This Could Hurt: A Novel

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Life Beyond Your Four Walls: The Millions Interviews Jillian Medoff

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Jillian Medoff’s When We Were Bright and Beautiful is a New York novel of a distinct period. At the novel’s center is the uber-rich Quinn family. On the outside, the Quinns seem to have it all—money, good looks, Ivy League education, whiteness—but all is not what it seems, especially when the youngest son is accused of rape. Medoff employs a kind of narrative hall of mirrors combined with a slew of unreliable narrators, leaving the reader eager to unpeel all the layers to get at the pith of this troubled family. I spoke with Medoff about her meticulous plotting, the isolating power of wealth, how the #MeToo movement impacted When We Were Bright and Beautiful, and more.

Marie Myung-Ok Lee: To not give away spoilers, let me talk about WWWBAB via other books. It feels very much in the great tradition of New York books like Claire Messud’s The Emperor’s Children. Did the milieu of this book come first, or did the characters? What kind of research did you do?

Jillian Medoff: Believe it or not, the Valmont, the luxury building at the heart of the novel, came first. Modeled after 740 Park, the Valmont is older, smaller, and more well-appointed, so it’s more exclusive. WWWBAB was conceived as a contemporary Upstairs, Downstairs, or Downton Abbey, and, like Bonfire of the Vanities, kicked off with a crime. The earlier incarnation tracked the interrelationships among the Valmont’s monied residents and the staff who serve them. The current version retains vestiges of these relationships, but it’s leaner, faster, and more focused.  
In initial drafts, a six-year-old girl named Cassie is kidnapped leaving the Valmont in a Town Car. She’s alone and her heiress mother, Eleanor, is accused of neglect. I wanted to explore class and privilege using parenting as the pivot. This setup was implausible, however, so I changed kidnapping to sexual assault, winnowed down the characters, and zeroed in on the Quinns. Cassie Quinn, now 23, narrates WWWBAB.
When I changed direction, I was about 10 months into the project. Since the setting and major characters stayed the same, I was able to repurpose my research, which included biographies of Wall Street titans like JP Morgan; TV shows and movies like Gossip Girls, Billions, Succession, Wall Street, The Godfather; and websites featuring lifestyles of the rich and famous—so, lots of blogs about luxury cars and wristwatches. 
MML: This novel has more twists and turns than an origami cube—can you tell me a little bit how you came up with the idea for it? 
JM: When I write, I typically begin with an image or a line of dialogue and let the story unfold. I don’t use outlines, which means I have a lot—a lot—of false starts. I’ll move forward tentatively, but the dialogue is a huge part of my interior process, so once characters start talking, scenes start to take shape. Instead of fleshing them out, however, I start over. This happens, like, 50 or 60 times before I’ll understand what the novel is about, and more specifically, whose story I’m telling and why. It’s slow and frustrating because I veer off on tangents for days, weeks, even months, and write many—many—pages that I end up cutting. On the other hand, working this way means I know the characters so intimately, they become part of me. I eat with them; I breathe with them. I feel them on a cellular level.
I worked on WWWBAB this way for about three years. But as I got to know the Quinns, and they became real to me, the story became increasingly complicated. By this point, I realized that the novel is a study of consciousness—specifically, moving from knowing something implicitly to acknowledging it explicitly. Cassie is telling you the story of her brother’s alleged crime, but in fact, she’s telling you about two crimes, and she’s the victim of one of them. This was an enormous challenge because I was writing two different books. The story flips after Part One, flips again after Part Two, and then the trial is in Part Three. It’s only after finishing the entire book do you realize what the novel is, and what I’m trying to accomplish. So, when I figured this out, I had to change my approach. Along with creating outlines and multiple timelines, I choreographed every detail, every action, every line of dialogue. Then, after I sold the novel, my editor asked me to cut 100 pages and rejigger the information flow all over again!
I had another reckoning a year later. The #MeToo movement exploded, and I got skittish. It was coincidental that I was writing about sexual assault at the same time the rest of the world was waking up, and the overlap overwhelmed me. Again, I considered changing the central crime. But seeing so many brave women come forward evoked a sense of urgency. Plus, I felt I could bring something new to the conversation by illustrating the complexity of survivors’ responses in a unique way. WWWBAB is a psychological thriller that moves quickly and covers a lot of ground, but the architecture is hyper-consciously engineered. Honestly, I couldn’t have written a book this nuanced and layered earlier in my career. It took 30 years and four novels—and lots and lots of rejection—to get me here.  
MML: Not to give too much away, but the idea of family in this book seems straightforward but then gets more and more complicated. Not just the legal idea of who is family, but who is chosen family and, when you grow up, do you get to un-chose? I really like the question the book poses: if adults go above and beyond to save a child, what does that child owe the family in loyalty when she grows up? Or, does the child owe the family anything, since it was never her choice, anyway? I think of when parents, especially often adoptive parents, demand some kind of spiritual payment or something for raising a child when the child never asked to be brought into the world, or adopted.
JM: I think every family has its own spoken and unspoken rules and rituals around money, responsibility, and loyalty. Sometimes it’s cultural, other times it’s circumstantial. Looking at the Quinns from the outside, it’s easy to envy or covet their level of uber-wealth, but Cassie makes it clear that for her and her brothers, money is both a noose and a trap. She wants to be her own person but isn’t sure how to do that, or if she even should. Is her inner conflict compounded because she’s adopted? Probably, but her brothers feel it, too, albeit differently. 
Similarly, loyalty and responsibility are expressed between parents and children in a variety of ways; sometimes it’s money, other times, it’s working in the family business or caring for a parent as they age. As Cassie says in the book, the rich have their own economy and their own forms of currency. Moreover, the higher a parent’s demands, the deeper felt the betrayal when these demands aren’t met. Parental expectations may not be expressed explicitly, but these expectations are communicated. This is what I’m trying to illustrate in WWWBAB, all the subtle and not-so-subtle messages that are imparted in a family; how we misinterpret behavior, how we tell ourselves stories about events we don’t, or can’t understand, how we believe myths about ourselves and each other. What do children owe their parents? What does loyalty look like? Ask a hundred different kids, and you’ll get a hundred different answers. 
MLL: As someone who also went straight to lucrative corporate work—namely, Wall Street—after college while nurturing dreams of writing novels, your nonfiction writing about how working in the corporate space gives you both freedom to write and material. That essay you wrote for Lit Hub was fascinating, especially now when in our culture the young aspiring writer in TV and movies is a young woman who somehow lives and writes in Brooklyn and has plenty of free time to hang out with her—meanwhile I still have PTSD over the exhaustion of working nonstop late nights and weekends on Wall Street. How did you plan your own path?

JM: I wrote the Lit Hub piece in 2018 to support my workplace novel, This Could Hurt. In it, one of the characters, Leo, reflects on how much he enjoyed talking to his therapist: “Therapists had a way of making his life feel scripted and thematic like he was the star of an action-packed feature film instead of an ordinary fool bumbling through random events.” In retrospect, my writing and corporate careers may appear carefully planned, but in fact like Leo, I’ve been bumbling around for 30-odd years. 
I started a corporate job when I graduated from college and never stopped working. At the same time, I wrote novels at night and on the weekends. I craved structure and financial security, but more importantly, I had no confidence in my ability to write an entire novel, much less sell one. So, I worked and went to work during grad school—NYU has MFA workshops at night—and then for the next three decades. Currently, I’m a senior communications consultant with a pension, a 401(k), and medical benefits; I’m also a novelist with my fifth book hitting shelves. While my life might look strategic and well-executed, I spend most of my days triaging projects so I can steal more writing time—just like I did 30 years ago. And now  I have a husband, three kids, and a dog, so I have even less time!
MLL: F. Scott Fitzgerald is of course known for parsing the nuances of wealth and class; he is often quoted as saying “the rich are different from you and me” but the whole quote is actually a lot more complicated: 
…the very rich. They are different from you and me. They possess and enjoy early, and it does something to them, makes them soft where we are hard, and cynical where we are trustful, in a way that, unless you were born rich, it is very difficult to understand. They think, deep in their hearts, that they are better than we are because we had to discover the compensations and refuges of life for ourselves. Even when they enter deep into our world or sink below us, they still think that they are better than we are.”
JM: I definitely think the very-rich are different from even the regular-rich. I also think they believe they’re “better,” mostly because they’re so insulated from the grind of normal life. This doesn’t mean they’re happier or more fulfilled—I mean, look at the Quinns. As a novelist writing about an uber-wealthy family, my job was to humanize each of them, which was challenging. But I kept thinking about Nate, and how purposeless he felt—if you’re born into a closed community, you don’t know differently. Of course, you can learn about life beyond your four walls, and understand it intellectually, but to experience it is something else entirely. We may envy the 1%, but the trappings of that life are soul-killing. It’s an isolating and lonely life in the long run, in some ways as isolating as being born into a Hassidic family or a cult. Sure, you may have more options if you’re wealthy, but you don’t know what you don’t know. That’s what I wanted to capture, the insularity of privilege—so that I could rip it open and twist it up to serve my own ends. 
MLL: What’s your favorite book about money? 

JM: Tough question! I’ll say one of my favorite books is Liar’s Poker by Michael Lewis. I’m captivated by the details of closed communities, especially those made up of men—prisons, fraternities, football locker rooms. I especially love reading about men and money. Liar’s Poker revealed the savagery of arrogant, privileged, white men who had access to titanic amounts of money with no oversight. The sense of entitlement is gasp-inducing. I’ll never forget one guy, Donnie Green, who stopped a younger salesman heading out the door to catch a flight. Green tossed the kid a ten-dollar bill and told him to take out crash insurance for himself in his (Donnie’s) name. When the kid asked why, Green replied, “I feel lucky.”

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