Interviewed by Calie Herbst
We had the absolute pleasure of chatting with Diary of a Wimpy Kid author Jeff Kinney, and it was every bit as entertaining as you’d imagine.
Jeff opened up about his writing journey, parenting, and what fans can expect from his Hot Mess Tour coming to Milwaukee’s Riverside Theater on Sunday, November 3rd.
Jeff’s humor is as sharp as ever—starting with a joke about who was late to the interview (spoiler: it wasn’t me!).
Don’t forget to grab your tickets here, and listen to the full interview on our podcast, This American Family.
Jeff: Just for the record, Calie was late.
Calie: [Laughs] Oh my goodness, Jeff! Well, thank you so much for joining us today. I’m so excited to talk with you today. My kids think I’m so cool. I’m sure you get that a lot?
Jeff: I really appreciate that. How old are your kids?
Calie: They’re 8, 10, and 13.
Jeff: Wow, that’s such a fun age. I envy you! My kids are 21 and 19 now, so we’re empty nesters.
Calie: Oh man, what’s that like? It must feel strange with all that extra freedom.
Jeff: You know, it actually wasn’t as hard as I thought it would be. Both times the kids left, we were really worried about how it would feel, but we’ve kept busy, and they’re thriving in their own spaces. It’s kind of the perfect setup right now. We still get them back for the holidays, summers, and breaks, so we get to be part of their lives in a different way. It’s actually really nice.
Calie: I love that. Okay, I want to talk about the Hot Mess Tour coming to Milwaukee, but before we get into that, can you take us back to the beginning? How did you get into writing and drawing? What’s your origin story?
Jeff: Yeah, so it all started in college. I had a daily cartoon in my school’s newspaper, and that was a great place to test out my ideas and get better at my craft. After I graduated, I tried to become a newspaper cartoonist, but nobody would take me! Eventually, I came up with the idea for Diary of a Wimpy Kid and worked on it for about 8 or 9 years before I showed it to anyone.
Calie: That’s amazing. I also read that when you started, it wasn’t actually meant to be a kids’ book?
Jeff: Yeah, that’s true. I thought I was writing for the humor section of a bookstore. Back then, the humor section had everything from Seinfeld’s autobiography to Calvin and Hobbes comics, and I thought Wimpy Kid would sit right in there. I imagined the readers would be people like my dad—he’s the one who got me into comics in the first place.
Calie: I love that. So your dad was a big influence on your love of comics?
Jeff: Absolutely. My dad introduced me to Carl Barks, who created Donald Duck and Uncle Scrooge McDuck. Those comics were epic—like these amazing, fantastical stories you’d expect to read in National Geographic. Once I discovered those, nothing else compared.
Calie: That’s so cool. So when the Wimpy Kid series really started taking off, how did that affect your family life? It must have been a big change for you guys.
Jeff: Yeah, it was definitely different. We’ve always had this dual identity. On one hand, we lived a pretty normal life in Plainville, Massachusetts. My kids went to public school, we stayed grounded. But on the other hand, we’d get to do these crazy things like visit movie sets, meet presidents, and go to the White House. Just last week, Jason Tatum from the Boston Celtics came to our bookstore, and I interviewed Hillary Clinton in Boston. It’s this weird double life, but it’s a lot of fun.
Calie: You live in a town called Plainville and get to interview Hillary Clinton. That’s kind of amazing! Speaking of Plainville, I read about the bookstore you created. Can you tell us more about that?
Jeff: Yeah, it’s been such a gift. Plainville has about 9,000 people, but we’re able to bring in some of the biggest authors in the world. We’ve had people like Matthew McConaughey, Doris Kearns Goodwin, John Grisham, Rick Riordan, and Dave Pilkey come through. It’s really special for the community because we’re bringing all this culture into our little town, and I often get to interview these authors on stage, which is an honor.
Calie: That’s incredible. I love how community-focused that is. So, I’ve got to ask—how do you come up with all your ideas for Wimpy Kid? Did you draw inspiration from your own kids when they were younger?
Jeff: Not really, actually. Most of my ideas come from my own childhood and perspective. My kids were different—they were athletes and played a lot of basketball, which was the center of their lives. So, I mainly use my imagination and reflect on my own experiences growing up.
Calie: That’s so interesting. Do you have a routine or process to get into that creative space?
Jeff: Yeah, I actually use something called systematic inventive thinking. It’s a way of being creative in a structured, almost scientific way. It helps me treat creativity like work—if you put in the time, you’ll get results. I don’t just wait around for inspiration to strike. I dig in and make it happen.
Calie: So, are you a morning writer or a night owl?
Jeff: I’m neither! I kind of fit in the middle. I’ll usually start around 9 a.m. and if I’m deep in a project, I’ll work until 1 a.m. sometimes. But I need those long stretches to really dive into it.
Calie: Wow, that’s some serious dedication! Okay, let’s talk about the Hot Mess Tour. What can people expect when they show up?
Jeff: So, the idea is that I’m trying to get out of the writing business and into the restaurant business. [Laughs] The show is about opening a restaurant, and we’ll bring family members on stage to act as waitstaff and go through some challenges. There’s a bit of drama, some comedy, and a lot of audience participation. Last year, we did the No Brainer Tour, which was a game show format, and before that, we had a full rock concert. So, this year’s show is different, and it’s going to be a lot of fun—though I have to do some acting, and I’m a terrible actor!
Calie: [Laughing] I love it! It sounds like a blast. But you don’t have to do these tours at this point, right? So what keeps you going?
Jeff: I think there’s a huge opportunity to stand out. A lot of authors will just do a reading or a Q&A, but I want to give the audience something different, something entertaining. Plus, it’s a great way to celebrate the release of the book after being stuck at my desk all summer. It’s like a reward for all that hard work.
Calie: Alright, we had a few reader questions come in, and one that stood out was: “What if my kid only reads Diary of a Wimpy Kid and won’t move on to more serious books?”
Jeff: I think kids need to meet books at their level. There’s a big gap between picture books and chapter books, and I think graphic novels and books like Wimpy Kid help bridge that. These kinds of books keep kids reading, and eventually, they’ll find new challenges.
Calie: Another reader wanted to know if you’d ever write something more advanced for kids who grew up with Wimpy Kid.
Jeff: I’ve thought about it! I’m not sure what that would look like yet, but if there’s a need, I’d be open to it. I have an idea for a new project that’s different, so we’ll see where that goes!
Calie: You’ve been a part of so many kids’ reading journeys. But we have to ask, how do you think technology and screens are affecting kids’ reading habits today?
Jeff: Oh, that’s the million-dollar question! There’s no one answer to it. We live in an attention economy where screens are competing for everyone’s time, including kids. But as authors, it’s our job to grab a share of that attention by writing good stories and creating engaging content. We have to make reading as compelling as screens—and that’s a challenge, but one I’m always up for.
Calie: So what’s next for you? You’ve got the Hot Mess Tour, but what’s on the horizon after that?
Jeff: I’m working on a screenplay right now for a Diary of a Wimpy Kid project with Disney+, and we’ve got several films lined up. I really enjoy writing screenplays, so that’s been fun. I’ve also been toying with the idea of doing a book of Wimpy Kid comics—something a little different but still related to the series.
Calie: One last question: If you could give just one piece of parenting advice, what would it be?
Jeff: Hmm, I’d say take a breath and appreciate the privilege of having kids or a family of any kind. Parenting is a long game, and my wife and I try to think of it in two phases—parenting young kids and then parenting them as adults. We hope the work we’re doing now sets a good foundation for the future.
Calie: Thank you so much, Jeff! We’re so excited to see you in Milwaukee on November 3rd at the Riverside Theater.
Jeff: Thanks, Calie! I really appreciate it. See you then!
Don’t miss Jeff Kinney’s Hot Mess Tour at the Riverside Theater in Milwaukee on Sunday, November 3rd! Grab your tickets here and listen to the full interview on our podcast, This American Family.
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Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.