Jennifer E. Smith

First Draft, Ep. 100: Jennifer E. Smith - Transcript

Date: June 21, 2017

The original post for this episode can be found here.

[Theme music plays]

Sarah ENNI: Welcome to First Draft with me Sarah Enni. Today I’m talking to Jennifer E. Smith, bestselling author of THE STATISTICAL PROBABILITY OF LOVE AT FIRST SIGHT, THE GEOGRAPHY OF YOU AND ME, HELLO, GOODBYE, AND EVERYTHING IN BETWEEN, and more. Her newest novel, WINDFALL, came out in May 2017, and was recently optioned for film by actress and author, Lauren Graham. So exciting!

Jennifer E. Smith is maybe the nicest person I’ve ever met in real life. I first met her at the North Texas Teen Book Festival, and I’ll be honest, I was nervous to approach. She’s a big deal author with lots of books, and she used to be an editor, and she just seemed so cool. I’m so glad I plucked up the courage to say hi, because in addition to being nice—and arguably being way more important than nice—Jen is curious, and thoughtful. A romantic with a practical streak, who spends a lot of time considering how luck, or chance, or serendipity, can upend and shape someone’s life.

The day I got to hang out with Jen ended up being a rainy one in New York. I had run for blocks along the entrance to Central Park, trying to hail a cab along with every other panicked tourist, my hair growing frizzier with every step. Thankfully, Jen and her apartment were an adorable respite. And I had so much fun talking on her comfy couch, watching through a huge pane glass window, as the city rained itself out.

So, dig out your Hunter rain boots, breath in the ozone scent of humidity proof, extra-strength, Pantene hairspray, and enjoy the conversation.

[background sound of rain steadily falling]

ENNI: So, Jennifer… hi!

Jennifer E. SMITH: Hi! How are you? Thanks for having me.

ENNI: Oh, my gosh! Thank you for having me over to your house. I so appreciate it. We’re in the middle of a New York whirlwind, so…

SMITH: Well, I’m very glad you’re here, on a rainy day in New York.

ENNI: Unexpectedly rainy, I will say. I got a little bit caught in it.

SMITH: Yeah, we didn’t see this one coming.

ENNI: So, on the podcast we like to start at the very beginning, which is: where were you born and raised?

SMITH: I grew up in a suburb of Chicago, just forty-five minutes north of Chicago, called Lake Forest. Then we moved to a little town called Lake Bluff after that. It’s a really nice town. It was a lovely place to grow up. Actually, all of the John Hughes films are filmed there, so you can sort of get an idea for what that’s like.

ENNI: Really? So, growing up, how was reading and writing a part of your life?

SMITH: I was a huge bookworm. My parents were very encouraging of it. I would always sneak down the stairs and ask for fifteen more minutes before lights-out. They loved that I was a reader, but in a kind of baffled sort of way. They are not terribly creative. My dad was a lawyer, and my mom owned a wallpaper and fabric store, and they were very practical. So, I think they were always tickled by the fact that I was such a big reader.

My mom, now that she’s retired, she’s in three different book clubs and reads everything. But at the time, I remember occasionally I would find the odd Mary Higgins Clark book lying around. The mass market paperbacks. But not much more than that. And my dad, still to this day – other than my own books, which he reads all of them – basically every year on vacation, he takes the same John Grisham book with him. He reads the first two chapters and then puts it aside again, and then the next year has forgotten the first two chapters, and starts it again. So, he was not a big reader. I think they thought it was great that I did.

ENNI: Where do you think that came from?

SMITH: I don’t know. I feel like it’s being right-handed or left-handed. You’re either a reader, or you’re not. From a really young age, I learned to read very early. I devoured everything I could get my hands on. My mom would drop me off at the library often, with spare change for the pay phone so I could call her when I wanted to be picked up. Of course, I never wanted to be picked up early, so I would just keep the spare change, and I would save it until the library had a book sale and then I would buy a lot of books with it.

ENNI: That’s perfect!

SMITH: It is perfect. So, it was right from the start. After all of the fifteen more minutes, fifteen more minutes, of reading before bed, I remember I would lay on my stomach in the wedge of light from the doorway – from the hallway – and just keep going. I couldn’t get enough.

ENNI: I’m always curious with people whether it was escapist. What kind of books were you reading?

SMITH: When I was really little, I loved THE BABYSITTERS’ CLUB and a lot of series books. I was a real horse kid, so I read a lot of SADDLE CLUB, all of the BLACK STALLION books; really animal books. I loved WHERE THE RED FERN GROWS. I loved TUCK EVERLASTING and BRIDGE TO TERABITHIA. I didn’t read a lot of fantasy, I read a lot of contemporary. I guess it wasn’t called contemporary then, but I read a lot of realistic fiction. It wasn’t so much escapist as… I remember always being thirsty for more. I think there was a real shift from reading – I loved, loved, loved BABYSITTERS’s Club, and SADDLE CLUB, and all those books – but I do remember a shift when I started reading BRIDGE TO TERABITHIA and those types of books, where it’s not even so much about the story as the language. You just get lost in the book. That was a real revelation to me at the time. That started a whole new era of books.

ENNI: So, those seminal middle grade books, kind of set your mind off…

SMITH: Yes, definitely.

ENNI: Were you doing any writing?

SMITH: I was. When I was in fourth grade, there was this school-wide short story contest that I won. I wrote this story about a girl and her horse, obviously [laughs]. I had no expectations, and no thoughts of writing to that point. I mean, I was nine, or ten. But, it hadn’t occurred to me that writing might be a thing that I liked. I think there’s a natural progression from reading to writing at a certain point, but for me it happened really abruptly with that short story contest. I won, and because of that I got to go downstate to the University of Illinois with my parents for a weekend. We got to listen to writing workshops. We got to meet a bunch of authors. But, it was just mind boggling to me… the whole thing. We got gold foil stickers on our stories, and from that point on, I just carried that thing everywhere with me. It was a really, really, big deal for me.

ENNI: So, it’s not like you won it, and you got to read it out loud, and “Hurray!” This was a really big deal.

SMITH: Yeah, it was a big deal. I think it wasn’t even school wide, I think it was district wide. And mine got plucked from the group, and because of this – I truly like to think I would have become a writer at some point anyway, I would have found my way there – but that really was a huge turning point for me.  From that point on, I fancied myself an author [laughs].

ENNI: Well, yeah! And now I think we take it for granted that authors are visible, and accessible to kids. But, even when I was growing up… none of that.

SMITH: It was a huge thing to get to meet people, and to know that there was a job out there, that was writing stories. That was a mind-boggling thing.

ENNI: Well, we’re gonna get to it, but that seems like a “Hinge Moment” which is really exciting. But you said your parents were really practical, where they kind of tempering…?

SMITH: When I was little, they loved the fact that I wrote. I remember my mom actually saying, when I was younger, “You could be a children’s book author one day. You could write these kinds of books that you’re reading all of the time.” Which was, obviously, so sweet and encouraging.  When I got much older, I think they started being like, “Ooh, this isn’t going away.” To an extent, saying you want to be a writer is like saying you want to be an astronaut, or a ballerina. It’s a job that’s totally possible, but it’s not wildly practical. Which my parents were.

So, they were encouraging. But really, a lot of the encouragement I got along the way was from teachers, and librarians, and people who saw the way I responded to books, and the way I wrote my own stories. When I was in seventh grade, I precociously started writing a novel, that was not a real novel. But, my seventh-grade English teacher was so encouraging about it. We would have a free-writing time in class, and she was always kind of amazed that I was doing this.

I look now - and I meet so many teens and younger kids when I go out and speak to them about my books - and I can’t get over how many of them have written novels, or novel-length things. Or many, many books. And I think it’s amazing. But at the time, I think my teachers were like, “Hm. That’s cute she’s doing that.” It didn’t seem to be quite as much of a thing.

ENNI: I wonder about that. This is something I thought about. I got the chance to go on tour with Veronica Roth, and eavesdrop on her many interactions with fans, and I noticed exactly the same thing! So many of them are writing. So many of them are taking it really seriously. I’ve seen all of these, really ahead-of-the-game teens, who are taking themselves and their writing seriously. It makes me really impressed, but it also makes me worry – in this dumb maternal way – like, “You should keep writing. Take yourself seriously.” But also, “You don’t need to be published right now.” Like, “Just keep writing and being a person.”

SMITH: I totally get that, because at any age you’re at, when you finish the first thing you finish, I think you’re first instinct is to run out and try to be like, “Here world! Here’s this thing I finished.” Whether you’re thirteen, or fifteen, or twenty-five. I used to be an editor, and I used to see that all of the time. People finishing something and being so… it’s a huge accomplishment to get to the end of a book. And look, the only way you know if you can write a book, is to actually sit down and try to write one.

And so, the instinct when you get there… I did the same thing. Not with my novel that I wrote in seventh grade, but the first novel that I wrote after college. You’re so proud of your accomplishment. You’re so eager to get it out into the world, that then you sit back, waiting for the world to be like, “Yay!”

And often that doesn’t quite happen. It takes time. It’s a craft that has a lot of stepping stones to it. And you need to go through those. But, in practice, it was a great thing to do. So much of writing a novel is about craft, and layering, and working on the narrative. But a lot of it is just sitting down and writing a beginning, a middle, and an end. To attempt that early on is a great learning experience.

ENNI: So, you kept writing.  Were you sharing with any friends? I know teachers, and librarians, but…?

SMITH: No, not really. I think a lot of it, at that age, was just for me. I continued through high school. In high school, I was really lucky to have one of “those teachers.” You know? A teacher who made all of the difference. I can’t remember if it was my freshman, or sophomore year… but, Mrs. Aronson [?]. Who, I was just on tour for WINDFALL, and she came to one of my events. I haven’t seen her since high school. And she brought her sixteen-year-old daughter, which was just incredible.

She saw what was going on. I was writing so much, and she started meeting with me after class. I was turning in so many more stories than were due, and she would read all of them. She would give me notes. And she kept them all in a pink binder that she called her Jen Smith Binder. It was so sweet.

When she emailed me to say that she was gonna come to the event, she told me that her sixteen-year-old daughter has read all of my books, and that she actually still has the pink binder, and they read those stories too.

ENNI: No way!

SMITH: Which made me cry.

ENNI: They got the director’s cut of Jen Smith!

SMITH: It made me cringe a little too, but it made me cry. It was so nice. She made a huge difference. And there was a national literary magazine for high school students, called Merlyn’s Pen. And she, from freshman year, started encouraging me to submit a story to it. It was a real deal. You got paid seventy-five dollars if your story got in, and it was published only quarterly. It was a really big deal. I turned in so many stories over my four years there. And it actually wasn’t until right before I graduated that one of my stories got accepted. It was a culmination of her work with me through high school and everything.

And then my parents told me not to cash the seventy-five-dollar check, because it was my first income from writing. That we should frame it instead. It was really sweet, they were saying that it was gonna be the start of a long career. But we never framed it. So that was seventy-five-dollars down the drain. I don’t where that check is now.

[Both laughing]

ENNI: Oh no!

SMITH: But it was very exciting.

ENNI: It’s always incredible to me when people discover their passion so early in life. I think that’s such a gift. Were you still like, “Author, author, author”?

SMITH: I was, “Writer. Writer. Writer.” Which I think is a different thing than author. Probably because I grew up with very practical parents, I was always pragmatic about it.  But I always knew I would write, no matter what. That was something that I loved to do, and I was passionate about. I didn’t expect to ever be an author. When I went to college, I was an English major with a minor in Creative Writing. But I remember, through high school and the beginning of college, I always thought, “Well, I like to write. What’s a job you can do with that?” For a long time, I thought about journalism, even though it really wasn’t for me. That style of writing I didn’t like. Now, there’s so many creative ways to be a non-fiction writer, but when you’re at a high school newspaper, it feels pretty rigid.

ENNI: Limited, yes.

SMITH: So, it just wasn’t for me, but it was the only thing I could really think of. I went to college, a school called Colgate in Upstate New York. And there was a class there that was incredible, it was called Living Writers. Every week you would read a book, and the author would come in at the end of the week and you would get to ask them questions, and talk to them about the book.

It was a big reason why I went to the school. They only had that class every other year, and it was kind of a big deal. It was run by this writer, Frederick Busch, who has since passed away. But he was a great short story writer and novelist. It was the first time, other than in fourth grade, when I really got to meet authors. And the idea that you could read a book, have a question about it, and then actually get to ask them was – again now, I think there’s so much more access to authors – but even when I was in college, it felt much farther away somehow.

Elizabeth Strout came, and Justin Cronin, and Ha Jin, and all of these amazing authors. It was just incredible anyway, but mid-way through they had an agent, and an editor from New York, come up. And that was the moment when I listened to them talk to us about what they did, and what the job entailed. For some reason, it just never occurred to me that that was a thing you could do. When you’re such a big reader, and you just want to be close to words, that you could get a job helping to make books possible.

And so, from then on, that was the goal. When I graduated from college, I knew exactly what I wanted to do. I wanted to be an editorial assistant, and I wanted to do it in New York, and I wanted to do it at a publishing house, and I wanted to do it in print and in fiction. It was so specific that it was hard to get a job, because I didn’t know anybody in publishing. I remember that whole summer, my parents being like, “Get. A. Job. Widen your net. Just apply for anything.” They would come up to me with newspaper advertisements wanting people to work for a website at O’Hare, or an airline. And I was like, “No! I’m going to work in New York City. I’m gonna be an editor one day.”

I was always still writing, but my dreams kind of shifted into publishing in a way which was kind of a combination of the practical and creative.

ENNI: It’s strange that we culturally have… books are omnipresent. They really are everywhere. But our understanding of where they come from…

SMITH: It’s magic!

ENNI: Yeah, totally! In this broader sense, they just appear. And people don’t really think about it.

SMITH: Even now, I think there’s a bit more of an awareness, especially if you’re a bookish person, about editors. But I often end up talking to people about publishing. There’s people who design the jackets, there’s copywriters who write all of the jacket copy that you read. There’s page designers, there’s proofreaders. There’s so many jobs. So much goes into the making of a book. And it’s fascinating, and wonderful, and if you’re a person who loves to read, the idea of shepparding a manuscript from a Word document on your computer, to a hard, rectangular object on the shelves of a bookstore… is so cool.

ENNI: It sounds like your high school experience of working with this teacher, was a lot of applying critical analysis to your own work. That a lot of people don’t get around to until later. Obviously, you heard from an agent and an editor, and were kind of like, “Agenting – no. Editing – yes.”

SMITH: Ironically, then my first job was with an agent [laughing].

ENNI: Oh, my god, hilarious [laughing]. Tell me about that, and then I want to talk about the transition to editing.

SMITH: So, as I was home for the summer, and my parents were like, “Please, for the love of god, get a job.” I was applying to everything. And I remember I had a few interviews at Random House, where I eventually worked years later. I just remember standing in the lobby of that building, I don’t know if you’ve ever been in there?

ENNI: Uh-uh.

SMITH: It’s probably twenty feet high with bookshelves, and I had this moment where I was like, “I will sweep the floors of this place. I just want to work here so badly.” I didn’t get any of those jobs, but I did eventually get a job working for a literary agent named “Binky” Urban at ICM, who is a complete legend. She has been a huge mentor of mine, and I totally lucked into this job. I was so clueless, it was ridiculous, when I think back on my interview with her. She represents all of my literary heroes. Toni Morrison, Haruki Murakami, Donna Tartt, E.L. Doctorow, everybody! Just incredible, incredible authors.

And I walked in there, basically being like, “Hi, I like to read, and I want to be an editor.” And she was like, “Work for me for a year, and I’ll help you get a job as an editor.” But I ended up staying for three years because I was learning so much. I was getting to help edit Cormac McCarthy, and Jennifer Egan, and Kazuo Ishiguro, and Richard Ford, and all of these amazing authors I was getting to do very hands-on work with.

And Binky, my boss, had never had an assistant before then who had wanted to be an editor, and who was a big reader. Often, a lot of the assistants at the big agencies come from more of a business or a law background. And I just wanted to read and I wanted to edit. So, it was wonderful. It’s a tough job to go into, at the beginning. There’s such a steep learning curve, and I learned so much about the industry that way. And got to meet so many of my heroes. So many amazing authors. It was incredible.

ENNI: Getting the opportunity to work with names like that, right away, must have been very humanizing. And taking some of the intimidation out of it?

SMITH: Yeah, for so long, you’re thinking of authors as these giants. And they are. Many of them are… all of them are. Anybody who writes a book is a giant in my eyes. But, three months before I got that job, my graduation speaker at college was Anna Quindlen. And three months later, she was represented by Binky. I was chatting with her on the phone every day, and getting to know her. That alone was such a cool thing. And to get to see the process behind these books. I knew, right from the get-go, that agenting wasn’t for me. I think it takes a certain kind of personality, and I was just laser focused on editing. But like I said, just to be able to have this bird’s eye view of that kind of office, and those kinds of writers, and deals and processes, was so enlightening. It was awesome. I still look back, and it was pure luck.

I got an interview to work for an agent there who did the royalties and data. And she saw my resume, and had a phone interview with me, and it turned out that Binky was looking for somebody then. And she suggested that she meet with me, because I might be better suited to work with actual literary agents instead of collecting data. I’m so lucky. I feel incredibly fortunate. To a certain extent, I feel everything that has happened to me since then has come out of that experience.

ENNI: It sounds like you were learning a lot while you were there, but you stayed there for three years. In hindsight, it’s so smart that you did. Any amount of time you can spend on that side of it, and getting really savvy, before you jump across [to writing].

SMITH: I wrestled with it a lot, because it’s hard to stay at a job where you know you don’t want to take the next step in the job. But, at the same time, the first six months to a year, I wasn’t doing that much hands-on work. I’m making it probably sound more glamorous than it is. You’re also doing so much assistant work. You’re answering phones, and you’re getting lunches, and you’re doing all of the correspondence, and you’re looking at the slush pile. You’re doing everything. And Binky, like I said, had never had an assistant who wanted to do editing before. So, she didn’t rely on me at first, when we were still getting to know each other.

There was a moment where there was this big author who was going to switch agents, and she was taking meetings with a few big agents. And Binky, I remember, was like, “You order all her books for me. I need to read them this weekend.” And the box of books came, and I walked them into her office, and she was like, “Ugh. That’s a big stack.” And I was like, “I know, but… you’re gonna love this one. And this one is one of my favorite books ever. And this one…” I had read a few of them. And she kind of looked at me with new eyes, and was like, “Okay. Here’s what we’re gonna do. We’re gonna split the pile this weekend, and we’re gonna come back and talk about them.” And that was a real turning point.

Probably a couple of months later, she asked me to look at a proposal that she felt was geared towards a younger audience – of a book that was geared towards a younger audience. And it just started gradually. By the time I left, I was lucky enough to get to… you know like I said? Jennifer Egan on her book THE KEEP? I did three or four drafts with her before they sent it to her editor. I got to work closely with Richard Ford on THE LAY OF THE LAND. There were so many books that I got to work on in a really tangible way, as it progressed. So, it became harder and harder to leave, because I was becoming more and more involved, on a ground level, with the development of these books.

ENNI: You carved out the editorial niche in that particular [situation]. You’re like, “I am the editor.”

SMITH: Yeah, exactly. So, I felt the things I was learning were very much transferable when I was gonna decide to make a leap eventually.

ENNNI: And then you knew all about agency stuff, and how they worked.

SMITH: Yeah, and then eventually when I did become an editor, it was so nice to have seen that side of the business. And then eventually as I was writing as well. I always do feel like I have this 360-degree view of the industry, which is sometimes a little daunting because you almost know too much. But sometimes it’s really, really helpful [laughs].

ENNI: So, at this point, you mentioned that being an assistant, especially for an agent of that caliber, is ninety-five hours a week, I’m sure.  And I know you were growing editorially – you couldn’t not, reading all of these amazing books – but was writing on your own still a thing?

SMITH: I was still writing my own stuff, but I was getting up either very early in the mornings, which didn’t always happen because I was in my early twenties in New York City, and there were a lot of late nights! But, I used to also try to carve out four hours every Sunday. I would basically rope those off, and that was really when I got most of it done. I like to say early mornings, because it makes me sound like a busy person [laughs]… a diligent person. But it was really Sunday afternoons.

I remember, even then, not necessarily thinking anything would come of it, but just the kind of stories I wanted to tell. I look back now, and think about how crazy it was. Because often I had a roommate, and we always had friends over, and everybody would be hung over on the couch on Sunday afternoon watching a stupid movie. And I would be like, “Okay you guys, I’ll be in my room. I’m gonna go write for a little bit.” And they must have looked at me and been like, “What? What?”

I guess maybe it’s like saying you’re gonna go knit, or something. It was a hobby. But I was so diligent about it, that I kind of look back at my younger self in awe. But, I was always doing that. Eventually, probably two years out of college, I had finished a novel that I was really proud of. I didn’t want to tell anybody at ICM, where I was working, for two reasons. One: because I didn’t want anybody to think that was the reason I was there. I very much wanted a career in publishing, and that was important to me, and I wanted to make sure that was understood. And two: because I wanted to make sure that I knew I could do it on my own.

So, I made a list of agents, and I sent it out to a lot of them, and I got a few offers of representation. I sort of narrowed it down, and decided on somebody, and I went to go tell my boss that this had happened, and she was sort of stunned. Because I had never mentioned that I wanted to be a writer. And she said, “It kills me to think of you being represented anywhere else. Can you buy us the weekend, and can I read it? And can I give it to another agent here?” Who was a younger agent, and had a very similar sensibility to her – was sort of here protégé in some ways - and that’s my current agent [laughs].

It was a really hard decision. They came back after the weekend, and they both loved it. And I had mixed feelings about it, because at that time, I didn’t have plans to leave there yet. I knew I would at some point, but it felt too close. I had this worry that I had to, “Send in a revision to my agent,” and then pass her in the hall, and it would be awkward. I thought, “Let’s keep it separate.” I also was worried about telling people, “Yay, I have an agent!” It was this big, exciting thing. And then you tell them it’s where you work, and feeling weird. Even though I had gone the extra mile to make sure I would have been able to go elsewhere.

ENNI: I could not agree with you more, and I can totally relate to this. In a selfish way, you’re like, “I never want anyone to think that I only got this because I was here.”

SMITH: One-hundred percent. So, I ended up, after a lot of thought, deciding to go with – her name is Jennifer Joel - and she’s now been my agent for over ten years. I love her and I adore her and I am so, so happy I did that. Because while there were moments of awkwardness in the final year I was there, and she was technically representing me – she hadn’t sold anything until I left, so it wasn’t too far down the process – but now it’s like home.

And whenever I go to meet with her about something, I get to see Binky, my old boss, who has still been such a big part of my life, and reads all of my books, and weighs in on all of my career decisions. And all of the other agents there who I had gotten to know so well over the three years. And they feel like family, and they treat me like family. It’s this really lovely thing to feel the kind of foundational part of my New York experience has continued to be a driving factor in my writing. I really lucked out. The whole thing worked out really, really, well.

ENNI: That’s incredible. Had the kind of books you were writing changed from high school to when you began to take it seriously?

SMITH: So, I was always drawn to realistic, contemporary books. I think it’s what I had always read, and what I always wanted to write about. There wasn’t even a question. I feel like I don’t have the imagination to write… I am so impressed by fantasy. I read dystopian, I love it. I am the biggest Harry Potter nerd. I love all of it, but my brain has never been able to bend in that way. This has always been what I wanted to write. I guess the main thing that changes is that the first two books I wrote – which neither of them got published in the end – were essentially YA, but I did not yet know I was writing YA.

I think a lot of current YA authors have a story like this, where I think my first one, the protagonist was eighteen. And the second one, the protagonists weren’t even teen-aged. There was a moment where, after the first one went out and got roundly rejected, I had this moment where I was waiting by the phone. I think she sent it out on a Thursday, or a Friday, and on Monday I remember walking in a being like, “This is it! I’m gonna get my offer.” I couldn’t wait to get the call. I was so naïve. I think part of that was because the only experience I had in publishing was in this office where everybody was a rock star – all of the writers that they worked with [laughs].

ENNI: Of course, because Cormac McCarthy would be getting a book deal out of that on Monday. Yes, it’s so true.

[both laughing]

SMITH: And so, I was crushed. I wallowed for a little bit, and then I picked myself up, and dusted myself off, and started writing another book. I look back now, and I think how crazy that is that with no encouragement and, in fact, with a lot of discouragement, my first instinct was to sit down and open up another blank document and start again. But I did.  And over the next year to year-and-a-half, I wrote another book. That one got roundly rejected as well. It was after that, that my agent Jen said, “You know, your voice actually feels like YA in a lot of ways. Have you ever considered trying to write that?” It was so new at the time, which is a weird thing to say because, in a way, it’s always been there. But as a category, it was new. I think the first thing I did was I read a lot of YA.

ENNI: I was gonna say, had you been reading YA to that point?

SMITH: I had been reading Harry Potter, and I had been reading the big stuff. But, I went and I read everything that was out there. This was ten years ago, so it was LOOKING FOR ALASKA, and Sarah Dessen, and all of these amazing books that I had missed because of my age, or my circumstances, or for whatever reason. And I was like, “Yeah, this is what I’m writing.” Or, “This is what I should be writing.”

I wrote a book proposal and I wrote the first sixty pages of my first book THE COMEBACK SEASON. It’s about two Cubs fans who fall in love. I’m a massive Cubs fan, and always have been. And my agent, Jen, is a very big Yankees fan, and it was a time when we were talking about baseball a lot. And the idea just kind of came to me. I wrote the beginning of it, and showed it to her, and she was like, “This is great. I want to send it out.” And she ended up only sending it to – she had had lunch not that long ago with this editor, Emily Meehan – who was my first editor, who I love. And she was with Simon & Schuster at the time, so she only sent it to Emily, who loved it, and bought it. This was actually the last month that I was working with ICM, I had already given my notice. I was going to grad school at St. Andrew’s in Scotland.

I had sort of had this moment where I said, “I love New York, and I love publishing, but I don’t want to wake up in ten years and never have done anything else.” It was time to leave ICM. I was gonna try to get a job as an editor, but I wanted to take a year in between to just write, to be completely indulgent with my own work. For so many years, it was taking other people’s manuscripts, and reading other people’s books, and pouring so much creative energy into that, that I wanted to just write on my own.

So, I sold a book right before I went to Scotland. I was able to use the advance to pay for grad school… for most of it [chuckles], it was a small advance! And I spent the year at St. Andrew’s finishing that book, and writing the very beginning of the next one.

ENNI: Wow! Actually, this has been provoked in me by all of these conversations that I’ve had, like you were saying – you are either born left-handed, or right-handed – it’s just the truth over, and over, and over again with writers.  You look back, and you’ll be like, “Well, I don’t know. I just spent every Saturday…” for no reason. No discernable present reason.

SMITH: Right! It could so easily turn out to be nothing. A friend of mine was recently talking about this, with another creative profession. That you could look back on it, and it could either be looking back as to stepping stones as to where you are now, or as time that just went up in smoke. But you don’t know at the time, you’re just doing it because you love to do it. It’s like you have this internal barometer that’s just pushing you towards it.

ENNI: It’s a very mysterious thing to me. It’s this beautiful and odd thing that – most especially when we are teens – you are sort of brave in these crazy ways. I look back at stuff that I spent hours on in high school, and all of those things are still in my life.

SMITH: It’s totally brave, because you don’t know if it’s ever gonna pay off. You don’t know if it’s ever gonna turn into anything. It’s brave to put a pen to paper, any time you do it. It’s brave to pour a piece of yourself onto the page. It’s one of the bravest things you can do. To put yourself in someone else’s shoes, or to tell your own story. Or, just put yourself out there in that way. But it is a crazy thing to do when you take a step back.

[both laughing]

ENNI: Yeah, yeah! Looking back at…

SMITH: We are all totally nuts!

ENNI: It’s true! It’s true. None of this makes any sense. But the fact that there’s a passion, and a desire.

SMITH: Especially when I look back at those first two rejections, which I took really, really hard. I mean, those were books I spent ages on, and carved out time from a busy life, and poured myself into and loved. And truly really believed in. The truth about publishing is that there are – and I say this from having worked at the other end of it for many years – is that there are so many great books that get passed on all of the time.

It is less about if a book is good or not, and more about if somebody connects with it in a visceral way. It’s like matchmaking, you know? But at the time, I didn’t understand that. It hurts, regardless. And it was hard to move on from those things. I’m glad I did, but it’s a hard thing to do. I’m so grateful that the crazy twenty-three and twenty-five-year-old me sat down and opened that blank document again. Because I wouldn’t be here if I hadn’t. But, I also look back and am like, “You were a nut! What were you thinking?” You got up again the next morning, and you said good-bye to all your friends, and you walked into your room, and you closed your door, and you were like, “Now I’m gonna start writing four hundred more pages.” And put yourself out there, all over again.

But, I look back too, and think about how I wouldn’t have written THE COMEBACK SEASON, which was my first one to get published, if I hadn’t written those first two that didn’t get published. I learned so much from those books. And I took very specific things I learned from them into the next one. And then my first two books, THE COMEBACK SEASON and YOU ARE HERE, I’m very proud of those books. But, they didn’t sell a lot of copies. And it wasn’t until my third book, THE STATISTICAL PROBABILITY OF LOVE AT FIRST SIGHT, that I sort of broke out a little bit. And I would not have written that book if I hadn’t written the two quieter ones.

When I say stepping stones, I mean it very literally. When I look back on my career, I can trace a path from book to book to book. I can say, for sure, that if you took out any one of those bricks, that the rest of it probably wouldn’t have happened.

There’s no such thing as failure, because everything leads to the next thing. In all of my published books, I’ve written, many times, one-hundred pages of a book in-between that I’ve abandoned for whatever reason. But, I had to do that in order to get to the next thing. It feels, I realize, a little maybe “Pollyanna-ish” to say that, because writing can be very hard, and it’s a struggle. And rejection sucks. And sitting down to that blank document is not easy, and it’s a sacrifice, and it’s hard. It’s the whole Hemmingway thing, where you sit down, and you open up a vein, and you bleed. But, like I said, from where I sit now I look back and it’s not a straight line… it’s steps.

ENNI: Yeah [sighs], it’s so true. The thing that kept me going for a long time was, “This time spent is only wasted if you stop.”


ENNI: I hadn’t actually done the math on that and realized that you were a writer well before you were an editor. That’s really interesting.

SMITH: Yeah, I was doing them simultaneously for a really long time. So, I wrote the first book while I was in grad school and then started the second. And by the time I had spent this idyllic, amazing, incredible year at St. Andrew’s where - after working full-time, and writing for three years – all of a sudden, my only job is to write.

[both laugh]

ENNI: And be in Scotland, my god!

SMITH: And be in Scotland. It was wonderful. Then I came back and I got a job as an associate editor at Random House on the adult side. At that point, my second book was still not quite due, so I was working on it. So, right from the beginning I told them – I don’t think my first book was even published yet – I think I started that job in September and my first book came out in March. So, I told them up front like, “I’m doing this too.” And they were okay with it. It helped that there was a bit of separation, where I was editing on the adult side, and writing on the kid’s side. So, it wasn’t tangled in any way… it was just time.

ENNI: I want to talk about the development of both careers. Because I’m so interested in how they inform one another. You were working in adult versus writing for children, and I don’t often get to talk to people who are also editors, so it’s very interesting to me how the two skills overlap? But I’m also really interested to hear how you developed your own list as an editor, and what kind of things stood out to you, and how that was different from what you were being inspired by within yourself?

SMITH: I think the great thing about being an editor is that you like what you like, and you go after that. For me, I was always very lucky to work under either bosses when I was an assistant, or under editors-in-chief who were very encouraging of me. Sometimes you feel like, “Should I be trying to acquire books that are more commercial? Or, books that are more this-or-that?” And I was always lucky that they said, “You know? You have great instincts. Go look for the books you want.” Which were generally… I loved books that were kind of that line between literary and commercial fiction, and that had great voice, and a lot of heart. That was always my description of what I was looking for.

When you are coming up, you have to bid against a lot of other editors who are much more experienced than you, and I lost a lot of books at first, before I acquired my first one. I lost Liane Moriarty’s book, WHAT ALICE FORGOT. It was me against the editor who eventually got it, and her career is now incredible. But that was the first book I ever bid on was that book, WHAT ALICE FORGOT, which is terrific.

Eventually, the first book I bought - it kind of comes full circle – was from Binky Urban, my first boss. I was very lucky in that way because she knew me, and she thought I was a great editor and she trusted me in a way that agents - who I was trying to get a lunch with, so that they would send me their stuff - didn’t know me. And so, she sent me a book called THE PRIVILEGES, by Jonathan Dee. Which was the first book I ever acquired, and I love more than I can say.

And everyone should read it, it’s amazing!  I’m not biased at all. It was a finalist for the Pulitzer Prize. So, it was a huge big deal for me as an editor. I am so proud to have been involved with that book, and it was a great toe-hold into doing more.

ENNI: So, you’re gonna be a challenge here [chuckles]. I’m trying to figure out how to talk about both at once, because this is so fascinating. Because you are living dual lives. Helping an author realize their vision is so different from working on [your own]. I’d love to hear if there are any specific examples of this that you can give us, about how you relayed what you learned helping other authors, to how you grew your own career, and thought about your own work.

SMITH: Yes. Whenever I meet somebody young who wants to be an editor, but also would love to be a writer, I always tell them that it’s incredible. Because being an editor is like a master class in writing. You can’t read that many manuscripts – both terrible ones that are being submitted, or amazing ones that you get the opportunity to work on; sometimes read eight or nine drafts of – without it affecting your own writing. It ups your game. I often meet writers who can’t read while they write, and that was never an option for me. I totally respect it, because I understand that you want to preserve your voice, and you don’t want to be influenced by anything. But, that was never an option for me, because I had a day job… which was to read.

But it actually upped my game, I think. But, the other thing I tell them, is that it’s an insane thing to want to do in terms of time and creative energy. Because I think people sometimes have this vision of editors that they’re sitting in this oak paneled room, with a glass of brandy, and they’re editing, and being brilliant. And that’s not what it’s like. You are in meetings, you are running around, you’re taking phone calls, you’re doing emails, and you take all of the reading and editing home with you. And there are manuscripts to read, always, that are being submitted. And you have to read them quickly because often they get bid on very quickly. And I was an intense, hands-on editor. I read books eight or nine times.

So, it’s tough because you are pouring so much creative energy into somebody else’s book, that you often don’t have anything left for your own. So, there’s not a great solution to that. It’s basically that you have to want and love books. There’s no substitute for passion and that’s what drives you. I am undoubtedly a better writer for having been an editor, and I’m undoubtedly a better editor for having been a writer. But, it was a challenge to balance them. As my writing career broadened and I was doing more travel and I was having to hit more deadlines, they were very understanding with me. They let me work from home a lot, and have a bit of a flexible schedule, and that really helped. But, there still were days when it felt like that well of creative energy is finite.

And so, that was the really hard part… not having the energy. When I first got to Random House, I was writing my second book. And after I finished that, I had a drought period of writing where neither of the books had sold very well. They were asking me to write something more commercial. I didn’t have any ideas that were commercial, and I turned in a few half-hearted ideas to them and they didn’t love them.

There was this moment where I sort of threw my hands up and was like, “Okay, I’ll just take a break.” It was the first time ever that I really took a break, and I thought, “I’m just starting out in editing. Let me try this. Let me put all my energy towards this.” And for probably nine months, or a year, that’s what I did. Towards the end of that, after letting the fields lie fallow, I got the idea for THE STATISTICAL PROBABILITY. Which the joke of it is that I thought it was not a commercial book, I thought it was my quiet love story, book of my heart sort of thing. I wrote it with no expectations, and it was just such a wonderful thing to do; to recapture what that felt like.

Then it sold and there weren’t a lot of expectations with the publisher for it, and it ended up building up a head of steam through foreign sales, and film sales, and word of mouth. The irony is it ended up being my most commercial book in some ways - my most commercially successful book I should say - which is just another reason to always write the book you want to write.

ENNI: That’s so funny, because I was gonna ask if that idea felt different?

SMITH: It was a joy. It was the book that I was waiting [for]. I didn’t have a publisher for it. I didn’t know if I’d ever get published again because my sales track record wasn’t great. I had literally no expectations. And I remember they took it to the Frankfurt Book Fair, and I had never sold in any foreign territory, and the book has since ended up selling like thirty-three, or something like that.

I remember getting the first offer, and I was just jumping up and down, and so excited. Because I was like, “That’s so cool! Someone’s going to translate my book into another language.” I had zero expectations for it. The whole thing felt like this happy accident every step of the way where I kept saying, “It’s like the icing on the cake, everything [that] is happening. But there’s so much more icing than cake.” [Laughs]

ENNI: [laughing] That’s true! It might be helpful right now - we keep talking about commercial, and I think I know what that means – but I think you are in a really great position to define that. Do you want to explain what you mean by it?

SMITH: When I was an editor, and I was talking about how I always looked for books that were kind of at that intersection between literary and commercial, what I mean is, basically beautiful, gorgeous writing but a story that has a hook to it. A story that you can talk about in a couple of sentences that has the elevator pitch, and feels like there’s something to hang your hat on in terms of marketing or publicity. And you’re sort of forced to think of it that way when you work in the business, because there’s so many books coming in. And so many books as editors that you want to acquire.

But a publisher only does a certain number of books. And so, you really need something that the departments, who are going to eventually spend six month to a year [on] - as you often do as an editor - crafting a book, and making it the best book it can possibly be. And it’s wonderful, and you’re so proud of it, and happy with it.

But eventually, you have to turn it over to the people who have to put a cover on it, and figure out a marketing plan for it, and bring it out into the world. And so, the more you can give them to work with [the better]. I think one of the best examples of the first huge book I ever acquired as an editor was called THE LANGUAGE OF FLOWERS. It was this book that was just gorgeous. Beautiful, beautiful writing, and this amazing story. Part of the story had to do with the Victorian language of flowers. And it was about a girl who had grown up in foster care, and she didn’t speak. She kind of spoke through her flowers. It was this amazing – I’m not pitching it very well [laughs] – but it was this amazing pitch that everybody felt like they could really sell.

So, that was the way I used to think about it as an editor. And that definitely seeped into my writing a bit too, I think, without me even realizing it. I think STATISTICAL PROBABILITY was the first higher concept book that I had written. I did that unconsciously. The idea just popped into my head and, like I said, I just went away and was writing this book that I wasn’t sure what would ever come of it. But when I look back now, I can see why that idea was different than my first two books.

ENNI: The commercial part of it is this plane flight, right?

SMITH: Yeah, it’s [about] a girl who misses her plane by four minutes, and because of that she ends up – she’s on her way to her father’s wedding, to a woman she’s never met before - and because she misses the plane, she ends up sitting next to this boy who’s on his way to London for another reason. And the whole idea is that they both meet each other, at the moment they most need to be meeting each other. But it’s all about like, “Imagine what would have happened, if she hadn’t missed the plane by four minutes.”

The truth is, you’re not writing in a vacuum. You can write in a vacuum if you want to, but if you’re writing to want to be published, part of being published is finding an audience. And there are ways to help that along. I remember very clearly saying to my agent, very early on, about one of the books that didn’t get published – which is probably the reason it didn’t – I remember saying to her, “I would rather write a beautiful sentence than a great plot.” And she was like, “Well, you need to do both.” [Laughs]

I am not a plotter, I don’t plot out my books. I have a hard time with writing something very commercial. But I think there was a shift that happened to me when I started sitting in editorial meetings once a week and listening to all of the books that people brought up that they wanted to acquire. If every editor is bringing, say, one book to the editorial meeting that they love, out of hundreds of things they’ve read. And then you think, all of those books they’re bringing up, only one or two of them is gonna get through. And then the one or two that get through, that’s one of however many books on that season’s list.

I just started seeing that you need a way to talk about the book in order to get other people interested in reading it. Because that’s the whole point of all of this. And so, I do think sometimes people use commercial in a slightly derogatory way, and it’s not. And, by the way, if you want to write a blatantly commercial book, that’s awesome, too! There’s no wrong answer here. Everybody is writing what they’re passionate about, and that’s what makes it so cool.

Again, there’s no right way to do it, and there’s no wrong way to do it. You have to write the book you want to write, which is the best advice I’ve ever gotten. An author friend of mine once said - I was struggling with this when I was in that one year period where I wasn’t sure if I was ever gonna publish again - and I was trying to do all of these fuzzy pitches, and he was like, “You gotta write the book you want to write.”

And it’s so simple, but I think that all of the time. When you can see that somebody’s put their heart into it, and there’s talent, it almost doesn’t matter what it is. I’m a firm believer, having worked in the industry for a long time, that the right book finds the right editor. That the good stuff flows to the top. And it is a business where there’s a lot of luck, and it’s a lot about timing. And there’s a lot of injustices in the way the industry has been set up, for sure. There’s a lot of problems with it, but I’m an optimist. It’s probably evident by the books I write, but I’m a big believer that the right book will find the right editor. It has to, right?

ENNI: I love that. I’m with you. Maurene Goo [listen to her First Draft interviews here and here] and I were talking about how optimism seems to be more efficient and useful than negativity [both laughing]. That seems sort of an optimistic realism. It seems to me like an easier, and more useful way to get through life, than believing in regrets.

SMITH: I’m with you guys.

ENNI: I love that you really allowed yourself this fallow period, that’s pretty brave as well.

SMITH: [laughs] I don’t know if that was brave, that was kind of like, “End of my rope! Okay I’ve got these two things going on, and this one is clearly not working, and it’s clearly not going anywhere, so I’m just gonna focus on the one.”

ENNI: This is the second interview, within however many weeks, where I’ve had someone say, “Nine months.”

SMITH: Yeah, maybe that’s the magic number.

ENNI: It’s like one school year, you know? It’s like a Hogwart’s year. You’re like, “I need to just take a backseat on this one.” And then it kind of is renewal, all about input for a little bit.

SMITH: Yeah, I think this is a career where there are setbacks both big and small… morale. And often the response to a big setback is to say, “All this time and energy, and hope.” Honestly, that’s what hurts almost more than the time and energy, is all the hope you put into it. And then that gets crushed. There’s only so many times, at least for me… you know those punching bag things that bop right back up? So, you can do that a few times, but sometimes you just need to collect yourself and lay on the floor for a second.

[Both laughing].

I think that was the case with me, is that it hurts after a little while, and if you want to be a real writer you, of course, have to have thick skin. And you have to have rejection. But we’re also thin-skinned people who have feelings, and pride. So, I never thought I was gonna give it up forever. But, I just needed to take a beat.

For me, ideas are also very hard. Once I have an idea, I can write pretty straight through, but not always – actually, that’s a total lie [laughs] -  but, it’s easier once I know what I’m writing. And I can only focus on one idea at a time. And when I finish that, there’s always a period of panic where I’m like, “Oh, my god. I have no other ideas. I’m never gonna think of another idea again.” So, sometimes that lasts a month or two, and in that case, it lasted nine months, or a year.

I think, because it lasted longer, and I was coming into it on the heels of some rejection… I was having a moment. I’m glad I pulled out of that.

ENNI: Out of the moment.


ENNI: You put in a lot of time in editing and you built up this world around that.

SMITH: Yes. I feel so lucky to have gotten to do it. I was an editor, I worked at Random House for seven-and-a-half years. I was an editor with my own list for maybe five of those. It is a huge privilege to get to work on somebody’s book. To take them through the process with you, to have them trust you. Editing is so subjective; as is writing; as is reading. And you are making gut calls on these books about what you think would make them better. And it doesn’t always mean that somebody else will think that made it better. It’s a situation where there has to be a lot of trust, and I was so lucky. I worked with so many amazing authors.

Eventually, I left. Random House was wonderful, and they let me keep cutting down my schedule, and they really wanted to keep me. By the end, I was really only acquiring a couple of books a year, and they were books I was intensely passionate about. It was a wonderful situation. But, what kind of happened was, I started feeling guilty too often. If I was editing, I was worried that I wasn’t spending enough time on my own writing, or my own deadline. And if I was writing, I would constantly be like, “Ah, I should check my email in case an author needs me.”

They didn’t put pressure on me. And neither did my authors, nor my bosses; nor my editors and publishers for my own stuff. I kind of got tired of always feeling like I wasn’t doing either one at one-hundred percent. And I wanted to see what it would be like to throw myself wholeheartedly into one career, instead of always being two places at once.

ENNI: It’s that Ron Swanson quote, “Whole-ass one thing.” [laughs]

SMITH: [laughing] Yes, exactly. I wanted to whole-ass one thing. When I left, they asked if I wanted to keep any authors and work freelance, and I only kept one, Lauren Graham. Who is wonderful and a fantastic writer. It’s been really great to still have a toe in the water, and to still continue to work with her. She comes from an industry where people wear all sorts of different hats. So, I think it was never odd to her, at all, that I wrote as well. So that’s made that editorial relationship very easy.

So, when she still sends me work, I feel that spark of excitement to edit something. To dig in and to use that part of my brain. And I do miss it. So, who knows what will happen down the road? For now, I’m very happy to be writing fulltime. But I do miss that chapter.

ENNI: You’ve said in several interviews, that you focus on “hinge” moments. Do you want to talk about what that means to you?

SMITH: Yeah, I’m kind of obsessed with these moments in time that act as hinges. Days where there’s a really clear split between a before and after. Where yesterday, your life was one way, and tomorrow, your life will be totally different. So, [in] STATISTICAL PROBABILITY, it’s meeting this person on a plane. And [in]  THIS IS WHAT HAPPY LOOKS LIKE, an email goes astray and sets a lot of events into motion. In THE GEOGRAPHY OF YOU AND ME, it’s a blackout in New York City, and she meets a boy in the elevator because of that. And HELLO, GOODBYE, AND EVERYTHING IN BETWEEN is the night before college, which is, of course, such a hinge moment. You’re literally entering a different life from everything you’ve known. And then WINDFALL, of course, is winning the lottery. Which, I’m not sure anything captures that quite so well.

ENNI: Before we talk about WINDFALL too explicitly, do you want to give the little pitch for it?

SMITH: It’s basically the story of a girl named Alice, who has been in love with her best friend Teddy for years. And on his eighteenth birthday, sort of as a joke, she buys a lottery ticket. And he ends up winning one-hundred-and-forty million dollars which, of course, changes everything. And they’d kind of been on the brink of something happening the night before. And then they wake up, and everything’s different.

And so, it follows what happens from there. It’s always interesting to explore the aftermath of these kinds of earthshaking moments.

ENNI: That’s what I want to get at, and I totally bugged you with this question when you were at your event in L.A. with Lauren Graham. And so, I’ve thought about it since. I need to ask this in a different way. But I love that, because this is something I think about a lot - and I think you clearly have an interest in this stuff - but I’d love to hear from you, how you differentiate serendipity from luck. Because, as I expressed to you before, I personally have a strange relationship with the word luck, because it’s used so often to discount effort and skill and…

SMITH: Accomplishment.

ENNI: Totally. And I think serendipity is this other thing. And you kind of dance with both of them.

SMITH: Yeah, I’ve thought about that question a lot since you asked it. It was a really good question, and it still is. And I’m just as guilty as anybody of kind of chalking things up to luck often times. I think I probably used that word ten times in this interview, talking about my career path. It’s hard because, yes, there are things in life that happen because of will. And there are things that happen because of outside circumstances. Often, in my novels, it’s outside circumstances that play a big role. I think it’s actually a weakness of mine as a writer, that I grow very fond of my characters and I have a hard time writing bad guys, essentially. I like to write about situations that arise from something external happening.

ENNI: Oh, I see what you’re saying. Rather than writing Darth Vader, it’s the lottery.

SMITH: Exactly, something happens in the world, or happens through fate, or through timing, or through misconnection. And these things then set other things in motion. So, it feels very much when I’m writing - especially in a book like WINDFALL - about luck, which is a huge topic of discussion in that book. Is the world a random place? Or is luck a factor? If something bad happens to you, or if something good happens, are you going to automatically [be] waiting for the other shoe to drop? These are questions that Alice wrestles with quite a lot in the book, because she’s somebody who’s had something really terrible happen to her in her past. And she can’t believe that that would be luck, or fate, or…? That has to be randomness, because how can she believe that this was meant to happen?

Whereas, the other characters have slightly different views on that. I don’t know that there’s an easy way to sum up answer to your question. I do think about that a lot, and I haven’t quite come to any conclusions. But I kind of have to split it in terms of internal motivations, and external events happening. And whether you’re pin-balling off the world, or you’re internally making decisions and working hard doing things. It’s kind of an inner volition, I guess, versus external circumstances.

ENNI: I really love this concept of you dealing with people who are constantly wondering like, “If this small thing hadn’t happened…?” The “what-if” questions feel so particularly poignant for a teenager, right? Because it’s the first time. I remember starting to get those letters from colleges. It was the first time where I had whole doors to potential futures just shut. Through nothing that I could have had any control over. And it was really wrenching.

SMITH: I think I say something in the book similar [to that]. They are talking about choosing colleges, and they say, “If you choose one thing, your life goes one direction. If you choose the next one, it goes in another.” And that is [it] in every possible way. If you think back, if you’d gone to a different college, you would have had a whole set of different friends. You might have had a different boyfriend, you might have had a different girlfriend. Anything could have been different, and I’ve always been obsessed with that kind of Sliding Doors feel to things.

So, it’s totally fascinating to me to explore. And I come back to that theme, in various ways, because I’m endlessly fascinated in my own life. I believe in stuff happening for a reason. I once was in a crazy situation, I was in a massive earthquake in New Zealand with my sister. And there were very distinct things [that happened]. We were thinking of going into a cathedral, and then we decided to go to lunch. And if we hadn’t done this… the cathedral collapsed. At lunch, we were going to sit inside, and then we decided to sit outside, at the last minute, because we saw that there were heat lamps. And if we’d sat inside… the roof of the restaurant collapsed.

There were all of these kinds of moments where you see - that’s obviously a very intense example of it, it was life and death, literally - but you see if you go left this happens. If you go right, this happens. And it’s this weird “choose your own adventure” thing.  And I am fascinated by that because there are so many iterations of that in story, and in life, and in circumstance. And I never tire of exploring that sort of theme.

ENNI: I’m interested in how that works with you being an optimist? I’m with you on the optimist thing, and then when you start talking about fate – I also believe that things happen for a reason. But I think that the reason is that we make narrative sense of our own lives. So, the things that happen, happen for a reason, because you choose to take away from it lessons; you make it a positive way.

SMITH: Yes, I actually agree with that. There’s almost a snowball effect. You gain something in every… choose your door. And you carry that with you. I think you can be both an optimist, and a believer in faith. I’ve thought of so many iterations of this because in the book, Alice’s cousin Leo - who she lives with because she won the worst lottery possible, her parents died a year apart from each other when she was little - and because of that, she believes the world is a random place. Whereas Leo has never had anything truly, truly bad happen to him. He’s had challenges, and he’s had setbacks, but he’s never had anything truly awful happen. And because of that, he feels like he’s always waiting for something terrible to happen. And then you have Teddy, who wins the lottery, who’s also had a really tough time, in certain ways in life, and he’s like, “Well, this happened, and I’m due something good.”

So, to take these three characters, with very different world views, and to play them off of each other in this extreme situation – literally money falling out of the sky – [it]made me think really hard about all of these questions. I don’t have answers to all of them. And I think maybe that’s why I keep going back to them, because I still don’t have the answers. But, it’s endlessly interesting to me.

ENNI: And here is an impossible to answer question for you! One of the things that has been most interesting throughout all of these conversations, is that some people are energized by exploring similar themes consistently in their work. I certainly love it when I look at an author’s work and I feel like I know what some of the things are that they’re gonna grapple with. I like finding themes throughout people’s work. But then, I’ve had a few writers say that they feel consistently going back to the same things in their work, makes them feel like it stunts them as writers. Where do you land on that?

SMITH: I think that every time I set out to write a book that strays very far from the themes that I’m most fascinated by, my subconscious pops up and somehow they’re there again. And it’s not a bad thing, but sometimes I feel like it almost happens against my will. I’m thinking that this is gonna be about something totally different, and then it turns out it can be both different and have a core to it that asks some of these same big questions. If you’re talking about the big life questions, there’s a finite amount of questions and an infinite amount of stories to try and answer those questions.

ENNI:  Yeah! Good quote, love it. Excellent! Okay, I have to ask you this question, just because I know you’ve answered it a million times. We were talking about a lottery book, people are gonna ask…

SMITH: Have I won the lottery? I have not.

ENNI: Did you secretly win…?

SMITH: You are currently in my apartment right now, so I feel like the answer is probably clear [laughs].

ENNI: [laughing, then in a deadpan voice] We’re in a mansion… there’s a pool. Have you been preoccupied with the idea of a lottery?

SMITH: I had never played the lottery before I won this book…. oh! Slip of the tongue! Before I wrote this book. I’d played scratch-offs in college. I think the first time a friend ever was like, “Here, play scratch-offs.” And I won forty bucks, and I was like, “Ooh, that was easy.” And then I never won again. So, I hadn’t really played. And shortly after I sold the book, I played the numbers from the book in Powerball, and did not win [laughs].

But, I wanted to write a lottery book for a really long time, because I do think it’s one of those moments of great change, and I thought it would be really interesting. I’d been thinking about the lottery so much since I wrote this. First of all, I did a lot of research into young lottery winners, and I think the more you read about them, the more you actually don’t want to win the lottery.

In the book, Teddy offers Alice half of the money because she bought him the ticket. And it’s not too much of a spoiler - because it’s early on - she says she doesn’t want it, because her life has already changed in a major way once. And I think for a lot of readers, that’s hard to understand. For me, it was very easy to understand. I think there’s gradations of winning the lottery, and it would be nice to have some extra money, but that kind of massive fortune really throws a wrench in your life. I think some people use it to be a force for good… certainly. But, a lot of people, it actually clobbers them.

It’s been interesting to think about. One of the huge bonuses of writing this book has been getting to talk to teens, especially, and everybody about what they would do. And it cracks me up, because people know what they would do down to the dollar. Some people would be like, “Yup, I would spend an eighth of it on this, and I would spend an eighth of it on that.” They know exactly… and they’re like, “I would first pay off this. And I would put it in this account. And then I would put this in this account.”

But talking to teens, especially, they are so generous and big-hearted. Honestly, at this rocky moment of the world, and the country, it has restored a lot of faith for me. Because I was giving away galleys a few months ago, and I just threw out the question, not even thinking about what I would get back, and I said on Twitter, “To enter, just tell me what you would do if you won the lottery.” And the answers were unbelievably wonderful. They all wanted to help their parents, because they had helped them so much. They wanted to build libraries, and give to charity, and start foundations, and save animals. It was so heartening to read that. It made me wish that more young people won, and it made me wish that more of the types of people who follow me on Twitter - which is to say, nice, big-hearted, bookish people – won.

It’s a really lovely thing to think about all of the good you could do. And there’s a big theme in the book that has to do with charity, and volunteering, and random acts of kindness. Those are things that have always been important to me. And it was really fun to write about them, and to hear what other people do - whether you have a jackpot or not - ways to put goodness out into the world. So, that’s been a really wonderful side-effect of this book.

ENNI: That’s so great. What a cool way to fill your Twitter feed with that awesome stuff.

SMITH: I know, it was really nice.

ENNI: Do you want to do advice as one last little thing?

SMITH: Yeah, sure!

ENNI: I’d love to hear advice as a writer and as an editor.

SMITH: I know this has been said many, many times but, read, read, read. Part of the reason why editing was so helpful to me as a writer is because that was my job. And the more you read, the more you get a sense of rhythm, get a sense of what you look for in a narrative. What keeps you turning the pages, what clicks for you. And what I was talking about before is that nothing is a failure, honestly. And I’m not saying that in a pithy way. I genuinely believe that it all counts, and it all builds into the next thing.

So, don’t be afraid of failure. I often meet writers who can’t get past the first paragraph, or the first page, because they’re so worried about it being perfect before they can move on. Don’t worry about being perfect. A first draft is a celebration of all that can go wrong on the page. Just do it. Just write it. And if that’s not your book, the next one might be the one that hits. But, you will have learned so much from writing that one, that the next one will maybe be the one.

ENNI: It’s like an iceberg. I think that’s a useful way to think about even a particular book, but certainly a whole career. It’s like, this is the whole Instagram thing, or social media thing, right? Don’t compare what’s over the surface…

SMITH: Comparison is the thief of joy. Do not compare.  It’s hard not to in this world, but you’re right. You won’t see all that goes into it, that’s below the surface of the water. You only see the shiny top of it all.

ENNI: You don’t see the four-hundred-thousand words, and the deleted documents.

SMITH: And you don’t see the failed manuscripts in the drawer. And you don’t see the book that you abandoned at one-hundred pages because it just wasn’t working, which took you one-hundred pages to figure it out. It happens a lot. It happens to me. It happens to every writer I know. So just write boldly, write bravely, write because you love it, because there’s no other real reason to do it. That’s the core of it.

ENNI: Yay! What wonderful advice! Thank you so much Jen.

SMITH: Thank you, again. Happy reading everybody!

[background music]

Thank you so much to Jen. Follow her on Twitter @jenESmith, and follow me @sarahenni, and the show @firstdraftpod. You can find the show on Facebook and Instagram as well, but for show notes with links everything Jen and I talked about, as well as my favorite quotes from this and every episode and the link to sign up for the First Draft newsletter, check out

My magical intern, Carter Elwood and I, are updating the website, by-the-by. So, if you have any suggestions, drop me a line. In July, I have two events in the Los Angeles area. On July 11th, I will be celebrating the release of Julie Buxbaum’s newest, WHAT TO SAY NEXT [listen to her First Draft interview here] at the Barnes & Noble at the Grove. Julie is amazing, and I’m so excited to be MC’ing her launch event. Also, that book has the cutest dang cover, so do yourself a favor and check it out.

Then, the very next day, July 12th, I will be appearing with Ameriie, Nicola Yoon, Cindy Pon, Christine Riccio, Tina Burk, and Andrew Smith, to celebrate the release of BECAUSE YOU LOVE TO HATE ME. The amazing short story collection which features a story written by moi! I just got a final for reals copy of the book, and it is so pretty. It’s out on July 11th, so preorder your copy now! Links, as ever, in the show notes.

If you like what you heard today, please do leave a rating and/or review on iTunes. Every five-star review makes me feel like luck is truly on my side. Thanks so much to Hashbrown for the theme song, and to Collin Keith and Maurene Goo for the logos. Thanks to super intern, Carter Elwood, and to transcriptionist-at-large, Julie Anderson. And, as ever, thanks to you Powerball hopefuls for listening.

[music fades]


SMITH: Although, maybe one of these days I’ll just write a Darth Vader character into one of these books.

ENNI: Ooh! A Jen Smith book with Darth Vader would be really cool!

SMITH: I don’t know if I could get it all the way… I feel like it would be a pretty mellow Darth Vader.

ENNI: Ah! I would love that too.

[both laughing]

[music continues to fade]


Every Tuesday, I speak to storytellers like Veronica Roth, author of Divergent; Linda Holmes, author and host of NPR’s Pop Culture Happy Hour podcast; Jonny Sun, internet superstar, illustrator of Lin-Manuel Miranda’s Gmorning, Gnight! and author and illustrator of Everyone’s an Aliebn When Ur a Aliebn Too;  Michael Dante  DiMartino, co-creator of Avatar: The Last Airbender; John August, screenwriter of Big Fish, Charlie’s Angels, and Charlie and the Chocolate Factory; or Rhett Miller, musician and frontman for The Old 97s. Together, we take deep dives on their careers and creative works.

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