Chad Capellman had the opportunity to talk with world famous author Jeff Kinney, whose 16th book in his Diary of a Wimpy Kid series, a sports-themed book called Big Shot comes out on October 26. Jeff talked about how he figured out how to put together a sports-themed book, the surreal nature of many parts of his life, including the jump between writing in isolation to encountering fans around the world, seeing his books come to life in live-action and soon in 3D animated Disney, the responsibility he carries after once being named one of Time Magazine’s 100 most influential people, his thoughts on the current state of the publishing industry and how he fits in it. Jeff also talked about his perseverance, how he was guided to his target audience and the importance of perfecting your craft in an age of instant, connected feedback.

Podcast Highlights

2:10 – About his 16th Diary of a Wimpy Kid book, Big Shot, and how his love of sports influenced it:For years, I’ve been trying to figure out how to write a sports book. But I couldn’t crack it because I thought if I have an image of a ball on the front of a book, That’s going to turn off everybody who’s not in into that particular sport. So if I have a soccer ball, non-soccer fans would not want to read it, et cetera, et cetera. And finally, I realized that I just need to write a book about sports in general because everybody’s had some sort of sports experience and most of us weren’t the star athlete. So I put a bunch of balls on the cover. And Greg is sitting in a hoop and he’s spinning a soccer ball in his hand. He’s also got a hockey stick and an ice skate on. So I hope that the message to kids is “this is a book about sports and that everybody will find something funny in the story.” “

3:29 – On the connections between the University of Maryland’s basketball resurgence when he was a student there, his comic strip Igdoof, and the creation and promotion of Big Shot: “It was really fun when we were at Maryland together because Maryland just seemed to crack the code on basketball. It feels to me like that’s when they started to get really good. I felt like that’s what really tied me to Maryland, which was really fun because I had to transfer from Villanova. I always felt like a transfer student, but basketball was something I could own. And we were in the ACC at that time and we were playing against these legendary teams in North Carolina, Duke, and what was really special about that era was that kids were staying in school, sometimes ’til their senior year, really good players. So you had a team like North Carolina who had Eric Montross and George Lynch, and then also Jerry Stackhouse, and Rasheed Wallace. And so it was really cool to play against those teams back then.” 

It’s funny, actually that ties into this moment. I drew a picture of Igdoof who was my short, three-haired character, soaring above a bunch of kids who are looking up at him. He was soaring about to dunk the ball, the Michael Jordan dunking pose, that famous poster. And now Greg Heffley, who really sprang from Igdoof, I just drew that same image the other day with Greg soaring above his teammates getting ready to dunk the ball. And so there’s a pretty direct line between the two.”

6:14 – On writing a sports focused book for those who aren’t good at sports: “What I’m trying to do in this book is to write about all those things that happen in sports. Especially to the kids who aren’t so good there are humiliations and degradation that we don’t really talk about, or that kids wouldn’t really have a label for. It’s the coaches coaching the players on the floor, but the players on the floor are doing poorly. So the coach yells at the bench players who obviously don’t have anything to do with what’s going on the court. And then Greg is like, I tried to look like I was ashamed because I think that’s what he wanted. I’m trying to write about the real feelings and real experiences that kids have, especially the bench riders.”

7:26 – On the impact of once being named one of Time Magazine’s 100 most influential people: “It was funny when I got a call from Time Magazine. I got this message and they said, Hey, congratulations, you were picked for this honor. And I literally thought it was a joke. And I thought somebody was pranking me. So I had to trace the number back. And I was shocked when I found out that the call was coming not from inside the house or from Time Magazine’s offices. That was really super weird because I don’t even think my third book was even out yet. And, the series was doing well, but it was not a cultural phenomenon or anything. So it was weird, and it felt unearned. But I have kept it in my mind over these years, is that I do have a privilege of, because I have this kind of built-in audience and a responsibility to that audience to entertain them and sometimes inform them. “

9:22 – On how old he was when he decided you wanted to be a writer and what motivated him to become one? (h/t Mateo and Liam):  “It was in college that I got a comic in the newspaper in the Diamondback. Prior to that, I actually got a comic in the Villanovan, Igdoof also, but I only went there for one year. And I really decided that I was going to be a newspaper cartoonist, and I tried after college, I tried for about three years. Didn’t get my work accepted by anybody. I just didn’t have the artistic chops to qualify for the comics page. And so I went about it a different way. I really wanted to get published. And I had this idea for Diary of a Wimpy Kid, and then I worked on it for eight years. So that’s the long answer to your short question.”

10:16 – On pivoting to focus on a different target audience: “In all of the years I was working on Diary of a Wimpy Kid I was writing for adults. Back then we had some great cartoons in the paper like Calvin and Hobbes and Bloom County, some really smart stuff, The Far Side. And I always saw those things as being aimed at adults because adults read newspapers, mostly. And so in writing Diary of a Wimpy Kid that was the frame of reference that I had, which is that adults read comics. So I was trying to write something that was aimed at the nostalgic adults, like the way The Wonder Years is aimed at adults who are revisiting their childhoods. So that’s how I wrote it. And then when my publisher took it in house, they decided that I had actually written a children’s series and said that’s how I became a children’s author, really on accident.”

11:27 – On what made him decide to write in the style he does and his approach to the illustrations. (h/t Christian): “The style I’m trying to write authentically as a kid. I’m not sure I always achieve it. But that’s the goal. Like whenever somebody writes a review and says, “You can’t detect the adult behind the kid,” that’s definitely what I’m going for. And then my artistic style, Igdoof was my comic in college and the style was a little bit more elevated, a little bit more detailed than Diary of a Wimpy Kid, but when I started to draw Diary of a Wimpy Kid, I decided to create this kind of low style or this simpler style. And I learned a lot about cartooning. I learned that cartooning is really the art of simplicity and maximizing your impact with as few lines as possible. So I was trying to write and draw in a kid’s style, and in doing that, I made some discoveries about cartooning.”

12:27 –  On what his favorite book is or was as a kid. (h/t Liam and Dominic): “I really liked a book called Tales of a Fourth Grade, Nothing by Judy Blume. I liked just about everything by Judy Blume and eventually I discovered fantasy so I really liked the Hobbit. And then there was a series called the Xanth Series, and that was like fantasy, but also really funny. That was, I think my favorite series growing up.”

12:59 – On how much he thinks about those books during his process now: “I think that probably Greg Heffley wouldn’t exist, if not for Peter Hatcher, who was the protagonist in Tales of a Fourth Grade Nothing, so I wouldn’t say I actively think about it, but that character who was not a special kid or not a heroic kid, I think he gave me permission to write about a flawed character. Holden Caulfield actually is another character who’s not really a hero and not really an antihero either. I don’t think about the Hobbit very much when I’m writing a Diary of a Wimpy Kid, but I did do a book called Rowley Jefferson’s Awesome Friendly Adventure and in that one, I definitely was drawing on my fantasy books that I read growing up.”

13:51 – On how long it takes him to write one of these books. (h/t Sebastian) And how the process has it evolved: “It takes me about seven months end-to-end to write a Diary of a Wimpy Kid book. And then the last three months, maybe the last four months are like super intense. Really, and truly 12 to 16 hours at my desk a day. And that’s brutal. So if I was writing at a more reasonable pace it, and I was good about managing my time, I think a book would take about a year.” 

14:24 – On how he gets ideas for his books (h/t Elijah), and how much of it is based on his real life (h/t Sebastian and Dominic): “Great questions. The way that I get my ideas for my books is, at the top level, that idea of, okay, this book’s about a road trip or this one’s about the family going away on an island adventure, that just usually comes out of my own experiences. In the early days, the first five books a lot less so these days. There’s a lot more invention these days and in the first book, there was a lot more recall. And the way I get my ideas in a micro sort of way is I use this process called systematic inventive thinking that helps me to formalize the creative process.”

15:14 – On the process he follows and how he stays motivated (h/t Christian): “I think that my books are a little bit more like a newspaper comic which has a longer lifespan. There’s something about cartoon characters, where we want them to live and live. We want them to be reliable. Imagine if Donald Duck had only existed for a five-year span, it would be really different. Calvin and Hobbes, we got a little bit of that because I don’t know how many years he worked on the strip, let’s just call it 10 for sake of argument. That was actually a very unusual situation where a cartoon character existed and then stopped existing in a way. At least in, in terms of new material. And I think that one of the things that keeps me motivated is that I know that a lot of cartoonists who did their thing for a while, did it for decades, so I’m not even into my second decade right now. Charles Schultz ended up at 50 years.”

16:15 – On what inspired the “cheese touch” (h/t Christian): “The cheese touch is this thing, it’s like cooties and it is an imaginary thing that’s passed from one person to the next. There’s a piece of old cheese on Greg’s playground, under the basketball hoop. And somebody touches the cheese it starts the cheese touch, and then it becomes a whole thing. The inspiration was that there was a basketball court at my church and right under it appeared one day a piece of cheese and the kids who went to the church school, there was some sort of episode there, where I think a kid was made to eat the cheese. That’s what gave me the idea.”

17:10 – On the origin and impact of Poptropica (h/t Christian): “I now no longer work for Poptropica, but it’s a website that I started. And in those early days it was incredible. We had hundreds of millions of subscribers from all over the world. And it was really cool. We told stories in the form of island experiences. So one might be a mystery island and another might be a vampire island. And it was such a privilege to write this stuff and have kids get exposed to Greek mythology for the first time or the Chicago World’s Fair for the first time. And so mobile came in, and once kids started playing Angry Birds and things like that, it made things a lot more challenging because we were web based. But it was a great run. That came out the same year that my first Diary of a Wimpy Kid book came out.”

18:14 – On the publishing industry in general and what it needs to be thinking about in 2021 and beyond?: “That’s a great question. Diversity first and foremost. I think that my big takeaway from the past five years of publishing is how underrepresented minorities are. And it’s criminal. A lot of the gatekeepers are white, and so a lot of stories aren’t being told, right? So I’ve seen that growing more and more in a positive direction that people are getting their stories told that might not have five years ago. And some real superstars in literature are making a name for themselves right now. So I think that’s the biggest thing.” 

19:06 – After taking a few years to get his break, what advice he has for others looking to get started: “I think mastering your craft is so important. Like I think that teenagers are growing up in a world that’s very interesting because they can publish content on social media that doesn’t have gatekeepers and the audience’s reaction to the content determines its success. Like we didn’t have anything like that, you and I, growing up. We could put something in the newspaper and then maybe you get a letter to the editor, but nothing that was like instant. But I think what that also does, is it discourages the long game. Somebody who really wants to get good at something, it’s hard to go underground, work on your craft and then pop up when you’re ready. And I think that I think that also creates a big opportunity for people who have the will to get really good at something. But I would just say for anybody who wants to be a writer or a creator to work at it for a really long time. Like right now, I wish I had a new project that I knew was going to take me 10 years to get ready for, because I would know how to go about that. And then I’d know that when I popped up and wanted to share my work, that I would’ve put in the work.”

20:41 – On the surreal nature of working in isolation and then connecting with fans around the world: “It’s really interesting. I write these books in isolation right now I’m sitting in a dark room, where I’ve written a few books. I wrote a few books in a cemetery in Plainville. During COVID, I’d go in there with a blanket and a bag of. Double Stuf or Mega Stuf Oreos, and I write this thing, and then I get to go out in the world like two months later and meet people who have already read the thing. In fact, that’s why at the top of the show, I was surprised that you’ve read it because it feels like there’s this kind of moment where it’s unleashed on the world. And we’re not quite at that moment yet. So it’s really cool. It’s weird. It’s humbling. Especially when I go to some far corner of the world, like Australia or Brazil or someplace in China or something like that, and the kids have read this thing I worked on in my car. It’s as cool as you could imagine it, but it’s really hard to wrap your mind around it as well.”

21:57 – On what his life is like within the publishing world:“Yeah, it’s interesting. And you’re going to want to play the world’s smallest violin for me here, but if I were to go to a comics convention — and I’ve been to a few — I don’t fit. I’m not a newspaper cartoonist. I’m not a comic book author. I’m not a letterer. And my work isn’t really considered to be real comics. And then if I go over to a writing convention, it’s the opposite, right? I’m not really considered to be a real writer because I do these kind of cartoon books. So I don’t feel like there is a perfect fit for me. And that’s actually fine. I used to chase that a little, chase that validation and I don’t anymore. And I sort of flipped the script a little bit, because now I’m a bookstore owner. So instead of going to all these conventions and these places where I’d meet other authors that way, now the authors are coming through the bookstore. And in there, I’m in my comfort zone because I feel like that’s a better hat for me to wear than to try to fit into these other categories.”

23:11 – On what the process was like for creating a bookstore: “It’s been interesting indeed. I live in this little town called Plainville and we had at the center of the town, this old decrepit building. It was a general store from the 1800s and we took it down and then built this bookstore. And we did it. So that we’d have kind of a feeling of pride of place. And there were lots of different ways we could go. Are we going to be at children’s-only store? Are we going to really feature Diary of a Wimpy Kid? Are we not? How many people are we going to hire, et cetera, et cetera. And it’s been really interesting. It’s been a wild ride. Really the biggest authors in the world. We’d get big politicians. We had Ruby Bridges this week, Henry Winkler. We had Chelsea Clinton. We’ve had Hillary Clinton, Rick Riordan and Dav Pilkey, John Grisham, Neil Patrick Harris, just about everybody up and down the ladder. So it keeps life interesting here in Plainville.”

“An Unlikely Story is the name of the bookstore. And it felt like a good fit because we planted this thing in a place that didn’t really need it or want it. We put a bookstore in the middle of a downtown that really needs an update. And it was a lot like Field of Dreams. It’s if you build it, they will come. And luckily people are coming.”

25:18 – On his approach to writing about COVID (h/t Dominic): “I did, there’s a book I did, which was my last one called Diary of a Wimpy Kid, The Deep End. And it starts off with Greg saying, basically he loves his family and all, but he doesn’t need to be stuck inside with them 24 hours a day, seven days a week. And he concludes by saying that what they need is a vacation from each other. And I was acknowledging the pandemic, like anybody who read that would know what I was talking about, but I also wanted to future-proof the book, so that some kid 10 years from now who read the book, wouldn’t be thinking about the pandemic. So that’s the way I tried to thread the needle, but I don’t think that I’ll write about the pandemic exclusively. Partially because a lot of terrible stuff has happened during the pandemic and death and dying are no laughing matters. But also because I think that the legitimate pandemic jokes are played out. It’s been done. How many jokes can you make about Zoom calls and, wearing your yoga pants all day and things like that. So I didn’t want to be derivative or repetitive.”

26:59 – Does he have any new book series planned? (h/t Mateo): “I do have a book series called Rowley Jefferson’s Awesome Friendly Adventure. And I have three books in that series and I don’t know if I’ll continue it. I like it a lot. I want to make sure there’s an appetite for it. And I think there is. But I don’t have any new book series planned.”

26:49 – On what it’s like working with Disney: “That’s a lot of fun. So we have an animated film coming out. It’s just Diary of Wimpy Kid One, basically. And it was really cool to take the book as it is on the page and bring it into that 3D animated world. We did four features Diary of a Wimpy Kid movies with Fox where we jumped right to live action. So that was a different medium and a different play. It had its advantages. But we’re now trying to do something that’s a little bit more faithful to the look and tone of the series.”

27:27 – On what the technology aspects of the process is like: “It’s really cool. It goes from this kind of animatic, which is like a 2D really rough drawing situation to this kind of loose wireframe situation where the characters are moving in space and then it just jumps to this third level, which is this incredibly lush, animated world. And I’m a producer and it’s been really fun to sit in that seat where we’re coaching the actors through their lines. I can’t name the names of the actors, but we’ve had some A-level talent, it’s wild to be running through the airport with my earbuds on while I’m watching some famous actor record their lines. And then I’ll like text something to the director and then, 10 seconds later, the actor’s reading their lines differently based on my feedback. For a person who lives in Plainville, Massachusetts is pretty heady.”

28:31 – On what’s the challenges of getting his original books into this format? I think tone is actually a challenge because Greg Heffley is really a complicated character, right? He’s messy. He’s imperfect. He makes mistakes. He’s not the best friend. Sometimes he’s a bit of a jerk, and that’s where I get a lot of my humor from, is that you laugh at Greg because he’s a little full of himself. And one day life is going to beat him down a bit. And then you take this kind of content and you put it into the Disney world and it’s interesting because Disney has a different aesthetic. They have a family audience. So you sort of have to smooth out the rough edges a little bit and show a lot of growth in the character. In my books, I can’t show growth, right? Because these are cartoon characters who can’t really change. They’re like sitcom characters. And then in the feature world, whether it’s Disney or somebody else, you have to show growth and momentum and positive intent in order to tell a good story.”

30:30 – On how he approaches writing about stress and mental challenges in youth sports: “We ran into some issues because I had some jokes that worked well. And then when the stuff was going on with Simone Biles and in the challenges she was having and she was articulating so well, I was like, oh gosh, I can’t do this. I can’t do this joke about falling off the balance beam anymore. The pressure that Greg would feel in the Olympics because I don’t want it to read as a response to that kind of situation. I think that Greg, the diary format, it allows him to speak directly to the audience in a way that would be a little bit harder if I spoke about him in the third person, I guess you could say. So I think there’s this sort of directness and also there’s an eagerness from Greg for the reader to be on his side. So I think Greg has always trying to cajole and convince which I think makes it more likely that he’s going to be forthright.” 

31:32 – On being the worst swimmer on his high school team after Chad shared he was on his: “I was also the worst swimmer on my high school swim team, mostly because I didn’t show up for practice. And then at the end, they wouldn’t give me my varsity letter.”

31:56 – Does he plan to end any of the series with a bang? (h/t Christian): “Great question. I’m well aware that I’m heading towards book 20. And although that, won’t mean much to the kids who are reading the series and cruising along, it feels like a big milestone to me because that feels like a moment that I could go forward or stop. So I don’t know if I would end with a big bang. I’ve learned enough from big bang endings, like Brett Favre and Mike Tyson and whoever you want to name retiring, that sometimes the retirement doesn’t last that long. So I think that I would definitely give myself an out, or a way back in”