Jenny Jackson, PINEAPPLE STREET: A Novel

Jenny Jackson, PINEAPPLE STREET: A Novel

GMA Book Club Pick alert! Zibby speaks to executive editor and debut author Jenny Jackson about Pineapple Street, a vibrant, witty, and deliciously funny intergenerational story of wealth, family, and love, as experienced by three Brooklyn women. Jenny describes her 20-year career in book publishing, the inspiration behind this story (she lives on Pineapple Street in Brooklyn!), and her book’s fascinating exploration of generational wealth. She also talks about her experience writing a book as a lifelong editor and shares her best advice for aspiring authors.


Zibby Owens: Welcome, Jenny. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss Pineapple Street: A Novel. Congratulations.

Jenny Jackson: Thank you. I’m so happy to be here. I’ve listened to you interview all my favorite writers. It’s kind of surreal. I’m excited.

Zibby: I’m excited because you’ve sent me so many great authors. They’ve come out of your creativity lab over there. It’s nice to be on this side of things. For listeners who do not know, first of all, give your background because I was just referencing you sending authors. Tell everyone your whole background as editor and also, maybe before we even get into the book, how you even got into that field of working in publishing yourself.

Jenny: I’ve been an editor at the Knopf Group for twenty years. I’m a vice president, executive editor. I started out by going to the Columbia Publishing Course. I knew that I wanted to work in books. I didn’t really know anybody who worked in books. I had one friend in New York City. I moved to New York thinking I might just come for a summer program. I fell so deeply in love with the city and with publishing. I just had to stay. Twenty years later, here I am. I came on as an editorial assistant at Vintage, so part of this same group. I laugh whenever people ask me for my résumé. I’m like, it’s one line. I took a job, and I stayed for twenty years. I’ve basically done the same job for twenty years, but I’ve had the enormous fun of publishing a really wide range of books. That’s one of the things that’s special about Knopf Doubleday Group. I’ve worked with Cormac McCarthy and Emily St. John Mandel, but also Kevin Kwan and Helen Fielding on the Bridget Jones books and J. Courtney Sullivan, Katherine Heiny, Helen Ellis, Chris Bohjalian, a really incredible range, which is just so fun intellectually.

Zibby: Oh, my gosh. Some of my favorites in there. It’s so great, the authors that you represent. So awesome. Pineapple Street, your debut novel, when did this even begin to percolate? What’s this novel about, first of all? Let’s go to that.

Jenny: It’s a family story about women and money that is set in Brooklyn Heights. I wrote this novel at a really weird time. I started it towards the end of lockdown. I was living on Pineapple Street. Really, my neighborhood had become my whole world because our office was shut down. I wasn’t ever taking the subway anywhere. We weren’t seeing people. I was just walking around the neighborhood basically talking to myself. The novel grew out of me daydreaming very much in Brooklyn Heights. We had spent the first couple months of the pandemic with my in-laws in Connecticut, which was amazing and also really weird. When did you last live with another family, and especially as an adult? My husband and I have been together for seventeen years. I love his family, but it’s not my family. I was thinking a lot about in-laws and family dynamics and then thinking a lot when I was home about Brooklyn Heights. Then I read this article in The New York Times called “The Rich Kids Who Want to Tear Down Capitalism” about millennials who reject the notion of inherited wealth. All these ideas clicked together for me. It turned into this novel about a family in Brooklyn Heights where the youngest sibling decides that she needs to give away all of her money. Obviously, people in the family think that that’s a pretty wild idea.

Zibby: The other sister also, we find out, has different relationships to money and makes different decisions along the way in her life as well. They are all, in their own ways, dealing with this. I was trying to take away, what is Jenny trying to say about wealth? What is your thesis on the whole thing? Is it ridiculous for people with inherited wealth to try to give it all away? Is that what everyone should be doing? Do you have no view and you’re just poking fun? How do you feel about it? How is the reader meant to feel at the end?

Jenny: Obviously, you ask me the hardest question of all right off the bat.

Zibby: Sorry.

Jenny: I would say my thesis is that in this world, we’re all trying to be good. That is our greatest struggle, all of us, every single day. What being good looks like is different for everyone. I have often been blown away because there are people who are celebrated in society for all of their amazing, good deeds and generosity towards causes, and then you meet them, and they’re maybe not the nicest people. On the other hand, I had the chance to meet this guy once who runs a very large company that makes missiles and instruments of war, and he was just a really charming, nice person. I’ve struggled for a long time with how those two things can coexist and how nobody is actually altogether good or altogether bad. My thesis in this is that we’re all trying to do our best. Money is an interesting vehicle to do good, so I wanted to examine how people who have money as a resource think about being good.

Zibby: It’s so interesting. The inherited notion, especially this very WASP-y family, they’ve had money trickle down. There’s not as much as there was. It’s not like there’s new — I’m struggling to explain.

Jenny: They’re old money, yes.

Zibby: It’s old money. What does that mean to their identity now? How does it inform what they should do to be good? All the different kids take a new path. They are lucky enough to be able to make the decisions that they want to make, all three of them, really. There are so many things that you describe with the parents that are so funny and societal and of that time, even the mother bringing her own food to the dinner party. It’s just such a perfect thing, or when she finds out something so horrible that’s happened to one of her daughters, just being like, “Okay, tennis at six?” It’s also the customs of that old money that I feel like you take apart. Wealth is the one bucket, but it’s also these societal things, almost in the way that Kevin Kwan, your author, really looks at society and finds the humor and finds the things that maybe they don’t notice about themselves. There’s something about this that reminds me of that just in that way. Totally different worlds, of course.

Jenny: I love that. I think you only need to look around to realize that we’re in this moment of extreme social upheaval. I love thinking about micro-generations and how our attitudes towards everything, money included, are really based on our birth year in some ways. I’m forty-three. I’m what we call a geriatric millennial. I was born on the cusp of being a millennial and being Gen X. My attitudes towards money are really different than the attitudes of people who are now in their twenties. I spent a lot of time over the pandemic with my assistant, who is in her early twenties and who is an incredibly smart, amazing person. We have really different attitudes about money. I grew up with that attitude that you do the best you can and make the most money you can. You enjoy the fruits of your labor. She is a lot more socially minded than I was in my early twenties. I think that for families now, adult children have a very different relationship with money than their parents did. That’s what I really enjoyed poking at in this novel.

Darley, the oldest sister, her relationship with money really is related to her marriage because Darley was unable to ask her husband to sign a prenup. She’s given up access to her trust fund. She just felt like, I was given a great education. I married someone with a great education. Between the two of us, we would be able to look after ourselves. Then she stops working when she has her second child. When her husband gets fired, things get more complicated. Her storyline was one that I felt very close to. My best friend from college stopped working when she had kids and has spent a lot of time grappling with finding her intellectual life meaning without a job. That’s something she and I have spent an incredible amount of time talking about, whereas I think her mother probably didn’t have that same struggle because raising children was her job. I think that women our age feel like — Zibby, I’m sure you’ve thought a lot about this. Being a mom is a lot. It is a full-time job, but we also feel a lot of pressure to also work and also have a lot else going on. It puts this character in an awkward position. Then it’s added to by the fact that she has really built a life around having a lot of money, and her access to it is drying up.

Zibby: I have to say, I’m just finishing Marion Nestle’s memoir. She’s the famous food politics person. She’s in her seventies or eighties now. She was saying these issues were there for her. She was going through all the same issues. She was a scientist. She’s got a PhD and all this stuff. Not that this is related to your book, but just to this conversation. Back then, there were still those same things, only there weren’t as many outlets. You could feel just as much drive to want to get out and do something, but there weren’t even the places to go. I know we all know this. Even Jessica Gross, too, in her book wrote about how even hundreds of years ago the moms would be like, I can’t believe my husband’s off at war, and I have to be here nursing. It’s one of those things that is constantly wrestled with. I feel like there’s never a good answer. Yes, Darley right in the middle of it.

Jenny: Then the second character, Sasha, has, also, a different relationship with money that’s wrapped up in her relationship with her husband. Darley is a middle-class girl who marries into this family. It is such a classic genre, the fish out of water. I had so much fun writing about this family through the point of view of someone who would think it was perfectly fine to drink bubbly water out of a can. Her mother-in-law is absolutely just beside herself that someone would do such a thing.

Zibby: Meanwhile, her family is throwing beers off a ledge or doing whatever in the harbor, the way you painted them. You also have this other subplot, which I won’t give away because it comes later, but with secrets and loss and all these extra feelings that are so intense. How does a family that’s used to not really dealing with feelings so much handle it when someone has the intensity of feeling, and so much so that she doesn’t even want to tell anybody about it? How does the permission to share across different families really affect everyone in that whole ecosystem?

Jenny: I think that WASP culture is an interesting place to start when we talk about repression or not wanting to talk about problems. I think it really spans a lot of different cultures. We’re told to put on a stiff upper lip or put on a happy face. Then also, the fact that this character has done something she’s ashamed of makes it really hard for her to confess to her family what she’s done. She experiences panic attacks and deals with it in the way a lot of people do, but a way that’s kind of unhealthy. I really wanted to talk about panic attacks and about anxiety and about mental illness because it’s absolutely more widespread than ever. Also, we’re all just accustomed to trying to power through when we’re having a hard time. The past couple years have been really hard for a lot of people.

Zibby: Very true. When you went through the actual writing of this armed with all of your editorial skills, did you feel like as soon as you started a sentence or a paragraph or a section, you were already editing it in your head? How did it manifest itself with your own words?

Jenny: It was interesting. I didn’t edit a ton as I went, but I reread a lot whenever I stopped and needed to start up again. I felt like whenever I sat down at my computer, I had to reread the previous chapter. It was getting back into the flow. It really helped me orient myself and get back into that headspace. I know that it’s so hard for people to stop tinkering and just let it flow. I’ve even heard amazing tips for it. I think Jojo Moyes was the one that said that she would sometimes turn her font white so she couldn’t see what she’d written so that she would just keep going. I love that. I didn’t get to that point, but I slapped my hands away and didn’t let myself revise much as I went. I just let it go. This book is three storylines. It’s three point of view. I wrote them separately for a while. Then when I was probably halfway through, I snapped them together and started writing A, B, C; A, B, C; A, B, C. The first edit that my editors gave me was, “You know, in the second half of the book, the characters really talk to each other. In the first half, you need to knit those together better.” I was like, oh, my gosh, I am so busted. That was the flaw in my process. It was how I needed to write it. That was something I had to go back and really work through because the characters weren’t talking to each other at first. It is so funny. A good editor can spot your Achilles’ heel so easily. I thought maybe I would be beyond that, but god no.

Zibby: How did you decide where to publish?

Jenny: It was a little bit scary, but I just decided to let my agent go out wide and send it around town. I thought, in some ways, I feel really vulnerable because since I’ve been an editor for twenty years, I know all these people. They’re my friends. Inevitably, a lot of people are going to pass on it, but hopefully, more are going to want it. I just thought that I wanted to have the real experience. I didn’t want to play it safe and send it exclusively to one person and keep it a secret. I thought, I feel proud of it. I like it. If I were an editor, I would bid on it, and so I feel certain that somebody else will. Let’s just let the chips fall where they may. Brettne sent it out. We had a bunch of calls scheduled. Then Pam Dorman and I had a conversation. Our editorial connection, it’s — you know that thing when you walk into a house and you know if you’re supposed to buy it or not? It really was like that with Pam. I was like, I just need to be with her. I don’t really even need to finish having conversations. Pam made an offer. I said, let’s just do it. This is who I want to be with. It really was a meeting of the minds.

Zibby: Wow. Did you consider publishing at Knopf, or you didn’t even send it?

Jenny: No, I didn’t send to anyone at Knopf Doubleday because imagine how awkward that would be, sitting in the marketing meeting and hearing how much money they were going to spend. I couldn’t do it.

Zibby: I know.

Jenny: Imagine if they felt they had to bid to be polite. That would be so awful.

Zibby: You’re like, maybe go up a little. I don’t know.

Jenny: Right, totally. look at your P&L. We can just adjust the price here.

Zibby: Totally, we’ll sell more copies than that. I don’t know what you’re thinking. Armed with all this knowledge, for the book to come out, is there anything that you’ve learned from all the authors, and I’m sure there’s a bazillion things you’ve learned, but that you’re really taking to heart, even in terms of marketing or publicity or what you want to have happen during your book journey? What’s going to make the experience satisfying for you?

Jenny: I love this question. The thing is, even moving back in time, I’m so happy that I wrote a book and decided to publish it because I know it’s made me a better editor. I know I will be a better champion but also a better line editor for having done this. I understand structure in a better way. I also understand something that I can’t believe it took me so long to figure out. I have certain writers who are reluctant revisors. They fight me tooth and nail. I say, hey, this needs to be twenty thousand words longer. They say, how about five? I say, how about fifteen? We settle. I used to think, oh, gosh, they just don’t feel like doing it. That’s not it. It’s that when you’re writing, you’re in this creative zone. When you’re not writing, it’s really hard to get back in there. These writers are just struggling to get back in. It’s not about will. It’s about that creative thing. I’ve already learned so much from being an editor. In terms of moving forward on the publication end, what I’ve learned from watching my writers, number one is, I have no desire to read bad Amazon or Goodreads reviews. That’s just not going to happen. I’ll confess that I have read a few Goodreads reviews, but I did it like a total narcissist. I went in, and I filtered to five-star reviews. I read a few of those. Then I shut it down. Is that crazy?

Zibby: No, it’s perfect. That’s what everyone should do. You’re absolutely right.

Jenny: I’m just not going to scroll down on Amazon. Of course, inevitably, someone tags you in a nice review on Instagram, but then you see below it, someone wrote, “Didn’t finish. Couldn’t get into it.” Then you spend two hours being like, couldn’t get into it? Why not? That is the path to madness. We don’t need to do that. I tell my writers not to do it, but I’m actually really not going to do it. Then also, I’m right now in the “say yes to everything” mode. This is such a ride. You only get one chance in your whole life to publish your first book. Whether or not I ever even publish a second one, I’m so aware of how special this moment is. I’m enjoying every second of it because it’s brief. It’s exciting. It’s fun. I’m just soaking it all in.

Zibby: That’s awesome. I love that. I feel like sometimes the perspective of this age or whatever — I’m a little older than you. The knowledge that these things are so temporary — I feel like back when I got married the first time, big things would happen before, and it was all about the stress and the event. Now it can be just like, no, the whole thing is the fun part, the whole thing, before and after.

Jenny: I also think publishing your first novel in your forties rather than in your twenties is awesome because I actually know that this was the best book I could write. I feel really proud of it. I feel like it’s a better book than I would’ve been able to write when I was in my twenties. I honestly know that not everyone will ever love anything, and that’s okay because my goal is to make people who love it have a really fun time reading it, get something out of it, have amazing conversations with their friends, think hard about their relationship with their spouse, with money, really enjoy it. For the people who don’t, that’s okay too. Being able to have that attitude about your work, that you’re excited for the fans to embrace it and that’s all that matters, you’re excited for readers to get something out of it, it’s a healthier attitude than I probably would’ve had as a younger person.

Zibby: It’s really great. I really enjoyed it. Your sense of humor is so great. Your wit and how you look at things as this societal recorder of sorts, it’s just so funny, and even when you say things like — there was some line about having kids. Somehow, she got pregnant. You’re like, it was the regular way, but isn’t it always just a shock when that happens? There are just so many lines where I’m like, oh, I’ve totally said that.

Jenny: Kevin Kwan is such an inspiration for me. One of the reasons I’m inspired by him is Kevin told me that he kept a post-it note over his desk with the word “joy” written on it. He wanted to remind himself as he wrote that that was his goal, was to make his reader feel joy. I did the same thing. I was writing it in the back half of 2020 and the front half of 2021. I just desperately wanted to feel joy. I wanted to make other people feel joy. That was the goal. I learned that from Kevin.

Zibby: Amazing. Now the both of you have brought me joy, so that’s great. Double whammy here.

Jenny: Thank you.

Zibby: So you’re not going to write anything else? You’re not sure?

Jenny: I would really, really like to. I would really like to. Gosh, once you’ve gotten the bug for how fun it is — when you are writing a great scene and you finish it and you immediately want to call your husband in and read it out loud to him, even though he’s actually really probably not in the mood and trying to do nine other things, that is so fun when you make something and you’re like, god, this is so good. It’s so fun. Once you’ve tasted it, I know it’s kind of irresistible, so I’m probably going to try again because I just want that feeling again.

Zibby: That’s awesome. It is addicting, addictive. Yes, totally. Now that you’re at this stage, what advice would you give to aspiring authors?

Jenny: I think the advice is that the right book will come to you. When it’s easy, it’s easy. When it’s hard, it’s hard. It’s okay for it sometimes to feel awful. Every book tries to kill itself at least once. You need to just stick with it. Inevitably, there are going to be parts of it that are so much fun to write. Inevitably, there are going to be parts of it that are so hard to write. You’re going to think, I can’t believe I’m even trying to write this. I should give up. I should try something else. Don’t. Every book feels that way sometimes.

Zibby: That is excellent advice. Jenny, thank you so much. This has been so much fun. Thank you for the book. It was delicious, seriously, just totally delicious. I savored it like a great, fun meal that I felt a little bad about. Overate because it’s so great.

Jenny: That means the world to me. I’m so glad.

Zibby: Thanks for coming on. Good luck. I’m so excited to watch you just soar with the publication.

Jenny: Thank you.

Zibby: Bye. Have a great day.

Jenny: Bye. Hope to see you soon.

Zibby: Hope to see you soon.

Jenny Jackson, PINEAPPLE STREET: A Novel

PINEAPPLE STREET: A Novel by Jenny Jackson

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