Episode 327: Cindy Chupack on Determining What You Want Your Book to Do for You

Sep 09, 2020

Cindy Chupack is a TV writer/producer whose credits include Sex and the City, Better Things, Divorce, Modern Family, Everybody Loves Raymond and I’m Dying Up Here.  She recently directed her first feature, Otherhood, now available on Netflix.  She has written two comic memoirs: the NYT bestseller The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays and The Longest Date: Life as a Wife. Now divorced, her latest “chapter” was published recently in Katie Couric’s newsletter, a piece called Love in the Time of Covid-19. 

She's also one of the kindest, most modest people alive. Proof: that bio above, which she gave me, doesn't even mention the fact that she has won Emmys and Golden Globes. As in: multiple. We met when we both contributed essays to the anthology Girls Who Like Boys Who Like Boys and in the years since, I've watched her straddle the line of author, TV writer, director and storyteller, among several other pursuits.

In this episode, we talked about how important it is to figure out ahead of time what you want your book to do for you, how likely it is to have your book adapted into a TV show or movie and the difference between writing a memoir and a book of essays, among many other topics.

 

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EPISODE TRANSCRIPT:

Anna David:                  00:00                Here we go. Hi Cindy.

Cindy C:                        00:02                Hello Anna.

Anna David:                  00:05                I was reflecting this morning or since we've been in touch again about when we met and how, and I am not blowing smoke, you are just one of the kindest, you treated me like I was a writer really before I was a writer. And you have no idea how much that meant, it's true.

Cindy C:                        00:24                Ah, I think you always were a writer. So that wasn't that hard to do.

Anna David:                  00:28                Okay. So we met at a dinner party that Tom [inaudible] and Melissa De Le Cruz had for all the contributors to their anthology, Girls Who Like Boys Who Like Boys. And I just remember it was this long table and like every woman, my age slash every personal life, I was obsessed with Sex in the City. And I was like, Oh my God, I heard there was someone who wrote on Sex in the City here. And you were just looking. And I think that night, well, my first book was coming out a few months later, a year later. And I literally [inaudible] you that night. I was like, would you write a blurb, which now that I'm asked for blurbs, I really quite understand what an imposition that is. And you were like sure. And you did!

Cindy C:                        01:06                That was before I realized what an imposition blurbs were early on in my career. And I was so excited somebody wanted a blurb from me.

Anna David:                  01:17                That's how I used to feel. And now I'm like, ah, no.

Cindy C:                        01:22                No, because you, you start to sort of feel like your blurbs are kind of a currency and you don't want to just give them to anybody. And but anyway, I still stand behind my blurb for your book. And I love that first book Party Girl. It was so cute.

Anna David:                  01:35                Thank you. I, so, okay. So what's interesting about you as opposed to anyone else I've ever interviewed. Is that being an author is kind of a secondary career for you? Probably really a hobby?

Cindy C:                        01:49                No, I love it. I still love it. I mean, and no, it's not. I mean, that's sweet of you to say it, what it is part of what I thought about what I wanted to talk to you about, which is sort of what your goal for your sales and your book, like what part of your career is it, or is it what you're counting on paying your rent or is it something to supplement or a stepping stone? So we can talk about that. But for me I sort of, I started out thinking I wanted to be a journalist and I wasn't good at hard news. And then I wrote like a comic essay that sold to a magazine and that started my TV career, but I continued to write those like one-off comic essays. And because I was in journalism school where you weren't supposed to have your opinion in a piece that was very objective. I really liked comic essays where it's like first person and you can just be yourself and I'm inspired by other writers who do that kind of writing. And that kind of just, I did on this side, but it was so exciting to me every time one was in a magazine back when there were magazines.

Anna David:                  02:47                Back when there were those things that we picked up and read.

Cindy C:                        02:50                You might see someone reading it on the subway or something.

Anna David:                  02:54                Well, and so, I mean, people would probably hate you to know that that's how you got into TV and you've talked about it before, but what in God's name was in this essay that made this whole ball start rolling? Who was that for?

Cindy C:                        03:08                It was for this magazine called New York Woman, which was edited by Betsy Carter. And when I moved to New York out of college and had this cheesy, like it was like an advertising job at one of the first online things. Cause I'm a hundred years old. So it was like, you had to explain what that was going to mean online shopping. Okay. So I was writing for that. And then I read New York magazine all the time. And there was this back page essay that was like a comic essay that I loved. And I just wrote this piece one night, New York Is, and it was all these things about New York. It's in my first book, between Boyfriend's book. And that essay, I just, it was kind of like all my observations as an outsider in New York, like New York is when a woman raises across the room to ask whose dress you're wearing. She is not asking from whom it was borrowed, but for the name of the designer, because I was such a girl from Oklahoma living in New York.

                                    04:05                So it was just a bunch of those. And it got published and a TV writer, producers saw it encouraged me to think about writing television, but from that one piece, which was kind of like the flare I shot up, I always think of it. I mean, I wasn't thinking of it as that at the time, it was my sense of humor. It was kind of like meeting me without meeting me. And so that started this path of writing essays every so often for magazines and also thinking about television writing, but it wasn't like I immediately got in, I came here and took classes and worked on shitty shows for a long time. And but it did definitely contribute to my career. And then as I continued to write pieces about dating that contributed to me eventually getting on Sex in the City when Sex and the City happened and becoming my book. So it was all sort of part of a plan. I didn't really have planned out.

Anna David:                  04:55                So basically, when you were submitting specs, did you also submit those dating essays or you just kind of had a name as a dating writer?

Cindy C:                        05:03                Well, I barely had a name like I was doing like one a year, I think, you know, for different magazines. And but, and when I first started writing television, I was writing with a partner. And so I couldn't use those dating essays. Cause when you're writing with a partner, you have to, you know, be a team. So those were my individual essays. So it wasn't until we kind of broke up as partners. And I was looking to make my name on my own, that Sex in the City was just starting and I had these essays I'd been doing all along. So it was sort of like having the, having the goods when I needed them.

Anna David:                  05:35                And so when in this, your Sex in the City and the city career did the, Between Boyfriend's book come out?

Cindy C:                        05:44                It was so I'd written these like once a year, these essays and then because of Sex in the City, Glamour invited me to be a columnist only because it was the Sex in the City writer. I mean, I guess I earned it because I was using dating stories all along, but it felt like nobody would have cared, but then it was kind of a big thing to be able to say the Sex in the City writer was writing a column for Glamour. And I took it kind of with an eye toward knowing that I would have to produce an essay every month that could become a book because I loved like Meryl Marco's books that were comic essays and Cynthia Jaimal who wrote a great book called Get Your Tongue Out Of My Mouth and Kiss Me Goodbye. She writes great.

Anna David:                  06:28                Oh, don't know that one.

Cindy C:                        06:29                So I had these, you know, sort of heroes who wrote this sort of book. And I always thought I'd love to try to do a collection. So I thought that column would push me to get enough done. And then, you know, I did all along, so when I was writing that column for Glamour, they would want you to edit the pieces to make it like good advice for women. And I felt like I don't know what I'm doing because if I knew what I was doing, I would be married instead of writing this column. But so I saved what I called the book draft as I was writing those essays, which was sometimes not that different than what they published, but it was just my pure vision, which was more like commiserating. And that kind of became the tone that I loved for books and for writing and for writing for women. And even for TV writing for women, just kind of commiserating rather than trying to tell people what to do.

Anna David:                  07:18                Yeah. Yeah. It's like, if you'd known what to do, you wouldn't have been able to write the pieces.

Cindy C:                        07:22                Yes, yes. But when Between Boyfriends but came out, so that came out while I was still working on Sex in the City. I didn't want Sex in the City on the cover for reasons that I can't remember. I thought it would be cheating somehow. I don't know what I thought, but anyway, I didn't want it on the cover identifying me. Cause I felt like it was sort of trading on this thing that wasn't, I didn't create Sex in the City. So anyway.

Anna David:                  07:47                Do you regret that?

Cindy C:                        07:47                I mean that book did well and like, you know, it, wasn't New York Times bestseller.

Anna David:                  07:56                Okay. So you have this piece that I think about all the time that is just is about how it is the New York Times bestseller, but compared to Liz too, you know, I had Greg Barrett on the podcast like two weeks ago.

Cindy C:                        08:09                Oh, he's so funny.

Anna David:                  08:10                So funny, but and it's very interesting to get the story of what happens after you have the number one New York Times bestselling book. But so you.

Cindy C:                        08:21                He's talking about Greg Barren and Liz Tachillo who had the number one bestselling book, He's Just Not That Into You. I had the number 27 for a week. New York Times bestseller.

Anna David:                  08:31                Which still counts. And you have this hilarious line in it that you were like, they're on Oprah, I'm on Liza. Liza at night, which was like maybe a radio show or something.

Cindy C:                        08:41                It was, and it was taped during the day. You're talking about the essay I wrote for the New York Times book review, which was this piece called the, Between Boyfriends Book Tour. And it really was, I was reflecting on it when I was going to do your podcast. It really was thinking about what my goals were for this little book, what the readings were like, how I had to send out these emails and do these like tiny little readings at bookstores. And then He's Just Not That Into You came out. And so I said, I used to be the writer from Sex in the City who wrote a book until two other writers from Sex in the City, wrote a book called He's Just Not That Into You. And then I realized, well, we're just not that into my book

Anna David:                  09:20                Well, it's all relative, because truly being one of those writers that they send on tour to have six people show up is you are the rarefied group of the people with book release.

Cindy C:                        09:32                Right. I know I took, I talked about in that essay, a friend of mine who was trying to set up his own readings at bookstores, and he got banned from bookstores basically even to buy books because every publisher only gets a certain number of authors in a bookstore. At least that's how it was then. And so you can't arrange your own.

Anna David:                  09:49                I know that's I was just writing about this because until I got into publishing my own books, I just believed my publisher when they said no, that bookstore doesn't want you. So I've had to work out this resentment towards Skylight Books for like two decades, not understanding that they, the publisher just wanted other authors in there. Now with my own books, I call it book soup. I'm like, you want me to, but we love it. Bookstores do want our books. It was the sort of that publishers are often working against the writer.

Cindy C:                        10:19                Right. They had other books that were bigger priorities. Yeah.

Anna David:                  10:22                So what was, and I realized it was a while ago, but what was your launch like for that first book? And then we'll talk about your second book

Cindy C:                        10:31                For that first book Between Boyfriends. But then I was on Sex in the City at the time. So there was a pretty extensive tour and people were pretty eager to talk to me on the radio or in interviews because I was on the show and I could answer questions about the show. So it was a platform. My book alone, I don't know if it would have made such a splash, but I stand by the writing of it because it was the same tone, you know, because I was writing both. But and I love that that's the kind of book, cause it was about well, I should tell the story of how I picked my, I was so lucky to pick my editor. But there wasn't, so I had these essays and I wanted to put them together in a book, a collection of essays. And when I sent it to agents, there was one agent in a really fancy agency who said, like, if you made this into more of a memoir, like really crafted it into a story instead of separate essays about dating, this could be a great book. And I thought, I don't have the time or the energy or the interest in doing that right now. And I don't quite know the shape of this story because I'm still living it. So there was another editor who saw my collection and she said, maybe we just need an organizing principle, like from breakup to your next boyfriend, which really helped me organize this group of essays. Cause then I could figure out what was missing and kind of put them in chronological order and create different sort of stages of that. And because it was so that helped me in so many ways. And it was interesting just to realize, maybe don't go with just the fancier agency. Cause you ha like the idea of being a fancy writer. Cause I wasn't really a fancy writer. I just wanted to do my book of essays. But I, but anyway, that sorry, what were you going to say?

Anna David:                  12:17                And really the difference between, it's always amazing to me, what is considered quote literary, and then what is considered like chicklet, like literally same books could be considered one or the other. It's very bizarre.

Cindy C:                        12:31                No chicklet. It's a very ghettoizing name. You know, there's not like a dicklet sort of version. No, but I will say that, that book, because it was about a stage of life that people just go through. Cause no matter how old, it wasn't really a time, even though it's probably outdated as far as dating is so different now. And it's so much more online. People still seem to read it when they are going through a breakup or give it to friends going through a breakup. So it's one of those kind of evergreen topics. I think that's why that book has kind of continued to do okay. And just be out there or be even just, you know, traded around with friends, which makes me happy.

Anna David:                  13:13                My favorite, favorite essay is the one about when you were dating the married man and you thought it was him calling to have phone sex, and spoiler alert. It was a dirty phone call.

Cindy C:                        13:28                That I entertained for a while and then felt, yeah, that was an essay called Rock Bottom as the name implies. I'm not proud of that, I believe in submitting your very worst. I mean, especially for me writing about women and dating, I feel like you have to admit your flaws and your worst moments. It's really not about revenge and taking anybody down or blaming the other sex so much. And I think those books and essays, when you read them, you can sort of feel that the motive is anger or revenge. But I was really just trying to figure out what or trying to make sense of it and sort of commiserate with other women going through it and admit my worst moments, which was dating a married man and having phone sex with some random stranger I thought was him, well, we didn't go all the way.

Anna David:                  14:19                You realized, I still remember. You're like wearing a tee shirt and he's like, what are you wearing? And maybe you lied about what you were wearing.

Cindy C:                        14:26                He said like what? Yeah, yeah, yeah. You have to read the essay, get the book or read the essay.

Anna David:                  14:36                Get the book. But Oh yes. You know, I talk about this quote a lot, but Mary Carr says, if anyone's going to be an asshole in your book, let it be you. Because I think that you can feel those vendettas I've been guilty of writing those vendettas make no mistake, in essays. I don't think in books, maybe in books too. And you can feel it and you don't like the writer as writer.

Cindy C:                        15:00                Yeah, you have to kind of take yourself down before anybody else does. And you'll still feel horrible when other people take you down. And if you write a memoir, you might be aware of this, but I feel like the reviews, it can be really hurtful because they're basically reviewing you as a person. There was this one Atlantic review, even though it wasn't a literary writer, there was a very long review in the Atlantic, which of course I burned ceremoniously with my friends cause it was like, it didn't matter. And then my dad mailed it to me for some reason. That's another story. But yeah. I feel like you have to have a pretty thick skin that people are going to talk about you, the author, and cause you're revealing a lot and they might sort of take you down.

Anna David:                  15:44                Yeah. I have a friend who wrote a book that was reviewed in the New York Times where I will never forget this line that said, you don't just dislike the book, you dislike the writer. And it's just as low as you can go, to spell that out. So cruel.

Cindy C:                        16:02                Yeah. Well at least that reviewer admitted it. I feel like that's sort of what is behind it sometimes when you can certainly tell.

Anna David:                  16:11                I once got a review that said I felt that the author was lying and it was my most personal book and I wrote her, I've never done this. I wrote her. And I said, you can say anything you want about my books, but don't tell me I was lying. She actually wrote back and said, I'll tell you the truth. I'm a fashion writer. And I was given this, I was assigned this book review and I didn't know what to write. I mean, it was really big of her to admit that. Yeah. You just don't know what's going on with those writers. So, the launch back then was a book tour? Parties?

Cindy C:                        16:51                Yeah. Well there was a party. I think, I feel like I might've ended up throwing my own party. There was in the same way that I didn't want Sex in the City on the cover. I think some magazine was willing to throw a party, but they were going to have, it was going to be like an advertisement in the magazine, which happens all the time. But at the time I was this girl from Oklahoma who had, I thought I had certain principles, but I didn't want that, which seems stupid. So I think I threw my own. But anyway, yeah, so we had a party that I threw, which is totally fine to do and it was fun. And then and then there was a little bit of television and there was like one Today Show appearance. That was probably the biggest uptick in everything. But I did find that I really liked radio because I didn't have to worry about what I looked like. Or if I was making weird, too many gestures with my hands or if I felt fat to be on TV or whatever, good reasons you could just sort of be yourself and it's pretty intimate and I liked it that way.

Anna David:                  17:54                So what would you say people's greatest misconceptions about a book launch are?

Cindy C:                        18:00                Well, getting back to what I was starting to say, I feel like you really have to figure out your goal for the book. And I mean, I was trying to write down what I thought some might be, I mean, do you want to be famous? Do you want to make a lot of money? Do you want your book to be in every single house and be a bestseller and be a household word? Or do you just want it to get to a few people who are sort of going through what you wanted to write about? Is it revenge? Which we've already identified as not the best reason. Proving something to yourself or your family or teachers who said you weren't a writer. Are you honoring someone like you're trying to write a book about a relative or something that you care about? Social change? Or is it like a stepping stone in your career? Like you want to be a TV writer and you want to put this out to show, you can write comedy or so I feel like that's a step that some people don't really think about and it really needs to drive then what kind of publicity you want to do? How much you care about all that? And then also is it like your sole income, in which case you really do have to push it and worry about every book sale and or is it something that you're trying to do on the side to enhance your career or something? So that's part of it.

Anna David:                  19:18                Great. I mean, and God help you if it's your sole career, because I think I know two people that have ever made a living as an author solely. Okay. So let's say that most people are like, Hey, the fame sounds great. What should they do?

Cindy C:                        19:36                Well then I guess you do try to figure out I mean, first of all, you're hoping that your book is actually going to be something that might be in the Zeitgeists or might speak to a lot of people in this moment. And maybe your very quirky personal thing won't be that thing. But I still believe you have to write what you want to write and write from the heart and hope that lands. But then I think trying to sort of identify your strength, cause you will have people tell you everything you need to do, which is a lot like Anna, you probably do it really well, but you should be making videos and on all sorts of social media platforms and blogging. And I heard your interview with Chris Voss, who's like so interesting and such a master marketer, but he's so strategic. I mean I just, sometimes you're just a writer who wants to write a good book and you don't really want to have to figure out how to be the master marketer. But if you want to be famous, you may have to figure that out.

Anna David:                  20:35                Yeah. And even then there's no guarantees, but yeah. I mean, Chris Voss, do keep in mind, he's the master negotiator. So he can negotiate something like this. You know, I remember him saying in that interview that he watches Ted Talks to understand how to articulate a story in a way that people think is interesting. And he's just talking about for the interviews, my God, if I was concentrating that hard on presenting myself, I'd never get around to presenting myself. That was just, that would stress me out.

Cindy C:                        21:04                I know. Right. And then you just want to be authentic or in the moment, but do you really need to prepare and know exactly what your talking points are? And I mean, one thing I realized for me is just trying to figure out where I'm most comfortable and can do the best. Like even down to the clothes I wear because there's people that tell you what you should wear. But I found if I just felt comfortable and good in what I was wearing, even if it wasn't exactly what would be the best on camera, then I did a better interview. So that makes a difference to me. And like I said, radio, I loved, I realized that I kind of loved Call-in shows or where there was a Q and A, because I really enjoyed that. Being able to be spontaneous and answer in the moment. And so there's certain places maybe you're going to shine, but yeah, there's all those, I mean, there's so many ways now, like a Ted Talk or all the podcasts or, you know, there's so many ways to get your message out there to different people. And I think you probably have had other people who are better at marketing than me.

Anna David:                  22:08                You know what I was thinking, I may not have anyone as good as writing something that'll get in the Zeitgeists is you, cause you said that very quickly, but how would you have been really good at that, consistently? How would someone do that? Or is it something you can even chase down?

Cindy C:                        22:26                Well, I know I listened to your interview with Anabel Gurwitch, who I've done some book readings with and toured with and I love, and she definitely does that and I thought gave a good explanation of how she identifies that. But for me, sometimes it's as simple as like, what are my friends and I actually talking about and worrying about like, what am I really worried about right now or confused by, and is it something that not anybody's really articulated, at least not in the way that I might. So I've actually kind of written about stages of life. Like that first book was Between. Boyfriend's book. My second book was The Longest Date: Life As a Wife, a stage, which has just ended for me, in my divorce. But I stand by it. Anyway, and so I kind of, even from the beginning, my first essay that was in New York woman, it was about New York. I kind of like taking on things that feel like everybody's experiences written about it. What new thing could you possibly have to say about dating or marriage or New York? And just trying to figure out what my way of saying it would be and kind of talking about in a way I haven't heard.

                                    23:38                And in my second book, The Longest Date: Life As a Wife, a big driving motivator of it was I had gotten later in life, was older when I got married, I still wanted to have a child and all the fertility stuff we went through, everybody I knew was going through because so many women have careers that go later until, you know, don't get around to having a kid till later. And so fertility and just trying, I found so trying. And I felt like there was nothing that was written that had kind of a sense of humor and just a coping strategy and was just going to be honest about it, the ups and downs and all the bargaining you do with yourself. And just be honest about the weird decisions you have to make, if you're going to use an egg donor and if you're going to adopt. And so I really, it was something that everybody goes through and that everybody, I mean, not everybody goes through fertility problems. But I felt like so many people I knew were dealing with it and there wasn't something out there and it was something I would have liked to have read. So then I'll write it.

Anna David:                  24:42                Great advice too. Yeah. If it's, you know, rather than doing global research, you do research among the people. You know, that is a niche. If they are people you know, there are other groups like that all over.

Cindy C:                        24:54                Yeah. Well, that's what I've learned that I find so reassuring about the world really is there's these common issues, even though infertility is, it's almost like a luxury problem because you have to have a certain amount of means just to even deal with that if you're having trouble having a baby. But I think these issues of motherhood and your fear of becoming a mother and how it will change you, and what marriage means and, you know, attaching your life to someone and all the compromises you make, those sorts of issues are so universal and the issues of friendship. I mean, I found that even as a girl from Oklahoma, writing on Sex in the City, that felt so specifically New York and this sort of frothy, upper echelon, New York, you still meet people from all around the world who so relate to that show and those women, because of the core issues you're talking about are relatable. So I think it's good not to get caught up in what I think is a little bit of a trap of like, do I have anything interesting to say about this that nobody's said, or are my problems luxury problems, or is what I'm going through with infertility, not nearly as bad as everyone else I know who's been going through it. And you start kind of comparing yourself and disqualifying yourself as only women can do, before we ever put it to paper. And really just, if you're truthful about your specific situation, I think that really speaks to people. And then you have the defense that you're just speaking your truth. You're not trying to speak a universal truth. You're speaking your truth, but I think that's what ends up touching people.

Anna David:                  26:26                God, that is such good advice because I talk to people all the time who say, well, what's unique about my story and it's actually ironically, it's the specificity of your story that's going to make it universal. I mean, that's brilliant,

Cindy C:                        26:43                Right. Yeah. I think because people want to feel, you're telling the truth and that you're opening yourself up and it starts making them think about their own story and what they're going through and their feelings can be so similar, even if the specifics are different

Anna David:                  26:59                And having written a book of essays and a memoir, a memoir of a certain time in your life, what would you recommend to people? How were the experiences different?

Cindy C:                        27:10                Well, the memoir about marriage, it was similar in that. I still wanted to write about it in essays. I mean, that's the only way I know to write a book. I think I get very intimidated by the length of a book, and the idea of an overarching memoir. I started writing that book about marriage five years into the marriage. And I sort of joked that I'd always said, I want to have a baby in five years. And I've been saying that for like 20 years. And so now I finally had gotten married and I wished we had five years just to be a couple, but we needed to try to have a baby right away. And then it took five years of infertility and everything more than five. So when I started writing the book, it was five years in, and we were still on the journey of it. But I still started figuring out what are the things about marriage and the adjustment to marriage, and also about a baby quest that could be an individual essay. And I do a lot of storytelling shows, which should be done too, which I love. I think that's such a great way to force yourself to write an essay. Cause a lot of times you can read them. You don't have to just say them.

                                    28:10                And there's storytelling shows all over the US pretty much if you just Google it in your town and there's ones about motherhood and there's, you know, ones that are just open and there's some that are funnier, and some that are more poignant, but I found that to be a great way to test out essays. And so I wrote one about like thinking we were going to try an egg donor and you know, all different stages of this. And then I put them together into a memoir that was more cohesive and I had a really good editor for that one. And he said at the very end, once we did, we adopted our daughter. She was like, so how has your life changed? This whole book has been this journey. You have to write the chapter on how your life changed, which wasn't anything I really planned. And I wasn't sure what I had to say about it, but being forced to write that essay, it's one of my favorite essays I've ever written. And it was really interesting to see at the end of the book that I did have a journey and an arc and something I learned, but I didn't know what it was when I started it. I can't remember if that even answers the question you were asked.

Cindy C:                        29:08                Yeah, well it does. And it brings me to, you know, other people who are intimidated by the idea of writing a book to actually write a book, have to know that you could write a book of essays and it can become a book without you having to do very much.

Anna David:                  29:24                A chapter basically. Yeah. Like bite sized pieces, I always think of it, cause I can sit down and write a pretty long essay and like I've written some for Modern Love and I love Modern Love as an example of just a really good essay. But I think a really good essay has a beginning, middle and end and has a journey in it. Then if you put those all together, you can have a really nice collection. And there's usually is some order to the things you're talking about even if you don't quite know what that is yet. And maybe you could think of a chapter of a book the same way, even if it's not a memoir, just this bite size piece of the journey of your book, you're going to do that today.

Anna David:                  30:01                It's so much less daunting. Speaking of Modern Love, but I just had this funny memory. So you and I both had essays from that book purchased as a Modern Love and they, and it was, it was crazy. I didn't know what Modern Love was. I didn't know that that's really crazy that Modern Love would pick two essays from the same book. And so I remember walking into our first reading, you are not there. Maybe you weren't, maybe you were coming, you weren't there yet. And this guy who was in the anthology comes running up to me and he's like, Oh my God, I was introduced as the Modern Love writer. I loved her so much, blah, blah, blah, blah, blah. And then I remember Tom walked up and he was like, that's not Cindy Chupack, that's the other one. And he was like, Oh, and walked away.

Cindy C:                        30:44                That's still pretty great. You know, I taught a memoir. Well I taught a class one time for Northwestern alumni with Hope Edelman. Who's a great writer. Who's written a lot about grief, lots of memoirs and books. And we were trying to figure out how to teach a class about how to tell your story, whether you're going to make it a TV show or an essay or a book or a memoir. And we decided to boil it down. Cause we didn't have that much time with students into let's just challenge everyone to write a Modern Love essay. And it's actually a great challenge for anyone thinking of writing a book because it does. And so many of those do get optioned into a book for one thing. But even beyond that, it forces you to kind of crystallize like this crisis moment where you learned something and kind of the heart of what you want to talk about. So people think they want to write about like when they ended up on a blind date and they realized they had a lump in their breast and it became breast cancer. Like that's this crisis moment. Even if you're thinking, I want to write a book about my whole breast cancer experience, there's some moment maybe that would be really to grab an audience. And that would be the one you choose to write a modern love essay. And so it's not about an exercise to sort of figure out your, if you have something that maybe could be a book.

Anna David:                  31:58                That is great advice. So what else would you recommend somebody do for a launch? Because you may say, Oh, I'm not that marketing person, but I, you understand human beings, in a unique way, I would say, that's why you're so successful. So what else would you recommend?

Cindy C:                        32:18                Well, I am totally a homework person. Like just to be on here. I asked you to give me your favorite three or three that you loved and or that you thought would be good for me to listen to. And so I listened to Chris, not to single anyone out, but I listened to what was it, Chris? Chris Voss, Joel Steinin and Annabel Gurwitch. And so I always do homework like that before I'm going to be on a show or interviewed by a magazine or anything. I try to make sure that I really know what kind of stuff they've done and try to see what I think works or doesn't work about interviews. And I think that helps and it's nice to just be familiar with it. It's hard sometimes. I mean, hopefully you're so busy that you don't have time to do that, but I just like launched. I just wrote and directed my first movie Otherhood for Netflix. And they did kind of a publicity tour for me, which was great because they had it all set up and we went like outlet to outlet. And you know, there was a hair and makeup person doing me before, which was kind of great. And so I could sort of only worry about where I was going to go. But even then I still tried to research in each city, like what we were, what that station was like, or just get a feel of whatever I could, if it was a radio interviewer, find out a little about them or read their biography, whatever I could just so that I felt a little bit comfortable there.

Anna David:                  33:36                That is so respectful. And I will say, here's a tip that you just gave me. You're the very first person I've ever said, Hey, would you do this? And you said, what are your favorite three episodes so I could listen. You could say that and not even listen. And you will impress the hell out of the person, seriously. Now I, you know, and then another thing I wanted to ask you about people, many people dream of having their book optioned and made into either a TV show or a film, what would you recommend for someone who has that goal?

Cindy C:                        34:07                Well, it's partly your, it's hard to, you know, anticipate that might happen. I mean, I'm even in that industry and yet my books have never been optioned for something like that. I've tried to make my books into like a TV pilot, but it's always kind of like translating. It's something that gets less interesting to me. Once you start fictionalizing, it enough to cause there's something about memoirs that are like, we talked about the specificity of first person, and it happened to you and you're telling it like it is. And then when you adapt it for TV or film, if you try to do it, you're then creating characters to act out this. Cause it's probably not somebody playing Cindy Chupack on the show, somebody playing Sandy, something. Sort of married to someone, something like your, whatever. I feel like it starts to get diffused a little bit. So adapting your own thing is hard, I think. And then letting it go and letting someone else adapt, it is hard. And I've adapted like in a [inaudible] book. That's still hasn't gotten made into a movie, but that was hard cause he's such a good writer and so funny that I want to do include everything. And he even told me that sometimes it's easier to adapt something where you like the plot, but you don't love the writing so much because and also if it's shorter, like taking the short story and adapting it. So there's so many reasons that it might be complicated to adapt a book. But anyway, I would say. So I don't know if I'm the best person to talk to about that, except for that. I know, you know, your agent can play a big role in it, your book, agent, and may work with other agents who sell to the industry and they can really push it and help make that happen.

Anna David:                  35:52                Yeah. I mean, not to be a contrarian here, but I had, you know, so I had one book that was, that's been bought over and over again, our optioned, and one that they try and our successful TV producers tried to make it into a TV show. And nothing happened, and nothing happened and now I've taken over, but I will say it's 15 years after the book came out. So I have, it was a novel. I have no devotion to the characters. I'm not at all clinging to it. And I wrote the script and now something's happening with it.

Cindy C:                        36:22                Well, that's an interesting point because you had some distance from it also, it was a novel, not a memoir. So that may make a difference too. And yeah, it's true. Maybe, you know, like, and maybe it's something that you thought at the time could be a TV show and made into a book and then it will be made into a TV show. So, I mean, there's definitely, there's no rules to these things and it's probably personal, isn't that helpful.

Anna David:                  36:49                I mean, I think it's good news that there are no rules to any of this. So Cindy, thank you so, so much if people want to find out about you, I discovered that you don't even have a website.

Cindy C:                        37:00                I used to have this one website and then Apple like phased out that tool that I was using. And I just never got around to getting it back together. And there were days where I felt like it seemed really strange that I had one because I would look at my heroes who were like TV writers and movie directors and they didn't have one. And I thought, why do I have to update a website and write it in the third person? Like anyway, I have the same kind of love, hate relationship with social media too.

Anna David:                  37:28                I noticed.

Cindy C:                        37:29                Yeah, I just am not that present. I just really like writing and trying to write. But anyway, if you Google me in the New York Times, you can find my essays or you can read my books or you can watch the TV shows that are listed for me on MTV. And anyway, I'm just happy to, like, my goal is really to try to write stuff that speaks to people and leave it somewhere. They can find it like a TV show or a book and then it will be there when they are going through that stage of life and need it.

Anna David:                  38:00                I love it. Thank you Cindy so much. And thanks you all for listening. I will talk to you next week.

 

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