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First Draft Episode #316: Kerry Winfrey
July 29, 2021
Kerry Winfrey, author of romantic comedies Waiting For Tom Hanks, Not Like the Movies, and her newest, Very Sincerely Yours. She is also the author of YA novels Love and Other Alien Experiences and Things Jolie Needs to Do Before She Bites It.
Welcome to First Draft with me, Sarah Enni. This week I'm talking to Kerry Winfrey author of many books, including romantic comedy Waiting for Tom Hanks. She's here to talk about her newest rom-com, Very Sincerely Yours. I so loved what Kerry had to say about leaning into your natural voice, how Adam Lambert kept her going through a quarter-life crisis, and her four-step plan to get published, among many other goal-setting systems that Carrie has put in place to help her kind of keep her sanity as she navigates her way to seeing her work on the shelves. There's a lot of great kind of practical tips in there.
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Okay, now please sit back, relax and enjoy my conversation with Kerry Winfrey.
Sarah Enni: Hi Kerry, how are you doing today?
Kerry Winfrey: Hi Sarah. I am great. Thank you so much for having me on.
Sarah Enni: I'm so glad that we could finally make this happen. And I'm so excited to talk about Very Sincerely Yours, but I want to get a little bit of background, about you, and then talk about your YA, and your writing for the internet. Before we get to all that, I would love to start at the very beginning, which is where were you born and raised?
Kerry Winfrey: I was born and raised in Bellville, Ohio, which is kind of in between Cleveland and Columbus and a very, very small town.
Sarah Enni: How was the reading and writing part of growing up for you?
Kerry Winfrey: It was a really a big part of growing up. I was definitely a really shy kid. So reading was kind of like my number one hobby. I was not a joiner, so I was not into team sports. Books were my sports.
Sarah Enni: I want to ask about writing. I read a very funny, cute story about you as a kid that you were kind of writing before you could even read.
Kerry Winfrey: Yes, definitely. I would dictate stories to my mom to write down for me. But the thing is that they were all heavily plagiarized from either Disney stories, or I was really into Judy Blume's Superfudge. And I would just rewrite that. I thought that if you changed a couple of words, it was not plagiarism. So I was like, "I'm just gonna rewrite these stories and make them my own."
Sarah Enni: I'm always so curious about people who find writing that young. Did you very quickly turn that into knowing you wanted to be a writer?
Kerry Winfrey: Yeah, and I think it's because that was a thing I got a lot of praise for, teachers really like it when you're the kid who can write a story. And I was always the one who would win the awards, or win the story contest, or have my story read out loud in class. And because I was so shy. I wasn't great at communicating with people verbally, but the fact that I could communicate with people this way, and get a lot of praise for it, I got addicted to that.
Sarah Enni: That's so interesting. What kinds of stories were you writing at that time as a younger person?
Kerry Winfrey: It was a lot of fairy tales because I was really in to Disney movies. So a lot of things about forests and not at all what I write now, much more fantasy based.
Sarah Enni: I'm interested in you being a shy kid and finding expression through writing. It sounds like you were sharing it in contests, and the teachers, and stuff like that. But were you using writing at all in a way to forge connections?
Kerry Winfrey: Honestly, almost too much. For someone who was so shy, I was very pushy about my writing. I clearly remember me writing all these poems and reading them non-stop to my neighbor and my mom being like, "You need to stop. You need to let her go."
Sarah Enni: Oh my god that's so funny. Oh, so sweet.
Kerry Winfrey: Even then, I really just didn't have any shame or any fear of rejection, at least. It's a good skill to get early in life.
Sarah Enni: Yeah, I wish I could tap into that. Did you keep writing all through high school? What was your focus in college? What was writing like as you kind of shifted to adulthood?
Kerry Winfrey: Yeah, so I did keep writing all through high school, but I didn't really have much of an outlet for it until I did go to this summer camp here in Ohio at Kenyon college, they have something called Young Writers at Kenyon. And I was able to go to that. And it was such a big eye-opening experience for me as someone from a really rural environment.
I had great teachers, but we didn't have a ton of opportunities in our school. And to meet all these kids who knew about all these things and had like student literary magazines, and they read the New Yorker. And I was like, "Wow, this is the life". So I did major in creative writing at college. That was my undergraduate degree.
Sarah Enni: What was that experience like? Creative writing degrees can be kind of all over the map. How was your experience?
Kerry Winfrey: It was good. And I think part of the reason it was so good for me was because I went to a college that wasn't really known for writing. Because, like a lot of 18 year-olds, I had no clue what I was doing, picking a school. Like I went to Miami University in Ohio and they are known for business, they're not known for writing. So to this day, I don't really know why I picked it. I think I was just like, "That looks nice."
And I remember at the time, there was a rumor about the Olsen twins going there and I was like, "That would be cool." So, it seemed like a good bet. It kind of worked out though that people weren't very competitive, I guess, in the writing program. It wasn't like a cutthroat environment. There were talented people there, for sure, but I didn't feel a ton of pressure, which I think was kind of good for me in a lot of ways.
Sarah Enni: Right, cause what you hear about when people have bad experiences is sort of a too critical environment. Also, I'm interested in what kinds of things you were writing at that time.
Kerry Winfrey: I feel like a lot of creative writing programs, I don't know if they're different now, but we focused almost entirely on short stories. So that was it. I know there was a class about young adult literature, but I didn't take it. I had no sense that I wanted to write commercial fiction. I thought I was going to be like George Saunders (author of Tenth of December: Stories, Lincoln in the Bardo, and A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life, and many more short stories and collections), or Lorrie Moore (author of Birds of America, Who Will Run the Frog Hospital?, and many more short stories and collections), cause that's what we were reading. And I loved those things.
And my professor kept telling me, "You're writing dialogue like a TV show." As a way of saying, "Don't do that." Or like, "This book feels like YA." As a way of saying, "Don't do that." Which is funny because now I write dialogue that feels like a TV show, but in commercial fiction, that is a good thing.
Sarah Enni: Yeah. I was gonna say that's like, "Yay!"
Kerry Winfrey: So it took me a really long time to figure out that, even though I loved literary fiction, that wasn't really where my voice fits.
Sarah Enni: It can be really rocky to discover what, or in an instance like yours, what we're talking about is voice, right? And sometimes it's a struggle for people to find it. But other times, if you have a pretty defined voice right out of the gate, but it doesn't fit wherever you are, or whatever you think you're trying to do, or whatever you think you should be doing, for whatever reason, that can be kind of really hard. Were you frustrated? How were you feeling?
Kerry Winfrey: That was definitely how I felt. My voice has always been very clear. That was not the thing I had a problem with, lots of other things in writing I had problems with, but voice was always there. So it took me a really, really long time. And I think it wasn't until several years after college, when I actually started reading a lot of YA that something kind of clicked. It was a lot of first person, very voice-y. And I thought, "Oh, okay, this is much more my vibe than the depressing short story that I've been trying to write, that don't really fit my voice at all."
Sarah Enni: This also reminds me of something that Marla Frazee (is the two-time Caldecott Honor-winning author and illustrator of The Boss Baby, A Couple of Boys Have the Best Week Ever, All the World, and many more. She joins us to talk about the Farmer series: The Farmer and the Clown, The Farmer and the Monkey, and The Farmer and the Circus, out now), said in our episode, which I keep thinking about over and over and over.
She's also a teacher and now she teaches people who write picture books and illustrate picture books. And she said that we so often devalue what we're naturally good at because it feels like it should be hard. Like we should have to suffer for it, or something. But naturally writing dialogue like a TV show, there's a place for that, obviously, which you found eventually. But that's sounds like a very relatable experience to be kind of having to figure it out.
Kerry Winfrey: And even now, sometimes, there's a part of me that's like, "Should I be writing weird short stories instead of what I'm writing?" Even though I don't actually want to do that. But you spend four years studying something and you do kind of start to think that's the only way to do it.
Sarah Enni: Right. Oh, that's so interesting. So you thought you were gonna be a George Saunders-esque short story writer, which a lot of us, oh my god, the dream. Who doesn't want to be like George Saunders? But what was your experience like leaving school? Or how did you think about what you wanted to do? And were you serious about writing books?
Kerry Winfrey: It took me a lot of years to figure out what I wanted to do. I mean, relatively speaking. I'm only 35 now, so it wasn't that long. But it felt like a long time, at the time. I moved back home because I didn't have any sort of a job. I graduated in 2008, right when the recession was starting.
Sarah Enni: Yes. You and I are exactly the same age, by the way. And we're like, "Welcome to the real world. It's horrible."
Kerry Winfrey: Yeah, you can't get any job. I mean, I couldn't get hired anywhere. And also being in my hometown, there were not a lot of employment opportunities in general. So I ended up working in manufacturing for like four to five years. I was in the office. I was in the customer service side. So I worked at a manufacturing plant, which is so bonkers to me because that definitely does not fit my personality. But yeah, it was like 98% men and me and just talking about steel and stuff like that.
Sarah Enni: That's so interesting. Also, I have to say that's very Ohio. That's very like the movie of Ohio.
Kerry Winfrey: It is!
Sarah Enni: So what was your creative life like during that time?
Kerry Winfrey: It was, I would say, bad.
Sarah Enni: [Laughs] "I would say bad!"
Kerry Winfrey: Yeah [chuckles], I could not figure out how to make a career out of writing. I didn't know anyone who had done that. I didn't have a blueprint for that. So in my town, no one's writing novels there. Most people don't have creative jobs. Some people do go to college for creative things, but not a ton of them. So I didn't really know what to do.
And I spent a lot of time avoiding it and getting more and more miserable the longer I didn't write. For a while, I was like, "Maybe I'm gonna be just really great at customer service in the manufacturing industry." And the problem is that I was not. So that was not gonna work for me. I was not great at it. I never learned about the products we were selling. I still could not tell you what we made there. I don't understand it.
So it did, it took me a really long time. And I think it was reading YA that kind of made me realize, "Oh, maybe there is something I could write that would be an actual job for me." And that's when I started writing about YA on the internet, which was very, very helpful for me.
Sarah Enni: I read an interview with you, where you had talked about this time as your American Idol years.
Kerry Winfrey: Oh my gosh, yes. I got really into the Adam Lambert, Chris Allen season. I had this tiny apartment in my hometown. It was $350 a month. It was part of a Victorian house. I could hear my neighbor through the walls, smoking and coughing every night. It was depressing. My parents lived there so my mom and I would watch American Idol together and talk about it. And then the next day at my desktop, I would read recaps of American Idol. And I was like, "This is what I got. This is what's keeping me going. It's Adam Lambert."
Sarah Enni: Right. And I bring this up because in that interview you had talked about this time as like, you were sort of lost, not sure how to move forward. And this relates to Very Sincerely Yours in a way, which is part of why I'm thinking about it. But that's also really relatable, you know? Your quarter-life crisis, which we all come due for, but that's very moving. I would like to hear about what it was like to have books come back into your life in any way, or the idea of writing coming back.
Kerry Winfrey: Rediscovering books and writing, I don't a hundred percent know what set me off, although I think someone in my family... one of my grandparents had died recently and you know how sometimes that does make you take stock of what you're doing with your life? It makes you realize that you don't have forever. And I knew I did not want to work at that job forever. So I started reading a lot of books. And I had this, this is like so nerdy, but I'm very goal-oriented. I had a four-step plan for how I was going to get into writing.
And the first step was start a blog, which I did. And I would post, at first, not just once a day, but twice a day. And I don't know what I was writing about. And my second step was, get published somewhere locally. So I started writing for a local newspaper. And my third step was get published nationally. Which, when HelloGiggles started, right away I emailed them and was like, "Can I write a column about young adult books?" And they said, "Yes." So I was like, "Wow, three steps down right away!" And the fourth step was publish a book, which is kind of a harder step than the rest of them.
Sarah Enni: It's a bit of a leap.
Kerry Winfrey: Yeah.
Sarah Enni: It's kind of exponentially difficult, those steps. I read somewhere where you were talking about this four-step process, and I love it so much. I just think that's sweet, but also incredibly useful. I love talking to people about this kind of stuff. Where practically, you were like, "I have this big goal. How can I break it down into manageable chunks?" And that held you accountable. Like emailing HelloGiggles, that's an intimidating email to write.
Kerry Winfrey: Yeah, it was. But I don't know if it was that I felt really desperate, but I was not concerned at all about rejection, like that did not set me back at all. I had a little spreadsheet of all the different places I was submitting and who accepted me and who rejected me. And I just thought it was very motivating. And I don't know why, because I'm afraid of most things. But for some reason, the rejection involved in writing has never scared me all that much.
Sarah Enni: I'd love to hear about your time reviewing books for HelloGiggles. You had a column for young adult books, but how did you think about the parameters of that? And how did you develop that? I love this stuff.
Kerry Winfrey: At first, I kind of just wrote about whatever I wanted. When they started their site, it was kind of like no rules, wild west, you can just write whatever. And I don't even think it got edited at all. So I really could just write in my voice these long rambling columns about whatever YA book I wanted. Things that had not come out recently, like things from years ago, there was no real theme. I just picked whatever I wanted.
But I was doing it once a week, which is a lot. Reading a whole book, and then trying to write a whole column every week, was kind of a lot of work. And now I'm thinking, "How did I do that?" Because I had a job too, but it was really fun. And also, I think it was the best education I could have gotten in writing was by forcing myself, not only to read so much, but then to think about it and write down exactly what I liked about every book. It was really helpful.
Sarah Enni: I was gonna say, that's almost like, I mean, you did creative writing for undergrad and in some ways this was your self-assigned master's degree in critical reading for this genre.
Kerry Winfrey: But I would say a self-assigned master's degree would be a very me thing to do!
[Both laugh]
Kerry Winfrey: The same thing as like a four-step plan.
Sarah Enni: I love it. Just thinking back to that time, what are some of the big takeaways from reading that many books, and reading and analyzing that many YA books? What were some of the big things you noticed?
Kerry Winfrey: Well, this was the hardest thing for me to grasp was that those books were finished, edited books. And I had the hardest time trying to put that together with what I was writing, which was at the time, not very good. And at one point I had an agent reach out to me from reading my column and say, "Oh, do you have anything to send me?" And I'm so embarrassed now that I sent her this awful, awful partial draft that now I look back on it, I think, "Oh my God, I can't believe I showed that to another person."
But I wasn't quite there yet. I still had to write a few bad books before I could write something that another person should see. But it was definitely just helpful to see how so many people put together story structures. Like later on when I wrote romance, reading so many romance novels, you get the beats of the story down, and they kind of just become in your brain. You don't have to think about them so much. You just kind of understand how the story works.
Sarah Enni: But YA is, I mean, tell me if I'm right about this. Cause my impression of romance is that there are kind of rules, there's a little bit of guardrails around romance. And that's not so true in YA, which makes it a little bit harder to get your arms around.
Kerry Winfrey: That's definitely true. Because YA, I mean, it's just an age range. It can be anything. And romance, you do have the rules. Like you have to have the happily ever after. And then among that, there are things people really like, or don't like. So yes, romance has more rules. YA is kind of like, whatever.
Sarah Enni: It's like just the broader fiction universe, which you can do anything. So being able to read widely in it, isn't so necessary. I mean, I think still to this day, you can tell when someone publishes a YA and they're not really well - this is an opinion I'm sharing - sometimes I read a book and I'm like, "I don't think this person has read widely in the young adult genre, or category." It's a little clunky unless you're really steeped in it.
Kerry Winfrey: Exactly. Every once in a while someone gives an interview where they say, "Well, I wanted to write a YA book that has sex in it, or swearing in it." And you think, "Well, okay, so do a lot of YA books."
Sarah Enni: Yeah, so many have for the last 40 years.
Kerry Winfrey: Yeah. You can tell they haven't read any in the last 40 years. Exactly. So yeah, I think that familiarizing yourself with what's actually being done in the genre that you're writing now, is really important. And you can definitely tell when someone hasn't done it.
Sarah Enni: Yeah. Okay, I would love for you to lead me from [pauses], I think here is, in your timeline, where I'm a little mixed up. You're writing for HelloGiggles. You are writing Love and Other Alien Experiences, which becomes your debut book. And you're doing A Year of Romantic Comedies, I think, at the same time. Is that right?
Kerry Winfrey: Yes. Yeah.
Sarah Enni: Lead me through that. What was going on at this time?
Kerry Winfrey: Well, most importantly, I was no longer working in manufacturing, so that made my life a lot easier. I had a writing-based day job that didn't make me miserable. I know people often will say, "You should have a day job that has nothing to do with writing so you can really focus on writing when you're not there." But I would also say you need a day job that doesn't feel soul crushing. Because it is hard to work if ... there's a difference between not loving your job and hating your job.
So I did get a much better job that fit me a lot more. So I think I had more mental energy to work on all those things. And when I was writing Love and Other Alien Experiences, I was not used to writing a book. I was used to writing blogs, or columns, or things that got feedback right away. And so I really did miss getting feedback. It felt very lonely to me. So that's why I started doing The Year of Romantic Comedies. I needed another project where I could be posting it once a week and have people read it in real time and hear from people right away.
Sarah Enni: You know, that's so funny. I didn't think about that. But yeah, reading poems to your neighbor, going to a creative writing program, which has a workshop element to it. And then writing columns and blog posts. So satisfying. Obviously you're the kind of writer that was born wanting your work to be read. And that's not always true and I think it's important to note that it also doesn't ever have to be true, people can write for themselves their whole lives.
But when you are someone who is so focused on that, then yeah, going into the writing cave for a year with no feedback can be a little bit unnerving, I would imagine.
Kerry Winfrey: Yes. And I know there are lots of people who just love writing for writing's sake, and I do too. But for me it is always with the goal of being read and connecting with another person through that writing. I wouldn't want to write just for me, I'm definitely doing it to be published.
Sarah Enni: I mean, I relate. That's how I feel too. And it can be a struggle, especially once you reach like five or six months and you're just really in the story by yourself, it starts to be a little forest for the trees. And you're like, "Is this even a book? What am I doing?"
So we'll get to Love and Other Alien Experiences and your unique publishing experience with that book. But I do want to just pause on A Year of Romantic Comedies for a moment, because I loved that tumblr so much. It was such a joy to read. I'd love for you to tell listeners what that tumblr was about.
Kerry Winfrey: Basically, I love romantic comedies, I have ever since I was a kid. And I wanted some kind of another blog project to work on when I was writing my book. And I didn't want to just blog about my life because nothing was happening other than me writing the book. So I was like, "I need something else to write about." And I loved writing about books. And I watch a lot of movies. So I thought, "Well, maybe I'll just watch a rom-com, one every week, and write down all my thoughts on it. And people love rom-coms, so it sounds fun."
And I have always wanted to write a rom-com, so I also thought, just like how I learned about YA by reading so many books, maybe I could learn more about romantic comedies by watching a ton of them. And I definitely did.
Sarah Enni: Once again, I have such a big place in my heart for people who give themselves homework. I am one of those people. So I love that you're like, "I'm gonna give myself an MFA in screenwriting, specifically for romantic comedies."
The blog was really a learning experience, even to read it. Because you tasked yourself with watching, I mean, 52 rom-coms, you're gonna get some stinkers in there, some were very mixed results. So reading your analysis about why things worked and why they didn't and what made something romantic versus kind of saccharin, I loved that stuff. I'd love for you to just talk about some of the biggest things that you took away from that experience.
Kerry Winfrey: I would say the main thing I took away from it was kind of what we were talking about with YA, how you can tell when someone hasn't read the genre. You can really tell when someone doesn't actually have a lot of respect, or love, for romantic comedies. Because they don't understand that you can't just go by the beats and have all the grand gestures, and meet-cutes. That's not really enough. You also need to have chemistry and you need to have a love of the story to make it work. And you can always tell the movies where someone really cares what they're doing and the movies where someone doesn't.
Sarah Enni: I just re-read a review of You've Got Mail, which I think you said was your favorite. And talking about what makes Nora Ephron's rom-coms just stand above the rest. Do you mind just sharing that with our listeners? Cause I thought it was such a good point.
Kerry Winfrey: Well, I would say that a good romantic comedy needs to have some sadness in it. They cannot just be light. Her movies are so funny, and they have such great dialogue that we all still quote today. But I think the main reason why they stick around, and why people find them so meaningful, is the really deep sadness in all of them. Like in Sleepless in Seattle, Tom Hanks' wife died. In You've Got Mail, he puts her out of business and she's so sad about the death of her mother. And none of those things are things that can be fixed by the end of the movie. And falling in love doesn't fix those things, but it does make them more bearable.
And it kind of reminded me, I'm just listening to your episode with John Green right now (#1 New York Times bestselling author of many young adult novels, including The Fault in Our Stars and Printz-winning Looking For Alaska, joins to discuss his new essay collection, The Anthropocene Reviewed. He is also one half of the vlogbrothers on YouTube and co-creator of educational series Crash Course. Listen to his First Draft interview here), where he talks about hope and how hope with all lightness in it doesn't mean anything to him. And that's exactly how I feel about romantic comedies too.
Sarah Enni: I loved how he talked about that in his essay about Harvey, which is not a rom-com, but it was a movie that meant a lot to him. And he said that it gave him a sense of hope that wasn't bullshit. And I relate to that so much. And that's what you're saying. These stories are textured, and difficult, and complicated, and that's what makes them feel real.
It's funny to talk about realism with rom-coms because there's an element of wish-fulfillment in romance stories, but I think that's only a surface level understanding of what's happening. You want to be compelled by something. And human beings are compelling when they're uncomfortable and flustered and trying to deal with stuff like we all are, you know?
Kerry Winfrey: And romantic comedies are never just about falling in love. It's always the character's dreams and their passions and their hopes along with those things. And hopefully by the end, they get some sort of resolution with all of those story lines together.
Sarah Enni: Yeah. I love that. And I think you and I specifically talked about, I remember at least, our exchange talking about Keegan Michael Key and Playing House being such a wonderful example of a leading man who works because he is just so clearly enamored with the person that he's interested in (Kerry wrote about his performance here. I spoke with Lennon Parham and Jessica St. Clair, comedians, actors, and screenwriters behind Playing House, in this interview.)
Kerry Winfrey: Yes, I feel like that's the best quality a rom-com dude could have is like, you need to be obsessed with the lead. I don't like a guy who's a bad boy. I'm not interested in that.
Sarah Enni: Exactly. And for anyone who hasn't watched Playing House, I'm gonna link to that in the show notes, cause it's a great example. If you're writing romantic comedies, it's a good one.
So I love that you kind of give yourself this thing to come to. It's also nice that you gave yourself something to write every week that is non-fiction. It's a really different medium, it's a break from writing your first novel. But how was the writing of Love and Other Alien Experiences going? I'd love for you to lead me through how that book actually got to be out in the world.
Kerry Winfrey: It's kind of a weird story because it was published twice through two different publishers, so there's a lot going on. It was published through, I guess they were a book packager. At the time, they were called Paper Lantern Lit. But they were doing this new program for eBooks only, where you would work with them on a book idea you already had.
So I had this book I was working on, but it wasn't really working. And it was all about someone who gets nominated to homecoming court as a joke, because that actually happened at my high school, which is like such a teen movie story, a nightmare.
Sarah Enni: Oh my gosh! To you?
Kerry Winfrey: No, not to me. No. But somebody in another class. So it always stuck in my head as like, "That sounds like a movie. Not like something that would happen in real life."
So I had this book I was working on about that and they had an open call for submissions. And I was very determined that I thought this was the best thing for me. It was like another step in my plan. So I was like, "This will be great. I'll get some help in writing my first..." Well, it wasn't really my first book because I did have others, but you know, "I'll get some help in writing this and maybe that will help me actually finish a full draft for once."
And luckily everyone that I worked with, I worked with an editor named Angela Valez, who now has her own book coming out soon (author of the forthcoming Lulu and Milagro’s Search for Clarity.) And then I worked with an editor named Alexa and she was great too. And now she's an editor somewhere else.
And they were both really, really wonderful. It was actually a great editing experience for me because they were very hands-on. I was writing the book with a contract already, which is not usually how you write your first book. So I had deadlines all the way through.
Sarah Enni: Which for you is very helpful, right?
Kerry Winfrey: Yeah. My hardest thing is always, if I don't have a structure, I'm in a bad place, that's hard for me. So that was really great for me.
Sarah Enni: That's great. And it is unique, as you say. Did you present them with half a book or a few chapters? Or what did you actually show them to begin with?
Kerry Winfrey: I think it was probably about half a book and an outline. And then we worked on a new outline together that was, frankly, a lot better than what I had.
Sarah Enni: Sometimes I feel like growth doesn't happen steadily all the time. Sometimes it's like you shed the skin, it's like the snake cycle. And those shedding of skin is like one big moment. And then you sort of level up, I think. So when I was thinking about your experience of having help come in on this book, that's what I was thinking of. Was like someone coming in, even on the outline stage, and you're sort of piecing it together and learning and leveling up.
Kerry Winfrey: Yes, and it was. This was another experience that was kind of like an MFA because I wouldn't just turn it the whole book. I would turn it in chapter by chapter and get their notes on it as I worked on each chapter. So it felt more like how I've heard like writing for TV, or something works. I had other people giving me notes constantly. It was really nice. I really enjoyed it.
Sarah Enni: Yeah. Well, it was more like a blog, right?
Kerry Winfrey: Yeah, exactly.
Sarah Enni: So, actually, I'm asking specific questions about this book, but do you mind pitching that book for us just really quick so listeners know what it's about?
Kerry Winfrey: It's been a long time since I pitched it, so forgive me if I'm a little bit rusty. But it's about a girl named Mallory who is agoraphobic, so she does not leave her house, and she attends high school via webcam. She gets nominated to homecoming court in what she thinks is a mean joke from her classmates, but the prize is actual money. So she decides to try to win to kind of show them that she can do it, and also to get the prize money.
And she ends up working with this very popular, lovably dim guy from school to do it. And the book is really about her coming out of her shell and dealing with her trauma, but in a fun way.
Sarah Enni: So you were working with Paper Lantern Lit, it was going to be released as an eBook. What was the next step? Because it did, as you say, have another life as a hard cover book as well.
Kerry Winfrey: Well, I was very lucky that I just got an email from my editor at Feiwell & Friends. Well, the woman who became the editor from Feiwel & Friends, saying that she was interested in the book, she really liked it. And she wondered what we were doing about print rights. And I said, "Nothing, I guess." And then I sent her on to the people at Paper Lantern and I ended up getting a two book print deal through Feiwel & Friends, which was pretty amazing.
Sarah Enni: This is an interesting sort of behind-the-scenes moment, I think, for listeners. When you had eBook only, that did mean that the rights for this book could still be exploited in other formats, including hardcover, paperback, mass market, et cetera, et cetera. So that's what your Feiwel & Friends editor was seeing an opportunity to do. A book that she already liked. You can just bring it on. And a lot of the work's been done. Did you do any editing with her at all?
Kerry Winfrey: We did a little bit, there were some small things that changed, but not much at all. Because the editing before with my other editor had been so intense that honestly, I mean, it was in pretty good shape already. There wasn't that much that she wanted to change.
Sarah Enni: Interesting. And then how did Things Jolie Needs to Do Before She Bites It come about? Were you still working with Paper Lantern Lit as well as Feilwel & Friends?
Kerry Winfrey: Nope. At that point I was totally on my own, so it really felt like I got the training wheels off. Then I really had to write a book in isolation all by myself. And also in between then I'd had a baby. So when I was writing Jolie, I think I wrote it when he was like three months old. So it was an intense experience.
Sarah Enni: I can only imagine, that is definitely like writing in snips of time.
Kerry Winfrey: Usually I'd have a choice like, "Can I write or can I take a shower?" And a lot of times I would have to pick writing and it was rough for everybody in the house, but we got through it.
Sarah Enni: That's very impressive. So I would love for you to talk a little bit about like you have these two really personal YA books come out, you're really dealing with stuff in your own life and finding a way to do that. What was the inspiration to try an adult rom-com which is where you went next?
Kerry Winfrey: I would love to tell you that I was really calculated and I was like, "I'm gonna bust my way into a new age range." But I was not. Basically, I had written My Year of Rom-coms blog and I noticed I was getting so many more emails and messages about that blog than I was about my YA books, by a long shot. People really liked reading the blog and they liked talking to me about it.
And I thought, "I wish there was some way that I could just turn this blog into a book." And I couldn't come up with a way, because no one knows who I am. They don't really want a book of essays by me. You need a different sort of platform for that. And I couldn't figure it out.
And then one day when I was breastfeeding my son, I had this little notebook where I would write down every time he ate and every time he pooped, and I had this title come into my head, Waiting for Tom Hanks, and I wrote it down in the breastfeeding poop journal. I was like, "Oh, I really like this title. What if somebody was as obsessed with romantic comedies as I am, but it was ruining their life because they didn't understand that that's not real life." And so that's where it came from. The title came before the actual book did.
Sarah Enni: I love that, that's so perfect. What you're describing is the hook of the book, really, arrived.
Kerry Winfrey: Yes.
Sarah Enni: And the title, which is convenient. You just did a good job, briefly, but can you just pitch that book for us really quick?
Kerry Winfrey: So it's about a woman named Annie who lives in Columbus in a neighborhood called German Village, which I picked because it's very cute, kind of like a movie set. And they had just filmed a movie there with John Travolta. And I was like, "What if someone else filmed a movie there? But it was not John Travolta?"
So she is obsessed with romantic comedies and she wants to write her own, but she's writing internet content at the moment, and living with her uncle who is like a big D & D fan. And the movie starts filming in her neighborhood, a romantic comedy. And she ends up literally running into the lead actor in a very rom-com way. And she ends up getting a job on the set of the movie and hanging out with him, even though he's totally not a Tom Hanks type, she thinks. And of course, because it's a romantic comedy, you can kind of tell where it might be going.
And it was fun because I got to put in every single rom-com cliché that I had just spent a year watching and all of my own personal thoughts about romantic comedies. And it was really fun to both celebrate those things and talk about the ways in which they're not realistic, or helpful, to people at the same time.
Sarah Enni: Okay, there's a few threads with this that I want to explore. First, from a craft standpoint, here you've explained how you have the title, you have the hook, and you have your own research, a year of researching, by watching these movies. How did you flesh out the actual book and the characters? How did you start there and get to the final result?
Kerry Winfrey: Well I feel like, in a lot of ways, this was the easiest book I've ever, or will ever write, just because I had all the story beats in my head. I knew that I wanted this to be a romantic comedy about romantic comedies. So it needed to follow all of the beats, but in kind of a self-aware way.
So the plot, once I realized she was going to be working on a movie set, falling in love with a movie star, it's not that I wanted it to be a cliché, but I wanted it to be that story that you're familiar with. Someone that finds themselves in that story, but doesn't realize it, or doesn't want to be. And giving me a way to talk about that.
So basically I just thought like, "What character would be best in this situation?" Every rom-com has a wacky best friend or like a lovable older relative. So it was fun to kind of think about everything I'd watched and what I loved about those movies and then put all those things into the book in kind of a meta way.
Sarah Enni: Yeah, writing a book that's a commentary on the thing that it also is, could get kind of cute, or could lose some of the veracity, or some of the emotional connection. So how did you kind of thread that needle?
Kerry Winfrey: I mean, perhaps some people do think it's too cute, I don't know. But in my mind, I just really wanted to go for it. At the time, rom-coms were just starting to become a thing in print, like Jasmine Guillory's book had just come out (New York Times bestselling author of romance novels The Wedding Date, The Wedding Party, While We Were Dating, Party of Two, and The Proposal. Hear her First Draft interview here.)
And I knew that that was the kind of book I wanted to write because this was not gonna be a super steamy book. And I liked how her covers looked, you know? How they had the illustrated look. And I thought, "Well, that fits what I want." Because this is more of a nineties romantic comedy than it is a super steamy romance.
And I remember when I sent it to my agent. At the time, I don't think that he represented any romance at all cause I got my agent through doing YA. And I remember him being like, "Okay." He was into it, but he was like, "Well, how are we gonna make this stand out?" He was like, "Maybe we should try making it edgier." And I was like, "I can't do that." Like, "I cannot."
I think Train Wreck had just come out, the movie with Amy Schumer. And I was like, "All right. Well, I physically can't write something like that. This is not who I am. This is not gonna work. So what if we went the other direction and went even sweeter and like very into the rom-com angle." And he was like, "Okay, go for it." And I did. And thankfully it worked out. I feel like we hit at just the right time when everybody wanted to read rom-coms. It was very good timing.
Sarah Enni: You'd written the second book, a sequel to the first one, how were you thinking about where you wanted to go from there? I'm sure the temptation, or maybe the pressure, or the assumption, that you'd write another in that series was there.
Kerry Winfrey: Well, my deal with Berkeley was for two books. So it was just for Waiting for Tom Hanks and Not Like the Movies. So I needed to write a new proposal and I would've loved to write another book in that series, but I didn't have any other stories to tell. So I couldn't really. There were only so many characters in the book and most of them at that point were already in relationships. I'd really painted myself into a corner.
So I started writing this other proposal and I worked on it for a really long time. And I knew in my head that it was not working, but I really wanted it to work. So I was just pretending that it still was, and I was continuing to really plug away at it. And I sent it to one of my writer friends who's my first reader, to see what she thought.
And meanwhile, I went to go see the Henson exhibit at a local science museum. It was all about his life and the Muppets and Sesame Street and Fraggle Rock. And I'm a big Muppets fan. I've always been into Jim Henson. And while I was there, I was really struck by how dedicated he'd been to his job, basically his whole life. He's one of those people who kind of always had known what he wanted to do.
And then I was also struck by the fact that he was kind of hot in all of his pictures.
Sarah Enni: Ha-ha! Yeah!
Kerry Winfrey: I was like, "This seems like a romance hero but who's a puppeteer." I feel like that hasn't been done a lot and someone who's really into their job, but their job is not like being a businessman. It's like being really good with kids and hosting a TV show.
And so I got this idea and I thought, "Who would juxtapose with that type of character? And is someone who doesn't know what they want to do." Which was interesting to me because normally when I'm writing a book, it is about someone who knows what they want to do and they are getting over the obstacles to get that thing. And by the end they get it.
But I feel like a lot of people in my life don't know what they want to do. And maybe that's also interesting too, is trying to figure out, "Well, what do I want?" And I'm obviously someone who's always known what I wanted to do. So it was interesting for me to explore that, too, and having those two people meet.
So I started working on that proposal and my writer friend gave me my feedback about my other proposal. And in a nice way, she was like, "This is not very good." I was like trying to rewrite Waiting for Tom Hanks again. And it was not working. And I thought, "Well, what about this one?" And she was like, "Yeah, that's a lot better". So I was able to send that to my agent. And the first thing that he emailed me back was, "This guy is giving me Mr. Rogers vibes and was Mr. Rogers hot?" And I was like, "I don't know how to answer that. Was he?"
[Both laughing]
Sarah Enni: I mean, you know, your mileage may vary, right?
Kerry Winfrey: So I had to do some convincing and be like, "Well, have you ever seen like a young male picture book author?" Like, "You know the vibe that those guys give off? That's the vibe I was going for." Not so much older man hosting a TV show. So once we kind of got on that angle, I could tell that it was kind of working.
Sarah Enni: That's so funny. You're like, "Are we talking about a grandpa here or...?" That's so funny. I have a bunch of questions about Very Sincerely Yours, but before I ask those, do you mind pitching that book for us please?
Kerry Winfrey: So it is about an almost 30 year-old woman named Teddy Phillips who gets surprise dumped by her boyfriend who she'd kind of devoted her life to. And so she realizes that she doesn't know what she wants out of life. All she has is working at this vintage toy store. That is a really fun job, but it's not something she has any sort of passion for.
So with the help of her best friends, she decides to do one thing every day that scares her. And one of those things is emailing this local children's television host that she has a crush on named Everett St. James. He has a show called Everett's Place and there are all these mom message boards about how hot he is and people love him.
So she emails him at the address meant for children to email in their questions. And they end up starting up a pen pal relationship, kind of, and having a lot of almost meets before they actually meet. And once they do get together, it's kind of a question of how do they balance their very different personalities and drives in life? And how does Teddy commit to a new relationship while not giving herself up to another guy's dreams like she did before?
Sarah Enni: Yes. Very well done. And as you kind of say, Everett, in some ways, came as a character first. I think that's so interesting because this is a third person, two point-of-view book, which is new, at least for your published work. So, did you always know that was gonna be the structure? Or how did you come to that?
Kerry Winfrey: When I started, I knew right away that I would have to do two different points-of-view and I had never written a book in third person before, not like since college have I written like that. So I was really scared of doing it, but I really wanted to do it. And I think just because I'd written so many books already in first person, you know what I mean? Like you need to kind of mix things up a little bit, so you don't feel like you're writing the same book over and over because that would be mind-numbing.
So I knew I had to do something a little bit different. Normally I have a very hard time getting into the head of the love interest because I'm in first person with the main character, but this time that character came to me really quickly. And so that was a lot of fun. I got into his head very easy. I always feel like it was the right decision to write in two points-of-view and third person.
Sarah Enni: When I've talked to people that have written explicitly romantic books, romance books, honestly, so they have that structure of happily-ever-after, that are two points-of-view. Part of what makes falling in love so amazing, and terrifying, is that you don't know what is going on with the other person. And you don't trust your instincts. The not knowing is the scariest part of that whole process. Right?
So I just am so intrigued by people who set themselves the task of making something very romantic and suspenseful in the way that romance has to be, when you do know that both sides are falling for each other.
Kerry Winfrey: Honestly, I've never thought about it that way before, but you're right. And I know, based on what I've heard from readers, that most romance readers really prefer two points-of-view. That's the main comment I look at from people who tag me in very nice Instagram posts about my book will say, "I love this, but I really wanted his point-of-view." So for some reason, people do really want that.
I think maybe it's like you said, you need to know that this other character isn't a jerk. Maybe that really is the main thing. If you're just looking at someone and they're mysterious the whole time, some books that works really well. Like a book where the structure is that the love interest is in love with the main character the whole time. Then maybe that works better, but I don't know. That's tricky.
Sarah Enni: It is right? But that's so fascinating that that's what you've heard from people. And maybe, maybe that whole, the scariest thing about falling in love in real life, IS the reason. Because when you're reading a romance book, you don't want to be scared that it's not gonna work out in some ways.
Kerry Winfrey: No, that makes total sense because yeah, the appeal of a romance novel is you know what's going to happen. It's like a safe space because you know that they're going to end up together. So yeah, maybe that is it.
Sarah Enni: On your Instagram, I think you said, "Everett's advice, and Teddy's connection with him, ended up being inspired by all the videos from picture book authors that my son and I have watched during the pandemic."
And you just said that was helpful as kind of like, "No, this is the vibe that we're going for with him, not Mr. Rogers, but these other more contemporary examples." But I would just love to hear about that. That sounded so interesting as like a pandemic inspiration.
Kerry Winfrey: Oh my gosh, yeah. So right at the beginning of the pandemic a lot of children's book authors were doing like Instagram Lives, and stuff like that. And we watched a lot of them. We watched Christian Robinson, (illustrator of Caldecott Honor, a Coretta Scott King Illustrator Honor, and the Newbery Medal-winning and #1 New York Times bestseller Last Stop on Market Street, written by Matt de la Peña (listen to his First Draft interview here), and the #1 New York Times bestseller The Bench, written by Meghan, The Duchess of Sussex. His solo projects include Another and You Matter) the picture book author, did tutorials and things about feelings and stuff like that. We love those.
Carson Ellis, (author and illustrator of Caldecott Honor book Du Iz Tak?, as well as Home, In the Half Room, and many more. Hear her First Draft interview here), who I'm obsessed with, did a lot of stuff on her Instagram too.
But the one that we got the most into was Mac Burnett (two-time Caldecott Honor-winning author of Extra Yarn and Sam and Dave Dig a Hole, both illustrated by Jon Klassen (listen to his First Draft interviews here and here) and dozens more children’s books, including the Kid Spy series (illustrated by Mike Lowery), CIrcle (also illustrated by Jon Klassen), and the Jack books (illustrated by Greg Pizzoli).
At the beginning, it was every day, he would read one of his books and it was the called The Max Show Book Club. And my son and my husband both have hats for it. We got real into it. Then it went down to one a week and now he's not doing it anymore because he had a baby and he's busy, but we got so into that.
And just having that structure in our day, just knowing, "Oh, we can look forward to Mac Barnett reading us a story and we can all sit down and watch it and laugh at his jokes. And he's in his house too." And he was clearly trying to be comforting for these kids, but not in an overly way. He wasn't like saying, "Oh, it's gonna be okay." But giving them some semblance of routine in the reading of books. And I, myself as an adult, found that really comforting too.
So I was able to kind of channel those feelings into Teddy. And how would she feel being kind of un-moored in her own life and not knowing what she wants? She's not in the midst of a pandemic, but she doesn't know what's next in her life. And in a way she's kind of approaching things like a child because she's kind of starting over right at the beginning. So she's getting this advice from Everett that's meant for a five-year-old, but it still feels very relevant to her life. And that's how I felt when I watched like Christian Robinson talk about feelings. I was like, "I have a lot of feelings too right now."
Sarah Enni: Oh my God. And Teddy, in the book, is almost 30, as you say. And as a grown woman, like what is more attractive than a man who is like, "I have the ability to talk about my feelings." Like, "I am demonstrably, emotionally mature." It's like, "Yes!"
Kerry Winfrey: I know. And I've read so many books, and written so many books, about men who aren't good at expressing themselves, or men who are kind of aggressive, or macho in some way. And that's not ever been the kind of man that's been in my life, either as a family member, or a friend, or a partner. Like that's not what I'm interested in, you know?
So it was actually much easier for me to write somebody who's, first and foremost, a kind person and who understands a lot about his feelings and wants to connect with people. And also, it just felt nice to talk about someone like that during the pandemic, someone whose job is connecting.
Sarah Enni: And then the third-person, dual point-of-view, I was thinking that it was probably useful, because Teddy, as your main character, is so unsure. And I related to it, I've had these moments in my life where I'm like, all of a sudden, you have to be like, "Who am I? And what do I care about? And where am I going?" And I really don't know.
But if you had been first person in that head-space for a whole book, it probably wouldn't have worked very well.
Kerry Winfrey: I know it would have been hard to write, or read. And I know that not everyone is going relate to Teddy. People are gonna be like, "Wow, that's so annoying. How could she not know what she wants?" But I do relate to that. That's like my American Idol years. And Teddy's going through her own American Idol years, it's just a different time. So I did really want to explore that, but you're right, it's nice to have it broken up with somebody who knows what they want and is very certain.
Sarah Enni: And from the third person, you can show the reader like Teddy is down on herself and unsure, but you can demonstrate to the reader, and let them in on like, "Well, she's a very competent person. She does have passion and she is such a good friend. And she shows up in all these other ways." So like, "She's gonna be okay. She's good. She's just having a moment."
Kerry Winfrey: Exactly. It was good to show other people in her life, that like her, and see her good qualities.
Sarah Enni: Yes. Her two friends were so patient with her. I was like, "Oh, these are very good friends to her." They're not just coming out and saying like, "Oh my God, you're so much better off." But that does lead me to the last thing that I have written down to ask you about this book. The first chapter is one of the most chilling breakup scenes I've ever read in my life!
Kerry Winfrey: Thank you.
[Both laughing]
Sarah Enni: Can you describe it? Or, I mean, it's the first chapter, so it's not a spoiler. It happens right away. But I was reading it like [makes a gasping sound] just like shriveling inside.
Kerry Winfrey: So the funny thing is that was not initially my first chapter. I initially started it with her at the store after having already been dumped. But then I was like, "Why wouldn't I just show this terrible breakup?" Like show her in the before, briefly, and then show quickly what happens to put her in the after?
So she's convinced that she's going to get proposed to, because her boyfriend has been so distant. And I feel like that's the kind of thing that advice columns, or women's magazines would tell you. Like, "It means he likes you. He's planning a proposal."
Sarah Enni: Or you would desperately tell yourself because you are so scared of the other potential.
Kerry Winfrey: Exactly. Because that's much easier than actually communicating with someone, is like assuming. So he tells her he wants to talk. So she plans this big, huge dinner even looks up like a Spotify playlist of songs to get engaged to. Which, that was fun to research, to be like, "What songs do people like to get engaged to?"
And he comes in and, of course, it turns out he actually wants to break up because he feels like their relationship is not working. And not only does he want to break up, but he's like, "You're gonna need to move out of the townhouse, like immediately." And it all happens while Celine Dion's, My Heart Will Go On is playing. Which makes it way worse because then you can never listen to that song, or watch Titanic again, without thinking about it.
Sarah Enni: But it's also like, there's a misunderstanding. It's actually, now in the moment I'm thinking of it, I just re-watched Twister the other day.
Kerry Winfrey: Okay?
Sarah Enni: This is gonna connect, I promise [laughs]. But in Twister, Bill, not Bill Pullman, um...
Kerry Winfrey: Bill Paxton.
Sarah Enni: Bill Paxton, thank you. Has one of those breakups that only happens in nineties movies, including in Sleepless in Seattle with Greg Kinnear. Where like at the end they're like, "Oh, we're so much lighter. We're so happy to be breaking up." Like these conflict free, literally no consequence breakups, that are just such like delirious dreams in movies in the nineties.
So he really, in Very Sincerely Yours, his name is Richard, which is so appropriate, just really feels like he's like, "Yeah, we're on the same page and this is fine. And it's not gonna be a big deal. You should just move out." And I was like wanting to jump into the book and just strangle this person.
Kerry Winfrey: Yeah. Because in his life, he's used to someone just making everything easy for him and he's like, "Oh great. Okay. Another situation where I don't have to do any work. Awesome."
Sarah Enni: Yeah. Yeah. "My emotional needs are always gonna be taken care of." And oh my gosh, I was just losing it!
This was so fun. Oh, I wrap up with advice, duh! But I want to ask about writing, as we said, when you're writing a rom-com, the ending is, there are no bones about the ending. It is like set in stone, sort of, what you are delivering on for readers. So I'd love to hear your advice for someone writing that kind of story about how you can maintain tension, even despite those structures.
Kerry Winfrey: That is a good question. And I'm the kind of person who loves having structure in place, I like having that structure there. But you're right. It is difficult. And you need to hit the same beats because people expect that, but you need to do it in a way that feels fresh, but also you can't change the ending. So that makes it hard.
So I would say my best advice is something I heard in a panel I did once with a YA author named Dee Garretson. And she said that you can give us the intention by giving it an unexpected setting. Like have someone have an argument, but in a funny place, and things like that. So I really use those a lot. Like have people fall in love, but in a place you don't expect them to fall in love.
And in Not Like the Movies, I had two characters get into a fight, but it was while they were at a bachelorette party and wearing those headbands that have little penises dangling off of them. But, I don't know if this is good advice or not. Maybe it is? But just keeping it unexpected in how you bring together the different elements of what you're doing. Like keeping the same beats, but making them happen in unexpected settings, or with unexpected characters.
Sarah Enni: Yeah. I like that. And then those are the opportunities to get into your like secret obsessions or passions, right? Like that's when sort of the unique angle on it sort of naturally brings to the story.
Kerry Winfrey: Yeah. Because it's like any kind of writing, even if you're writing the same idea, no two people are gonna write the same story. They're always going to be different based on your point-of-view.
Sarah Enni: I love that. Kerry, it's been such a pleasure to finally be able to chat and meet you. It was so fun. Thank you for giving me so much time today.
Kerry Winfrey: Thank you so much. I had a great time. This is like a dream to be on this podcast after listening to so many episodes.
Sarah Enni: Oh! Yay. I'm so, so excited we could do it.
Kerry Winfrey: Me too.
Thank you so much to Kerry. Follow her on Twitter @KerryAnn and on Instagram @KerryWinfrey. You can follow me on both @SarahEnni (Twitter and Instagram), and the show @FirstDraftPod (Twitter and Instagram).
First Draft is produced by me, Sarah Enni. Today's episode was produced and sound designed by Callie Wright. The theme music is by Dan Bailey and the logo was designed by Collin Keith. Thanks to social media director, Jennifer Nkosi and transcriptionist-at-large Julie Anderson.
And as ever, thanks to you, Keegan Michael Key for listening.
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