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Caroline Leavitt: Portrait of a modern novelist

Best-selling author Caroline Leavitt has had both towering highs and staggering lows in her long career. Here’s what she’s learned after 11 novels and several decades in the industry.

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Writers always gun for the hows and whys behind the latest best-selling smashes. We can’t help it. We ask: How did you do it? What are you doing that I’m not? How did you get to be so talented?

And: What makes you so special?

The harsh reality is that the vast majority of us will not pen the next Eat, Pray, Love or Gone Girl. Frankly, if we all knew exactly what it takes to go viral or pen a smash best-seller, we’d all have done so by now.

Cruel Beautiful WorldSo how refreshing it was to call up Caroline Leavitt on a sunny morning in June and hear her talk candidly about all the moments in her career, not just the best-selling ones. Granted, Leavitt is no stranger to success; her ninth novel, the New York Times best-seller Pictures of You, was a massive hit, undergoing several printings before the book was even released. Her follow-up, Is This Tomorrow, was both a New York Times and a USA Today best-seller. Her latest novel is Cruel Beautiful World, which was released in October 2016 to a wealth of positive reviews.


But behind that long line of success are decades’ worth of real hardship. Here Leavitt shares what I consider to be the “real” life of a modern-day novelist: There will be high points, there will be harsh blows, and you will probably have to teach, consult, or edit to make ends meet. All you can do is return to the writing, day after day – and never, ever give up.


Was there a specific moment you decided to become a novelist? Or did you just always know?


There was a specific moment. And it actually was when I was a little girl: I grew up in this very working-class neighborhood of Waltham [Massachusetts]. I was a Jewish kid and I also had really bad asthma, so I was bullied a lot. I spent a lot of time at the library, and I was always asking for books about kids like me. And of course the librarian could never find any.

So I just decided, “You know what? If there are no books for kids like me, then I’m going to write them for me.” And I started writing stories about this little Jewish girl with really bad asthma. My parents thought it was very cute and sweet, and my teachers thought, “Oh, that’s nice,” but I was determined. I just always knew it was going to happen.



How have you changed as a writer since then?

I’ve changed a lot. I got published when I was in my 20s, and my first novel was a sensation. And I thought, “Oh my God! It’s going to be like this all the time!”

Then books two through eight were failures. I had five different publishers. Three of them went out of business. Two of them did nothing for the book and wouldn’t take my calls. So I would get reviews, good critical reviews, but I had no sales whatsoever.

My ninth book, Pictures of You, was on contract with a big publisher, and the editor called me up and said “I’m sorry. We’re not going to publish this. I just don’t think it’s special.”


I started to cry. I said, “What do you mean? Can – can I make it special?”

She said, “No, nobody here thinks that you can.”

I said “Well, can I send you something else?”

There was a silence, and she said “No, I don’t think so.”

I hung up the phone thinking, “Well, that’s it, my career is totally over, because no one’s going to want somebody who’s had eight failed books, no matter what the reviews had been. This is it.”

So I called my agent, and she said “Don’t worry, don’t worry,” and I called all my writer friends sobbing hysterically, and one of them said, “You know what? I have an editor who I love at Algonquin Books. Why don’t you just write what the book is about, and I’ll see if she wants to take a look at it.”


So I did. And the editor, who was Andra Miller, said, “This looks interesting. I’d like to see the whole novel.”

I sent her the whole novel, and two weeks later, she called me up and she said, “We all love it here. We want to buy it.”

I said, “Do you know who I am? I really don’t sell books.”

She said, “You will now.”


It was amazing. They took that little non-special book and they got it into [several] printings before it was even published. It made the New York Times Book Review. They just gave me my career back.

So the way that I’ve changed is that I don’t think in terms of “success” so much anymore. Because I know how things can happen: You can have success, and then it can be taken away from you. Then you can have it again. So I just really focus more on the work. I love to write, and that’s what I’m going to keep on doing, no matter if I’m published again (or not published again).


All of your books end with this wonderful two-page, three-page list of acknowledgments of the people who have helped you bring the novel together. How important is community to you?


It’s totally important. I spent the beginning of my writing life on my own, all alone. I was too shy to show anything to anybody.

And all of a sudden the internet exploded, and I had all these writer-friends and a writing community. You could ask them questions! You could Skype them and you wouldn’t have to leave your desk!

I have three writing friends who email or Skype every day just to check in: “How’s the work going? Would you read something? Okay, let me read something of yours back. . .”

When you find someone who has your same sensibility, it’s just amazing. It’s just totally amazing. I feel like it’s really important to have a writer’s community, to help other writers, and to be able to ask for help yourself.



How do you think a writer should go about building a community?

Probably the same way I did it: Go to a lot of readings, talk to a lot of people. Don’t ask them things. [Don’t] go to a reading with a copy of your manuscript and ask people to read it.

Try to talk to people about things in life. Like if they have brownies they bake, you talk about brownie recipes. And you do the same thing on social media. You get on Twitter and Facebook, and you find writers you admire and you don’t talk to them about writing. You just wait until they say something about their dog or their cat, and you get to know them as a person, and see if you like them as a person and if they’re like you.

And what happens is when you do form a connection, then people say “You know what? We should have lunch.” Then you have lunch, and that’s how you make friends.


I know a lot of people say “Social media is terrible, the relationships aren’t real,” but they are real. Some of my closest writer friends [are] people I’ve met online, just from interactions and having conversations with them.


A lot of your reviews say things like “It’s gripping, but it’s beautiful; it’s lyrical, but it also turns pages.” How do keep those pages turning? Is that something you’re conscious of?

I wish I knew. I have no idea. When I’m writing, I always think, “This is so boring. Who’s gonna want to read this?”

But part of it is something that I learned from Robert McKee, [a] story structure guru. He talks about something called “the negation of the negation.” What this means is that you always want your characters to be in peril, but you want to make it as bad as you can.


So if you have something bad like, say, you’re getting married and your partner doesn’t show up. Well, that’s bad. But the negation of the negation would be: OK, you’re getting married. Not only does your partner not show up, but your partner runs away with your mom.

And then you think, “Well, what’s worse than that?” And what’s worse than that would be, “Your partner runs away with your mom, and they both get in a car accident and your mom survives, but your partner doesn’t.”

So you always try to think in terms of what would be worse, what would be harder for these characters. Because those are the moments when people really show their best selves. Also, those are the things that people don’t really talk about a lot, but they want to know about. We’re sort of afraid of it. So as a writer, you go into those dark places, and I think that’s what keeps the pages turning.


But it’s never anything conscious with me. I never really know what I’m doing.


What’s your best advice to other writers?

Never, ever, ever give up, because you never know what’s going to happen. And don’t listen to what people tell you. When I was in high school, my English teacher told me that I was a horrible writer, that I would never be a writer. In college, I took a class with a professor who at the time was a famous writer. He told me at the end of class that my work was garbage, and I would never make it, and I should think about being a nursery school teacher instead. I didn’t listen. I didn’t listen! I was devastated, but I kept writing and writing and two years later, I published my first novel. I sent a copy of it along with the New York Times review to the professor with a note saying “You were wrong!”

So you can’t listen to what people say. There are always going to be people telling you “you can’t do this,” or “I don’t like this.” There are so many writers who have gotten 80,000 rejections and then suddenly they sell a book and it’s a huge critical and commercial success. So you never know. Just keep writing.

Also, write what you want to write. Do not follow the market. Do not look at the books [that] are best-sellers and think, “That book is selling, I’m going to write that too!” No. Write for yourself first, and that’s how it will become universal.



What would you say is the most difficult part of being a writer?

The first is a practical thing: Paying the bills. Before Pictures of You, it was really difficult, because I had to have a day job as well as find time to write, and I couldn’t have a day job that was so all-encompassing that it would use up all of my mental facilities. So I had to find these jobs that would pay enough but yet would be “stupid” enough so I could do them without really thinking. That’s really hard.

Even today, I still do other stuff because I have a son in college. And other writers I know, they still teach, or they do manuscript consulting, or they’re married to wealthy people, so they don’t have to worry about that. That’s the main issue.

The other issue is learning to deal with the solitude. You have to love it. I never liked going to a “job-job,” where you had to socialize all the time and you had to go to meetings and that kind of stuff. I love the solitude of being at home, making a schedule for myself and not procrastinating too much. And that’s something that’s difficult that you have to learn.


And the last part is you have to have faith that you can do this, and that you believe in yourself, and you’re not going to let anybody stop you. Because those are the people who make it: The ones who don’t give up, who have the grit to keep going on and persevering no matter what. And then finally you will find success that way. I’m sure of it.


How did you find time to write when you were holding down a day job?


It was really hard. It was really, really hard. And the first thing was that I hated the job. I mean, I hated the 9-to-5.

So my goal was always: I have to get out of here. I would write on my lunch hours, and then I would get yelled at for not going out with coworkers for lunch. I would carve out 2 hours each night to write. I would write on the weekends. I was really lucky to have such an understanding husband who also kept weird hours, because he’s a writer and editor, too. But what’s difficult is I work all the time. We both work all the time now. But it’s work we love, so it doesn’t seem like work. You just have to be really disciplined, and you have to really want it. No matter what.


Last question, and I know it’s one you always end with when you interview other writers: What haven’t I asked you that I should have? 


This is a question that writers always want to know: “How do you get your book to the movies?” That’s the big payoff.

And the answer to that question is: You just don’t give up, and you have to realize that the movie business is a thousand times worse than the book business because there’s so much money at stake. People will promise you everything and deliver nothing, and most movies don’t get made. So it’s like winning the lottery. It’s fine to think about it and imagine it, but don’t get your hopes up.

I’ve had options of five of my novels, and I actually had a deal that was made at Sundance for Pictures of You. This big star was going to star in it and direct it, and there was money behind it. And then the big star was offered another film for more money, and that was it. The deal fell through. And once the deal fell through, it was sort of like nobody wants to pick it up, because then they think, well, it fell through, so I don’t want to take something that fell through, whatever the reason. So you just never know.



For more on this best-selling author’s writing process, check out “How Caroline Leavitt writes a novel.



—Nicki Porter served as the editor of The Writer from 2016 to 2022; she previously served as its associate editor. Before helming The Writer, she worked as a food editor for Madavor Media and America’s Test Kitchen. She’s also written for a number of publications and spoken at writing conferences across the country. Learn more at








Originally Published