Author Josh Duboff and Alison Roman on the Aimless Drift of Your Early Thirties

Who better to pen a bildungsroman that delves into the world of glossy downtown media jobs than someone who just crawled out of one himself? After several years working as an entertainment journalist at Vanity Fair, Josh Duboff set off in 2019 to write his debut novel, Early Thirties, initially to process his own experiences as a hustling 20-something in New York City. Six years on, the book assumed its final form as a fictional account of the stiff transition one makes as they round 30, told through two friends, Zoey and Victor, who drift in and out of each other’s lives as they come to terms with the vagaries of adulthood. Fictionalizing his own coming of age left Duboff with something of a “vulnerability hangover,” as his friend Alison Roman put it when they got on the phone last week just before the novel’s release. In conversation, the two got to talking about instability, interview etiquette, and pandemic-era doom and gloom.

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ALISON ROMAN: Well, Josh, do you know what today is?

JOSH DUBOFF: What?

ROMAN: It’s the anniversary of COVID.

DUBOFF: It is the COVID anniversary. Has it been five years?

ROMAN: Yeah.

DUBOFF: That’s actually so insane. I still feel like it was three days ago.

ROMAN: Not to make it about me, but having just had a baby, it’s very similar to COVID in that you don’t leave the house and you do the same thing every day. And when you go out into the world you forget how to engage with people. What I didn’t do during COVID was read a single book because–

DUBOFF: I don’t think I did either, now that I’m thinking about it.

ROMAN: We all thought maybe that would be a cool time to get caught up there, but not a single one. It was terrible. But I did read your book and I loved it. Cool segue.

DUBOFF: That’s an amazing segue.

ROMAN: The thing that came to mind most when I was reading it was the fact that I’m no longer in my early 30s, and how distinct a chapter that is in your life. How old were you when you started writing this? Were you writing about your past or were you writing it in real time? 

DUBOFF: No. It’s funny, promoting a book called Early Thirties when I’m in my late 30s. It does feel odd in a way, especially because there’s a lot of semi-autobiographical stuff in here, reflecting on a previous chapter of my life. There’s a lot of emotions coming to the surface now that I’m talking about it, which has been why I haven’t been able to sleep the past three weeks. 

ROMAN: Just a vulnerability hangover?

DUBOFF: Yeah.

ROMAN: As a person who knows you, as I read it I was like, “I wonder how much of this is autobiographical or if this is just from working in the “industry.”

DUBOFF: I had a really funny lunch recently with a friend of mine, and the protagonist has a really dark, low moment in the book, and he was like, “I didn’t realize you had been in that situation.” He kind of just started the lunch assuming I’d written a memoir or something, which I totally get because I do that when I read other people’s stuff. I feel like so many of the writers that you and I both know write a lot based on their own lives. I get the impulse, but so much of the conversation I’ve had with people who have read early copies has been like, “Which of your friends is Zoey? Break it down for me.” My mom literally had eight nominations for who that could potentially be. 

ROMAN: Wow, eight?

DUBOFF: Yeah. And it’s not like this was exactly what happened to me, but I feel like I’m in a lot of the characters. There’s a gay guy in his 30s who works at a Vanity Fair-esque magazine, so obviously there’s a lot of similarities, but I feel like I’m as much in Zoey in terms of how she views the world and her objectivity and rationality about things. I think what you said about a vulnerability hangover is accurate, but in a weird way it’s opened up pathways in some of my relationships where I had a few friends read the book and then call me and with a weird emotional referendum on our friendship or something, because the book something sparked in them. 

ROMAN: I think everyone tends to make everything about themselves. Guilty as charged. Sometimes I wish I wrote fiction because it feels like you can really process a lot. Did you find that? Were you going through personal stuff and being like, “It’s a character.”

DUBOFF: Right after I left Vanity Fair, I was processing stuff and I was thinking about some of my experiences and how I felt working there. There were moments where I was like, “Oh, I probably shouldn’t include that,” or specific things, whether it be a celebrity interview or a dynamic with a coworker.  I did find myself self-censoring with what I was sharing and the emotions of it all. And my agent was the one who was like, “Just as an exercise, let’s take this into fictional terrain.” And it was shocking to me how it freed me up, and then it became this whole other thing. I mean, it’s vulnerable to share, but you don’t want to write about friendships that are still close.

ROMAN: It’s the juiciest stuff, and I think the best writing comes when you’re the most honest. Wait, did you not intend to write or sell a work of fiction?

DUBOFF: No, I definitely did. In the early days it was just me toying around and thinking, “This could be interesting to have for myself.” And then I was like, “I’m going to write a novel now.” And it was right at the beginning of COVID that I really said, “I’m going to write a book.” And it was off of my agents pumping me up. I knew I wanted to do a kind of character ensemble-y type of book. I would say I was coming out of my early 30s when I started really getting into it. I feel like I’ve read so much about high school, college, and coming of age. I love that kind of stuff. It’s such a weird time. The 20s feels like everyone’s in the same boat a little bit; you’re hooking up with a lot of people, you’re jumping around jobs. But then in your early 30s it does start to feel like things really start to get a little more concrete where people are getting married and choosing to have kids. Some people are getting really career focused, and things get a little more solidified in this way where it feels like you start fracturing a bit. 

ROMAN: Absolutely. Everyone has a little bit more money, everyone has a bit more stability, but you still find yourself to be an absolute mess and mostly adrift. Versus 50 years ago, when everyone had three kids by 32 and a job they’d been at for 15 years. These days people are starting over at 33.

DUBOFF: Yeah, especially in New York. It definitely does feel like here your 20s are really about exploration, experimentation, making mistakes. I also feel like that in my 30s now, but it’s a different level of issues you’re grappling with and things feel more real. 

ROMAN: Yeah. Well, that’s why I appreciate the distinction between early 30s and late 30s. There is so much change that happens. And if you’re in your early 30s, you cannot write about your early 30s. You simply must have some distance. When did you start writing it?

DUBOFF: Fall 2019 is when I really started writing it. It was a long process.

ROMAN: How much did the pandemic inform the book that you started writing versus what ended up coming to be published?

DUBOFF: I would say it shifted it a lot. I was way more focused on the “working at a celebrity magazine” part before COVID. It was a little bit more like a character who’s in this glamorous world, a bit of Devil Wears Prada energy. But as I’m sure we all did during COVID, I started thinking about friendships and connection and sort of where I felt in the social fabric of my life and my relationship with my parents, especially writing in my childhood bedroom in Boston with a Britney Spears poster on my wall.

ROMAN: Did you feel like the COVID aspect evolved from the time that you started writing to the time you finished it and turned it in edits? Many years passed, you became older, you experienced things differently, you went from presumably being in your early 30s to your mid 30s–

DUBOFF: Yeah, I sold it during my mid 30s and then revised it during my late 30s. 

ROMAN: Were there things you felt like you had to go back and elaborate on after you had some distance?

DUBOFF: For sure. I actually added two chapters after I sold the book… I don’t want to describe it too intensely. 

ROMAN: Where do the chapters fall? In the middle, or at the end?

DUBOFF: Towards the end, and they’re more focused on Zoey. I wasn’t expecting to add chapters, but I felt exactly what you’re describing, that something was different. Especially at that point after I’d sold the book and were working on the revision with my editor. I was back in New York and I had sort of “resumed” my normal life. My feelings changed a bit, maybe from some of the slightly darker emotions I might’ve had when I was starting to work on it initially. But I called my brother in a few instances where I was down to the wire and the final manuscript was due in two weeks. I was like, “Wait, do I keep this?” Because there were a few moments that feel really vulnerable, even though it’s fiction. 

ROMAN: Is your brother older or younger?

DUBOFF: He’s spiritually older, but literally younger. He’s my North star, and I’m so happy he encouraged me this way. He was like, “No, you’ve got to keep that stuff.” I’m so happy that I didn’t remove any of that, because it’s what people really vibe with. Also, the book was initially called “Congrats on Everything,” which was in the vein of something a bit darker, snarkier. I mean, the book is kind of dark and snarky in certain ways. But Early Thirties really changes the tenor. And I’m actually happy that we didn’t have that title until later on because I feel like I might’ve been a little too in my head like, “Is this capturing the early 30s energy?”

ROMAN: The title that you just mentioned definitely feels more Devil Wears Prada. It feels more career focused and snark driven, whereas this feels more coming of age.

DUBOFF: I have a few friends, including our dear mutual friend Caity Weaver, who still call the book “Congrats on Everything.” I feel like the title is living on. 

ROMAN: It’s a good title and I do think you could back-pocket it for your Devil Wears Prada moment. But having the perspective you have, working in magazines and interviewing so many celebrities, is the ultimate hide-behind-something. The focus is always on the subject and you can really hide behind a lot of shit. So having this book be the first time where you’re like, “I can’t hide behind anything except for the fact that it’s fiction”—it’s an intensely different chapter for you.

DUBOFF: My friend was asking me the other day. She was like, “It must be so weird being interviewed,” because my whole career has been interviewing other people. This isn’t nerve-racking for me, but I’m starting to do some podcast interviews and it is a whole different mindset. I was on Watch What Happens Live and it’s the silliest interview segment, but I was so nervous. I like being in control and asking the questions. That’s been more of a shift for me to contend with than I realized. 

ROMAN: Now that you’re the one being asked questions, is it tough to not judge the way that other people interview you? And will it make you approach your style any differently?

DUBOFF: I mean, my interview style is very conversational. I find that most people don’t interview that way, per se. When people do the 10 questions on a piece of paper, I start feeling like, “Oh, god…” But someone gave me the advice: “When you’re being interviewed, imagine yourself as a mob boss.” He’s like, “You need to channel more of that.”

ROMAN: I’m here or I’m not. Don’t even worry about me.

DUBOFF: Yes. Which is, as you know me well enough to know, not my default. But I like talking. I mean, I’ve really enjoyed my conversations with people who’ve read the book. We can really get into it. It’s actually funny, some of the conversations I’ve had where we can’t really spoil things or talk about the book, but we’re trying to talk about it in vague terms. There’s a lot of questions like, “What’s the spark for your characters?” Or, “What time do you get up every day and write?” And some of that totally makes sense as questions, but it’s funny because you’re kind of talking around what the actual book is about. And sometimes you get odd personal questions. Or just things that are like, “Who’s the worst celebrity I’ve ever interviewed?” And I’ll totally answer with anyone over drinks, but–

ROMAN: Here’s a pro tip: don’t answer that, ever. Nowhere is safe. No one is your friend, Josh.