Dollars, Cents, and Being Left With the Bill: Jillian Medoff on Breaking Up With Her Literary Agent

In 2008, after 13 years together, my literary agent and I parted ways. (To preserve her anonymity, let’s call her Michael Ovitz.) Between 1995 and 2002, Michael Ovitz sold two of my novels, including my debut, Hunger Point. By any measure, our partnership was a terrific success. Michael Ovitz and I were more than just agent-writer, we were mentor-protégé, friends, confidantes. She invited me to stay in her country home. I corresponded with her daughter. She met my parents. We bought each other gifts. “You’re a part of the family,” she liked to say.

Business isn’t emotional, but people are. This is especially true in the highly subjective book industry, where an author’s imagination, manifested on the page, is the product. Michael Ovitz is an attorney, and the smartest, savviest woman I’d ever met, like Ari Gold from Entourage, but with a maternal affect. Near the end of our first conversation, she asked if I had any questions. I was so wowed I could barely speak. “Who else do you represent?” I blurted out. “Can I see a client list?” (This was before agents posted their client rosters on websites, but Michael Ovitz was way-old-school, anyway. She wouldn’t accept electronic submissions, corresponded only by hand on heavy cardstock, and didn’t adopt email until well into the aughts.) “Oh, Jillian,” she said, chuckling at my farm-girl faux pas. “That’s simply not done. Those names are confidential.”

Seeing that list might have saved us both a lot of heartache. Michael Ovitz represented very few fiction writers; most of her clients were celebrated, erudite nonfiction authors who legislated U.S. foreign policy or sat on the New York Times editorial board. Typically, nonfiction is sold on proposal, which means an author works with an editor from Chapter One through The End. Fiction is different. Most novels aren’t sold until they’re finished, which means an author works with an agent to prepare the book for submission, which can take years.

In 1995, I was fresh out of my MFA program; Hunger Point was my graduate thesis. I had a corporate career—I still do—so I was well-versed in business fundamentals; and yet, when I met Michael Ovitz, my head emptied out. Suddenly, I was as starry-eyed, guileless, and histrionic as a love-struck tween. It’s mortifying to admit, but I brought to our partnership the same immaturity that a young wife brings to her first marriage. I tried too hard to please, I refused to speak up, I expected her to read my mind, and got resentful when she couldn’t. I know my personal finances down to the decimal point, but in an uncharacteristic move (one I still can’t explain), I let Michael Ovitz handle every aspect of our business, from contracts to royalty statements to editorial letters.

I met Michael Ovitz the old-fashioned way: through the slush pile. I sent a letter through the U.S. postal service (with a stamp! And an SASE!). Her assistant called a few days later, requesting the manuscript. A few days after that, I signed a contract that entitled Michael Ovitz to proceeds from, basically, anything I wrote, talked about, or thought about until the end of time. Although Hunger Point was completed, I expected Michael Ovitz to have editorial notes. Instead, she pronounced it “perfect,” stamped her name on the first page and started calling editors. When she asked if I had any objections, I shook my head. What the hell do I know? I thought. “Just do whatever makes sense,” I told her. Today, these words haunt me.

When pitching my novels, Michael Ovitz spoke to editors; digested their feedback; and then translated it for me—like a game of Telephone. In fact, until she and I parted ways, I never read the editors’ letters myself. So, I had no idea if she was parsing their comments correctly. Instead, I trusted that she had my best interests at heart and used her like a human shield. On one hand, this helped buffer the rejections (of which there were many). On the other, I ended up wholly dependent on her. Looking back, I’m aghast at how quickly, and easily, I surrendered my autonomy.

Worst of all, I also deferred to Michael Ovitz in aspects of money. Negotiations, contracts, royalty statements—all of it, like a 1960’s Betty Draper who let Don handle the checkbook. After reminding myself of my good fortune to have an agent who was also a lawyer, I signed publishing and movie contracts without reading them, agreed to whatever payments she negotiated, and never once opened a royalty statement. Truthfully, it was easier to let her handle the details, to nod and sign on the dotted line. It was easier to let her hear the painful rejections first and soften them for me. Michael Ovitz believed anyone who rejected us was wrong; I believed they weren’t only rejecting my writing; they were judging my character, my personality, and all my life choices. Of course, it was easier to let her handle everything. Of course, it was easier to give up my voice.

As time passed, and I became more dependent on Michael Ovitz, I started to feel trapped, then paralyzed. The more I deferred to her, the more I lost my way as a novelist. Once, casting around for my next book, I read an article about two women who developed a deep and abiding friendship in a nursing home. Before I could even finish my sentence, Michael Ovitz nixed the idea. “Way too depressing. Everyone dies, Jillian. Selling fiction is already hard; why make it worse?” Soon, it didn’t even occur to me to challenge her; I just shrugged and moved on. After all, what did I know?

Our relationship started to fray in year seven. It took me two more years to acknowledge this, and then another four to make a move. Agents and authors frequently argue over money, but Michael Ovitz and I never did. We struggled over the work; rather, I struggled to get the words down, and she struggled to sell them. Michael Ovitz was a brilliant agent, and terrific with nonfiction, but she was a less-brilliant literary fiction editor. While she could help get a novel into reasonable shape before it was sold, the bar for what was “reasonable” kept getting higher, and I couldn’t reach it, not on my own.

I’d work for nine, twelve, eighteen months on several chapters. She’d read them, often overnight, and come back with high-level feedback. (“Your main character is an asshole,” was one note. “Make him less of an asshole.”) Then I’d go away for another nine, twelve, eighteen months, and try to figure out what she meant. This period, the loneliest and least satisfying of my life, went on for eight years. But to leave would’ve been a betrayal—of her, of our partnership, of the all the time she’d invested in me. Besides, where would I go? Who would want me?

Michael Ovitz sold my first novel in 1995 and my second—actually third, as the one I wrote after Hunger Point didn’t sell—in 2000. Then I wrote a long, complicated family saga. That didn’t sell either, so I wrote another novel, also rejected. I considered these my own failures; my shame was unbearable. I felt lost and unmoored. The day after my 28th rejection, I called Michael Ovitz from an empty Dunkin’ Donuts on Twenty-third street.

“Why is this happening?” I was crying.

Her voice tightened. She didn’t like when I got weepy. “My mentor told me this is how it ends. First, they blame themselves, then they blame the publisher, then they blame you.”

“I’m not blaming anyone,” I insisted. “I just want to know what I’m doing wrong. Please, just tell me: what should I do differently? How do I get this right?”

Michael Ovitz was silent for a long, long time. It was chilling, that silence; it sliced me open. Finally, she said, “I don’t know what to tell you.”

I knew in my bones it was time to go. Instead, I stayed another year. I cared deeply for Michael Ovitz and believed she cared for me. But our relationship wasn’t a marriage, and my career would be stalled forever unless I made a move. Finally, I decided to quit, not writing fiction, necessarily, but trying to sell it. The grind was too hard. I wanted to be a normal person, live a normal life. But then a miracle occurred: I found a different agent.

In my severance letter to Michael Ovitz and her follow-up phone call, we both agreed that moving on made sense. We expressed our mutual admiration and affection. We wished each other much success in the future and signed off with love. It was all perfectly civilized. Even so, resentment roiled under the surface. Michael Ovitz expressed her anger by reminding me that, going forward, if I sold anything I’d written since 1995, she deserved a percentage of the proceeds. Then she sent me a bill for unpaid expenses ($1,000 for Xeroxes, messengering, and postage related to the novels she did not sell between 1995-2008); a bill that I, expressing my own anger, refused to pay.

To be clear: Michael Ovitz was entitled to every red cent. When I signed the contract that bound us together, I agreed to cover any outstanding expenses. Some agents consider these the cost of doing business and write them off, but legally, the $1,000 was hers. When I received the bill, I was shocked. For the past 13 years, Michael Ovitz and I had been a team, I was part of the family, a beloved kid sister. Together, we celebrated book sales, rave reviews, and movie deals; we mourned rejections, pans, and passes. Most significantly, she was privy to my private thoughts, shitty first drafts, and embarrassing hopes and dreams. Given all we’d been through, not to mention the hundreds of thousands of dollars, the bill smacked of rancor, of pettiness. Taking umbrage, I stuck it in a folder and walked away.

I never paid the bill, although it is being settled. For the past fourteen years, Michael Ovitz has been siphoning off a few extra dollars from my royalty payments. Slowly, steadily, my balance is dropping.

I’ve known my current agent almost as long as I’ve known Michael Ovitz. In fact, she was my editor on Hunger Point. A few years later, she joined a literary agency and rose through the ranks. As in many strong, enduring relationships, we started out as friends; over time, our feelings for and knowledge of each other grew and deepened. The beauty of this is that she understands, on a gut level, how novels work. Equally important, she understands how I work. Her notes are directive and specific. (“On page 23, Rob claims he would never cheat on his wife, but on page 65 we see him kiss Lucy. This is confusing for the reader.”)

Along with being patient, thoughtful, methodical, and caring, my current agent puts her heart and soul into everything she does, behavior that’s as risky for an agent as it is for a writer. But because she does, I trust her implicitly, which frees me up to write what compels me, without censoring myself or gaming the market. She treats me as an equal, and I treat her with the respect she deserves, which means maintaining boundaries, voicing my opinion, and having hard conversations.

Our bond, forged over 30 years, has helped me mature as a novelist and as a human being. Now, I’m a full participant in the business of my career: I read my contracts, review my royalty statements, and speak up while she’s negotiating. So far, she’s sold three of my novels, and we’re engaged in long, deep discussions about the one I’m currently working on. These conversations encompass every aspect of the book—why I chose this project, where my idea originated from, the novel’s architecture, the characters’ story arcs (two are best friends who meet in a nursing home). I’ll always be grateful to Michael Ovitz for changing my life, but I’m equally grateful to my current agent for resurrecting my career and guiding me forward. It is a privilege to have her in my life, and I never take it for granted. We’re not family, but we’re partners, through thick and thin, for the long haul.

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When We Were Bright and Beautiful by Jillian Medoff is available from Harper, an imprint of HarperCollins Publishers.