Book editor-turned-bestselling novelist Jenny Jackson to speak at book festival on Saturday

They say you should walk a mile in someone else’s shoes before you judge them, but how is the average person supposed to refrain from judging the super-rich when they can’t afford groceries, let alone thousand-dollar designer heels?

In her debut novel, Jenny Jackson gives readers a chance to see how the 1% lives without paying the price. All it takes is a jaunt down “Pineapple Street.”

“Fiction is, for me, the closest I will ever come to knowing what it's like to be inside someone else's life and someone else's experience,” Jackson said. “And studies show that reading creates empathy, and I can't think of a more important thing in our world right now.”

From book editor to bestselling novelist

As vice president and executive editor at Alfred A. Knopf, Jackson knows a thing or 10 about books—at least from the editorial side. But when a few key moments clicked into place, she got a chance to experience the book business from a writer’s perspective.

Like many authors, Jackson drew inspiration from her life. At the start of the pandemic, Jackson and her husband left New York City to live with his family in Connecticut. In six months of living with her in-laws, Jackson got a little more insight into what it means to live in another person’s world, learning the rules and routines that make up someone else’s life.

While Jackson’s experience was a positive one, others had a different story. Back in Brooklyn, one of her best friends received an invitation to move into her in-laws’ lavish brownstone as they headed upstate. The catch? They had to leave all of the in-laws’ belongings exactly where they were, meaning wacky discoveries became a regular occurrence in the swanky home.

Although the exact details of “Pineapple Street” are relatively new, immense wealth and privilege have been on Jackson’s mind for a while. From preschool fundraisers auctioning off child-sized Teslas to parties in extravagant homes with catering kitchens, Jackson said “living in New York has kind of been a 20-year deep dive into spying on rich people.”

But when she read Zoë Berry’s New York Times coverage of the uber-rich millennials tearing down generational wealth, the spark of inspiration became a living blaze.

Jenny Jackson's novel peeks under the gleaming veneer of wealth

Jackson’s stroll down this fictionalized version of Brooklyn's Pineapple Street lingers on an extravagant four-story limestone owned by the Stocktons, a family whose lavish lifestyle is funded by generations of real estate investments and inheritances. But while the home’s facade appears perfect, it’s exactly that—a facade.

The glittering picture of wealth starts to crumble as Sasha and her husband, Cord Stockton, move into the limestone. Now surrounded by her in-laws’ treasured (and expensive) belongings, Sasha feels cemented as an outsider in this unfamiliar world of immense wealth. Of course, it’s hard to feel welcome after discovering your sisters-in-law refer to you as “Gold Digger” behind your back.

Then again, maybe there’s a reason Darley and Georgiana feel so defensive of their brother and family fortune.

While Cord and Sasha move into the limestone, eldest daughter Darley Stockton thinks back to her decisions to quit her job to raise her two kids and refuse a prenup, thus giving up her inheritance. Darley has been burnt by money-hungry “friends” before, but she trusts her husband, Malcolm, wholeheartedly. But when Malcolm is wrongfully fired from his job as a consultant in the aviation industry, she can’t help worrying how her family will react.

Where Darley is hyperaware of others side-eyeing her money, Georgiana seems completely unaware. As Georgiana scrambles out to retrieve a Cartier bracelet from a friend’s BMW, it’s easy to see why Jackson called her the “delightful brat” of the family. But as her obliviousness withers into anxious awareness of wealth inequality, the tension on Pineapple Street rises beyond family squabbles.

While Jackson isn’t entirely sold on the idea of “Pineapple Street” as satire, the humorous moments are significant. Whether it’s Tilda’s obsession with themed tablescapes or Darley’s kids’ fascination with a dead pigeon, that laughter has a purpose.

“We've read and seen a lot of movies, TV shows, books that eviscerate the wealthy,” Jackson said. “And while I'm all for it, and that's fun, I thought it might be more interesting to write a book about real people having real moral struggles with their wealth. And to do that, I wanted to have them be sympathetic so the reader could sort of understand what it might feel like.”

“Pineapple Street” also helped Jackson be a little more sympathetic in her role as an editor. Although she’s seen the publishing process from the other side many times before, this one brought her face-to-face with the author’s fear of breaking a fictional world somewhere in the many rounds of revisions. Even after emerging with a fully intact story and a better understanding of her authors, Jackson felt the novel wasn’t quite complete.

“I started writing a novel so I would have a place to put my brain during a stressful time,” Jackson said. “This sounds so crazy, but I didn't know that I could do it. Once I understood that, even when I typed the last sentence of my book, it wasn't done until somebody read it.”

With invested readers comes productive conversation, even in the neighborhoods that inspired the Stockton family. Jackson was delightfully surprised that people are open to discussing wealth when the invitation is extended via a novel with bejeweled twists and humorous turns.

While the real Pineapple Street might be quite a trek for most Savannahians, the fictionalized version of the extravagant limestone is just a quick read away. As Jackson prepares for the Savannah Book Festival, she looks forward to bringing these conversations to a whole new crowd—no Louboutins required.

If You Go >>

Jackson will speak about “Pineapple Street” during Festival Saturday at 5 p.m., Feb. 17, at the First Baptist Church Sanctuary, 223 Bull St. For a complete schedule, visit savannahbookfestival.org.

This article originally appeared on Savannah Morning News: Book editor-turned-bestselling novelist Jenny Jackson speaks at book festival