The Book Drop


The Indefatigable Caroline Leavitt

By Jon Michaud


In this month's Book Drop, Jon Michaud talks to New York Times bestselling author Caroline Leavitt about her new novel Cruel Beautiful World


In 2011, I had the good fortune to publish my debut novel with Algonquin Books of Chapel Hill, on the same spring list as Caroline Leavitt’s Pictures of You. It was a debut of sorts for Caroline, too—her first book with Algonquin after a decidedly mixed experience with a number of other publishing houses. Pictures of You came out a month before my novel and was a huge hit from the get-go, garnering critical praise and making the New York Times Best Seller list. 


Given such accolades, I was surprised when, a couple of weeks before my own publication date, Caroline got in touch, saying that she’d loved my novel and wanted to do an interview with me for her widely read blog. I didn’t know at the time that Caroline does this a lot. She is endlessly supportive of other novelists, especially emerging writers. “I’m just so amazed that after all these years, I have even a little clout to help someone else,” she told me. “I’m delighted to be able to use it in the service of another writer.” For that reason, among others, she is almost universally adored by her peers.


Caroline will be appearing at the Center on October 4th with Rick Moody to launch her new novel, Cruel Beautiful World. Set in the late sixties, the book tells the story of Lucy, a teenaged girl who runs away with her high school teacher. Cruel Beautiful World not only gives us Lucy’s point of view, but also those of the family members she leaves behind: her sister Charlotte, and her adoptive mother, Iris. It’s a gripping, emotionally wrenching novel about independence, loyalty, and the end of the Summer of Love. 


When I asked Caroline about the origins of the new novel, she said that there were three sources that came together to inspire her. The first was the memory of a high school classmate and friend who was engaged to an older man who was “a tad controlling.” Caroline later learned that when the girl broke off the engagement, her fiancé stabbed her 43 times. The second source was Caroline’s own relationship, a decade after high school, with a man who, among other things, monitored everything she ate. “I went down to 93 pounds and he began to criticize how I dressed, and when I snuck out to stuff a candy bar down my throat, I felt him stalking me.” Thinking of her high school friend, she ended the relationship. But the novel didn’t fully come together until four years ago, when she came across an Internet notice from her murdered friend’s sister. “After all these years, she still was haunted, and she was asking people for anything they could remember. Then I knew I had my story. All that it was missing was the sister.”


Cruel Beautiful World went through 30 (yes, 30) drafts before it was ready to be published. “I used to just follow the pesky Muse and end up with an 800-page novel that made no sense,” Caroline says. She credits the influence of John Truby for the more tactical approach to writing and story structure she uses now. “Truby doesn’t deal with plot points, or act structure. Instead, he [talks] about moral choices, reveals, reversals, and asking a question that haunted you, the writer, and discovering the answer through the writing of the book.” With Cruel Beautiful World she says, “I figured out the moral components first, for all of the characters and then I wrote a detailed 30-page outline.” That took about six months. And then she started writing. Even with an outline, there were lots of surprises. “I do try things out and improvise.” 


Caroline says she showed the manuscript first to a group of four trusted readers, who suggested edits before she sent the book to her agent, Gail Hochman, who also requested a revision before passing the novel on to Andra Miller, Caroline’s editor at Algonquin. “[Andra] had me rewrite it three times! But you know, I loved the rewriting process. I loved seeing the book get deeper and more multilayered. Andra had me change the whole tone of the book, and it made a tremendous difference.” Any reader of the novel will be able to see the gleaming results of all that authorial and editorial labor.


If you follow Caroline on social media, you’ll know that she is candid about the struggles she goes through as she writes each book. Here’s a trio of recent postings from her Facebook feed: “Wide awake at midnight thirty worrying about my writing,”; “I have to get into the Writing Jungle today but I can’t stop alphabetizing my office right down to the furniture”; and “Is it insane that I’m writing two novels at once?” She told me that this frankness about the process is a deliberate ploy. “I wanted to disabuse people of the fantasy that writers have it easy, that we sit and dream, and eat chocolate and whoosh! There goes another novel out to be published! It’s hard. It’s really, really hard. I wanted every writer and every reader to know that it really is a career, it really is a job, and the stakes are really high because you are putting such personal stuff out there.” 


For aspiring writers, Caroline advises perseverance above all else, pointing to her own experience. “My first novel, Meeting Rozzy Halfway, made me a sensation. And then my next seven novels were absolute failures. I had a few great reviews, but no sales, no tours, no one knew who I was. I bounced around from publisher to publisher. Pictures of You was rejected by my then agent as ‘not being special enough,’ and I knew that it was over for me. Who would want to take on a writer’s ninth novel if she had no sales and no following?” Algonquin, of course, turned it into a bestseller.


“You never know how a book is going to do,” she says, “so you can never, ever give up.”






The Book Drop is a monthly column of thoughts, trends, and tidings from the desk of our librarian, Jon Michaud. 


Jon Michaud is the author of the novel When Tito Loved Clara, named a best book of 2011 by the Barnes & Noble Review. He was Head Librarian at The New Yorker from 2003 to 2012. Prior to that, he worked in libraries at Time Inc. and the U.S. Environmental Protection Agency. A regular contributor to The New Yorker’s Page-Turner and Culture Desk blogs, Jon also reviews books for The Washington Post. He lives in Maplewood, New Jersey with his wife and two sons where he is at work on a new novel.


You can find him on twitter @jonmichaud