Zibby Mag

Book jacket biographies don’t tell us nearly enough about the authors we love. That’s why Zibby Mag launched the Author Snapshot, giving readers an inside look at the lives and work of our favorite writers.

This week we are featuring Jenny Jackson, a Vice President and Executive Editor at Knopf whose debut novel, Pineapple Street, is the March pick for the GMA Book Club!

What was the inspiration for your debut novel Pineapple Street? Did you actually live on Pineapple Street, and how much of your own experiences or observations did you weave into this Brooklyn family story?

I can’t decide whether I have a wild imagination or literally none at all because with Pineapple Street all the big stuff is made-up, but all the little stuff is absolutely true. Unlike the characters in this novel, I don’t come from a prominent real estate family, I didn’t inherit thirty-seven million dollars, and I didn’t even grow up in New York. But I did have a hopeless crush on an older co-worker when I worked at a non-profit, I did spill cocktail sauce all over my dress at a fancy wedding, and I did absolutely freak out when my children picked up a dead pigeon with their bare hands at the Brooklyn Heights playground.

I was living in an apartment on Pineapple Street when I wrote the novel. It was Q3 of the pandemic (I have now decided to start talking about Covid like our ruthless and disorganized employer), and I was working from home, bored and lonely, spending a lot of time walking around the neighborhood and missing my friends. One of my closest friends had just moved into her in-laws’ Brooklyn Heights brownstone with her husband and child and kept telling me the funniest stories about life surrounded by his family’s detritus. Meanwhile, I came across this article in the New York Times by Zoe Beery called “The Rich Kids Who Want to Tear Down Capitalism” about socially-minded millennial heirs who feel their inheritance is at odds with their morals. Somehow these three things—my Brooklyn Heights neighborhood, my friend in her in-laws’ brownstone, the idea of a rich child rejecting the family fortune—clicked together and became the basis of Pineapple Street.

It was such a weird time, being home, never going to parties or cocktails or lunch, never getting to laugh or gossip or flirt, and so I poured all my pent-up social energy into the book, creating characters who could do everything I desperately wanted to be doing.

You’ve been the editor of many beloved authors over the years. What was it like to move from the editor’s side to the author’s side? How has this experience been similar to or different than what you expected?

I feel like I’ve studied at the feet of the masters. Getting to edit writers like Kevin Kwan, J. Courtney Sullivan, Katherine Heiny, Jennifer Close, Lauren Fox, Gabrielle Zevin, Chris Bohjalian, and Emily St. John Mandel has been like sitting in the front row of the most amazing literature class of all time. I’ve learned different things from each of them. I’ve learned how to write a joke from Katherine Heiny, I’ve learned how to establish voice from Jennifer Close, I’ve learned how to turn up the volume in places from Kevin Kwan.

When it came to the writing process, I found the move from editor to writer was fairly natural, but when it came to the editorial process, I was surprised by how hard it was! I wrote the book entirely in close third person with a rotating POV. It’s a great way to write a book because whenever you’re struggling with one character or storyline you can just pick up with someone else. But when it comes to editing and making structural changes to the book it becomes like a game of Jenga! Figuring out how to move pieces without upsetting the other timelines is mind-boggling. Then I was also surprised at how vulnerable and sensitive I felt about the editorial notes. When my editors didn’t like a joke or didn’t like a new scene I felt totally deflated, but when they wrote “haha” or “love this” in the margin I was buoyed. As an editor, I always make a point to put encouraging notes in the margins and this was a good reminder to keep doing that!

What do you hope people take away from Pineapple Street?

Well, I have always felt like you catch more flies with honey and a spoonful of sugar helps the medicine go down, so my goal was for this book to be joyful and enjoyable, but I do want people to read and consider what it means to be good. Having a positive impact can mean different things for different people, but for the characters in this novel, characters born into extreme wealth, it means they have the power to drastically change lives. At the center of this story is a moral reckoning. Georgiana, the spoiled youngest daughter, does something really bad, and when she hits rock bottom, she realizes that she has to change. Her money gives her the power to actually do that. I hope readers are inspired by Georgiana.

What can you share about the TV series adaptation of Pineapple Street?

It’s been exciting! The book was optioned for TV by Picturestart and they hired a writer and showrunner, Sarah Watson, who was the showrunner for The Bold Type and a writer on Parenthood. She and I have emailed and Zoomed and I am so happy with how she sees the characters and how she plans to adapt them for the screen.

What books do you recommend people read after finishing Pineapple Street?

If you haven’t read Laurie Colwin, I suggest you do so immediately. Maybe start with Family Happiness. You should read Katherine Heiny’s Early Morning Riser, Jennifer Close’s Marrying the Ketchups, Meg Mason’s Sorrow and Bliss, and Nick Horby’s How to Be Good.

What are you working on right now?

I’m leaving Pineapple Street and heading to my hometown of Ipswich, Massachusetts, for a novel about marriage. Ipswich is famously the home of John Updike and the setting of his novel, Couples, and when that book was published it scandalized the entire town. I’m drawing a lot of inspiration from his legacy but definitely hoping to avoid scandalizing anyone!