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Featured Writer Friday: Caroline Leavitt

Posted: April 12, 2019 | By:

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This Q&A with Caroline Leavitt is the first of many features showcasing the wisdom and experience of the talented writers and editors in our network. These award-winning and bestselling authors and editorial experts know  the writing and publishing process inside and out.

Caroline Leavitt is the New York Times bestselling author of Pictures of You and Is This Tomorrow, as well as the critically acclaimed Cruel Beautiful World, Girls in Trouble and eight other novels. A recipient of a New York Foundation of the Arts Grant in Fiction, an IndieNext Pick, A Costco Pennie’s Pick, a Goldenberg Fiction Prize winner, and a finalist in both Sundance Screenwriting Lab and Nickelodeon Screenwriting Fellowships, she was also longlisted for the Maine Readers Prize. She’s a book critic for the Boston Globe and People Magazine and she teaches novel writing online at both Stanford and UCLA Extension Writers Program. Her work has been in Salon, The New York Times Modern Love, Real Simple, New York Magazine, and more. Visit her at www.carolineleavitt.com.

Tell us about your publishing journey. How did you begin writing, and how did you break into the industry? When did you know you could make a career out of it?

I grew up a shy, asthmatic kid in Waltham, and while other kids were out playing, I was in the library reading. I loved stories so much, but I didn’t want to just read them, I wanted to write them, and I started young. My older sister and I both wrote what we called “novels,” on pads of paper, illustrating them as we went along. In high school, I made up books to write book reports on, and I was so good at it, I wasn’t caught until my senior year, when my teacher was so enamored of the book, she went to look for it. In college, at Brandeis, I got more serious, getting into a writing class taught by a then famous author. But he hated my work and he humiliated me in class, telling me I’d never make it. That made me more determined. After college, I kept sending out short stories, and kept getting rejections. But then there was this Young Writers Contest, and on a whim, I sent a story in, and I won first prize! I was flown to Manhattan, agents came calling, and they wanted the story to be a novel, which they immediately sold to a publisher.

My first novel, Meeting Rozzy Halfway, was a phenomenon, and I thought it would continue that way. But my publisher went out of my business, and then my next publisher went out of business, and then I bounced around from publisher to publisher. I wasn’t selling any of work. Nobody knew who I was. Worse, my 9th novel, Pictures of You, was rejected on contract as “not being special enough.” I cried. I knew my career was over now, because who would want to buy a 9th novel from someone who didn’t sell books?

But a friend got me to her editor at Algonquin, who bought the bought and when I told her, “I don’t sell books," she laughed and said, “You will now.” They took that non-special book and put it into six printings six months before it was even published. Its first month out, it became a New York Times bestseller. And I’ve been with them for my next three books, the fourth one coming out in Spring or summer of 2020.

Do you have any quick tips for working with editors?

Working with editors is a collaborative process. I always tell clients I work with that sometimes I point out flaws because their intention wasn’t clear. And sometimes I can be wrong. You have to listen and figure out whether or not the editor’s ideas work for you or not, and if they don’t, you don’t use them.

How do you know if an idea—yours or someone else's—is strong enough to develop into a book?

For me, it’s a gut feeling. I get a kind of deep rush, where I feel this is a book I would want to work on or read.

What does your writing routine look like? How do you stay productive and overcome blocks?

I’m at my desk every day and it’s become a necessary routine for me, almost an addiction, so I never stop writing!

What's your best piece of advice for someone looking to be a full-time writer (ghosting or otherwise)?

Never, ever, ever give up. Keep working, keep trusting yourself, keep going. You’ll succeed.

What are you working on next?

A new novel and a pilot script! I’m very excited.

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