CHARACTER—PLUS PERSEVERANCE—IS DESTINY: A Talk with Jillian Medoff about Craft and the Writing Life

Jillian Medoff’s novel I Couldn’t Love You More was released in mid-May, had its fifth printing less than two months later and was just featured by Jennifer Weiner as a Best Summer Read on CBS Sunday Morning. But as Jillian told me in our Head Butler interview, this success has not come easily. After an author/blogger event at Greenlight Bookstore, curated by Ron Hogan of, Jillian and I decided to continue our conversation for the She Writes community—focusing on craft and the challenges of the writing life.

To kick things off, watch this video clip in which Jillian describes the genesis of her new novel and its climactic “Sophie’s Choice” moment.


Gretl Claggett: Let’s talk about choices—in writing and life. What’s the connection between the two?

Jillian Medoff: Because I don’t write with outlines, my choices emerge unconsciously, and then as the story grows, become increasingly more conscious. I’m obsessed with finding patterns—in my literary life and my actual life. Writing novels is one way for me to make sense of the world’s randomness.


GC: If you don’t outline, how do you develop a successful structure?

JM: I jot down a sentence or two and take off from there. Over time, characters evolve. Once they start to speak, I hear them in my head and they become real. Then, from these characters, a story emerges. My theme song is a quote from Heraclitus: “character is destiny.” I derive all my stories from my characters, which is why they have to be genuine. If readers don’t believe my characters, why would they believe anything they say or do?

In my first few drafts, I get to know the people I’m writing about. In subsequent drafts, their actions become more and more refined. This means I spend a lot of time writing material I never use. I suspect this is a much more difficult way to write than if I plotted the entire story in advance, but that wouldn’t be as interesting for me. I write the way I like to read, with plot twists and secrets revealed to me as I chisel away at the story. I go forward and backward, writing a few chapters and then starting over. As I make my way through each draft, I write notes to myself. I also create several timelines, all of which are refined again and again. There’s the backstory timeline, the timeline of the action in the story, and the timeline of how this action corresponds with real life.

Because I don’t spend a lot of time strategizing, my first drafts are really, really awful, and I have to revise again and again and again to carve out the story and get the words right. I’ll write fifty, maybe a hundred drafts of a book over the course of four or five years.


GC: How do you keep the material fresh with new twists, turns and surprises without losing control of the structure and through-line—especially when you’re writing, revising and editing a novel for such a long time?

JM: Although I always have structure and plot in the back of my mind, my major concern is character development. As I get deeper and deeper into my characters’ lives, they become more complex and act in more complex ways. Readers may not like or condone the things my characters do, but I’m fairly confident that they all behave consistently, largely because I’ve lived with them so long and know them so well. Similarly, many readers have incredibly strong reactions to my characters—positive and negative reactions—because they seem like living, breathing people. Sometimes, though, a plot twist that I love—that truly catches me by surprise—doesn’t service the story, and I have to delete it.


GC: What compelled you to reveal your rejections and failures in "This is a True Story", an essay at the back of the book?

JM: To talk about writing without addressing rejection or failure is to leave out the most important piece of the entire craft. This novel would not have been—could not have been—a success if I hadn’t had ten years of rejections before it was published and years of ups-and-downs before that.

I did spend many years writing a novel that I thought would change my life. I haven’t re-read it in a long time, but in my memory of the book, I can understand now why it didn’t sell. The characters were moody and (oh, I hate this term) unlikeable; it was a dark story; no one was redeemed; the humor was snarky. But at the time, I loved it—and so did my agent—and the experience of seeing thirty publishers reject it was very painful. But—and this is important—I never regretted writing it. Working on that book taught me a lot. I figured out how to craft a man’s perspective, which is vital to the novel I’m writing now. I learned a lot about time shifts and pacing and maintaining a consistent tone as well as balancing multiple points of view. Was the book a failure? Sure, absolutely. Am I a better, more careful writer for it? Yes, absolutely.


GC: Besides being a writer, you’re a mother of three and have a corporate job. How do you do it? And what advice can you offer to others juggling family and work responsibilities with the writing life?

JM: I work hard, that’s true. And I’m very busy. But I have a wonderfully supportive husband. I’m also very clear that my writing life is just as important as my corporate life, even if it doesn’t pay as well anymore—and may never again. However, of all the choices I’ve made in my career, the most significant was reaching middle management at my corporate job and staying put. Rather than run a practice or oversee a department, I purposely stay at a level for which I’m overqualified. So I work four days a week, and write my books on Fridays, at night and on my lunch hour. I could teach a master class on compartmentalizing. I’ve trained myself to maintain a laser-like focus on whatever I’m doing at that exact moment. There’s so much to do and such limited time, but once I fixate on something, I can make it burst into flames.


GC: We’ve talked about failure. What about success?

JM: I don’t know if I consider myself a success. I’m proud of my books, certainly. I’m proud of myself for persevering. But I also want more, more, more. To be clear, though: I’m not competing against anyone else—I’m only competing with myself, and I never win. I’m harder on myself than anyone else could be. At the same time, I know that with each novel I’ve written, I’ve taken on larger themes and more complicated plots, so my work is improving. Someday I’ll be the writer I want to be. I’m not there yet, but I’m also not giving up.


For Jillian’s thoughts about “Women’s Fiction” versus “Literary Fiction” and the biases of media exposure and reviews, watch this video clip.














Photo by Marion Ettlinger
For Jillian Medoff’s web site, click here.

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Comment by Daphne Q on July 23, 2012 at 7:06pm

What an interesting interview. I'm afraid I'm not a good enough writer yet to write without an outline, but it obviously works for Jillian


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