Holly Kowitt on Cutting Good Jokes, P.G. Wodehouse, & the Principal’s Underwear (Which Is Missing!)

We’ve been fans of Holly Kowitt for longer than any of us care to remember. And now, our nine-year-old is a fan. And so it goes. When we heard the title of Holly’s new book, we howled, we roared, we had to have it! The Principle’s Underwear Is Missing! What more do you need in a kids’ book? Since she’s one of the funniest, most creative, and most successful writers we know, we thought we’d pick her brain on books, writing, principals, and yes, underwear.

Photo of Holly Kowitt smiling

Holly Kowitt

The Book Doctors: Why in heaven’s name did you decide to become a writer? And having made that decision, why did you decide to write books for kids?

Holly Kowitt: I first became a writer to get illustration work! My cartoon-like drawing style made me a tough match for most children’s books (this was pre-Wimpy Kid) so I had to create my own projects. Which turned out to be a good thing.

Part of ending up in children’s books was random– my first entry-level job just happened to be at Scholastic. Being there naturally made me focus on kids.

TBD: What were some of your favorite books when you were growing up, and why?

HK: Harriet the Spy was my all-time favorite. The characters were so alive to me—so real and quirky—and, like Harriet, I wanted to be a writer. I also loved Beverly Cleary’s Fifteen, a low-concept, timeless coming-of-age story with the best first line ever: “Today I’m going to meet a boy…”

TBD: What books are you reading currently, and what books have you really enjoyed lately?

HK: Should be reading: Evicted by Matthew Desmond

Secretly reading: I Represent Sean Rosen, a middle grade novel by Jeff Baron.

Recently enjoyed: The Uncommon Reader by Alan Bennett and The Daily Show: An Oral History.

TBD: As an illustrator as well as a writer, how do you get these two parts of your brain to cooperate with each other? What are some of the advantages and disadvantages to wearing both hats simultaneously?

HK: The cartoons give me an extra way to hook reluctant readers, and add a loose, fun energy. Plus, they’re a blast to draw. The disadvantage is sometimes the text gets robbed to let the illustrations shine. It’s hard to cut a good joke, even when you realize it works better as a picture.

TBD: I just did a Google search of your name and the wordunderwear, and I got tons of hits. Did you ever think your life as a kids’ book author would lead you down this dark path?

HK: Ha ha! Children’s Book Rule #8: Use the word “underwear” whenever possible.

Cover of The Principal's Underwear is Missing by Holly Kowitt; two students run under the title

MacMillan

TBD: The Principal’s Underwear Is Missing: That may be the greatest title I’ve ever heard. How did you come up with it? And what was the inspiration for the story? Have you ever had underwear go missing? Have you ever been involved with principal’s underwear?

HK: I tried to invent the most catastrophic scenario possible for my heroines—and I think I found it. My approach to a story is always: what’s the biggest problem I could give this character? No, it’s not torn from my own life!

TBD: How do you capture the voice of the kids so well?

HK: Obvi it’s, like, crazy-hard. Some combination of subway eavesdropping, The Urban Dictionary website, profiles of twelve-year old YouTube stars, Seventeen Magazine, and Shop Jeen on Instagram gets me in the ballpark.

TBD: What was your inspiration for the story?

HK: I got the idea from Jeeves, the P.G. Wodehouse series about a rich, dimwitted young man and his very smart butler. I thought it would be fun to set the story in middle school, where a ditzy, super-popular 8th grader teams up with a 6th grade nobody. The Queen Bee has a habit of getting herself into trouble, and it’s up to her brilliant younger friend to get her out.

TBD: What’s this story about?

HK: Becca, a bookish 6th grader, accidentally zonks the school’s most glamorous 8th grader with a volleyball. To make it up to her, Becca tries to do Selfie a favor. But she accidentally grabs the wrong shopping bag—one containing a very personal item. Even that wouldn’t be so bad, if Selfie didn’t immediately lose it.

It’s the story of a friendship that holds constant surprises. It’s about exploring an off-limits older world, and finding out how it’s better (and worse) than your own. It’s about challenging the unspoken rules of middle school, and doing what’s right. It’s about losing the principal’s underwear.

TBD: We hate to ask you this, but what advice do you have for writers and illustrators?

HK: Billy Crystal’s ex-manager once told him to “leave a tip” with his stand-up act—to go deeper and more personal. After I finish a chapter, I go back and try to squeeze in an extra ten percent to make it funnier, weirder, realer. So my advice is to always give your work that extra push. You won’t be sorry.

Holly Kowitt has written more than fifty books for younger readers, including the Loser List series. She lives in New York City, where she enjoys cycling, flea markets, and West Coast swing dancing. Find her online at kowittbooks.com.

Arielle Eckstut and David Henry Sterry are co-founders of The Book Doctors, a company that has helped countless authors get their books published. They are co-authors of The Essential Guide to Getting Your Book Published: How To Write It, Sell It, and Market It… Successfully (Workman, 2015). They are also book editors, and between them they have authored 25 books, and appeared on National Public Radio, the London Times, and the front cover of the Sunday New York Times Book Review.

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About David Sterry

David Henry Sterry is the author of 16 books, a performer, muckraker, educator, book editor, activist, and book doctor. His first memoir, Chicken, was an international bestseller, and has been translated into 10 languages. “As laconic as Dashiell Hammett, as viscerally hallucinogenic as Hunter S Thompson. Sex, violence, drugs, love, hate, and great writing, what more could you ask for?” – The Irish Times.

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