Jessica Fein: Welcome. I'm Jessica Fein, and this is the “I Don’t Know How You Do It” podcast, where we talk to people whose lives seem unimaginable from the outside and dive into how they're able to do things that look undoable.

I'm so glad you're joining me on this journey and I hope you enjoy the conversation. 

Welcome back to the show. Today we are diving into the extraordinary life of bestselling author, Caroline Leavitt. You might know Caroline from one of her best selling novels like Days of Wonder, With or Without You, Cruel, Beautiful World, Pictures of You, just to name a few.

But the story of Caroline's personal life is just as dramatic as any of her books. From family curses to medical [00:01:00] miracles, From heartbreak to literary triumphs, Caroline has been through a lot. She has turned adversity into art, setbacks into stepping stones, and personal pain into powerful prose.

Caroline and I talked about how embracing your inner Pollyanna isn't about blind optimism, but about finding the strength to keep moving forward. We explored the healing power of storytelling, The importance of persistence in the face of rejection and how sometimes the most powerful thing you can do is simply refuse to give up.

Caroline's books have been translated into a dozen languages, and two of her novels are now in shopping agreements for film. She's a book critic for People and The Ethel, and she writes a blog for Psychology Today called Runs in the Family. Caroline is also the co founder of A Mighty Blaze, which connects writers and readers online.

Without further ado, I bring you Caroline Leavitt.[00:02:00] 

Welcome to the show, Caroline. 

Caroline Leavitt: Thank you so much. I'm so excited to be here. I really am. I thought your book was remarkable and I think you are remarkable as a person. So that makes this doubly wonderful. 

Jessica Fein: Well, it's like triply and quadruply wonderful for me because, first of all, to have you say that means so much to me.

And I'm such a fan of yours, both in terms of your writing and who you are as a human being. And I've devoured so many of your books. before I knew about your backstory. Oh, yeah. Once I started to learn more and more about what your personal life has been like over the years, I could imagine how your life has informed your writing.

And that made your writing so much richer for me. You know, I even want to go back and be like, now that I know, but I'm sure many of our listeners are in that same boat, people who know you for your writing, and don't know what you've been through. [00:03:00] Right. You know, I think of myself as a whack a mole, right?

Somebody who continues to get whacked down and I pop my head back in. Yeah, me too. Yes, I was going to say, like, you are the epitome of whack a mole. So let's bring everybody up to speed and start with what was it like to grow up in your family? 

Caroline Leavitt: It was really hard. It was really, really hard. My father was actually an abusive brute.

He was really terrible, but my mother would not divorce him. My mother was alternately incredibly loving and incredibly full of rage because of her situation. My sister was my best friend until she was 17. When she began to have mental health issues, and it was really, really hard for me. She estranged herself from me five years ago, because she felt that I had stolen her life.

And it was a really terrible woman for me to get over. So I was always told that the Leavitt women were all cursed, that all of us were going to have terrible lives. And every time something terrible happened to me, my mother would say, See, I told you, I told you. [00:04:00] So I just sort of retreated into books and stories.

I had really bad asthma also as a child. So I wasn't this asthmatic little girl with an unhappy childhood. I was, you know, a ballerina in Spain or, you know, a mechanic in Africa or any number of things. And I began to really want to write stories. I also was bullied very much as a child for a variety of reasons.

You know, wheezing is a very funny thing to children, unless you're doing the wheezing yourself. So that was hard. My parents also, for some inexplicable reason, lived in a very working class Christian neighborhood and where we were the only Jews there. And I was not liked because of that. People would ask me, where are your horns?

And they would sometimes dig their hands into my hair. So it was really, really, really a rough time. But once I started writing, it helped. It soothed me. And I was determined to change things in my life the same way I could change them in a story. [00:05:00] And it really, really helped. So that was my childhood. 

Jessica Fein: And you had told me that you were mocked for being a Pollyanna.

Caroline Leavitt: Oh, yes, that's right. My sister and my mother always felt that because of the Leavitt Curse, that they would always say things like, well, it's just our luck that this bad thing is going to happen, or you know, if my mother had a headache, she would say, oh, it's a brain tumor, and I would try to make things better.

And I would say, well, you know, maybe it's just a headache, do you want to take an aspirin? Or if something terrible happened to my sister, I'd say, well, you know, it doesn't matter. You can do this instead. And it enraged my mother and my sister. They used to say, stop with the Pollyanna stuff. It isn't helping.

It isn't helping. And I began to realize that they need to feel bad, not that they like it, but they needed that drama. And they needed to feel that. This was their control that everything was going to be horrible. She might as well get used to it. And I determined if they wouldn't listen to me, I was going to listen to me.

And I began to tell myself, okay, childhood is bad, but when [00:06:00] you're 17, you can go to college and leave. Or, you know, this other thing is terrible, but you can change it or you can get over it. And I noticed that they weren't really happy about that. When my first marriage fell apart because my husband was cheating on me for five years and vanishing and all this stuff.

My mother told me not to divorce. My sister told me not to divorce. They said, you'll never find anybody else. Somebody else will pick up your husband immediately and you'll be left alone. You won't have any money. You won't have any happiness. Don't do it. Don't do it. And if you do do it, then you have to come and live at home.

And I said, no, I'm not going to do that. And I went to New York and I was happy. And I always felt that they felt they didn't want to see that example. So I was the Pollyanna of the family. But I take certain pride in it because I think that's not a bad thing to be. 

Jessica Fein: It's certainly not a bad thing to be, particularly in that context.

But then one thing after another [00:07:00] continues to happen to you. And we'll talk about that. But I'm wondering, Did you ever buy into it and say, Oh my God, maybe there is a Leavitt curse? 

Caroline Leavitt: No, no, never, never. I refused because I saw how unhappy, my mom was totally unhappy until her last years when she fell in love in her 90s which was incredible.

My sister is still very, very unhappy. When I kept offering her things, you know, that I would pay for her to go back to school. So she could get a real job that I would help her. She was divorced or this and this. And I began to see the more I tried to help, the more resistant she was. And I began to realize, well, I can do stuff for myself.

And I was determined every time somebody told me you can't do this, or I'm really sorry this happened, but you have to expect this now I would say, no, I don't, I don't, I have to really try. And I would succeed on some level. I never believed it and I still refuse to believe it. I won't believe it. 

Jessica Fein: What do you think accounts for, even from a young age, [00:08:00] for you having such a different outlook and an attitude than the people closest to you, than your family, and being able to say over and over again, sorry, I don't buy into that?

Where did that come from? Were you just born that way? Or is that something that happened along the way?  

Caroline Leavitt: I think I was born that way. I mean, my mother told me that from the moment I was born, I was this really happy little girl. I mean, I became very, very shy because it was sort of, if I wasn't shy in my family, I would be yelled at or hit or whatever.

But she said, from the start, that was my personality. And I was like, And I loved hearing that and that actually helped me get over my shyness a lot to realize, okay, I can do this. I can do this. I mean, I don't want to say that it was easy. I don't want to make anybody misunderstand. It wasn't easy. It was like a really long process.

But now when I look back, I think, Oh, good for me, good for you.

Jessica Fein: That's right. Good for you. Because you do end up leaving that marriage and you say, no, this isn't for me and I'm not buying into the curse and you get engaged. And then…

Caroline Leavitt: Yeah, [00:09:00] I got engaged to this great guy, we lived together for four years and he was really young, you know, we were both really young and he was healthy and two weeks before our wedding, he just woke up and said I don't feel really well and we were about to go to the ER and he literally dropped it in my arms and he had some kind of heart malfunction that nobody knew about and I I just, I just fell apart.

I mean, I did fall apart, but I always was determined that I was not going to go home and live with my mother who wanted me to do that. I was not going to give up. I mean, my friends would say, Oh, well, you know, at least you had that relationship and that will carry through the rest of your life. You know, that was when that stupid statistic was wrong where it said when you reach 40, you have as much chance of getting married as being shot by a terrorist.

It was like some stupid thing. And every time somebody would say that to me, I would say, that's not going to happen. That's not going to happen. And I've seriously looked for statistics, which said that people who had had happy relationships could find it again. Cause you know how to do it. [00:10:00] I mean, it did take me five years.

That was really hard. And you know, I had to go to grief therapy and regular therapy. But I was very conscious that I'm going to do this. I'm going to have this. And when I met my now husband, it was really scary because I kept thinking, what if he dies? You know, like, what if he died? What am I going to do?

I cried through my whole wedding ceremony. Cause I kept waiting for him to collapse. And then he. Did it. And I remember, you know, my mother, my sister said, Oh, well, you were very lucky. That was luck. We never have that luck. And my response would always be, it was a luck. I worked really, really hard to get this happiness.

And you can too. 

Jessica Fein: You know, that's so interesting to me. My sister died suddenly at age 30 of a heart condition that was not known. And I remember a conversation she and I had once because she had had a little bit of a charmed existence from the outside, what would look like, you know, she met this most wonderful man and they got married when [00:11:00] she was 25 and they had this most spectacular child.

And I remember she said to me one time, you know, people say, Oh, everything comes easily to you. And she said, that's such a dig because that doesn't show. How hard I've worked for the things that I had. Right. So when you say that, and you know here earlier we were talking about this feeling of being a whack-a-mole, and the more I'm hearing from you, I'm thinking your sister and your mother were the ones holding the hammer.

Caroline Leavitt: Yes. That's right. That's right. Right. The big problem my sister had with me as she felt that everything comes her, it comes easy for me. And she would say like. When I would try to be comforting her about something, she would say, Well, you don't know because everything comes easy for you. I would call her up and cry sometimes.

I mean, when my fiancé died, I cried. I said, I'm so upset. Please come and visit. She would say, I'm not coming to visit because you're going to be all right. Everything comes easy to you. And I kept thinking that's so insulting because it doesn't. You have to work at it every day and, you know, always try to reframe your [00:12:00] thinking to the positive.

Jessica Fein: And then you meet your fabulous husband, you struggle and you eventually have a baby. 

Caroline Leavitt: Yeah. And here it comes. Here it comes. I had a bliss. I had my son when I was 44 and, you know, I brooked all the odds. They said it's going to be really difficult and I had like five miscarriages and I finally had one that took.

And I was so happy and I had a perfect pregnancy, perfect delivery. Everything was easy. And then just as I was ready to go home, I noticed my stomach was like. And I asked the doctor and the doctor said, Oh, that's nothing. It's just, you know, probably a blood clot from the delivery and we'll just clean it up.

So the next thing I remember is I woke up in a hospital room and it was, I was terrified. Everything was black and white and I couldn't move. And I knew that everything that had happened before wasn't real. I just had this feeling like this was my reality and I had to get out of it. And someone came towards me in a suit [00:13:00] and then everything went black.

When I woke up again, there were all these doctors around my bed and I thought, Oh, I'm in a TV show. This is really weird. And they were saying, do you know where you are? Do you know who you are? Do you know what happened to you? And I looked up on the wall and there was a huge photograph of Max, our baby.

And underneath it said, get well, mommy. We miss you. And I thought, you missed me, where am I? And they had a doctor come in and they told me that they didn't know what was wrong with me yet, but it was something really, really serious. And they were going to try to find out. And I was sort of out of it. I kept saying, can I see my baby?

And they said, no, because we don't know what you have. You can't see your baby. And it turned out there was a small stature woman from Germany who was about ready to retire and she said I think I know what this was I've seen this once before and she wanted to do a test for it. It was something that in postpartum your body produces a protein that stops all your blood from [00:14:00] clotting.

So they didn't know what was going on. I had like five emergency operations. They put me in a coma, a medically induced coma. And they said every time they would open me up, it was like the shining, like blood would just pour out and pour out onto the floor. But meanwhile, they're telling me all this, and I'm in the haze of morphine.

So I'm just laying there saying, Oh, uh huh, uh huh, uh huh. So this doctor said, I think that's the protein. And the hospital did not want to test for it because, first of all, the test was very expensive. And second of all, the treatment was really expensive and insurance wouldn't pay for it. And my husband said, just do it.

Just do it. I will pay for it. So they did it. And sure enough, it was that protein. So I had three more months in the hospital. I had a hundred transfusions. They would come in every morning and say, don't move. Anything could cause a bleed. They were afraid my brain was going to bleed. And at the same time, I would say, you have to move because otherwise your muscles are going to atrophy.

They began to give me something called memory blockers. So, I couldn't really remember what was going on at the end of the day. And then I [00:15:00] was on morphine. I was hallucinating. And finally, they let me go home. Finally, they let me go home. I had to relearn how to walk. All my hair fell out. My skin turned gray.

I was on steroids. So, I was really big. And when I would walk outside, I just remember a group of teenage girls saw me. There wasn't a MoMo because I couldn't fit in anything else. I had no hair so I had like some kind of thing on my head and they were snickering at me and I thought, oh my god, but I turned around because I was, I was crying and my husband came out and he said, never mind.

And I said, I have to cover up more and he said, no, it's warm out, you have to cover up less. Let's go buy you a sleeveless dress. And he made me go and buy this little dress, and as soon as I put it on, I felt, he's right. Like, screw them. Screw them. I'm going to be okay. The hardest thing was that my baby didn't know who I was after.

Jessica Fein: How old was your baby at that time? 

Caroline Leavitt: Six months. 

Jessica Fein: So you had been sick from the time that you gave birth. Six months later, you now come out. 

Caroline Leavitt: [00:16:00] I came out, and I was allowed to hold him, but very carefully, because they didn't want me to bleed. And he would cry. I mean, when I would hold him, he would cry. He would reach for his dad.

Jeff was really great and he said, I'm going to give you two time to bond. And every day Max would be in the bed with me and we would just, I would try to play with him. I would read with him. I would smile with him. And then finally, after a few weeks, he like put his little hand on my face. I thought, Oh, okay.

And then we became really close, like super bonded. So that was that. It took another year for this to resolve, but then they said, you won't come back unless you get cancer or unless you get a repeated bouts of the flu. And I had to go check in with the doctor for five years, twice a week. And then I stopped going because I couldn't, I just, it was too depressing.

But now to anybody out there who worries about that, they now have cures for this. So don't worry. 

Jessica Fein: Well, thank God that the doctor who was about to retire hadn't retired yet. 

Caroline Leavitt: She was great. She [00:17:00] was amazing. It was a really hard time. You know, I had to go back to work because my husband, if this sounds like a soap opera, but my husband was the one earning money and he was fired for spending too much time with me.

So I had to go back to work. To work and so there I am with in the moves and stuff and it was really hard and I saw people's faces when they saw me but I sort of turned it into my Pollyanna moment where I realized you know what it doesn't matter what you look like it doesn't it really really honest God does not matter.

You know, before this happened, I used to be, I don't know, I would wear these little mini skirts and tight tops and bury myself. And I always thought that, you know, I could attract a lot of male attention. And I thought, you know what? I don't have any of those things anymore. And it doesn't matter. And it didn't matter.

I mean, my husband would tell me every day that I was beautiful when I most decidedly was not. And it didn't matter. You know, it just, it just didn't matter because I was happy about it. So that part went away. 

Jessica Fein: That part went [00:18:00] away. And then, I don't know where along the lines you wrote With or Without You, but I loved that book.

And Of course, our main character, Stella, in that book is in a coma. 

Caroline Leavitt: She's in a coma, yeah. And she wakes up.

Jessica Fein: So tell us about that and when you decided that that piece of your real life story was going to become a main thread in one of your books. 

Caroline Leavitt: It's really interesting because it's actually the second of my coma books.

The first book was this book called Coming Back to Me, which was really, really true to what had happened. And it was a very dark. book. And it didn't end with hope. It just ended with this woman saying, well, I'm alive right now. And I was still having all these, because of the memory blockers, I had all these PTSD stuff.

I would be in the supermarket and I would see this packaged soup and I would start to shake. And I didn't know why. And what I would tell Jeff, he would say, well, when they allowed you to eat in the hospital, that was the only thing you can eat. Or I would see somebody with a striped shirt and I would feel nauseous and I would [00:19:00] have to stop.

And it was because that was the hospital curtains and I was sort of remembering it. So I went to a therapist and I said, I have to do something about this. I'm afraid to go to sleep. I couldn't sleep because I was afraid I was going to go back in the coma. I'm afraid of all kinds of stuff and I can't live like that.

And the therapist said, was talking to me and she said, you know, I think you wrote the wrong book. And I said, what do you mean? And she said, you should write a book about another woman coming out of a coma whose experience is totally different from yours. And I thought about it and I thought, okay. I thought, okay, I'll make this woman, Stella, remember everything in her coma because I remember nothing.

And I will have her come out of it not, you know, bleary and hallucinating. She's gonna come out of it with a new talent. And it was the happiest book I ever wrote. I mean, I was so happy when I was writing it, and I always felt like Stella, that character, cured me of a lot of my PTSD. I still have moments, but now I can sort of brush them off.

But it changed from, you know, the ending of the [00:20:00] first comic book was, well, I'm alive right now, and that was all I could have. But the ending of the Stella book, it was almost magical. It was like, anything can happen now, and that can be a good thing. And that was just so happy for me, and that was so healing for me.

And it taught me what a gift writing has been for me through my life because it's really helped me navigate this terrible stuff. And the funny thing is a lot of times people will say to me, you're such a goofball in person. Why do you write these dark books? And I always say, well, it's because I write dark books that I can be a goofball in person.

I put it all in my work and it allows me to be really, really happy, which I am. 

Jessica Fein: I love that. And the book where you had the hope and where you've had the happy shiny is what in fact was healing. So it's not only getting the dark out, but maybe writing a character. But it's right. bodies what it is you want to carry forward.

Caroline Leavitt: Yes, that's exactly right. That's exactly right. It's not like I dismiss that terrible things [00:21:00] happen. They do. They happen all the time and you can't be prepared for them. But it's like there's always a fork in the road and you can choose what you're going to do with that. And I know you're just like that too.

Jessica Fein: thank you. Well, I'm wondering because you have tragedy in your books and you have triumph and in your personal life you have tragedy and triumph, right? 

Caroline Leavitt: Oh, yeah. 

Jessica Fein: How do you balance the tragedy and triumph in your storytelling in a way that A, is healing for you as you talk about, and B, is so riveting for the reader?

Caroline Leavitt: I wish it weren't so, but I've come to learn, at least for me, that tragedy has made me have more empathy, more compassion, and as you know, it makes the joys So much deeper and better and incredible. I mean, I'm grateful every day for everything. I mean, every little thing it's, I notice it and I'm grateful for it.

It could be just like a really good sandwich and I stop and I think really grateful for that sandwich. It changes you. It changes you. And [00:22:00] again, it's work to get there, but it changes you for the better because I, I understand that you can't have the joys without the sorrows and vice versa, but the sorrow can bring you deeper joy.

And it does. It does. 

Jessica Fein: I so agree. And you and I have had the opportunity to chat about this mingling of joy and sorrow before, but you know, it's interesting because sometimes when I'm talking with people about that very thing, they'll say in a negative way. Well, that just sounds Pollyanna. That's the word they'll use.

And here we are saying being a bit of a Pollyanna is almost what saved you. 

Caroline Leavitt: It saved me. It absolutely saved me. I mean, when I was grieving my fiance, I got it in my head that. Whatever makes me feel better and helps me get through the day, it's okay to do. I've spent a fortune on psychics and mediums, and I, like, got into a bad relationship because I thought, well, maybe that will make me feel better.

And I don't regret any of it, because it's almost like saying, well, I'm going to [00:23:00] try. Like, why not try? And if it sounds Pollyanna, maybe it is, and so then you move on to something else that does work. But it's, it's the way I live. It's the way I live. 

Jessica Fein: And there are far worse things one could be than Pollyanna.

Caroline Leavitt: That's right. That's right. You're making me want to get a t shirt now that says Pollyanna and proud of it. 

Jessica Fein: Yes. Okay. That's going to be our merch. We're going to get our merch. 

Caroline Leavitt: Oh, yes. Yes. Yes. I'm proud of it. 

Jessica Fein: Okay. Well, let's talk about Days of Wonder. This is a book that I just love. It's your latest. I've been shouting from the rooftops about it.

Anybody who follows me has read about it. So first of all, tell us a little bit about that book. 

Caroline Leavitt: Okay. Well, this is a story within a story, which is one of deep resilience. I met this woman a few years ago on the advice of a friend of mine who said, you're going to love her. Everybody loves her. I met her. I loved her.

We became friends. And then one day at dinner, she said, I have to tell you something. And I thought, Oh, I hope she's not sick. Or I hope there's not this. And she told me that when she was 15, she [00:24:00] had committed a murder. And I just, froze because I didn't know what to think. But she was very calmly telling me that she was a wild child as people are at 15 and she did do it.

And she went to prison for just five years because she was a minor. And she said while she was in prison, she got her GED, she got a college degree, and she decided she was going to change her life. And when she got out, she moved out of the country where she was living. She changed her name and she started a profession where she was very, very successful at it.

The only thing she couldn't do is she was very wary of having relationships with people. I actually had trust issues because, you know, when people found out, oh, you murdered your murderer, they would pull away. I thought that that was incredible. Then she told me that when she was in her 40s, she actually was outed.

Somebody found out and she did indeed lose jobs. She lost relationships, but she didn't give up. She said, okay, I'm going to move again, change my name again, do this again. And she had, [00:25:00] and I was just so full of. Compassion and admiration, because it's not like somebody like Charles Manson, who murders and you ask him about it and he says, well, let me out.

I'm going to do it again. I have no regrets. This was somebody who really realized she had made a mistake and she was trying to atone for it by being the best person she possibly could. And I thought, wow, that's, you know, that's so great. And I did not want to invade her privacy. And I promised that I would never reveal her identity, which I never have.

And I wanted to like. Change the story so nobody would ever say, I know who that is, that's blah, blah, blah. So I made it into two New York City kids. And I turned the murder into attempted murder. But the book is based on that whole thing about, you know, what does it really mean to be forgiven and to try to be a better person?

Because my heroine does the same thing where she feels that she did this terrible thing and she changes her name. She moves away and her big problem is she cannot get close to anybody because you know how can you get [00:26:00] close to somebody if you're always hiding away a really important part and it's just about how she comes to understand what she did and how she can live in the world as a better person and I just, I just love that story.

It was like seeing my whole mode of being be related to a real person. And that was really healing for me to write that because I felt that, you know, I've written a lot about an estrangement because my sister is a strange for me and her own daughter and a grandkids, and it's sort of like when you do something wrong, there's a difference between owning it and say, well, what can I do to make it better?

How can I go on and be a better person or just closing down and saying, no, I don't want to deal with you at all. I don't want to deal with you at all. That was sort of what I was writing about, you know, human connection is so, so important that it's worth, you know, maybe putting yourself out there and risking somebody not accepting you.

And if they don't accept you, that's fine, you know, find somebody else who will. 

Jessica Fein: It's interesting because I think that's so true in your own [00:27:00] story about putting yourself out there and taking the risk over and over, given what you've experienced. And, of course. One of the places that's very important in this book, Days of Wonder, is Ann Arbor.

And I loved that you even talked about Literati, the bookstore, which is a terrific indie bookstore, and it's a place that's been important to both of us. So tell us about how the setting and the place Your work comes to be and how much you put your own places that you love in your books. 

Caroline Leavitt: When I first went to college, I went to Brandeis Great University, great education, but it was, you know, it was set in my hometown and it's a really small school.

It was only 2000 people in the whole school. And I went to visit a friend of mine who was going to school in Ann Arbor, and I walked into the city and it was, it was electric. There was so many interesting people walking around and there's so much stuff going on, so much arts and culture. And I just fell in love with the place and I felt I belong here.

I have to go here. I have to have to go here. And I came home and I told my [00:28:00] parents, I'm, I want to transfer out of Brandeis. And they said, Oh, you can't leave Brandeis. It's such a great school. I said, no, I'm really unhappy. And I got them to allow me to transfer by saying, look, it's going to be much cheaper because Brandeis was so, so expensive.

And I got in. And as soon as I got there, it was like being in heaven. It was just being in heaven. I loved everything about it. It's the perfect mix of nature, cause it had this beautiful arboretum you could go everyone way into, and city, and that it was buzzy and busy, and it just felt like possibility.

And I loved it so much that I stayed there for an extra five years after I graduated. I would never have left except that I met my first husband there, and he was going to law school in Pittsburgh, so I left too, but I just, I would have stayed there forever. I never would have left. It was Perfect, perfect place.

So I needed a place for my character. I wanted her to go to a place of great hope that she would love and not want to leave and that would be very nurturing for her. And as soon as I thought that, I thought, well, Ann Arbor, of course. And I still have friends there, so I got to talk to them and, you [00:29:00] know, say, oh, is this place still there?

Or what's new? And, you know, I wanted to throw in Literati, because they're so great. It was just so much fun. It was like I got to be back in Ann Arbor. I was writing it. I love doing that. I want to write about Ann Arbor all the time now. 

Jessica Fein: As your life circumstances have changed, do you find that the stories you're drawn to tell have changed?

Caroline Leavitt: Oh yeah, that's a great question, but yeah, definitely. My first few books, there was no hope in them whatsoever. I mean, even, even though I had hope, they were really, really difficult. I mean, my first novel was very autobiographical, two sisters, one has mental health problems, the other doesn't. Ends really badly.

You know, ends with a suicide. Second book, again, it was like a mother daughter, ends very badly. And I don't remember when, I think it was actually after my fiancé died that I started to say, you know what, I have to give these people some hope at the end. Maybe they don't get what they want, but they get what they need.

So it's more balanced and true to life. But now I'm just [00:30:00] interested in writing about how people change as they work through tragedies or whatever happens to them and how they find happiness and how precious that happiness is. I would never say my books are Pollyanna, but it's definitely different. I'm interested in writing about different things.

I'll never write a comedy, but they're definitely happy, hopeful. Books which say you can do this, you can find happiness, and that's what's important to me. 

Jessica Fein: We have so many writers who listen to the show and I know people would love to get some advice on how do you create a life of writing? Do you have a couple pieces of advice you could share on that?

Caroline Leavitt: Yes, it's really hard and it's even verging on impossible these days because my publisher was just swallowed up by another big conglomerate and that stuff happens and people leave all the time. The first thing to remember is that a writing career is not always like this, going straight up. It can be highs and lows.

The important thing is the people who are successful never, [00:31:00] ever give up. Do not give up. Do not give up. I was very, very lucky with my first novel, but on my ninth novel, it was part of a three book deal with a big publisher, and they rejected it. They said, we're not going to publish it, and I had that moment of feeling, oh my god, what am I going to do?

If you have nine books out, and nobody really knows who you are, which was the case for me at the time, I felt I'm not going to get a publisher. Bye. I decided I was gonna reach out to everybody I knew who was a writer. I just wanted comfort. And I reached out to all these people, and of course they all comforted me and said, don't worry, don't worry.

And one of them actually said, I'm gonna take your book to my editor. I have a new editor at Algonquin. I think she'd like this. And I had no hopes at all, but the editor called me and we talked about the book, and she made me a really modest offer. My agent said, you should take it. So I took it and I told the editor, I have to be honest, I don't, you know, I don't sell books.

Nobody knows who I am. And the editor actually said, oh [00:32:00] honey, that's got to change. And I thought, yeah, really? And I saw what they did. And they got that book into six printings months before it was published. It got on the New York Times bestseller list the first week out. This was picture view. It became a pennies pick, which meant it was in every single Costco in the nation.

And when I got my first royalty check, I thought it was a mistake because it was so much. And then I actually called the publisher and said, I think you made a mistake. And they laughed and they said, no, no, no, we didn't. We didn't. But the great thing about all of a sudden being hugely known and famous and everything else is I looked at it differently.

I thought, oh. Okay, this is nice, but it's not everything. You know, it's not everything. It changed the way I looked at my writing. And since then, you know, when my next book came out, it was the day that Trump was elected and nobody came to any of the bookings. And then there was a pandemic, but I always kept it in my mind.

You know what? The important thing is what I need to focus [00:33:00] on is the writing. And that's what writers out there need to focus on. Don't write to the market, write to what haunts you, write to what is meaningful to you. That's what makes it unique. That's what's going to get you there. Write from the heart, dig deeper, be the canary in the coal mine, go to the places where most people don't want to go.

I mean, that's why your book was so compassionate and beautiful and wonderful because you took on a hard subject. You know, the loss of a child and made it something shining. You know, shining, if I can say that. And that's what I wanted to do. So I feel like who knows where my career is going to go. I could have another failure.

I could have another success. But that's not what I think about. And that's not what any writer should think about. Write the book you need to write. Write the book that you need to read for yourself. And do not give up. I don't care if you have 80 rejections. The 81st could be where the world cracks open.

That's my advice. Yeah. 

Jessica Fein: Oh, I love that advice. That's fabulous. And since you brought up the pandemic, another thing [00:34:00] that you have done is you have really shined a light on so many other authors. And one of the ways you've done that is through A Mighty Blaze. Can you tell us about that? 

Caroline Leavitt: But yeah, A Mighty Blaze was really amazing for me because I've been fired for most every other kind of corporate or business job I've had.

So for me to start a business is ridiculous. But the pandemic started and just as I was about to fly out to Houston and give a talk in front of 200 librarians and Al Gollum called up and said, no, everything is canceled. Everything. There's no tour for anybody. Bookstores are closing. We don't know what's going to happen.

And I hung up and I thought, what am I going to do? My poor book, my baby's coming out and who's gonna read it? And I, all of a sudden I thought, nothing is canceled. Nothing is canceled. I'm not gonna let this happen. So I made a video for Algonquin of myself giving my speech with like the hand motions and everything else.

And I sent it to them and I said, maybe you can send it to the libraries. And they said, what a good idea, we're gonna do [00:35:00] that. And I thought, well, maybe I can help other people. So I put the video on Facebook and I put out a call and I said, you know what, any of you who your tours are cancelled, I've started the Nothing Is Cancelled Book Tour.

All you have to do is make me a video on your phone, one minute. You have to call out another writer because we're all in this together. And you have to call it an indie bookstore. And I thought I'd get 10, 20. I got 200 in the first two days. And after the first week, you know, all I was doing, I was working and putting these videos up.

Ron Charles from the Washington Post called me up and he said, what are you doing? And I said, I have no idea. And he said, well, keep doing it. So I kept doing it. And I was really lucky that Jenna Blum, another wonderful writer called me and said, look, I have a lot of business acumen, would you like help?

And I said, Oh my God, please, please, please, please. So she, we went in and she developed this marketing plan for us. She was amazing. She said, okay, we're going to do this. And then we're going to contact the Authors Guild, Publishers Weekly, the [00:36:00] Boston Globe, the New York Times, and we did all that. And they all responded.

And all of a sudden I was getting all these interviews and all these people wanted to support us and all these writers. And I thought, this is crazy. This is. crazy like I don't know how to do this and Jenna said well I don't either and it's gonna be fine and we're gonna do this and it started to grow so we needed to interview authors like big authors Jenna said I don't know how to do that and I thought well I'll go to all the authors I've ever reviewed so first I went to John Irving because I had written him a letter years ago And he actually wrote back to me because he said I hadn't asked for anything.

So I wrote him a letter and I said, John, I'm really sorry, but I'm asking for something this time. And I told him about the project. And he said, yes, he would do it. And it was so terrifying for me, you know, to interview big authors, like scary. But I did it, and he was very wonderful, and it made it, and once he came on, all these other authors wanted to come on.

Elizabeth Stroud, and J. Courtney Sullivan [00:37:00] is coming this Friday again, and George Saunders. It's a dream job, because I get to talk to writers, and I get to help writers. And it's not just big writers. I read very widely, and if there's a small book from a small publisher that I love, I figure, well, I'm the co founder, I can do what I want.

So I, I prove them all. Um, and I do whatever I can when I can, and it's a fabulous thing because you're giving back to the community. It's just wonderful. It's like giving back without expectations, and it's just made me feel meaningful and great, and it's just a really good thing to leave a mark in the world and to be of service to other people is, again, it sounds Pollyanna ish, but it's a wonderful thing.

It's really a wonderful thing. 

Jessica Fein: Yes, and again, a way in which we are now redefining the word Pollyanna. So what are you reading now and what else is on your reading list? 

Caroline Leavitt: Oh my god, this book is incredible. This is J Courtney Sullivan's The Cliff. It's all about possibility and the history of places and how they [00:38:00] impact people.

It's just absolutely fabulous. I've finished this other book. It's called The Most. It's very, very small and it's about this 1950s housewife and a day in her life when she's deciding, should I stay in my marriage? Should I go out of my marriage? What about the kids? She gets in a swimming pool to think about it and she doesn't get out by choice.

And it's just this beautifully written, gorgeous book. And I love it. Your book Breath Taking is just wonderful. And I've been telling people they have to read it. There's just wonderful, wonderful books out there. 

Jessica Fein: Thank you. Well, thank you for saying that. And your books are so wonderful. Last question. Are you working on a new book now?

Caroline Leavitt: Yes, I am. I'm actually torn between two lovers. I'm writing two books though. I'm doing final revisions on this book I'm calling The Inseparables, which is about what makes relationships and people inseparable and what makes that crack apart. And the reason why I'm doing revisions is when I First wrote it, I had set it in modern times and because it spans 20 years, I realized, Oh, I'm going to [00:39:00] have to write about COVID.

I'm going to have to write about 9 11. I thought, I don't want to do that. I just can't go there. So I decided to set it in 1980s New York city, which is really fun because New York city in the eighties was so gritty and so much fun. And I lived there then, and it was just a blast. And the danger was a blast too, when you're young.

So I'm doing that. Yeah. And then the next book I have 50 pages on and it's set in the 1920s, actually. So that's really fun because I, I really haven't written historical fiction that much, but the 20s is a wild time. So I want to do that. 

Jessica Fein: Awesome. Well, that's great. I, for one, am very happy. That means that I have two new books of yours to look forward to, which I will.

And in the meantime, Days of Wonder, if you haven't read Caroline yet, that's a great one to start with. I am so, so glad we had the opportunity to have this conversation. Thank you so much for being here. 

Caroline Leavitt: Thank you so much. I can't imagine having a happier time talking to anybody and just thank you. Thank you.

And everybody should read Jessica's book. [00:40:00] Breath Taking. 

Jessica Fein: Thank you. Here are my takeaways from the conversation with Caroline. Number one, many of us feel like whack a moles. Persistence can be a superpower. Number two, sometimes it pays to flip the script on family expectations. Number three, if someone calls you a Pollyanna, own it.

Choosing to focus on the positive and maintain hope might be your key to finding happiness. Number four, writing can be a great therapeutic tool. Try writing about your experiences or creating fictional stories to process your emotions. Number five. Ditch the metaphorical muumuu. When you're feeling vulnerable, try the sleeveless dress instead.

Number six. Find creative solutions to obstacles like Caroline did when her book tour was cancelled. Think outside the box to find alternative ways to achieve your goals. And number seven. Joy and sorrow really can live together. As Caroline said, something as seemingly simple as a really good sandwich can be a source of gratitude.

Thank you for listening to this episode. [00:41:00] I have such a great lineup of shows coming over the next few months. Take a minute to subscribe now and you will not miss any of them. As you're settling into fall and looking for a good book to curl up with, check out any of Caroline's many books, and of course, I hope you'll read my memoir, Breath Taking, available in whatever format you prefer, wherever you like to get your books.

Have a great day. Talk to you next time. 

music: I've got the whole world at my fingertips. I feel like flying. I feel infinite. I know that we're the kind that think along some other lines, but we'll be fine. Come along now. The sky is endless. Now we're limitless. We're limitless. Now. Come along now. [00:42:00] The sky is endless.

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now.