PHOTO: Gennifer Choldenko, author of award-winning middle-grade novels, photographed smiling warmly in front of a vibrant bookshelf.
Celebrated Author Of Al Capone Does My Shirts And Tales From Alcatraz Series
Gennifer Choldenko reflects on creating authentic characters, exploring childhood memories, and collaborating with bestselling author Katherine Applegate, while sharing insights into historical fiction, hope, and the power of imagination.
Gennifer Choldenko has a gift for finding the extraordinary in the everyday, for crafting worlds that feel both deeply lived-in and startlingly fresh. Her characters, from the inventive Hank Hooperman to the enduring Moose Flanagan, grapple with the challenges and confusions of growing up in ways that resonate across time and circumstance. Whether weaving intricate historical landscapes or conjuring the whimsical and wild, Choldenko builds stories that deftly blend grit with grace, realism with hope. Her voice—at once clear-eyed and compassionate—offers young readers not just escape but connection, understanding, and a sense of possibility.
What stands out most is the emotional honesty in her work. Choldenko’s protagonists often find themselves at crossroads where choices are ambiguous, where doing the “right thing” is entangled with growing pains, familial bonds, and self-discovery. Her stories reject simplistic resolutions, instead embracing the complexity that young readers themselves know all too well. Perhaps this sincerity finds its roots in her own childhood—a creative and playful time spent in Los Angeles, imagining mischievous tales, spinning jokes, and climbing literary heights on the staircase of the Pickwick Bookstore.
With a career spanning nearly every facet of children’s literature—from unforgettable middle-grade fiction like Al Capone Does My Shirts to her collaborative Dogtown series—Choldenko continues to challenge and enchant. Her newest work, The Tenth Mistake of Hank Hooperman, is no exception, a shining example of her ability to blend humour, depth, and humanity into storytelling that lingers long after the final page. Few writers can balance imagination and insight so gracefully, but Choldenko has built a literary legacy that proves it can be done—and done beautifully.
In The Tenth Mistake of Hank Hooperman, how did your childhood memories of your big brother influence Hank’s character?
Hank is a fictional character. But he shares some attributes of my big brother, Grey. Grey is a creative guy who now runs a children’s Shakespeare company. When we were kids, he was always coming up with imaginative games to play. The games and rhymes that are a part of Hank and Boo’s world are not the ones I played with my brother. But when writing the book, I tried to imagine what my brother would have done, if he were in Hank’s situation. Hank and Boo are 8 years apart. My brother and I are 5 ½ years apart. But I was surprised (shocked actually) how much I felt like I remembered what it felt like to be three while writing this book.
What inspired the collaboration with Katherine Applegate on the Dogtown trilogy, and how did your creative processes align?
Our collaboration just kind of happened. It wasn’t premeditated. We lived near each other and had lunch together a few times. After several discussions about authors who collaborated, it popped into my mind to ask if she might be interested in working together on a book. She thinks it was my idea. I think it was her idea as she was the one who kept bringing up the topic of collaboration. Anywho, as Chance would say, it worked out.
The toughest part was coming up with an idea that we both liked enough to pursue. The most surprising part was how close we became while writing the trilogy. (As of yesterday, it is officially a trilogy as we turned in the third Dogtown book to our editor.) Katherine Applegate is one of the kindest human beings I’ve ever encountered.
After concluding the Tales from Alcatraz series with Al Capone Throws Me a Curve, what drew you to explore new narratives like Orphan Eleven?
I love historical fiction. I love reading it and I love writing it. But for me, it’s tricky to find an original historical fiction idea that has real kid appeal.
Your books often feature young protagonists facing significant challenges. How do you balance realism with hope in your storytelling?
I’ve always hated kid’s books that make life look easy. All the protagonist has to do is do the right thing and everything works out. When I was a kid there were many many times when it wasn’t at all clear what the right thing to do was. Even looking back, I am not sure. I write the books I wanted to read when I was eleven.
I don’t try to balance realism with hope. I try to be honest. But I believe that who you are shines through between the lines. And I am a hopeful person.
With a background in illustration from the Rhode Island School of Design, how does your visual arts training influence your writing?
My mother, God bless her, helped me pay for RISD. She died many years ago, but whenever someone asks me this question, I hear her voice.
My career turned out differently than I thought it would. But RISD launched it. My first published book was written for a RISD class taught by the incredible David Macaulay. His words kept me walking down a path that did not seem the least bit promising. He said: “I don’t know about your drawings, Gennifer, but your ideas are incredible. I’ve taught lots of students over the years your imagination is really something.” I will be grateful to Macaulay for those words until my dying day.
You’ve held diverse jobs, from working in a ketchup factory to teaching horseback riding. How have these experiences enriched your character development?
My character development? Okay, that makes me laugh. So many assumptions you’ve made here. That I have character. That it is developed.
Most of the jobs I had taught me one very important lesson. I had better find a different job because I sure as heck didn’t want to spend the rest of my life making blender drinks.
Al Capone Does My Shirts received both Newbery Honor and Carnegie Medal nominations. How did this recognition impact your subsequent writing?
Winning the Newbery Honor and getting nominated for the Carnegie were astonishing, life-altering events. I’m not a star. I’m the kind of person that blends into the background. I go to parties and help out in the kitchen. Writing Al Capone Does My Shirts made me believe anything is possible.
What advice would you offer to aspiring authors striving to find their unique voice in children’s literature?
Read widely. Write from your heart. Be kind to yourself. Exchange pages with people whose opinions you trust. Make your work a little better today than it was yesterday.
