In the heights with Jenny Jackson

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Adam Sockel:

You are listening to Passions & Prologues, a literary podcast where each week, I'll interview an author about a thing they love and how it inspires their work.

I'm your host Adam Sockel, and today's episode is with instant New York Times bestselling debut author Jenny Jackson, whose book Pineapple Street has quite literally taken the literary world by storm.

It is a story of intrigue of the rich and the famous, and I jokingly told her it's a book perfect for fans of succession, which is extremely buzzy right now, of course. And so, if you're a fan of those types of stories, you are going to adore Pineapple Street.

In this conversation, Jenny and I discuss her massive love for where she lives, just Brooklyn Heights. It's a really fun conversation. She basically talks about the fact that during the pandemic, she was going on long walks and just became obsessed with the place that she lived.

She was researching the buildings, she was looking up the prices of houses, basically that same thing that we all do every single time we go for a walk. You see a house or a building, you're like, “Oh my God, I wonder what that is.” She took it to the nth degree of extremist because like we all did, she had time to kill.

I really love this conversation, it's something I was thinking a lot about. I am very active, I take my dog out all the time for walks. And in any neighborhood that I'm in with him, I find myself doing that same thing.

I want to get to know the place that I'm at. You find people that you see frequently on those walks, and you conjure up little narratives for yourself about, “What's going on with them? What secrets do they have? Who are these people?” Again, it's how stories form.

So, I really love this conversation, I extremely related to it. And listen, if you've ever been in a neighborhood, which we all have, I think you're going to love it as well. Before we get to our conversation, I want to give you a book recommendation.

This week, I read Claire Keegan's, Small Things Like These. It is a really quick story, it is about 115 pages, but it will absolutely shatter you.

It is set in 1985 in an Irish town, during the weeks leading up to Christmas, there is a coal and timber merchant named Bill, and he is basically just taking timber and coal to the various houses in the neighborhood so that they can keep their fires going and stay warm throughout winter.

And he basically encounters something really, really horrendous and shocking happening at a convent, and he struggles with what to do with it.

It's a story of hope, but it is going to floor you before it gives you that hope, I will admit. But I loved it, it's extremely quick. Like I said, I picked it up at the bookstore and just read it in afternoon. I think you'll really, really love it.

It's a very small story with big emotions, which is the thing that I love most about books. So, I think you’ll really like it.

And again, that is Small Things Like These by Claire Keegan. If you'd like additional book recommendations, you can always reach me at [email protected]. You can send me any requests for book recommendations there.

If you wouldn't mind taking a second to leave me a rating or review where you listen to podcasts, it helps people find me just a little bit more easily. And anytime you reach out to me at that email, [email protected], be sure to let me know, the things that you are passionate about.

Anyone who does that, once a month, I pick somebody at random and give them a bookshop.org gift card, so be sure to connect with me there, I love hearing from everybody who's listening in.

Okay, that is all the housekeeping. I am so, so excited for you to listen to this conversation with Jenny Jackson, author of Pineapple Street on Passions & Prologues.

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Okay, Jenny, what is something you are super passionate about that we are going to be discussing today?

Jenny Jackson:

We are going to be talking about Brooklyn Heights.

Adam Sockel:

Awesome, okay, tell me more, I believe this is where you live, correct?

Jenny Jackson:

This is where I live, and I've lived here more or less for 12 years, but most centrally in Brooklyn Heights for the last six years.

And during the pandemic, we didn't go anywhere. And so, I was just walking around and went so deep down the rabbit hole, learning about the neighborhood, looking at different buildings in the neighborhood, going on real estate blogs and reading about different homes in the neighborhood.

Definitely looking at how much they cost. I became a Brooklyn Heights nerd, I'm obsessed with the neighborhood.

Adam Sockel:

So, two things. One, I'm instantly already starting to see how Pineapple Street came to be, perhaps, but I need you to know, so I live in Cleveland, Ohio, and we like to joke like no one loves their city more than a Clevelander loves their city.

And so, I feel this in my bones, but what is it about Brooklyn Heights that you are so infatuated with, has made you fall in love with the neighborhood?

Jenny Jackson:

So, I love it because I think there is this very interesting paradox that in some ways, it is an extremely old neighborhood that is resistant to change. And the historical society has put in a bazillion restrictions to keep Brooklyn Heights the way that it is.

And there are all these amazing, amazing people who've lived in Brooklyn Heights — Walt Whitman, and then Truman Capote wrote In Cold Blood and Breakfast at Tiffany's at 70 Willow Street. Sorry, but I'm definitely going to tell you more about that because it's such an interesting story.

And there were homes of sea captains and there — it's a fascinating, fascinating neighborhood. Also, there are a lot of wooden homes in Brooklyn Heights. Building wooden homes in Brooklyn has been illegal for more than a century because of fires but they're historically preserved.

And so, there are these buildings that just don't look like the rest of New York. And also, God help you if you are trying to renovate and maybe add a patio or something to your house here because they will stop you at every single turn. Like they will block you because they're so resistant to change.

But then, moving on about why it's such a paradox; it's also in some ways an incredibly modern neighborhood that is full of famous people and hedge funders and investment bankers. And so, it's this funny mix of like the oldest church in Brooklyn is here, but the preschool associated with that oldest church has an NBA player who sends his kids there. So, it's this hilarious collision of old and new in this tiny little neighborhood.

Adam Sockel:

So, I feel like this is a — I don't want to say New York phenomenon, but specific neighborhoods of New York phenomenon, this like dichotomy between, like you said, these things that are going on that have been here forever. And you just get used to these “celebrity sightings” type of a situation. And I feel like it's such a unique aspect of living in specific pockets.

Again, I live in Cleveland, Ohio, like seeing a “famous person” is like seeing a Cleveland Cavs basketball player every once in a while, and it's because they're six foot nine and they stick out. Or seeing Michael Simon walking around, like our famous chef that we have around here.

But have you always been fascinated or was it really, like you said, during the pandemic, none of us had anything to do and you're just fell down that rabbit hole?

Jenny Jackson:

I think that there is this sick thing that all New Yorkers do. I'm actually going to go out on a limb and say all like 100%, which is obsessed over real estate. And that's just because living in New York is so hard. Finding a place to live is so hard, everything is overpriced. The whole process of getting an apartment is absolutely demented.

And I've moved a zillion times, I pretty much lived in different apartments every two years for 20 years just because somebody raises your rent, or a roommate is moving out, or you want to move in with your boyfriend or whatever. And so, we all spend a disgusting amount of time on either Craigslist, or I personally am a StreetEasy fan, though I also love Zillow, I love Zillow Gone Wild

Like I'm into all of it. I spend so much time on the Real Estate apps and I'm not trying to move, I'm on there for sport at this point, but StreetEasy is just like always been a fascination of mine. And it's a great way to look at where other people live.

And especially, I think StreetEasy became extra fascinating to me during the pandemic because we couldn't go in anybody else's house. We were only ever in our own house, so it was a way to kind of, I don't know, visit someone in a really sad, pathetic way.

Adam Sockel:

Well, it's the same. There's a TikToker who's … I think it's like apartments of New York where the guy just walks around and goes to everything from the smallest studio apartment you can imagine to — I think he's walked around Cher's apartment or something absurd.

Where there is this fascination of how other people live, how other people design their houses, what they pay for it. My two best friends live in San Francisco and Los Angeles, respectively.

Jenny Jackson:

Pretty pricey.

Adam Sockel:

Pretty pricey, exactly. And they both do very well, but we had endless conversations about houses when they were both trying to purchase houses and they were showing me like I was getting such sticker shock.

Again, I live in Cleveland, which I love, but from a number standpoint, I imagine I could probably purchase a home here in Cleveland for half of what it would cost to rent an apartment in New York City, it's just wild to me.

Jenny Jackson:

There's a fantasy element to it and there are people who just every weekend, for fun, go to open houses just to look at other people's homes. And when we have gone to open houses, it's been so funny to try and figure out like, “Are other people here because they're actually going to buy this place?”

And I'm going to be honest, I've toured apartments, there was just no possible way that I could afford. But I was like, “Oh my God …” but that apartment is on the base of Montague Street, the main street in Brooklyn Heights, overlooking the promenade.

There's basically this whole row of houses that overlooks the promenade is the most expensive real estate in all of Brooklyn, and if you give me a chance to walk into one of those places, I will pretend I can afford it and I will walk through it, absolutely.

Adam Sockel:

There is actually along those same lines, at a previous company that I used to work for, we … that show Million Dollar Listings.

Jenny Jackson:

Love it.

Adam Sockel:

So, our CEO, like someone in his family was on that show basically because he works in publishing. People are listening, and I'm not being very coy about this, and people know where I used to work, but the CEO of our company has an apartment overlooking Central Park in Manhattan because in publishing, you know this more than anyone else.

Like you have to be in New York to be involved in publishing, and we saw the episode for his apartment, it was one of the places he lives. And all of us were just like — not only was it a fascination, but it was a fascination of like, “Oh my God, we know the person.”

Jenny Jackson:

Yes, totally.

Adam Sockel:

What's that?

Jenny Jackson:

Did you invite yourselves over?

Adam Sockel:

I would've loved to, he's a very unassuming kind human being then you realize like, “Oh wait, he's making …” — he's a very successful human being, wait a minute, we're not living the same type of life.

And so, along those lines, when you were talking about having this fascination and this going to figure out like, “Oh, I just want to see what these people live like,” I have to imagine that is sort of how Pineapple Street, your book came to be.

Jenny Jackson:

Yes, I was living on Pineapple Street in a rental, a nice apartment, but renting an apartment above Joe Coffee, which is where the opening of the book is set. And I became fascinated with this other apartment a few doors down on Pineapple Street, purely because they have these huge bay windows.

And I saw through the window, those big Chinese vases, they probably pronounce it “voz,” chandelier, and a grand piano. And when I saw the grand piano, I was like, “Really? In New York City, a grand piano? Who has room for a grand piano?”

I thought that was the sort of thing that they were just photoshopping in when I was going on StreetEasy. I'm like, “No, this person has one.” So, I started dreaming about what it would be like to live in that palace on Pineapple Street.

And then a funny thing happened around the same time, my friend Allie was living with her husband and baby in a different part of Brooklyn. His parents left their brownstone in Brooklyn Heights during the pandemic and said, “Hey guys, you can move into our apartment, you can just like have it, move on in.”

But they hadn't moved out, and so my friend moved into this apartment that was just full, like the closets were full of her mother-in-law's clothes, there was no place for her stuff.

And so, that sort of clicked together with the other idea and became Pineapple Street, which is the story of an in-law moving into the Brooklyn Heights brownstone that belongs to her husband's family.

Adam Sockel:

And so, along those lines, it's one thing to, like you said, look on StreetEasy, Zillow and imagine what it might be like to live like these people. And I have friends who have grown up with money and I've gone to their houses before, but you really don't know.

So, how did you go about learning about these people's lives to be able to write a story that was believable and fun, but also, had all those intricacies that us normies may not understand?

Jenny Jackson:

Well, it is funny like in New York, you're just living cheek to jowl with people. And so, earlier, I was joking about the oldest church in New York in Brooklyn and how there's the preschool. So, that's the preschool that my kids went to.

So, not only is there like an NBA player there and other sort of celebrity parents, but there were also a lot of bankers and so on. And the school auction is like one of the funniest things on the planet because it's a preschool auction.

I brought my kids there, we were doing face painting, everything was mostly normal. And then you went over to the raffle ticket table, they were auctioning off a child-sized Tesla. They were auctioning off a Botox party where you could invite your friends over and a famous dermatologist would come over and give you shots in your face.

Like the stuff … this is a preschool, and the auction items were so funny to me. And so, I feel just by association, I get invited places and I snoop around once in a while, you get invited over for a play date and I have a four-and-a-half-year-old and a seven-and-a-half-year-old.

And she was like, “Okay, garden level apartment,” I'm like, “Okay, great.” So, I assume that meant that they live on the garden level. That's just the door they use, they own the whole building. And I was like, “Wait, where are the kids? Oh, they're two floors above us in a playroom, like what is this?”

Adam Sockel:

And you do it really well in Pineapple Street, but I feel like there's this delicate balance of telling a story like that where people read it and enjoy it or like I couldn't help but think of Succession while reading Pineapple Street.

I feel like I watched Succession because I am so infuriated by their life. And I feel like it's one of two things. You either can make it humorous and not approachable in a way that you don't feel like you're looking in on something or you can go the complete opposite where you're just like, “I'm going to make everyone absolutely hate every single person.”

Jenny Jackson:

Totally, and I feel like if I'm being honest with Pineapple Street, I very much want to have my cake and eat it too. I want for people to have fun reading it. I want them to like the characters because I personally, yes, I'll read a book with despicable characters, but I enjoy more a book where I've fallen in love a little bit.

And so, I want people to love these characters, but at the same time, I do want to ask some serious questions about income inequality and inheritance tax, and just the huge moment in history we're living through where inherited wealth is greater than it's ever been.

Adam Sockel:

Well, and then there's of course, the additional aspects of the people who inherit a lot of these generational amounts of money that no matter what they do with their lives, they can never screw up enough to lose all of it.

It comes with a privilege and a type of personality where they act like they're greater than thou, exclusively because they were born where they were born and when they were born. And you're absolutely right, it is really interesting.

And so, I am curious if you find yourself thinking about those aspects of daily life being where you live and you mentioned like, yes, it has all of these extremely wealthy people, but there's also, like you said, the place where Truman Capote wrote his books and stuff like that. Do you find yourself thinking about that often or are you able to separate it in your daily life?

Jenny Jackson:

I think honestly, one of the things that I've learned from Kevin Kwan from the writer, Crazy Rich Asians who I work with, is that when you're writing fiction, you can turn a place into a character, and you can do that by turning up the volume on the place.

And so, I definitely did that with Brooklyn Heights to make it more extreme than it is. The reality is that yes, there is that element in Brooklyn Heights, it's also a really normal place for most of us. Like there are a lot of old people in the neighborhood who've lived here for generations.

There are a lot of families with children who are in very normal-sized apartments. It's actually a pretty normal neighborhood too, and I think that in thinking about who I wanted to write about, I had fun pumping up the volume.

Adam Sockel:

Speaking of the writing process, I kind of want to nerd out about writing with you for a little bit because for people who may not know you're like “day job,” you have made a career out of being, a vice president and an executive editor at a very successful publishing house.

And so, going about, I guess A, what made you want to be on the other side of that process and B, as someone who has been an editor for so long how interesting was that about when you got an editor to work with. I imagine you are in a very unique place from a writing standpoint.

Jenny Jackson:

All of my editor friends were like, “Seriously, you're going to publish a book? You are brave. Like we know how hard this is for writers. Like seriously, you're going to do this?” So, I think maybe it was a little bit of a wild thing to do.

Do you know what's so crazy? I never understood this before, I wrote a book. I thought that people published a book because they wanted to make money, great. Or they wanted to be a writer, absolutely valid, because they wanted fame, fortune, blah, blah, blah.

I didn't actually understand that when I was writing the book, I wouldn't feel like I was finished until people read it. And so, the desire to publish the book was really about a feeling of artistic completion, about a feeling of sharing what I had made and wanting other people to feel the feelings that I had put in the book. And it's a way more emotional and psychologically involving thing than I had ever understood.

The editorial process was definitely different than what I had anticipated, which is hilarious because I've literally edited people for 20 years. I've given people editorial notes for 20 years. I've always tried to be really kind and given notes in a way that cheer leads people along, and that was really important.

I didn't understand how hard it was to go back in and write new stuff after you'd finished writing. It was so hard to get back in there. I did have to do a lot of reordering of the plot in editorial, that was difficult but intellectually difficult and achievable in the way that if you're coloring in a super complicated coloring book — clearly I have children right now, why am I talking about coloring books? But you just have to be patient and do it.

That part, the reorganization of the plot was about patience and diligence. Going and writing new stuff and getting back into the headspace that you were in when you were first writing is not about that, it's about some weird creative thing. A tap that you have to be able to figure out how to turn on again, and that was so much harder than I ever anticipated.

Adam Sockel:

There's so much goodness in what you just said. Well, I am querying a novel right now, trying to find a literary agent, which is the most fun part of the process. You get to get, oh no, all sorts of times. But the way you just described it, like when people ask me, “Why do you want to publish a book?”

I feel like I've never been able to encapsulate it as perfectly as you just did. I don't feel like it's done until … like A, yes, there is some of the vanity and wanting to have my name on the spine of a book. Like yes, all that is true.

But there is this last section of like, okay, I've written the book, I have a friend who is an editor who has edited it, so at least, it's manageable as a manuscript to query. But yes, all of the making some money would be great. And it's the wanting it to be out in the world so other people can read it. You so perfectly encapsulated that.

But the other thing that I haven't really thought about that I think you also nailed right there is, I wrote the last words of this manuscript over a year ago at this point. By the time I edited it and I had an editor look at it, and then I was ready to start querying it and now I'm going through that process, it's been at least a year.

And so, by the time I get a literary agent and then work with an editor, it will probably have been 18 months or longer since I was in that head space. What was that like? How were you able to channel that previous version of yourself?

Jenny Jackson:

I really wasn't sure if I could or not, and it scared me so much because they wanted me to add another 15,000 words and that is a lot. And they wanted to know more about Sasha the in-law, they wanted to know about her life outside of the family.

And there I work with the writer Katherine Heiny. She wrote Single, Carefree, Mellow and Early Morning Riser, she’s so funny. And I think it was with her novel Standard Deviation, I asked how the main couple had met.

As an editor, I wanted to know, “How did this couple meet?” And she said, “I don't know that.” And as an editor, I was like, what do you mean you don't know that? Like they're pretend people, you made them up, like just make it up.

And that information was not accessible to her and that was not something she could put in the book. I didn't get that, I get it now. There are things sometimes you don't know and anything you write doesn't feel right. And so, you just can't put it in there.

Adam Sockel:

The way that I like to think of a novel most of the times, unless it's a sweeping novel like Pachinko where it's like you're looking at five generations of a family. If you are looking at a story that even if it tells much of one person's life, like you still are kind of taking a timeline of a world that whether it's like the “real world” are a completely fictional made-up world.

Like you're taking a timeline of a space that you're playing in and you're putting brackets around what the story is going to be and that's the part you're going to tell. And so, you're absolutely right, the story that I wrote begins with an elderly man. Like if an editor were to ask me like, “What about the first 70 years of his life?” I'd be like, “That wasn't what I was writing about.”

Jenny Jackson:

No, and if they said you had to write it, maybe you could, maybe not. Like who knows? Is that information available to you? Maybe not.

Adam Sockel:

So, we're short on time and I want to be respectful of that and I feel like I could nerd out with you about writing for like hours.

But when you received those edits and you went back, as a person who has done this for so long, did you have an initial pushback of like, “I know better than you?” Or were you able to kind of remove the editor hat and just be a writer for this process?

Jenny Jackson:

I would say that the way that I reacted was really on par actually with the way that writers I've worked with have reacted. In that, at first, I was, immediately resistant, took some time, really soaked it all up. At the end of the day, took about 90% of their notes.

I couldn't take 100 because there were some things that just didn't feel right, or I just couldn't get to where it felt exactly right, and that's true with writers I work with too. Like no writer's ever going to take 100% because they understand their work the best and you're helping them move it along.

And so, I knew that I was working with people that I really admired. And this sounds weird to say, but I've been an editor for 20 years and the editors I chose to work with are more experienced than I am.

And I felt that if I was going to have any dumb ego about it, working with people who I was like, “No, categorically, they've done this longer probably help me get over a hump,” sorry if that's gross, but it probably did help me.

Adam Sockel:

I love that. Okay, I have two more questions for you. One will be really quick, but first, what do you want people to take away when they're reading Pineapple Street? What do you hope they leave thinking or having thought about during the story?

Jenny Jackson:

I hope that they finish the book and think about the possibility that we all have to change. Because over the course of the book, these characters all do change for the better. And also, even the older generation comes to have some real revelations. And so, I hope that the book makes people feel hopeful about our ability to change our culture and to change each other's minds.

Adam Sockel:

I love that. Okay, last question: I always have the author give us a recommendation of any kind. Normally, I say it can be like a movie or a food or something. I am going to make you do a book recommendation of your experience.

So, what is something that you think more people should know about or need to read? Or what's something you have loved recently that you want people to read?

Jenny Jackson:

So, it's a British author. Her name is Meg Mason, her book is called Sorrow and Bliss, and it was a sensation in England and Americans need to know about her.

Sorrow and Bliss is what I call the chocolate pretzel of a novel because it's sweet and salty, and you're like laughing and crying and she's kind of mean, but so funny, it's just blissful. So, Sorrow and Bliss by Meg Mason, mwah, chef's kiss, it's wonderful.

Adam Sockel:

That's absolutely perfect. Jenny, like I said, I feel I could keep you here for another two hours, but I want to be respectful, thank you so much for joining me today.

Jenny Jackson:

Thank you for having me. What a great conversation.

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Voiceover:

Passions & Prologues is proud to be an Evergreen podcast, and was created by Adam Sockel. And it was produced by Adam Sockel and Sean Rule-Hoffman. And if you are interested in this podcast and any other Evergreen podcast, you can go to evergreenpodcasts.com to discover all the different stories we have to tell.