Zibby is joined by novelist Jillian Medoff to talk about her latest book, When We Were Bright and Beautiful, which went through a number of iterations before publication. Jillian shares her concerns about writing a story focused on sexual assault in the #MeToo era, which books influenced this story’s twists and turns, and the role her sister played in crafting some of the plot and characters. The two also discuss the life experiences that inspired Jillian to become an author and how the writing process changes with each new publication.


Zibby Owens: Welcome, Jillian. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss When We Were Bright and Beautiful: A Novel.

Jillian Medoff: Thank you for having me. I’m thrilled to be here.

Zibby: My pleasure. Your book is really good. I was drawn in right away. I feel like your depiction of the brother-sister relationship, even though they’re not blood relatives, is so on point, and how close we all are to having our rights just taken away. Billy gets thrown in jail. From one minute to the next, you don’t know what’s coming. I’ve been talking to my family about this book. This is the book I’m reading. This is what’s happening. Maybe you should do a better job than I just did. Why don’t you explain what the book is about and also what inspired you to write it, why you wrote it, all that good stuff?

Jillian: I am a career novelist. This was my fifth book. Originally, I was writing a novel about — it was an updated Bonfire of the Vanities. It was in a luxury building like The Dakota. I thought, you know what would be so great? To do an upstairs/downstairs like Downton Abbey, but luxury building in the twenty-first century. I thought there should also be a crime. It would be looking at class, but I thought that I would do it under the guise of parenting. In the original incarnation, a young girl is kidnapped. Then her mother, who is an heiress, is held on negligent charges. It didn’t have enough to propel a 350-page novel. The whole idea of parenting, it was when you saw parents being punished for leaving their kids in their car. It just wasn’t as compelling an idea. I said, okay, the central crime will be sexual assault. The young girl actually became the narrator, who’s now twenty-three. The book opens where she finds out that her brother has been accused of assault by his former girlfriend. She comes home. The whole family rallies together. Then as the book unfolds, you realize there’s a whole other story going on.

When I approached the book, it was like, I really am delving deeply into this family, but I need to make the book interesting for me as a novelist, something more interesting to write about, and also how to make it compelling for me to keep interested. I could’ve written a straightforward narrative, but I wanted to do something a little different. By the time I was two or three years into it, the Me Too movement exploded. I was like, the market’s going to get flooded with novels about sexual assault. I felt like, how do I bring something new to the conversation? How do you write about sexual assault? I’m a white woman writing about a white family. How do I do something different? I said, what I’m going to do is a dual narrative where you read the first hundred pages, there’s a twist, and you realize, oh, wait, something else is going on. Then you read the next hundred pages, and it shifts again. By the end, you’re like, oh, that’s a completely different book than what I thought it would be. I was really influenced a lot by books like Trust Exercise, which was Susan Choi’s book. I don’t know if you read it. It was really great.

Zibby: She was on my podcast for it.

Jillian: I love the idea of taking a story and then completely subverting a reader’s expectations. I think the challenge with this book is that people will look at it and say, oh, I know that story. It’s like, well, you think you do, but it’s actually a different story than you think you’re getting into. Then by the end of the book, you realize, oh, my gosh, this book can be read two ways. I really was unsure if I could pull it off. Then with Me Too, I thought, do I go back to the kidnapping? Then I thought, you know, this is a really pivotal moment in American history, or cultural. I just want to take advantage of it and also write the most authentic book that I could write at this time in my career.

Zibby: Awesome. I love it. I love hearing all of that.

Jillian: It really feels like one long run-on sentence.

Zibby: No, it’s neat to know. I especially responded to when you were like, I wasn’t sure I could pull it off. It doesn’t seem, when you’re the reader, like there’s an uncertainty in what’s going on. Then here’s this author on the other end. Does this make sense?

Jillian: All the time. There’s a trial. I spent literally eighteen months doing everything I could to avoid writing the trial. I set the book twenty years in advance so we could refer to it but not have to go through it. I tried to get them to settle. There was this whole thing where the trial never really happened. Then finally, my friends were like, “You’ve got to do it. You just have to face it. What’s the worst that could happen?” I’m like, “I could look like an idiot.” They’re like, “You might look like an idiot anyway. That has nothing to do with book.” It was really rewarding. Then at the same time, it was so enlightening. I learned a lot. My sister is a litigator. She helped me with a lot of the technical details.

Zibby: Interesting. The character of the doorman, was that a remanent from the upstairs/downstairs?

Jillian: Yes. The opening scene in that book was where a little girl has her hand up and the doorman thinks she’s saying goodbye, but in fact, she’s waving for help. That was the image that started the whole thing. It’s been pitched to the movies. We’re talking about keeping that image in because it is this harrowing moment where Cassie is sort of taken away from her — her whole sense of identity gets skewed in the course of the book. You learn that she’s got a lot more going on underneath the surface than meets the eye.

Zibby: She’s also an orphan, which you learn as time goes on, and was taken in by the mentor of her dad and yet feels the allegiance of a blood sibling to her brothers and all of that. You have this very unsavory lawyer character. Tell me about developing him.

Jillian: The funny thing about him is he’s one of my favorites. The book is so closely — it’s Cassie’s story. She starts out saying, if this were Billy’s story… In fact, you realize it’s her story. She’s telling you everything you need to know in the very first hundred pages. You get the perspective of the lawyer only through her. The one thing about Cassie is that she is very sexualized. She uses her looks and her sexuality kind of like, not a weapon, but as a way of moving through the world. She’s really relied on — she’s smart, and she knows it. She really thinks that she’s got this lawyer down and that she and he are aligned in protecting Billy and protecting the family. It’s only when a few things happen that she realizes she’s not the smartest person in the room and, in fact, might be very, very, very uninformed about a lot. The painful part of the book is seeing her come into knowledge and realize just how closed off and lonely she feels.

Zibby: That’s like when she jokes with him that she’s a lawyer because she’d watched all these Law & Order episodes.

Jillian: My sister, actually, she says to me all the time — she’ll call me, and she’ll tell me about this case. She’s like, “Well, you’re a lawyer. You figure it out. What do I do?”

Zibby: How did you end up becoming a career novelist?

Jillian: I grew up always moving. My family moved a lot. I mean seventeen times. I went to seven elementary schools, two junior highs, and two high schools.

Zibby: Why?

Jillian: My dad was in sales. We’d move, and he’d take a different job or a different territory. It was chaos, real chaos growing up. Writing became a refuge. The idea of actually publishing a book, that was not in the stars. My goal in life really was just to be a middle manager. I also have a corporate career. It wasn’t that my parents didn’t want me to have ambition. It’s just, they didn’t want me to be disappointed. The way that they dealt with that is, don’t want too much. Keep your expectations in line. This way, you won’t be disappointed. One of the ways that I really dealt with a lot of loneliness and upheaval was to create these stories. I would just write these stories from the time I was five or six years old. They grew longer as I grew older. Again, I never really thought that it could be something you do as a job. Even as I was growing up, they were like, “Are you going to go into journalism?” I’m like, “No.” They’re like, “Are you going to go into PR?” I’m like, “No. I want to write stories.” I knew I would have to have a job, so I got a job. I wrote at night. Then I was dating this guy.

Zibby: Wait, what was your job?

Jillian: I do communications consulting. I started in marketing. Now I work with big companies helping them communicate with their employees, everything from 401(k) benefits to health care and stuff like that. I was at Deloitte and then Aon. Now I’m at Siegel. I went to school. I wrote at night. Then I was dating this guy. I was about twenty-seven. He was working for equitable real estate. He says, “They want me to open an office in Paris.” He said, “But I think I should go alone.” I said, “That’s okay because I’m going to graduate school.” I had not even applied. I have to have my thing too. I ended up applying to NYU. I only applied to one school. I got in. I just think, imagine if my life had gone differently. It was an evening program, so I could work during the day and get my MFA at night. Then my first novel was my graduate thesis. My whole life would’ve been different.

Zibby: Whatever happened to the guy?

Jillian: He moved on. Different girl. Different woman. He just wasn’t interested. I said, well, this is what I’m doing now.

Zibby: I think he needs a thank you note because if he hadn’t done that, we wouldn’t be here.

Jillian: No, not at all.

Zibby: Funny how life works. Tell me the story of how exciting it was selling your first book. Does it get less exciting the more books you sell, or not?

Jillian: Oh, no. The first time, I couldn’t really believe it. It’s such a strange thing to write something and then have your agent call and say, “We have an offer.” I grew up as a reader, but I didn’t know any novelists. I didn’t know any creative people that actually got paid for their art. When it comes to novels, you typically have to write the whole thing before you can sell it. Each time is its own — you never know. I was very lucky when I sold my first book because I write novels and not haiku. It’s more marketable to write a funny novel. It came at a time when books were expanding from being just funny or sad to being kind of bittersweet. My first novel was called Hunger Point. It was made into a movie. Then I had a second novel that didn’t sell. A third novel sold. Then I went through a really dark time where I just couldn’t sell anything. I ended up changing agents. It wasn’t until ten years later I sold another book. Each time has been unbelievable to me. I can’t believe it. I don’t take anything for granted. I’ve had a lot of rejection.

As a novelist, my goal is to get better but also to take on more interesting and different kinds of projects. The book before this one was a corporate novel. It had different viewpoints. It was really hard. The architecture and the structure was really complicated. Then I said, I’m going to go into this next one — this is going to be really easy. This ended up being even more complicated because when you’re writing a novel, you’re dealing with different timelines. Everything is so intricate and deeply plotted. It’s like a big puzzle. Then you hear things like, I wish this had happened. Readers say, I wish that had happened. It’s kind of like, to oversee or carry through an idea from page one all the way through page 350, and you’re dealing with time changes and different points of view, it’s really a complex undertaking. I just can’t believe not only that I kept doing it — every time, I’m like, okay, I’m done. I can’t go through this again. Then I sit down, and I get involved. It becomes this universe that I can sort of live in. It’s so gratifying when you get it right.

Zibby: Wow. Sometimes I’m like, I spend all my day talking to people who imagine worlds, and they don’t even know why or how it actually happens either. You know what I mean?

Jillian: I know.

Zibby: There’s no science or fact behind it. It’s all imagination and these alternate universes and these different ecosystems and people who seem quite real, but are they real? They just appeared in your mind. It’s really like, what am I doing? It’s amazing.

Jillian: Do you see any common threads through authors? I speak to a lot of authors too, just in passing. There seems to be the same consensus that starting is hard. Finding time to sit down and do it is hard. For me, it’s not hard to find the time. It’s to motivate myself. I’m very insecure. I’ll approach something like, oh, I can’t do that. I can’t pull that off. There’s no way. Then once I sit down and get into it, it’s like a weight lifts. I just start getting deeper and deeper into it. It’s just that first couple of steps into the pool that are really hard, you know?

Zibby: I totally understand. I also feel that way about the pool. I’m like, I know it’ll be such a luxury to just be in a pool swimming around, but ugh. I can’t even say this sentence. It’s ridiculous.

Jillian: I understand. Everything about the whole run-up is very hard. Even after five books or even seven books, because I had a couple that didn’t sell, I always start from a place of, there’s no way I could pull that off. There’s no way. I compare it to some male authors that I know. I’ve heard that, once I have an idea, I know it’s going to work. I’m just like, I don’t know anything. I don’t know anything. I kind of write the way I read, which is that it unfolds for me as I go.

Zibby: Do you like to read books like yours or other types? What do you like to read?

Jillian: I read everything, yes, including Bookends, which I found so poignant. How did that feel?

Zibby: I know, I’m sorry. For people listening, I’m in the midst of trying to do my own publicity for Bookends while doing my podcast, so I’ve got my two signs here behind me. Originally, I was going to swap them out from one interview to the next if I was being interviewed or doing the interview. Now they’re just double layered. It’s crazy. I don’t know when this episode is airing, but as we’re talking, it’s right before the book is coming out. I’m pretty terrified. I’m holding my breath. I had a month where it was an Amazon First Read, so I got used to it. I got through all the roller coaster. I’m nervous. I was signing books the other day at my local bookstore out here. I was just like, oh, my gosh, what if nobody buys them? What if they all sit in this big stack here for the rest of the summer and every time I walk in, none of them are sold? That’ll be so sad. I’ll be so embarrassed with the bookseller.

Jillian: First of all, you can always tell yourself that that’s a whole new stack, that they’ve all sold out and they’re just —

Zibby: — I know, but I signed them.

Jillian: You don’t have to look. I think the book is going to be a huge smash. I predict that.

Zibby: Thank you.

Jillian: I think that it’s exactly what people want right now. I really do. I’m very hopeful for you. I will be cheering out here. I think that one of the things that I have found is when you meet people that understand what it means to be a writer, and you might not even want to do it, but you feel compelled to do it, there’s this mutual language. You understand that it’s just something that had to come out.

Zibby: Yeah, I know. I’m like, why do I care so much? Then every time I tried to be like, it’s okay, I’m just going to put it aside, then it would come back. It’s like a stubborn bee or something.

Jillian: I would say, this is just for us. This is just for me. Nobody else has to see it. It’s just for me. Just get it down. Get it out. Move on.

Zibby: I had to do that, actually, when I talked to my editor and had the book deal and everything. I had to start writing a whole new version that would be this book. I remember this so well. I sat down. I was like, I can’t do this. I just can’t do this. I put in big letters in my Word doc, “No one will read this but me.” Then I started. Ridiculous.

Jillian: Have you gotten to the end of When We Were Bright and Beautiful?

Zibby: I have not.

Jillian: Okay. I’m not going to say anything.

Zibby: When you were saying it really changes in the last third, I was like, oh, yeah?

Jillian: When you’re finished, go back to the first chapter. You’ll realize it’s a whole different book. It’s one of these, oh, wow.

Zibby: I’m coming back to it. Thank you. This has been so fun. Thank you for coming on.

Jillian: Thank you for having me.

Zibby: I think admitting that vulnerability is so inspiring because so many people share it and don’t feel comfortable talking about it, so I appreciate you saying that. How great. Here’s to ex-boyfriends.

Jillian: Yes. I wish you the best with Bookends. I can’t wait to see you out there.

Zibby: Thank you. You too.

Jillian: This was such a pleasure.

Zibby: You too. Thanks, Jillian.

Jillian: Bye-bye.



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