Ilana Long: On Persistence and Flexibility

A stand-up and sketch comedy writer and actor, Ilana Long studied improv and performed at The Second City in Chicago. She first heard about pickleball when her sporty friend confessed that she was addicted to a game that was “like ping-pong but standing on the table.” Shortly after, Long picked up a paddle despite her utter lack of hand-eye coordination. She is the author of the picture book, Ziggy’s Big Idea, and her essays appear in multiple books in the Chicken Soup for the Soul series. Follow her on Instagram.

In this interview, Ilana discusses how her own love for the sport its based on helped inspire her new romance novel, Pickleballers, her advice for other writers, and more.

Name: Ilana Long
Literary agent: Elizabeth Rudnick, The Gillian MacKenzie Agency
Book title: Pickleballers
Publisher: Berkley Books
Release date: November 12, 2024
Genre/category: Romance
Previous titles: Ziggy’s Big Idea (Kar-Ben Publishing, 2014), Various Chicken Soup for the Soul titles.
Elevator pitch: A pickleball romcom where Dodge Ball meets The Hating Game.

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What prompted you to write this book?

The idea to write a sporty romcom arrived by accident in the spring of 2020 when my YA sci-fi manuscript, the novel I wrote about a tragic pandemic, ran into some bad timing. “I think people need a lift right now,” my agent had said. And knowing my background in stand-up and improvisational comedy at Second City in Chicago, she suggested, “Why don’t you write something funny about something you love?”

So, I thought, What do I love? Well. I love love. And I love…

…Maybe some of you have heard of pickleball? It’s like ping-pong, if you got to stand on the table. My own obsession with the sport actually began during the pandemic, when it was the perfect social and athletic way to play outside while standing six feet apart. Pickleball is a cinch to pick up. It’s pulse-pumping fun. And with all the camaraderie, flirting, and banter, pickleball is a hotbed for the courting scene. So that’s how my romance, Pickleballers was born.

How long did it take to go from idea to publication? And did the idea change during the process?

From conception to release, Pickleballers took about three and a half years. When I wrote the first draft, I was teaching high school in Costa Rica. In between my classes and during my planning period, I would push through my grading and prepping. Then I would write like a woman possessed. Now that I have stopped teaching to write full time, it’s actually more difficult to write. I am still working on organizing my time without the forced structure of a teacher’s schedule. And because I want to play pickleball too much.

The manuscript changed over time. Initially, I wrote Pickleballers as a comedy with a sprinkle of romance for added color. But as we passed the height of the pandemic, people were looking for uplifting reads, and romance blew up. So, I shifted the focus, and when Berkley Books picked it up, my editor Sarah Blumenstock helped me to pull the romance to the forefront.

Were there any surprises or learning moments in the publishing process for this title?

I could not believe how many grammatical and proofreading and other errors I made. I spent 32 years as a high school English teacher. For example, I had to learn to write out the number 32, when all those years I taught my students that they only needed to write out the number 10 and below. With Pickleballers, the copy editor’s style sheet detailed my errors in 17 pages. Hundreds of errors! And like Shakespeare, I managed to invent three pages-worth of new words, including picklebrawl and picklechasers.

Were there any surprises in the writing process for this book?

I’m not spatial or mathematically minded, so it was a struggle for me to keep track of the timeline in the book. I would write that something happened in the morning, and then an hour later, the sun would go down. Or the construction crew would be working, and the chapter was set on a Sunday. Eventually, I got so confused that I had to put every event on my Google calendar as if it was happening during the summer of 2025. I made sure all those dates lined up!

What do you hope readers will get out of your book?

Through the magic of pickleball, Meg Bloomberg regains both love (after a blindsiding divorce) and her art (after stepping away from her passion for painting). Trying the new sport gives her the confidence, the adrenaline bump, and social opportunities to move forward—so she can get back to her true self. I hope readers will see that stepping into something fresh and fun at any age can be rejuvenating. Between the sweet romance and the broad comedy, the story serves up the happy feelsies, and I hope my readers come away smiling.

If you could share one piece of advice with other writers, what would it be?

Persistence and flexibility! Getting published is a challenging road and I’d been at it for 15 years before hitting it right with my debut novel. Over a three-year period, I queried 143 agents. I faced quitting every time I was rejected or slush-piled, but I did not stop. When my pandemic sci-fi tanked when it ran up against an actual pandemic, I pivoted and wrote Pickleballers. And when my agent and editor suggesting moving it from a straight comedy to a romance, I shifted again. Folks in the publishing industry have an eye for what works and what will sell. As humbling as it is, I have to let go of my ego and accept critique with an open and willing heart if my goal is to get my books in front of readers.