How To Write a Bestseller

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S1: Hey, how to listeners? Before we get to this week’s episode, I want to let you know that starting today, how to we’ll be on our summer schedule, which means we’ll be appearing every other week. That does not mean, however, we are slowing down inside how TOS headquarters. We are still trying to solve your problems as fast as we can. So if you have a question or something we can help with. Send it to us at how to at Slate dot com and look for us every other week in your feed.

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S2: If you are in your 40s like I am and you’re a woman, you have earned a head full of stories in which someone better than you out there is doing this. Why should you even do this when there’s dinner to be made, when you already have a good job, when your children need you to write a book right now? There are so many forces that are at work that the first thing I want to say is congratulations for overcoming all of the fear, because I already know that you should be writing a book.

S3: Welcome to How to. I’m Charles Doing. If you remember back at the beginning of the pandemic, remember back then, there were all these articles about how we should make the most of this time at home. We should get in shape and learn to cook Cerrado and take up the guitar. And while you’re at it, why not write the great American novel? Well, we’ve got a lot of questions from listeners asking some version of that last one about writing a book, including this woman.

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S4: My name is Lauren and I live in the mountains in Colorado. I have two children and I work as a translator. I translate from Spanish and English.

S3: Lauren has always loved language. Her mom was a librarian and growing up, Lauren would hide in the stacks all day and read thinking about the books she was going to write someday. Her job now is translating legal documents. And so she’s still reading and writing all the time, but not the way she dreamt of as a kid.

S4: Currently, I write all day long, but I don’t write my own words. And so that’s kind of boring. And so I like the idea of creating something. You know, I don’t want to write a memoir. I’m not looking for that. And that is all I currently do is journal about myself. And I don’t like to reread it. I’m looking for how to take the jump from what’s right in front of me to, you know, a new idea and creating a totally different story.

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S1: Lauren thinks part of her problem is a lack of confidence that goes back to college.

S4: I was an English major, and at some point you have to apply for creative writing. And so I put that off and put that off. And then the day came where you had to turn something in and I turned in something that I wrote in high school.

S1: Lauren was rejected by the creative writing program that was more than two decades ago, but it’s still kind of answer. And since then, she’s tried writing a couple of short stories, but nothing ever seems to click. And so she just goes back to journaling. Why do you think you’re having trouble starting a novel?

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S4: Well, I’m not sure how to take an idea and work through it over time. I feel like I, I just kind of self criticize myself back to nothing and say, OK, that that was bad, you know, negative, negative, negative. And then and then I don’t do anything for a year or something.

S1: Lauren has this one idea that she really likes. It’s a novel that’s loosely based on her family history.

S4: My own grandfather found out when he was 75 that he had been adopted and it kind of rocked our whole family. His mother had died in childbirth. His father had given him up to a Norwegian orphanage in Chicago and also given up his six siblings. And my grandfather was adopted and the family that adopted him, their child had been sitting by an open window and was hit by a stray bullet in Chicago and killed him. And that adopted father went to the Norwegian orphanage and took home my grandfather and gave him to his wife, who was grieving and said, Here’s your new child.

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S3: Whoa. Yeah, I would definitely read that book. Wouldn’t you read that book, too? On today’s episode, we’re going to help Lauren start that book with the help of Taffy Britt Esther. ACNC, whose debut novel, Fleischman Is In Trouble, was one of the biggest books last year. TAFE has been testing tips for first time writers. So keep reading or listening.

S5: You know, just don’t put the book. Stick around.

S1: So to start, could you just introduce yourself?

S2: Sure. I’m happy, Brett Esser, actor. I worked full time at the New York Times magazine, and I am also a novelist. I am the author of Fleischman is in Trouble, which is now in paperback.

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S1: Daffy didn’t intend to become a novelist. She didn’t even tend to become a journalist. She started out at film school.

S2: And I have the same story as Lauren. I showed my professors a couple of things. My like in the 90s, my male professors who were like, this isn’t good. And right after college, I got a job in journalism because that was a thriving industry. Let us just have a laugh. And eventually I became someone who who wrote good stories. And the story I told myself as a result of that was, oh, it must be that you’re not a good creative writer. It must be that you’re a good journalist. And so you should be very happy for the success you seem to be having and go with it.

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S3: Toughies become particularly well-known for celebrity profiles. Like when she revealed the inner workings of Gwyneth Paltrow is poop empire or when indoor skydiving with Melissa McCarthy. But despite her success, things didn’t feel right from a creative perspective. And she was wondering what to do next when she had this lunch date.

S2: I went to go meet with a friend of mine who said, listen, I’m getting a divorce. And he had already moved out. The alimony was worked out. The child support was worked out. And he took out his phone and he showed me what it is like for somebody our age to be on dating apps. My mind was blown. I had never seen anything like this. And I knew by then that if I had never seen anything like it, it might be a good story. I left that luncheon on the street. I remember I was on Fifth Avenue, on the street. I called up my GQ editor and I said, I have to do a story about dating apps. And he said to me, you know, you don’t usually sound like a clueless New Jersey housewife in her middle age.

S3: But right now you do. Batarfi couldn’t stop thinking about what she’d seen, your friend’s experience and dating apps. It might not make for a good magazine story, but what about a work of fiction?

S2: And I pulled over literally into a restaurant and I sat down and I had my computer on me, like I always do. And I wrote the first 10 pages of my novel. Toby Fleishman awoke one morning inside the city. He’d lived in all his adult life and which was suddenly somehow now crawling with women who wanted him, not just any women.

S1: Taffy sent those first 10 pages to an editor she knew and he liked them. So she made a deal with herself.

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S2: I said to myself, I’m going to give you six months to write this. You won’t give it one more day than six months, but you have to do it because clearly there’s something in you that needs to be put to rest. And I have to find out if my screenwriting teachers were correct, that I am not a good creative writer. And I wrote that book in six months. I spent a lot of time with the same questions that Lauren has, which is the question of I think every parent who is a practical person and who wants to know that she’s not wasting her time doing this thing that she feels she wants to do. Lauren, is that does that sound right? That does sound right. You spoke about a failure or a perceived failure you had in college where you let your teachers opinions of it determine how to proceed with the rest of your life. And you relegated the thing that you wanted to do, which was be a writer into a hobby. Right. But ultimately, I’m going to say something extremely controversial. Journaling for writers is like a surgeon playing the game operation at home. Like, can I ask you, do you enjoy it while you’re doing it?

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S6: I wouldn’t say yes. What you’re saying is you lost my mind. You sound like you hate it, but I think it’s what people I mean, it’s definitely a tip of like.

S4: Well. Journal, journal, journal. Something will come of it.

S2: This is certainly not a necessary component of developing yourself as a writer. We only have so much time in the day. Your problem is that you’re too good a student, that you let too many other people tell you what you should be doing. But there’s this tiny voice inside of you that is screaming for you to pay attention, and you’re quieting it by journaling and pretending that that will put you on the road to something when really I think what’s going on here is that you’re journaling is a distraction from how scary it is to put something on paper and know that you have this great story. And I’m sure, Charlie, you agree, right? Like that story. It’s fascinating. It’s absolutely in my mind.

S1: So, OK, so let me let me ask this. So, Lauren, what have you is saying? Does that resonate with you?

S4: It does resonate with me. Definitely. And I really liked what she said about about journaling.

S6: I think that you’re right. I took my hand.

S4: And definitely the practicality of of having a life that has got to move on and kind of spending time in my head is doesn’t it does feel like a luxury.

S2: But now, if you were to think about all the time, you’re using journaling. Right. The better question you should be asking after hearing my story is why her and not me?

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S3: Here’s our first rule. It’s really easy to get bogged down to avoid writing because you tell yourself, I don’t know how to do this. But that’s often just a way to distract ourselves from the belief that we don’t deserve to do this. But you know what? You do deserve this. You can write a book. You just need to give yourself permission to start. When we come back, TAFE will tell us how to write your first sentence and then the next one. And then the one after that. Stick around. Hey, listeners, there’s another podcast we think you might enjoy on Ted’s podcast, WorkLife organizational psychologist Adam Grant takes you inside the minds of some of the world’s most unusual professionals to discover the science of making work, not suck on this season of work life. Learn how to procrastinate less and fight burnout, fix broken job interviews and negotiate better and a lot more. Find work life with that imprint where ever you listen to podcasts. We’re back with our budding author, Lauren, and her expert, Taffy Bert Esser, actor, and if you’ve ever thought about writing a book before, you probably know there is a lot of advice out there. I think a writer’s notebook is the best way in the world to immortalize bad ideas.

S7: I like to run and I like to walk in solitude. And I do my meditation and my thinking. So by the time I come to the blank page, I have many, many things to say. The blank page in the mind has to be filled before you can have the courage to face the actual blank page.

S3: That was Stephen King. Joyce Carol Oates and Jonathan Franzen. So, you know, people who know how to write TAPI, in fact, says some of her favorite advice came from Franzen.

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S2: He said that a lot of people think a book is about what happened, but the better version of a book is here’s what happened. Now, let me tell you how. And I thought that was so remarkable because it means that you don’t have to. You don’t have to have some big reveal about action. You have to have a big reveal about character. And the process of writing is very much the process of getting to know your characters. A good tip for that is to have someone in mind is to say, like, OK, the brother is a guy like Brad Pitt and the uncle is a guy like Charles du Hegg. And then you use that to fill in some space and make them who you believe that they that they are.

S1: Here’s the next rule. Draw your characters from people that you already know or that you observe in real life.

S2: Think about when you do it standing in line at CBS. And the story you tell yourself about the guy in front of you. Right. And now think about the ways you hate him. Could you also use those things to make him into something that you love? Because the work of fiction is empathy. The work of fiction is. Here’s a story that makes no sense to me. Here’s a story where everyone seems terrible now, create circumstances in which you understand why everybody would behave that way. So you think of a light plot. How did this happen? What’s the story of the bullet? Like, where did the bullet come from?

S1: Learn so this character, the one who who goes and in their child dies and they they get essentially a replacement baby from the orphanage. If that had to be someone whom you already know, some model that you’re using just to help you fill in the blanks, who are hers to you?

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S4: Oh, my gosh. I have not thought about that in that way. There’s a thousand ways it could go. And I wonder when you’re brainstorming like that when you brainstormed for your own book. How did you narrow down, you know, all of the of the ways that it could go?

S2: The first thing you do, and this is how I write any journalism, is you say what is interesting to me about this. You have to give yourself permission to not be the translation, but the source. Right. You have to be the person who has the idea. But the reason you don’t have that right now is only because a long time ago people said to you, you’re better working with other people’s material instead of writing your own. Someone said that to you when you were impressionable and you took that story and ran with it.

S1: Let me ask you this because because I think everything you’re saying makes a ton of sense to me. But even I as someone who, like, you know, has been writing for fifteen years now, like some mornings I wake up and sometimes I don’t even know where to begin. Like, what do you do with only six months to write a novel? What would you do on those days when you’re like, look, I actually don’t know where the scene is supposed to go. Right. I don’t know yet.

S2: What’s interesting to me, the thing that I would do is I would lock myself in a room and I would say, what is the book that I see myself writing? Like, what is the point that I need to make? The good news for Lauren is that one day she’ll look back and say, thank God for that pandemic, because it gave me something that is better than time. It gave me that lack of excuse. I don’t think Lauren, who has been assiduously journaling and making space for this this whole time, is going to have a problem finding the time. I think she’s going to have a harder time reminding herself over and over why her and not me?

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S4: I do have I do have time right now that that excuse is not there. I think the allowing myself to take the time is difficult. And then the actual appreciating the process and not not criticizing myself so much that I will just stop. It will be hard for me.

S2: Well, let me ask you this. Do you remember do you remember teaching your children how to ride a bike? Yes. Do you remember how you like the way riding a bike works is that it’s really hard to get to the fun part because even if you’re good, you wobble for a second. Yes. The problem with teaching your kids how to ride a bike is convincing them that the wobbly state is a temporary one and that one day this will become a machine that goes of itself. I’m here to tell you that one day your book will become a machine that goes of itself. All you have to do is write the first 30 pages Taffy.

S1: I’m sure you have this moment, Lauren. You probably have this moment. I have it all the time where I, like, sit down and I write something. I spend like 20 or 30 minutes, maybe 40 or an hour writing something. And I look at it. I’m like, Jesus, this is terrible. This is so bad. I’m embarrassed that those words came out of my fingers because, like, I don’t know what the hell I’m talking about. What do you do when what you write is bad luck? You’re a good judge of writing.

S2: Look, I think I know what I can do. But you don’t get to the good sentences if you don’t write the bad ones first. I actually heard this tip recently from Charles French, who is a mystery writer, that the first thing you should do is write the entire story in ten sentences, like think about how innately we know how to tell stories. I think that every writer would be a better writer if they sounded like they do when they talk. And I think sometimes that’s hard because again, Lauren, you’re such a good student. You’re reading legal writing all day. There is no way you don’t equate writing with some kind of formality. What you should be doing is is trying to bring your journaling self into your novel writing self. And you should maybe even start one chapter. Just write one chapter as one of your characters who is journaling.

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S1: Here’s our next rule. Write the bad sentences, tell the story the way you would with a friend. TV says one of her favorite tricks is to write. Here’s the thing. And they just launch into her story the same way she would if she saw someone on the street. And she only had a few minutes to talk to them. Lauren, if you were to say tomorrow, you’re going to sit down and you’re going to write five or ten terrible pages of your novel and you just accept it’s going to be bad. Would you be OK with it?

S2: I think that would be good. A great thing to have is a goal. That’s a word count today because some of your writing is spent thinking, some of your writing is spent pacing, some of your writing spent picking your nose and some of your writing time is spent on Twitter or Facebook or cooking while you’re figuring it out. If you write 500 words four days a week and then on the fifth day, you revise those those two thousand words and then on Monday start over again, in a year you will have finished a book.

S3: Tell me, what do you think about writer’s block? Like, is that something you’ve ever experienced? So glad you ask that.

S2: It’s my favorite question. I don’t believe in writer’s block. I wrote half of my book in the in the Nordstrom ladies room where there’s a couch and the other half with children sitting next to them watching TV with them so that they would have the illusion that I was spending time with them. Like I never asked my my sister, who’s a veterinarian. I never say to her, like, oh, you’re not blocked today, are you, because you have had surgery to do. This is a profession and you have to treat it professionally. But at its heart, writer’s block is the act of thinking about writing instead of doing it. And if you just remember that, you can always know that you could just write the next sentence. It might not be very good, but the one after that, probably Wellby.

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S1: Here’s our next rule. Just keep writing. That’s it. Just keep writing.

S4: But I do wonder. I mean, it sounds like Taffy. When you wrote your 10 pages, you had someone you trusted or someone at least that you knew that you gave it to. And at some point, that part scares me. Of who?

S2: Who am I going to you. No. Now would I trust. Think of it this way. I took a very powerful editor at one of the very few remaining publishing houses, and I said, here I took a dump on these 10 pages. Tell me if I have any talent. I risked a lot doing that. That was my brain trying to obligate me to something or to let it go. What if you said yourself, I’m going to write the first 10 pages without ever looking back? Because I worry that you are somebody who will edit it to death and never get to page eleven because it’s still not perfect.

S1: Taffy, how many of your those original 10 pages that you wrote in that restaurant? How many of them changed versus stayed the same in the final book?

S2: The first 30 pages are intact and everything else changed.

S3: It takes enormous courage to do something like that, to descend a bunch of pages to an editor or to a friend for that matter. But the only way you get better writing is by showing other people your work. Don’t let the fear of not being perfect stop you from writing and sharing a first draft that needs help.

S4: Well, I wonder what you would suggest. Would you suggest that it be someone who is a writer or someone who I trust with my feelings or.

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S2: I’m not sure I would tell you that you should not make it somebody who’s like a member of your family. OK. For the simple reason that in addition to how proud and excited they’ll be, they will also have feelings about this endeavor. And those feelings can often be pure. But undermining. I learned that I can’t let my husband read things until they are published because he can judge a piece of writing. I get too attached to his opinion. So I have a group of people I send my stuff to. And what I think those people are non-professional people that I know like to read like. Are you in a book club? Yes. Who’s your favorite? A lot. You’d have to name that person on the podcast. You should take your. You should take the person that feels really well read and who enthusiastically seems to read more than everyone else and say, would you mind reading these 10 pages?

S4: That’s really great advice. I really like that.

S2: And then you say, like, they’re they’re terrible. I just want to note, you think to not indicate that to that person that they hold your heart in their hands. All feedback is good information, but you have to figure out a way that it only goes in sheer brain and not your heart. And after the ten pages, if someone says this was interesting, you should know what your questions are for that person. And my questions are always, would you keep reading this? What did you remember most about it when you were done?

S1: Here’s our final rule. Find someone to be a trusted reader, not a cheerleader. You want to find the kind of person who would actually want to buy your book. And if they don’t like it, that’s OK. You should just try someone else. Not everyone is gonna like your work. And just because one person doesn’t, that doesn’t necessarily mean it’s bad. You should take feedback seriously. But don’t let it stop you from writing. Lauren, let me ask you why you want to write this novel, why you want to write the story of this guy and his child being killed by a stray bullet and going to the orphanage and getting a replacement baby. Why do you want to write that?

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S4: Well, I think maybe this story speaks to me about something I feel has been handed down in my family. And so I do feel like I can hone in on that. And I’m actually pretty excited to try.

S5: And why do you think it’s important to tell other people about that?

S4: That’s harder for me because it does feel selfish, and I think that will be that will take time for me to really value. But I I do think even if it’s just for me to tell myself this story. That’s the importance of it. That it’s important to me.

S1: What’s your favorite book, Lauren?

S4: My favorite book right now, I think, is of Mice and Men.

S1: There’s a great book. It’s a great book. And when you think about that, I mean, it was kind of selfish of John Steinbeck to say, like, I’ve got this story and it’s a kind of preposterous story. Right. Like, it’s these two ramblers. And one of them is is mentally disabled. And spoiler alert, the mentally disabled one gets killed at the end, like he’s like pulling on the heartstrings. It’s is this audacious kind of selfish thing. I never read it. But I guess I won’t. But are you glad that Steinbeck wrote it?

S4: I am. I mean, I do feel that. I feel. Oh, imagine who I would be if that book hadn’t been written. I mean, that book is important to me. And so, of course, that that is value beyond measure, I think. I think so, too.

S2: I think that I think that first of all, you know, I think about the fact that that that men never ask these questions. Right. Like, I have never had I’ve taught writing a lot and I’ve never seen a man ask me the question. Like what? Like what right do I have to take up the space? Like, why shouldn’t I have this? Why shouldn’t the world know what I’ve been through? This is not a selfish thing that you’re doing. This is a selfless thing that you’re doing. This is a generous thing that you’re doing. And again, this isn’t something that any human being should want to do. So the fact that you’ve been chosen to want to do it means that you have an obligation to do it.

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S1: And I think that’s really well put. I do, too. I would love to read this book.

S2: Lauren, I can’t wait to read this button because you’re going to name characters after both of us. And we’re going to go to your book party and we’re going to laugh about the time where you were journaling.

S3: Thank you to Lauren for reaching out to us and to Taffy Burdette’s or actor for her fantastic advice. Make sure to look for her book. Fleischman is in trouble now out in paperback. And a quick update the last time we checked in with Lauren.

S8: She had started writing her book when Robert lifted the Winchester at the North Avenue hardware store. He found it surprisingly heavy. His arms were scrawny, although most mornings he rolled up the sleeves of his white undershirt and flexed it himself in the mirror. At 13, he didn’t really have any muscles to speak of. With this shotgun in his hands, he felt just like he thought he would. Powerful, larger than life, a man to be reckoned with like the ones in the Chicago papers each day. Watch this. He told his brother and pulled the trigger.

S3: I cannot wait to read this book. Do you have a problem in search of a solution? If so, you should send us a note at how to add slate dot com. Or you can leave us a voicemail at six four six four nine five four zero zero one. We might have you on the show. How TOS executive producer is Derrick John. Rachel Allen is a production assistant in Merritt. Jacob is our engineer. Our theme music is by Hannis Brown. June Thomas is senior managing producer and Alicia Montgomery is executive producer of Slate podcasts. Giebel Roth is Slate’s editorial director of audio. Special thanks to Kevin Bendis.

S1: I’m Charles Du HIG. Thank you for listening.