I'm thrilled to introduce you to Caroline Leavitt, a bestselling novelist whose 12th book With Or Without You is coming out through Algonquin in August. Caroline and I had a chance to talk about everything from Story Structure (which she teaches at Stanford and UCLA), to how she comes up with her story ideas, to how to stay the course as a career writer.

Caroline will be visiting the Unlocking Your Story summer workshop next week, zooming in from Hoboken, New Jersey!

CAROLINE LEAVITT is the award-winning author of twelve novels, including the New York Times bestsellers Pictures of Youand Is This Tomorrow. Her essays and stories have been included in New York magazine, Psychology Today, More, Parenting, Redbook, and Salon. She is a book critic for People, the Boston Globe, and the San Francisco Chronicle, and she teaches writing online at Stanford and UCLA.

Her forthcoming novel, With Or Without You(Algonquin, August 2020), is a contemporary story of what happens to relationships as the people in them change, whether slowly or in one cataclysmic swoop.

“What if Snow White woke up and decided she didn’t much like Prince Charming? Something like that happens in Leavitt's latest novel... One character’s coma is only the first surprise in this satisfying story of middle-aged love.”STARRED Kirkus Review.

Also, Caroline's novel Pictures of You is being re-issued for its tenth anniversary edition. The story features two women running away from their marriages who collide on a foggy highway, killing one of them. The survivor, Isabelle, is left to pick up the pieces, not only of her own life, but of the lives of the devastated husband and fragile son that the other woman, April, has left behind. Together, they try to solve the mystery of where April was running to, and why.

KARIN GUTMAN: What first strikes me is how prolific you are. Would you describe yourself this way?

CAROLINE LEAVITT: It's so funny to hear that because everybody says that I'm always working. I was brought up in a household where I was told I was lazy all the time. So I always think that I'm not working hard enough and I'm not doing enough and I need to do more and there's not enough time. So I guess the answer is, yes, I am prolific but, no, I don't think of myself as prolific.

KARIN: Can you tell us the story behind publishing your first novel Meeting Rozzie Halfway?

CAROLINE: Sure, absolutely. Listen, I had a really difficult childhood. I was asthmatic and bullied and I spent a lot of time in the library reading and writing stories and I always wanted to be a writer. I was always told, “No, that's really not a profession.” I had very traditional parents. “You can be a school teacher or you can be a nurse and, best of all, you can be a wife and mother.” I didn't listen and kept writing and writing and writing, and when I got out of college, I started sending out short stories and they always came back, rejection, rejection, rejection.

And then in my early 20s, I entered this contest called A Young Writers contest and the prize was that they would fly you to New York and you would get your piece published in Redbook Magazine. I figured, “Oh, I don't have a chance. I don't think I write Redbook stories,” which at the time was very traditional. So I sent in a story about two sisters growing up in Boston, one was mentally ill, and I won the first prize. I was so surprised. Not only did I win, but all of a sudden the story created all this buzz and within weeks I had an agent, and then I had an editor who wanted the story to be a novel and that's what started my publishing career.

I had never thought it was going to happen so soon, I just thought I was going to be publishing short stories for a while and paying my dues. But it didn't make my career run smoothly, which is one thing that I think is important for all writers to know, that a writing career is not up, up, up. It's always up and down and up and down. I had a big success with my first book. My second book was a lesser success, and then books three to eight just didn't sell. It got to the point where nobody knew who I was and I felt like a failure and my ninth book on submission was rejected as “books to be rejected.” They just didn't want it.

I thought that, well, after nine books if nobody who knows who you are, and you haven't built an audience, then your career is over. So, as I was trying to think of what to do, a friend of mine had an editor at Algonquin who was looking for material and she sent the book to them and they bought it. They turned it into a New York Times Bestseller its second week out and got it in six printings. So, I've learned that a writing career can go up and down all the time and you just have to persist and keep writing and remember that it's the writing that's important, not the publication.

KARIN: Was that Pictures of You?

CAROLINE: Pictures of You was the one that gave me my career.

KARIN: When you say that it “gave you your career,” what do you mean?

CAROLINE: To me it meant that I could continue writing and I would have readers, because when it became the Bestseller, I had zillions of readers and people reaching out to me and that was really gratifying that people were reading my work and responding to it. I knew that it didn't necessarily mean that the next book would do the same level or that they could not vanish just like my second novel did, but it gave me an understanding that what was important was telling the truth on the page and not worrying so much about what else was going on. Now I'm established—people know who I am—but I can still fail and to me that's okay, because I also know I can still succeed. I'm thinking about the business very differently now than I did when I started out.

KARIN: Do you think that Pictures of You is better than the other novels you’d written?

CAROLINE: That's a great question, and it's one that I really thought about. No, it's not that Pictures of You was suddenly different from every other book I had ever done, and I wouldn't necessarily say that Pictures of You was better than any of the books that I wrote before that. I think it was the publisher; I watched what Algonquin did and they do things that no other publisher has done before. I saw them physically reach out to people who were book reviewers and say, “Listen, you have to read this book,” and the person would say, “Yeah,” and they'd say, “No, no, no, listen, really, you really have to read this book.”

They really put their careers on the line for this particular book; whereas before, I never even had a publicist assigned to me for some of my books. So, I would say it was definitely the publishing company.

KARIN: Do you now feel partial to Algonquin?

CAROLINE: Oh, yeah. Algonquin is my home now. I already sold my fifth book with them, and I don't want to go any place else, because they've been fabulous to me and everybody knows everybody. I can call up the publisher, the head of the whole thing and say, “Let's have lunch,” and we'll go have lunch. All the editors know each other and they all know the authors and all the authors know each other, so it's really more of a family feeling.

I was at Grand Central and Saint Martin's, and it was a very different experience. I couldn't ask questions and I was not part of any of the marketing. There was no marketing. Also editorial wasn't as intense as it is with Algonquin where my editor and I slave over every page. There's a lot of collaboration going on and a lot of conversation going on and trust and it just feels like they truly care about the work that the writers are doing. To me, that makes so much difference.

KARIN: Looking back, would you have done anything differently during that period after your first book came out?

CAROLINE: Well, let's see, it was a period of 16 years of trying to make it and slogging around.

I didn't know anything. I was a different person than I am now. I was painfully shy. I was in a very unhappy first marriage. I would never think of asking anybody for help because I was afraid. If I was back in that period, I would reach out more to people. First of all, I had a different agent during those years, so I probably would have gotten a different agent sooner. I stayed with my first agent because I was afraid that I wouldn't get any other agent who would take me. So, I definitely would have been bolder about it.

KARIN: It’s hard to imagine you as shy, because I feel like you've such a generous, open-hearted spirit.

CAROLINE: Well, I had to learn to be that way. A lot of it was Algonquin, too, because I had all these books and nobody had ever sent me out on a tour and Algonquin did, and all of a sudden, I was in front of 200 to 900 people and I had to be personable. A friend of mine was a media coach and I said, “How do I do this? I'm so afraid,” and she worked with me and then I discovered that the more personable I got and the more relaxed I was, the better they liked me. They would laugh and afterwards people would come up and say, “I'm so glad you told that story about being bullied as a little girl because that happened to me, too, and now I feel less alone.”

I began to realize, “Oh, this is what it's about.” It's not about standing up there and saying, “This is what my book is and you should buy it.” It's more about saying, “I'm a human being, like you're a human being and this is what I've gone through, and I tried to put it into art by making this novel and I hope it's something you'll respond to.” And the more I did it, the easier it became and I turned myself into a non-shy person, which is kind of remarkable.

KARIN: That is amazing.

So Pictures of You was your first experience with Algonquin?

CAROLINE: Yes. I had heard of them, of course, but at that time, I just thought, “Well, they're a small prestigious literary publisher, they'd never want me,” and to my surprise, they did. I learned not to depend on anybody else to give me my self-worth as a writer. I always tell writers you have to find it in yourself. You have to really dig deep and find it in yourself and then other people will respond to that.

KARIN: And now you’ve got a new book coming out with them…

CAROLINE: Yeah, With or Without You, it's coming in August, and then I sold another one called Days of Wonder, which I have to write. They do this wonderful thing where you can send them the first 70 pages and if they like it, then they'll buy it. And then you have a year to write the book, so that's what I'm doing now.

KARIN: So, you sent the 70 pages and they liked it?

CAROLINE: Thank goodness, but that doesn't mean it's getting easier to write the rest, especially now during a pandemic. It's really hard.

KARIN: You're finding it harder to write?

CAROLINE: Yes, it's much, much harder to write because everything feels so surreal. Nobody's on the street. I usually would go out and see my friends; my husband and I would always go out into the city and do things. There's a kind of stasis feeling and every once in a while, I realize again what's going on in the world is so terrifying on so many counts, that I can't work, because I keep thinking, “What can I possibly write that's going to help anybody or help me?” Most of my writer friends say, “Well, the business of writing is to create empathy and that's something that people need and that they could use more of, so you should just put your head down and try to do your work,” but it's difficult. It's a difficult time now for everyone.

KARIN: Can you share what the new book is about?

CAROLINE: Yeah, I can actually. It's about this young woman in her 20s whose early release from prison for an attempted murder that she and boyfriend may or may not have done when they were 15 years old. Because her boyfriend was very wealthy and came from a prestigious family, he did not get sent to prison, but she did. So the book is about her struggling to rebuild her life, to try to find this guy, and find out what really happened that night, because she doesn't remember it. Also when she was sent to prison, she was pregnant with their child and the child was given away, so she's looking for that child also. That's all I know about it. I'm going to find out the rest as I write about it.

KARIN: How do your ideas come to be… how do you find your story? I know you often use your personal life experiences as springboards for your novels.

CAROLINE: Yes, usually it's about something that's been haunting me for a long time and I really don't know the answer to some question about it. For me a lot of it had to do with my family. I have an adored older sister and we were really close for 17 years of our life, and then her personality changed and she's become estranged from me, which is really painful. I've been writing about it and writing about it and I realized that the question for me was, “What did I do and how do I get to be forgiven?” because she's not giving me the answer. She's just telling me she doesn't want to speak to me.

I thought, “You know, I should write something about this,” and then I happened to be talking to a good friend of mine and she was telling me about this wonderful woman who has all these friends and everybody loves her. So, I met this woman and I did love her and I said, “Oh, she's such a great person.” That was when my friend told me, “You know, I didn't tell you this because I didn't want you to have any pre-judgment, but she went to prison when she was 15 for a murder she committed, and she spent her whole life trying to become a good person because of it and she succeeded.”

Those two ideas struck with me and I thought, “Oh, now I know what the novel is about. It's about this constant yearning feeling of when do I get to be forgiven, what do I have to do, mixed with that feeling of what did I do?” To me, being 15 is so interesting, because most of the time kids that age are runaway cars. Your emotions are all over the place. You're not thinking things out. I guess I'm writing it to find out how this woman is going to be forgiven—and how is she going to end up feeling that yes, she now deserves a place in the world and should she have been imprisoned at all. So that's how it all came about.

KARIN: Will you do research?

CAROLINE: I have actually. I have a friend who runs a prison program for women in Massachusetts where as part of their parole they have to read books and have discussions, and she asked if I would like to come to one of their meetings. I absolutely wanted to go. There were about 20 women there and they were not very friendly at first. They were very suspicious and they wanted to know why I was there and what I was doing and I was really honest with them. The interesting thing is they started to warm up when I told them that I had never learned how to drive a car and I told them, “I'm nervous being here with you, because I want to do you justice.”

And then they started opening up. I asked if I could interview them about their experiences in prison and one woman burst into tears and said, “I have to think about it.” Two other women said, “Yes, you can talk to me.” I had long conversations with them. What was so interesting to me was that some of them formed their first real steady friendships in prison. They felt they were protecting each other and there was a kind of community and I liked that. So there were a lot of those details that I used.

KARIN: What is your writing practice like?

CAROLINE: Well, I have a deadline, which is really good, because it forces me to write. And also for my mental health, it's important for me to write.

For the next book I have the 70 pages I wrote a really detailed 30-page synopsis of what I thought might happen, which changes as I write. Every day I sit down at the desk around nine or ten and circle one part of the synopsis that I'm going to work on, just for the day. Maybe it's one or two scenes and that way it makes it seem more manageable to me. I don't feel so overwhelmed. I feel like, “Okay, I'm just going to do this part,” and it doesn't have to be chronological. Usually I can work for four hours and then I'm exhausted and I can't do it anymore. It's like the spark isn't there anymore.

Every day I try to do a little bit, even a paragraph and I used to be very consistent about this. Now with the pandemic, I'm not so consistent. Some days I wake up and I just feel depleted. I can't do it, and so I'll spend the day watching movies on my computer or I'll just take a walk with my husband or I'll read, or I'll teach my classes and do whatever else I need to do with the writers that I work with. It’s definitely not as consistent but I'm really trying. I'm struggling to get back to that because I need to, both because I have a deadline and because I know it feeds me. It's going to make me feel better.

KARIN: Do you adjust the synopsis as you’re writing?

CAROLINE: Yes, what happens with the synopsis is I'll write it out so I can convince myself I know how to tell a story—that I have beginning, a middle and a satisfying end—and then as I'm writing, of course, I'm making new discoveries so I have to throw things out and then I have to add things and everything changes. I re-jigger the synopsis all the time. I will go back and say, “No, now this particular thing can't happen. It doesn't make sense.” So, I'm going to have this other thing happen and it will usually change anywhere from 10 to 20 times as I'm working on the book.

KARIN: Interesting.

You teach story structure, right?

CAROLINE: I do. I teach story structure online, at both Stanford and UCLA Extension Writers’ Program. I have anywhere from 12 to 20 students in each class and it's 10 weeks and it's really intensive and most of it is online but every week we have a Zoom class so we can all see each other and talk and know each other. It's really, really fun.

KARIN: How do you go about teaching structure?

CAROLINE: I didn't learn about it myself until about eight years ago when one of my students actually said, “Do you know about John Truby's story structure?” At that time, I was the kind of person who felt, “No, I believe in creativity and the muse and I don't believe in any kind of formulas.” And she said, “This isn't a formula. Just listen to this.” She gave me these tapes and I listened and I was amazed. I was amazed because he doesn't give you a formula as much as he gives you an idea of the bones that every story should have.

Like every story should have a character who desperately wants something and out of that want comes action. So that's always a first step that I tell my students. You have to have a character who wants something and you have to know that there are stakes to it—like if he doesn't get this, what is going to happen that he won't like? And what does he have to give up to get what he wants? I also tell them that you can't always get what you want, but if you try, sometimes you get what you need.

I tell people that at the end, in terms of structure, you want the character ideally to have some kind of self-revelation where they realize, “Ah, I've spent my whole life trying to be rich and have a trophy partner and I struggled and I got those things, and then I realized, I'm not happy and now I realize that what I really need to do is quit that stupid job and go to the woods and be a gardener,” and then they do. It's that kind of change and realization that makes for a satisfying story.

So I give them beats of things that they should have, and every week we split it up and we'll talk about it. Like what's the moral choice? How could we make it deeper? What does a character want? Does it have big enough stakes and if not, how can we make it bigger? There's all kinds of toolbox stuff and I tell the writers, “Look, this is just a toolbox, and you can pick and choose the tools you want and you may find that you are the kind of writer who can't use any of these tools. That you just like riding on the seat of your pants and if that's you, that's fabulous, that's fine.”

KARIN: Everything you’re saying really resonates with me.

CAROLINE: Oh, I'm so glad.

KARIN: So, you give John Truby a lot of credit…

CAROLINE: Yeah, he changed my writing life. I don't agree with everything that he says, but I think he's on the money about the seven beats that you need.

KARIN: Did his approach to structure really change how you write?

CAROLINE: Yup. I used to write novels that would come out to be 800 pages, and I'd turn them into my agent and she'd say, “I can't send this out." She'd read it and say, "Let's try to figure out what the real story is and pare it down.” We'd do it that way.

There was much more hysteria in the process for me, because I never really knew what I was doing and I would go off on all these tangents and nothing would happen and characters wouldn't change. As soon as I learned story structure, it became so much easier because then I figured, “Oh, of course, this character has to do this and this should happen and we can go deeper here.” I just feel more in control. I tell my students, “It's like if you can think of a human being, every person on the planet looks different, feels different, acts differently, but we all have basically the same skeleton and that holds us up.”

Story structure is like your skeleton. Get the skeleton down and then you can add whatever kind of flesh and clothing and personality that you want, but it's the skeleton that's so important.

KARIN: Yes, I love how you talk about it.

You used the term “moral choice.” I've never heard of that. What does it mean?

CAROLINE: Oh, this is great, you'll love this. A moral choice is not about morality as much as what kind of person you are. It's putting your character between two terrible choices and what the character does tells you what kind of person he is—like say there's a guy, and his wife is dying of this terrible rare disease. There is a cure, and it's owned by one pharmacist. So the guy goes to the pharmacist and says, “I really need to buy this medicine,” and the pharmacist says, “Well, the medicine is going to cost $10,000,” and the guy says, “I don't have the money, please give it to me. It's the only thing that'll save her.” And the pharmacist says, “No, I'm sorry, it's $10,000.”

So the moral choice is… the guy can either say, “Well, I have to find another way, because I'm not going to get this drug from this pharmacist. He won't let me and the stakes are really high, and my wife might die.” Or he can say to the pharmacist, “You are inhumane,” and kill the pharmacist and steal the drug and save his wife. But in saving his wife, then he's going to jail, because he killed the pharmacist. So, when you have those two highly dramatic things, you put people reading in a position saying, “Oh, my God, what would I do?”

I always tell them about Jaws. You have the Sheriff. Is he going to close the beach and protect all the people and the town will ruin and he'll lose his job? Or is he going to keep the beach open and he'll keep his job and hope for the best? But meanwhile people could be eaten by the shark. The more of those kinds of choices you can give your character, the better.

KARIN: Meanwhile, tell us about your new book!

CAROLINE: With or Without You.

KARIN: I was fascinated by your recent essay in the Daily Beast that describes how you wrote TWO novels related to your real-life experience of being in a coma.

CAROLINE: Right, I got critically ill after the birth of my son with a mystery illness, so I was put into a medical coma for two weeks and I was sick for a year. The problem was that they gave me memory blockers so I wouldn't remember the pain and procedures, so my mind didn't remember any of this but my body did and I had all these post-traumatic triggers. So I was talking to a friend of mine who was a psychiatrist and he said, “You know, when you hypnotize a person and you tell them that they're burning, their skin can flame up. They can get blisters. The brain doesn't know the difference.” And he said, “You do that in your writings… why don't you just write about it and you'll heal yourself that way.”

So I wrote this book right after my coma that was called Coming Back to Me, which was about a woman like me who had been in a coma after she had a baby and she didn't remember anything. I thought it was going to make me lose these triggers and it didn't. I still kept having them. I was afraid to go to sleep and certain smells and certain colors would really upset me and none of the people who had been around me when I was in a coma wanted to talk about it, because it had been so traumatizing for them, too. So, I began to think, “Well, what if I wrote a book about a woman whose experience was different from mine? What if I wrote about a woman who remembered everything? Maybe then I could heal.”

So I created the character of Stella, who is aware of everything in her coma and outside of her coma. In fact, I made her better when she got out of her coma because she has a different personality, which does happen. She also has this extraordinarily miraculous new talent where she can paint really well and she can paint the inner lives of her subject. I did a lot of research and actually that's something that does happen in coma. People do awake with these astonishing new abilities.

KARIN: Wow.

CAROLINE: Suddenly they can speak a foreign language or suddenly they can be a virtuoso on the violin. I found that so fascinating and I wanted to write about that. So, the book is a lot about how we can re-make ourselves and what this does to the people who love us when we change, and what it does to our feelings towards the people we love.

KARIN: Have you noticed any shifts as a result of writing this second novel?

CAROLINE: Yeah, I have. I'm not bothered by colors or sounds or smells anymore. I still get unnerved when it's time to go to sleep, but I definitely feel free of the whole issue of coma. I think I will never have to write about it again, which is a nice thing to realize.

KARIN: Are there any promotional book events coming up that we can attend?

CAROLINE: Well, you can go to my website, www.carolineleavitt.com. There's a list of 30 different virtual events—some of them are with wonderful other authors that I'll be in conversation with. I know money is tight in the pandemic, but just calling your local library and asking them to order the book is a very big deal.

KARIN: Thank you, I will do that!

Caroline Leavitt is hosting the weekly Reedsy Prompts contest on July 24th! Each Friday, Reedsy posts five new writing prompts, and then challenges writers to submit a short story inspired by one of those prompts. A weekly winner receives $50 and is featured on the Reedsy site.

Caroline will be doing a “Reversals” theme. Here's a sneak preview of one of her writing prompts: “Every year one person is chosen to go to the moon, and this year, though you hid in terror, it is your turn to enter the rocket.”

To learn more about Caroline Leavitt, visit her website.

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