acts and good works. No, inside those columned, great-lawned homes were pirates for whom there was never enough. There was never enough money, goods, clothing, safety, security, club memberships, bottles of old wine. There was not a number at which anyone said, “I have a good life. I’d like to see if I can help someone else have a good life.” These were criminals—yes, most of them were real, live criminals. Not always with jailable offenses, but certainly morally abhorrent ones: They had offshore accounts or they underpaid their assistants or they didn’t pay taxes on their housekeepers or they were NRA members.

And worst of all, the biggest insult there was, was where this was all situated. It was at the tip of Long Island, which itself was a bunion on Manhattan. This luxury tip was so precariously placed and so prone to terrible weather, surrounded on most sides by water as the Hamptons was, that the most offensive part of it all was that such wealth was planted in such tenuousness. One bad storm and all of these houses were blown away. And you know how these pirates felt about that? They didn’t give a shit. Go ahead, let God blow the wrath of shame and destruction down on us. Not to worry, we’ll make a killing on the insurance, and also we have a place in Aspen!Despite her, let’s call it less than generous characterization of the second home-owner set in the Hamptons, Ms. Brodesser-Akner said, with a laugh and without hesitation, that she would want a second residence in the Hamptons if the opportunity presented itself. If her career trajectory continues along its current path, that’s not a far fetched reality at all.