Poured Over Double Shot: Jenny Jackson and Ann Napolitano

By Miwa Messer / March 14, 2023 at 6:00 am

Family dynamics, for better or worse, are front and center in these two novels from two striking voices in fiction.

Jenny Jackson’s debut, Pineapple Street, brings us to an upper-class suburb in New York City — an old-money family, new romance, heartbreak and the kinds of drama only the one-percent can deliver. Jackson joins us to talk about publishing as an author rather than an editor, the intrigue of Brooklyn Heights, how to write humor and more.

In Hello Beautiful, Ann Napolitano follows four sisters as they navigate their lives from the 80s to early 2000s through tragedy, love and what happens when our futures don’t go as we’ve planned. We talked with Napolitano about her emotional journey while writing this, incorporating obsessions into your work, how to know when a story sounds right and more.

Listen in as both talk separately with Poured Over’s host, Miwa Messer.  And we end this episode with TBR Topoff book recommendations from Marc and Jamie.

Featured Books (Episode)
Pineapple Street by Jenny Jackson
Hello Beautiful by Ann Napolitano
Crazy Rich Asians by Kevin Kwan
Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin
Bridget Jones’s Diary by Helen Fielding
Games and Rituals by Katherine Heiny
Dear Edward by Ann Napolitano
Little Women by Louise May Alcott
Commonwealth by Ann Patchett

Featured Books (TBR Topoff)
The Most Fun We Ever Had by Claire Lombardo
How It Feels to Float by Helena Fox

Full Episode Transcript

Miwa Messer

I’m Miwa Messer, I’m the producer and host of Poured Over and Jenny Jackson, if you’re a regular listener, you may have heard Jenny at the end of December when we were talking about Cormac McCarthy, who’s one of her authors over Knopf. But Jenny has a novel coming out and it’s called Pineapple Street. And it is a fast fun, smart— I love these characters. I love these characters so much, fun, fun read. And Jenny, it’s about as far from Cormac as we can get. There’s a little, you know, if you read Kevin Kwan’s Crazy Rich Asians, which Jenny was also the editor on, there’s a lot to like, in Pineapple Street, but okay, come on, you’ve got kids, you’ve got a big job, all of this stuff. How in the world did Pineapple Street come into the world?

Jenny Jackson

It’s actually related to Kevin Kwan, the way it came into the world. I was listening to Kevin Kwan talk about his process once and he said that he writes the word joy on a post it note and he hangs it above his computer. And every time he sits down, he just tries to write something to give people joy. I just did that, but for myself, so it was like, you know, Q3 of the pandemic of 2020. And I was not going anywhere and not seeing anybody. And I was kind of, frankly, just going nuts and waking up at like 4:30 or 5 in the morning every day and staring at the ceiling. And I thought, oh my God, I need joy. And I couldn’t see my friends, so I just sat down and started making them up and it was purely to save myself in a bad time.

This cast. I love these women and the men okay, there’s Cord, there’s Cord’s dad, there’s he who I shall not name for the moment because let’s let readers discover who Brady is. But the women of Pineapple Street are pretty great. Who showed up first?

Sasha showed up first. And I think you know; Sasha is the outsider, she is the skeptic, she is the fish out of water. And it’s so much fun to start a novel with a fish out of water. You know, she’s the first voice because they can kind of give it to you straight, for the reader. They’re like, hey, this world is bonkers and I’m going to describe it all because it all still strikes me as bonkers. Whereas the other characters, Darley and then Georgiana, they were born into this world, so they don’t know how crazy it is.

And we’re talking about life changing money— this isn’t “my parents are comfortable; we can do what we’d like.” This is almost money on a Crazy Rich Asian scale, almost. It’s Brooklyn Heights money in a new way. So, let’s talk about the setting for a second. How’d you get there? Are you a Zillow addict too?

I absolutely am a Zillow addict, like Zillow Gone Wild and Zillow Catastrophes, like I’m in it for the franchise. I was living on Pineapple Street when I wrote the novel. And as I said, not going anywhere or wandering the neighborhood. But I also think that Brooklyn Heights is just the most fascinating little piece of Brooklyn. It’s America’s first suburb. And it is, bizarrely suburban, considering the fact that you’re one subway stop away from Manhattan. I mean, leafy streets, big dogs, like people, they don’t just have little dogs, they have big dogs in Brooklyn Heights. That’s bizarre.

It’s also kind of fun to visit. I mean, I still live in the city and every now and again, if you have to run out there, it’s just like, where am I?

Cobblestones and I mean, there are little plaques on all the different houses to say which like sea captain lived there. We have Truman Capote’s house, we have the Moonstruck house, Walt Whitman’s. I mean, it’s a historic little slice of the city and it’s beautiful.

It’s also the perfect place for a young married couple to move into his childhood home.

Yeah, I’m not I’m not sure that there is a perfect place to ever do that. But if someone’s going to give you a free place to live in Brooklyn Heights, you’re going to say yes.

But that house, and that whole Cord and Sasha moving into his parents’ home, and his sister’s junk is still there. The minute you put us there, I knew I was in for a good time. But let’s talk about the setting. Let’s talk about the voice, because you have a cast that you’re juggling. We’ve spent a lot of time in this one neighborhood and within two blocks of each other.

Yes, it’s interwoven so that you sometimes are seeing the same scene from different perspectives. I mean, it all takes place over the course of about nine months, and they hardly ever leave town except once in a while to weekend somewhere or when Sasha does a runner and goes home. But otherwise, they’re really within the same couple city blocks and really just going through these family rites and rituals. The wonderful thing about writing a cast of family members is that as an author, you don’t actually need to do a lot in the way of calisthenics to come up with reasons for them to interact, get on each other’s nerves, get in fights, fall in love and make a disaster of things because somebody always has a birthday or a school recital or an auction or a fancy dinner or a gender reveal party that they must attend. There are just lots of great reasons that I could throw them all in the same pot, stir them around and watch it explode.

Okay, so here’s the thing, everyone gets their turn, sort of, as they narrate the story. So the multiple POV one, it’s fun for the reader. It’s definitely fun for the writer and solves a lot of problems because you know, you get stuck on one person’s POV and you need to move the story forward, you just go to the next person, but your day job, you’re an editor, and now you’re doing both things. This is a lot can we just talk about what that multiple POV means from the writer’s brain? And also, the editor’s brain.

Honestly, I keep saying to myself that I wish that I had written a novel 20 years ago, because I now understand structure in an entirely different way. I was very insistent that the structure of this novel be ABC, ABC, between the characters, we’re never gonna go out of order. You’re never— I felt very married to this structure. And it was, you’re right, it was easier to write in that structure, ABC, ABC, because when I hit a stumbling block, on to the next. Revision, from multiple POV, is madness, because they asked me to move up the storyline where Darley’s husband Malcolm gets fired, that used to happen halfway through the novel, my editor said, we really want it to happen in Darley’s first chapter. So, I had to pull all these strings and threads, and it was I mean, oh my word, it was so much harder to revise having written in this way. I don’t wish that I had written it differently. But now when I’m editing other people’s books, I’m gonna understand the limits that structure puts on a book so much better.

Well, I feel like I was really plunged into the story very quickly. I mean, between Sasha and then Darley, who Darley might be my favorite of the women, but I haven’t totally decided, but yeah, I think Darley is my favorite. But here we are and it’s like, oh, I’ve got the lay of the land. So, are we outlining?

No!

Okay, so you just sat down and wrote.

Yes, I sat down and I wrote, Sasha and I wrote a lot of Sasha and I wrote probably half of Sasha’s whole storyline. And the first half of the Sasha storyline is really about an outsider trying to fit in, about a woman who has followed her heart, but who’s in-laws really just don’t accept her for who she is. And then the next character that came to me was Georgiana. And Georgiana is a delightful brat. You know, she’s a decade younger than the rest of them. She’s wildly self-centered, she thinks she’s doing a great job adulting, but not one single bit. She for me, was like, just hilarious to write, she has this unbelievably painful crush, and it’s fun to write a crush, it’s fun to write a wild love affair. And then Darley came to me third, and because I’m also a mom with two kids, it gave me the chance to really tell a lot of ridiculous stories about my own children, like my own children did pick up a dead pigeon at the playground. And I’m like, well, that’s gonna happen in the book, you know. And then I had written about half of each of their stories and was like, alright, time to block them together. And so, I then got busy with some post it notes, blocked them together, and then wrote the rest of the book in order. But then I did have to do a lot of work to go back through from the beginning, and then stretch it through so that the chapters were really talking to each other.

You know, dialogue drives this novel so beautifully. I mean, I felt like I was eavesdropping on stuff. That was just, it was great. But that’s a really fine line to walk and not everyone does that, where you’re trying to always keep the story moving forward, without forgetting your characters. I mean, there’s some people who do story really well. There’re some people who do character really well. There are some people who can juggle all of it. You’re one of those people, but for you as the writer, how are you keeping track of where you want to be and where you need to go? I mean, is that just straight up revision?

No, oh my gosh, unhelpfully? I think it is, I don’t know if it’s like, what’s the equivalent for riding a bike? What’s something that you’re just like doing and not thinking about? It was that, but there are certain characters like Tilda and Tilda is the matriarch of the family and she is a ridiculous person and her dialogue was just— she was like, screaming at me and I was like, well, I gotta write that one down. I can’t believe she said that, you know, and so the more outrageous the character, the more tempting I was just to pour in all their dialogue because it was making me laugh so much.

I’m very glad Tilda is not my mother, but she’s a lot of fun to read. And also, her closet is slightly terrifying because apparently Tilda gets rid of nothing, she has never Marie Kondo-ed a thing in her life.

No, I am not particularly tall, and I find tall people in general intimidating. So, I was like, well, I’m gonna make her really tall and I’m gonna have her wear high heels all the time, because she’ll scare the crap out of me that way.

She is absolutely, absolutely her own person. Tilda and Chip, her husband, let’s say they both come with pedigrees. I’m choosing that word deliberately because it does feel like someone’s checking the horse for the teeth and making sure that the papers are there and all that, but then you throw in the Jehovah’s Witnesses and not in the way that people might assume when I say Jehovah’s Witnesses. Let’s talk about money in New York for a second, in real estate.

Well, it’s so hilarious to me that I didn’t even realize until I was like, I don’t know, not elbow deep, but wrist deep, in the novel, that the family was going to work in real estate. And I do kind of think of the Kushner family a little bit. I think of them as sort of like, the Cuomos meet the Kushners meet like, I don’t know maybe the Bushes or something. You know, like the family has been featured in Vanity Fair and they made their money originally by investing in New York real estate and then started buying up property in Brooklyn Heights. And then as residents of Brooklyn Heights know, so much of that neighborhood used to be owned by the Jehovah’s, all of these incredible buildings, like first of all the watchtower, the huge newspaper operation, the Bossert Hotel. And then, interestingly, when the Jehovah’s lived in Brooklyn Heights, part of the reason Brooklyn Heights does not have as sophisticated a restaurant culture as like Cobble Hill or as the neighboring parts of the city is because the Jehovah’s ate exclusively in their dorms. It’s fascinating. There were these huge apartment buildings, all of these apartments, none of them had kitchens, and they had big residential dining halls, which meant that there was just a huge population in the neighborhood that was never going out to eat. But then also, when they sold out these buildings, flipped them, they had to be gutted, because who’s gonna buy an apartment without a kitchen? My other favorite tidbit is that all these Jehovah’s buildings, many of them were connected with underground passages. Oh, let’s get on the YouTube and look at that, but there were underground passages that had laundry, that had little convenience stores and so people could, you know, just go underground from one building to the next. When the Jehovah’s moved upstate, and they sold these. They’re like— they had gotten permission from the city to have these underground tunnels. But they just had to fill them with cement, because can you imagine living in an apartment building and someone from another building can just like wander over through the underground tunnel? Teenagers smoking in about five minutes.

That and possibly building some skateboard ramps, but no, thank you. Yeah,

But so, the Jehovah’s in the novel, the Jehovah’s vacating Brooklyn Heights was an excuse for the Stockton family to double down on their investments in the neighborhood. And it means that they just own a huge swath of some of the most expensive real estate in Brooklyn.

Research. It sounds like there was some research, I mean, some fun stuff, obviously, too. But real estate in New York is complicated in way, especially commercial real estate, especially the kinds of parcels that you’re talking about. It’s not just you walk into your local realtor and knock on the door. So, you have to do a little bit of research.

Yes. And this is where it helps me out that there are so many New York bloggers who are absolutely obsessed with real estate, I mean, from like, Brownstoner, to the Brooklyn Eagle to the Brooklyn Heights Historical Society. I mean, I went down every rabbit hole there was and tried not to get too lost, because I didn’t do like, take a day off and research then go back and write I would sort of be like, oh, I want to write that, let me look around and see what I can find out. And then sometimes I find something interesting that I’d like scribbled down to tuck in later or something. But especially, you know, on Malcolm’s storyline with all the aviation investment banking, my first draft didn’t have as much detail about the ins and outs of investing in American Airlines and the possible merger with like a small South American airline. That was a lot of stuff that then I went and researched after the first draft.

I have to say to you, I was very happy when Malcolm popped up. I was like, wait a minute, not everyone’s white.

Not everyone.

I say that with love. But there are times where, you know, worlds get really small, and when you’re representing a certain slice of a community, and I was like, Wait, there’s a Brown guy. This is great.

I think it’s so fascinating to me to juxtapose how the Stockton family felt about welcoming Malcolm to their family versus how they feel about welcoming Sasha to their family. Malcolm for them feels much more culturally similar, because he’s rich. And I mean, we see this all the time. I’m not comparing the Stocktons to Trump in any way, but haven’t we seen over and over that, of course, Trump is racist, but he’s actually more classist, than racist— if you’re rich enough, then you kind of get a pass. And so, it was interesting for me to see how for the Stockton parents, Malcolm made perfect sense in their family. But then it’s Malcolm’s wife Darley, who’s really grappling with well, what’s it like to raise biracial children in a neighborhood that’s so white? And why are our friends so white? And why is our club so white? And why is our school so white?

Yeah, she has a moment where they’re visiting, outside, they’re in Connecticut. And she thinks, oh, this is great, we should move out— and it’s really not what it seems and that’s all I’m going to say because it’s just, the way you set it up, I got kind of excited, too. I was like, oh, maybe that is progress.

Right? Let’s head to Greenwich.

I mean, you are you’re writing about class, you’re writing about money. You’re writing about mobility in ways that are fun and poppy, and you let your characters do what they’re going to do. But they are wrestling with big ideas, and I don’t want to leave that part out. Because I mean, I felt like I was a little smarter after I read your novel without feeling like you fed me my cultural vegetables. I didn’t feel like you were saying now, hey, fellow New Yorker, you need to learn this. It was more like; can you believe these people?

Yeah, yes, I’m definitely a catch more flies with honey philosopher. But I was just so interested in the way that different generations look at inherited wealth. I mean, I was born on the cusp of Gen X. I’m 43. And I grew up with a really shallow view of generational wealth. I sort of you know, I grew up middle class, and I love watching Troop Beverly Hills and Lifestyles of the Rich and Famous, and MTV Cribs and my basic attitude was like, money. That seems cool. I would like some. And I think that the people who are on the far end of the millennial generation that people closer to Gen Z have a much more sophisticated view about money. Some of that is just because economic inequality has become even more stark while they’ve been growing up. Some of that is because they watched Occupy Wall Street, some of that is because they voted for Bernie or AOC. And it’s entered the cultural conversation in a different way. But I think people in their 20s now instead of saying that seems cool and I want some are saying, but what does it mean to inherit money? And how is that just and how can you be a good person and be incredibly rich at the same time? They’re saying I don’t know if that’s possible. And so I wanted my characters to wrestle with that. I wanted to have characters that represented different sides of this generational divide, to have to think on about how to be good, and what goodness means when you’ve been given more than your fair share.

Yeah, and I mean, we’re in this weird moment in America, where it feels like the 80s have come roaring back in all of the terrible ways. I honestly can’t really think about a lot of great things from the 80s and now granted, I was young, but you know, I can read newspapers and whatnot. Like there doesn’t seem like a lot of 80s legacy that we would want.

Just Madonna. That’s it.

Madonna. Great. Otherwise, now, the rest of it, and we’re living in it now. And I’m just kind of like, we did this before. It was not good. And just see this younger generation sort of like, yeah, that was gross. That was super gross. And they don’t quite find out that quickly, because otherwise we wouldn’t have a book but seeing Georgiana and Darley and even Sasha to a certain extent, I mean, Cord, her husband is very nice, man. He’s a very nice man. I think Sasha wrestles with things a little more than he does. And you know, the idea. And I think plenty of us have wandered through these houses that are stuffed with stuff and it’s because a great grandparent had it. And you’re just like, Oh, okay.

Yes, the brown furniture and the watches and the oil paintings and right Marie Kondo did not come for them. They saw her, and they said, No, thank you.

But it is a really clever shorthand. I mean, it really, like this idea that your stuff defines you. Yes. And yet, they’re kind of traipsing through the world. And Sasha has that to a certain extent, her family is very different from her in laws. But there’s a little bit of my stuff defines me. I mean, her brothers, her brother sounds slightly terrifying. And they’re very funny New England way. Very familiar characters. They’re huge. They’re just huge.

And they’re wild. They’re ill behaved. They’re wonderfully drunk and stoned.

They’re kind of defined by where they come from, and what they do and who they hang out with and the people they sort of adopt. There’s a backstory in there that we’re also going to let people discover.

They don’t think that Sasha has married into a cool family at all. In fact, they sort of think that their sister’s a social climber. They think it’s sort of gross that she all of a sudden has access to money and they’re pretty wary about the whole situation.

Yeah, and it’s frustrating a little bit because I mean, honestly, she just really loves her dude. She actually did just marry him because he’s the one for her kind of thing. And so to have all of these people on both sides for piling stuff on, there are lots of people who ascribe stuff to Sasha, where you’re just like, no.

They all bring their own class consciousness to interactions with her and because she’s the one falling back and forth on either side of the fence, she’s making everybody uncomfortable wherever she goes.

Although I will say when she and Darley are developing their friendship, I was quite enjoying that. I was like, alright, something’s gonna happen. But for the moment, this is really fun.

I think that Darley and Sasha share a sense of humor. And so, I really liked writing their conversations, because one of the things that Sasha and Cord have in common, one of the reasons they fall in love is that they share just a natural silliness, they have an attitude towards life, that is just they’re more inclined to try and find the funny in the world. And it turns out, Darley is able to let that side of herself show with Sasha. So that’s kind of how their friendship feels natural. Georgiana isn’t especially silly; she takes herself more seriously. And, you know, she’s younger, and she’s a pain in the butt, as we’ve said, and so she doesn’t find that same easy banter with Sasha. But it was fun for me to create that between the two characters, just an organic like, they get along and they’re funny together.

And the thing that I appreciate is everyone actually has an arc. There’s no one just sitting on the sidelines where you’re like, well, I need to have this person because it fits in the story. But everyone has an arc: like Malcolm goes through some stuff and Darley goes through some stuff and Georgiana definitely goes through some stuff, even mom and dad have a little bit of a tweak. And I mean, certainly Sasha and Cord, and it’s just, it’s really nice as the reader to be able to invest in all of these different pockets of story, and then it really comes together.

Good. I had a blast writing the end, and I’m not gonna give it away, but when I wrote the last lines before the epilogue, I like I made myself laugh, writing them. And I was like, oh, man, I don’t know if my editors are gonna let me keep this, but I like it.

Was that the biggest surprise for you?

Yes. But who knew that— I didn’t know this about writing, that sometimes something funny just pops out. And you’re like, Am I allowed to do that? I don’t know. Let’s try. I mean, it does sound like one of those things that writers say that always seems kind of like, fake. You know, like, it just came to me. A voice spoke to me. It just poured out. But once in a while. I mean, it really feels like, I don’t know, it’s coming from somewhere else. And it’s awesome.

But you’ve also worked with some very, very funny writers too. I mean, Katherine Heiny comes to mind, and I mean, yes, Gabrielle Zevin Tomorrow, and Tomorrow, and Tomorrow. Like, it’s not a consistently laugh outlet. But she has some moments in the book where you’re just rolling because it is so funny. I mean, that humor piece I do associate and actually I just interviewed Ayobami Adebayo and she and I were laughing so hard. Okay, Spell of Good Things. Not the funniest.

But it does have moments especially with Wuraola’s mother.

Yeah, exactly. And stuff like that. And I’m just like, I do associate that sort of underlying humor, with the work that you do when you’re not writing the story and I really appreciate that. But can we talk about some of your literary influences for a second? Because I feel like that’s something that is not easily or quickly learned and it’s something that comes with time.

Yeah. Interestingly, I think the kind of book that I’ve written, I hope is in line with what have always been my favorite books to read. Like, I’ve always loved Laurie Colwin, she’s been a huge influence for me. And then I read Bridget Jones’s Diary when I was in, I don’t know, I think I was a freshman in college and fell so deeply in love with Helen Fielding, and then I ended up getting to edit her last two books, which was just kind of full circle. And then you know, Katherine Heiny, Jennifer Close, J. Courtney Sullivan, Lauren Fox, Dolly Alderton, so many of my writers that make me laugh. And I think that one of the things I look for in my friends, definitely in my husband and my family are people who are smart, that can make me laugh. And that is what I want in, it’s not always what I want to read, but there’s definitely a time when that’s what I want to read something that makes me feel okay about the world and that finds the funny in it, you know, and so that was very purposeful.

Yeah. And also, I mean, I so appreciate humor that feels organic. That feels true to the characters that isn’t like someone trying to tell me a joke, because they’re like, I gotta work a joke in here writing to get a joke and it’s, oh, no, I just totally believe that person would make that crack. And like, we all say ridiculous things going through life, but to have that sort of space to breathe, because again, you and I know I said this earlier in the show. you’re wrestling with some pretty big ideas about class and identity and belonging and all of those things that make drama really great. But to have those moments were really, really funny stuff happens…

Well, Katherine Heiny definitely taught me a lot about building a joke, because Katherine Heiny, I mean, she’s both a novelist and a story writer and I think if you read her stories carefully, you can learn a lot about how to build in a joke. And the jokes are, as you said, they’re from character, you know, and it’s once you know the character, and then they say the exact thing that you knew or dreaded that they would say, and it’s so funny when they do.

Yeah, I just got my galley actually, for Games and Rituals, the short story collection and I started it, the bridesmaid dress. I mean, there’s some great stories in the collection.

I actually, I can’t walk past an airport bar now without thinking about the characters in Katherine Heiny’s story who spent a whole day at an airport bar.

Yes. And we’ve seen those people if you fly at all, you’ve seen those people.

I saw a woman drinking a glass of red wine at eight in the morning last time I was in the airport. And I was like, red wine at eight in the morning?! Hmm. Okay.

You’ve mentioned a couple of different things that you’ve learned being on the writing side of things, you know, certainly structure is different. And I love the idea of talking about structure with writers because I think it’s something that if it’s done, well, you don’t notice it. And if it’s not done, well, oh, you feel it. So, you weren’t necessarily outlining as you were going, you’re researching as you go. It sounds like voice is the thing that you latch on to first, as a reader as a writer as an editor. Am I right about that?

Absolutely. Yes.

So, for me as a reader, voice is part of structure. It’s not just dialogue. It’s not just like, it’s all of those things mixed up. It’s all of the things and you just know it when you hear it. It is the worst cliche in the world, but it’s so true.

Yes, yes. And in some ways, you can think about how voice occupies that narrow little window between the omniscient narrator and the character who you’re reading about in close third, that that little slice is kind of where the voice works or doesn’t work.

Okay, but when do you know that you have it? You know, as a writer, it’s not going to be the same moment as the editor, right?

Yeah. I mean, I think, as an editor or as a reader, I think within a first the first few pages of something you’re like, it’s not— do I like it or not? Because I will read about characters who are despicable. I will read about, you know, scary things, whatever. But it to me, it’s do you trust it? And as a reader, if after a few pages, I trust it, then I’m going to keep going and see where it takes me, I may or may not end up deciding to publish that or even finishing it as a reader. But do I trust it or not is the most important question, I think that as a writer, when you’re finding the voice, it’s like, you’re either in the zone or you’re not in the zone, and it’s either pouring out or it’s not pouring out. And if it’s not pouring out, then just call it a day and go for a walk or work on your taxes or whatever, because you’re not going to get it that day. I know that there are people who say like, writing is about sitting your butt in the chair, but some days, that’s a waste of time.

For me also, as a reader, like I don’t necessarily think it’s fair to say to someone, give it 50 pages, it really picks up from like, no, we kind of have, you know, whether you’re an editor or bookseller, in my case, like we kind of— it’s up to us to be able to say no, no, like, let’s get moving the minute it happens, and asking someone to give you an investment of pages, and pages and pages before there’s any kind of real payoff seems ill considered and definitely frustrating for me as a reader. I mean, there’s stuff that I’ve just dropped because I’m like, no, no.

Yeah, as an editor, I’m always saying like, don’t put the dragon at the gate. You don’t need to scare people off from getting into the book. And it’s interesting, because I confess that, you know, it being February and you know, our emotions being tied to the sun, I’m kind of in this little window of the year where I often want to read things that are uplifting, rather than things that make me feel crummy. But I started reading Age of Vice, which begins with violence and poverty, and but the voice is so good, that like, you couldn’t tear it out of my hands. I’m like, it may be February, but this voice is going to take me through the month.

That is always the thing that I want the most of and it is the hardest thing to do. And for me voice can’t be separated from language though, like it’s not enough— like voice is built off of great language. It doesn’t have to be beautiful, but it has to be great and it has to be precise in ways that only fiction can pull off and there were a lot of moments where you do it in Pineapple Street where you know, it’s the house of itself, or the new maisonette that the parents are living in, or it’s something that Darley says, or Georgiana does, or, you know, or Sasha, frequently rolling her eyes, it’s like a full body eyeroll from Sasha going, who are these people, but you do it in a single line. And I think that’s the kind of stuff where it’s not enough to just say, I’m going to move the story forward, though stuffs gonna happen. It’s more like, well, why am I so invested? Why? So, can we talk about your editing process for you, though, as the writer? Are we doing sentence edits kind of thing? Are we doing that level? Are you just doing the first pass? And then you’re going back and sort of picking around like, where does your agent come into it, where does your editor come into it? Where do you turn off your editor brain?

Yeah, I mean, I didn’t show anything to anyone until I had what I thought was a pretty perfect first draft, because I’m definitely not one of those people who’s like, hey, take a look at what I’m messing around with. It’s like, no, I also like don’t go to the bus stop in my pajamas in the morning. I’m like, that’s just not me. And so I didn’t show it for a while. And then I have the fascinating experience of being edited by three editors at once by Pam Dorman here in the US, and Nicole Winstanley in Canada, and Venetia Butterfield in the UK. And I’ve been on the other side of this, because when we edit Emily St. John Mandel, I edit alongside a candidate in the UK for Ayobami I edit alongside the UK, so I’ve been on all sides of this. And it is harder to edit as part of a team, but it is actually way hardest to get edits from multiple people at once, especially when they’re not always all in agreement on everything. But I, I kind of felt like, well, gosh, I have the opportunity to have three women who I revere, give me comments. So let’s bring it on and I’ll just like, you know, turn on the hose and all like yell mercy when I can’t take it anymore and it was amazing. Because yes, I did feel like, there were certain things that you know, that a certain editor was like, we have to know the intentions of this romantic— you know what I’m talking about, we have to know his intentions were and I was like, people do weird stuff in love, we’re not going to know that. So, there were certain guns that I stuck to. For the most part, I took almost everything they said. And I was, I felt like it was crazy how I was able to just be like, no, I understand. I’m the author, and I can’t see I get a little snowblind. So, you have to tell me, does this work? Does this not work? And they saved me from myself. On some a couple of dumb things I was trying to do.

I mean, granted, I’m just, you know, churning out lots and lots of copy. But having an editor and knowing that you have someone who can save you from the stupid thing is just, yeah, I, you know, whenever I do events, someone just like trust your editor, like people are asking for advice on they’re not just like, trust your editor, find an editor, you’ll need a team of people to help you sound like all of this is effortless.

Exactly. No. And it’s also funny, because I think a lot of authors have a few trusted readers and they, sometimes there are other authors, sometimes there are people from their book group. Of course, you never want to edit by committee. But I will say that it’s really ideal to have four or five people cast their eyes on it. Because if they all tell you one scene stinks— guess what that scene stinks. There were a few things I was attached to. And I needed to hear from three people that it was garbage and so I cut the garbage, but it is actually helpful to have a few people read something.

With all of the work that went into this book, do you miss Pineapple Street, I mean, not your old house on Pineapple Street, but Pineapple Street.

Do you know what I miss? I miss the feeling of in the mornings after I’d write for a while and then after I’d you know, get the kids fed and either off to school or stick them in Zoom with my husband, I would go for a run. While I was running, I would think about what I had just written. And then something new would come to me. And literally I would be like, trying to like scream dictation into my phone while running down the street. Like I gotta get home before I forget this, like burst in the door covered in sweat, just sit down at my laptop and be like “and then Tilda said this!” Just like get it all on the page. That feeling is so good and I would love to have that feeling again of just like, I have something so funny to say and I’m gonna write it down. You know, what a gift. I loved it.

So, does this mean we get more novels?

Oh, I hope so.

Okay, how in the world? Are you going to do this? I mean, we’re also back in the world. I mean, that’s part of it. Like, we’re not working from home as much as we were in a lot of cases.

I know. That’s the hard part, it turns out like social energy is the same thing as writing energy for me. At some point this summer I’m going to visit my brother; my younger brother lives in Hawaii. So, I’m gonna go out there and we get a one month, sabbatical every 10 years at Penguin Random House, I’ve been here for 20 years. So, I get my sabbatical. So, let’s see if we get a little something done.

So, there’s something percolating. Because, you know, that’s the other piece of conventional wisdom that we hear a lot of, is the whole, you know, have the second thing happening as the first one is coming out, kind of thing. And I know you’ve been through this a million times. I mean, some of my favorite writers are edited by you. But it’s really different. I mean, don’t you feel a little more exposed? I know, this is not auto-fiction. We’re not, yes, you lived on pineapple Street, whatever. This is not auto-fiction. But at the same time, writing and reading are really intimate acts. And I don’t know that everyone always considers that when they sit down to do the thing.

No, and you know, what is great. I’m glad that I waited to write a novel until my 40s. Because I think that I like who I am better than I liked who I was in my 20s. And I feel like, you know, not everyone is going to love any book, but I feel pretty great about it. And I feel like confident putting it out there. The thing where I feel exposed is that professionally, I pride myself in publishing my authors really, really well. I pride myself in making hits. And so, I do think it’s on me to make sure I do a good job with this book, too. You know, like, that’s where I feel a little exposed.

I can imagine turning the tables is, you know, not the most comfortable thing you’ve ever done.

No, but in life have you ever done anything that was really worth doing that didn’t scare the crap out of you?

No, no, straight up no. Yeah, no, I’m very glad you did it. I mean, I have to say, this book is gonna be a lot of fun to sell. And I do think that sometimes, and I love knowing that Kevin Kwan has this post it note—I run my life with post it notes, but he has this post it note that says joy over his computer. I just think that’s really charming. And why not have a little fun, even when we’re talking about big messy stuff, and imperfect people and everything else? Why not have a little fun? The jacket is great, too.

The jacket is great. They nailed it on their first try.

Are you kidding? No, that does not happen often. There are times where I open up boxes of galleys, and I’m like, oh, okay. I have to chat about this.

You know, they nailed that on their first try. And thank goodness, but also, because for work, I see jackets all the time, there was no dithering because I’m like, no, that’s categorically a good jacket. Yeah, what was done. So easy.

The things that you learn on the backside of books. I mean, that’s, that’s the thing, you and I both been doing this for a minute, you end up with knowledge you never knew you wanted or needed. And it’s really helpful. It is seriously helpful to understand how all of this works. One thing though, before I let you go because you have a day job, and I technically have a day job that isn’t always just talking. But if someone were coming to you for advice about getting started on that first novel, because we are, you and I are talking in February, obviously this is going to air update, but there’s always someone somewhere sitting around thinking, this is the time, I need to do this, I need to sit down and write this novel. What do you tell them?

I think that I look to Katherine Heiny, because Katherine had her first short story published when she was 23 and it was published in the New Yorker and then she didn’t publish again for more than 20 years. And since then, she’s published two novels and two short story collections. The thing that I want to take from that is that it’s never too late and you can tap into that creative vein, whenever you’re ready. It’s there. You just need to be ready for it.

And that seems like a really great place to end the episode. Jenny Jackson, thank you so much. Pineapple Street is out now. There’s a whole slew of fabulous books that you’ve worked on, that are out in the world, and everyone can go find them. But really, pineapple Street is out and that’s where they should start. Thanks so much. Thank you.

Thank you. I appreciate it.

Miwa Messer

I’m Miwa Messer, I’m the producer and host of Poured Over and I am so, so happy to see Ann Napolitano, Hello, beautiful.

Ann Napolitano

That’s so nice.

So the new book Hello Beautiful follows Dear Edward, which everyone has read, a lot folks have seen on Apple+ now. But Hello Beautiful is a little different., it’s a little different. So, an homage, a tiny bit, to Little Women set in Chicago.

Yes, although I didn’t intend it to be an homage to Little Women,it is, like very pleased that that showed up. But it wasn’t something that I knew when I started the book, I sort of just stumbled into that. It’s about four sisters who live in Chicago and they are very close knit, strong willed, young women in a family that has a lot of love and a lot of noise. There is a young man named William Waters who grew up, because of a tragedy in his family, he grew up in a home that had no love and no noise. And he sort of enters the Padavano family orbit and they take him in and sort of the collision between the way that he was raised and the world that they live in, changes all of their lives. At some point the for Padavano sisters in talking to each other start comparing about which March sister they are. And when they did that, you know, because sometimes the characters will say things that I wasn’t planning for them to say, you know, that’s part of the fun of writing. They said it I was like, oh yeah, there’s four sisters, like the March sisters, and there’s an outsider boy like Laurie who was lonely and was like peering in the window at the vivacious love filled room that the March sisters were in. And it’s very similar in my book that William is peering through the living room window, metaphorically, and wants to be part of what’s inside. So once that came up, I was like, oh my gosh, that’s so interesting. And I obviously I loved Little Women as a child and as sort of like a foundation block. Like all the books that you read when you were like eight years old, just sort of stick.

When did you start writing this though, because I mean, Dear Edward came out in January of ’20 and we are taping in February of ‘23. That seems like a really quick turnaround.

For me, it is unbelievably fast. Dear Edward took eight years and the book before that, that I wrote also took eight years. But actually, the timing is explained for me why— so Dear Edward came out in January 2020, and I went on book tour for like two months, basically and then in March, the pandemic hit. And I was supposed to go on like another wave of book tour, but it got canceled. And you know, I did some Zoom events. But basically, obviously, we were all home and particularly living in New York City, we were all home. And in April 2020 my father died in the beginning of the month, and he had been unwell, but we didn’t anticipate him dying so soon. And because of the pandemic, we were unable to go be with him when he died, and we were unable to gather after he died. So, it was like, so many people went through this. And it’s very difficult and sort of, you know, sort of unprecedented in all of our lives and all the ways that we were pulled apart from each other. And I started writing Hello Beautiful that same month, I had been thinking about the book for a while so it’s not like it came at me from behind a door. But it really took me and like pulled me in completely in a way that I’ve actually never experienced before. And for two years, it was like I was feverish with it. I was working through like my own grief and like sort of the isolation and my father’s death and the pandemic sort of threw my family of origin into disruption and disrepair. I ended up writing my way into this story that was dealing with all of these issues of connection and loss and grief. And it felt like I needed this story as I was writing it in the same way that like William needed the Padavano sisters, I needed the Padavano sisters. But it was so intense because I was like, I needed it right now and I had to write it right now. So, there was a compulsion to it and a sort of intensity to it that like I felt like saved me. But also, it was, you know, fairly intense is the only word that I can think of.

Hearing you say all of that I can only imagine what it was like living with this book and the two years that you’re writing it. I mean, you start in the 1980s. It brings us up through roughly 2008, right after sort of the recession starts. I mean, November of 2008 is sort of where we get to and we’re in Chicago. I wasn’t expecting…

Yeah, me neither. But the explanation for that is really the explanation for the title too. My mother has six brothers and sisters, and I grew up in northern New Jersey and all of them grew up around us except for one, my mother’s brother moved to Chicago like before I was born. And so, when I was a child, he would send me postcards that were addressed to “Hello Beautiful.” And I knew that he didn’t really know what I looked like, because he hardly ever saw me and he had like, a bevy of nieces and nephews. So, I felt like he was seeing that I was beautiful on the inside and since I was very shy and bookish, that like felt real and appropriate in a way that made me love that greeting. I had this vision of Chicago, and this neighborhood that he lived in Pilsen, which was covered with murals that like kind of lived in my imagination in the same way that like, Anne of Green Gables did, and Little Women, you know, so it lived inside me in this like, place. And so, when I started writing this book, it was like that place appeared again, and the father in the book, Charlie, that’s how he greets his daughters, whenever they enter the room, and he says, hello, beautiful, and he really sees what is beautiful in them in a very truthful way.

I have to say. There’s so much love in this book. It’s not overwhelming. It’s just, it’s a delight. You cover a lot of ground in this book, but there’s so much love, but I wasn’t expecting the 80s. It feels like that’s uncharted territory for a lot of writers like, we’ve got the postwar years covered, we’ve got the 60s covered, we sort of have the 70s covered, and certainly, you know, plenty in the last 20 some odd years. But the 80s— it feels like not a lot of people want to touch that and I’m wondering why you just start there?

Well, I’m a child of the 80s. I mean, I was born in 1971. So, my teenage years were the 80s. So, I have a great affection for that time. And I also I think because of the age I was during that time, there are ways in which the Padavano sisters are naive perhaps to the world around them and I was naive in the same way. The first out gay person I knew was when I went to college, like, which is unthinkable now, like, that would be impossible. But that was the way the world was, you know, for many people at that time. So, it was a very familiar ground for me because I was similar to their age during that time,

Who showed up first. I mean, there’s Julia, there’s Sylvie, there’s Cecilia, there’s Emmeline. I mean, we’re gonna put William off to the side for a second, but of the Padavano sisters who are all, they’re so great. Who did show up first?

Julia. Yeah, she’s the first one who appears in the book. And she is the oldest of the Padavano sisters, and she’s the leader and she is very directive. She is like a natural director, and she wants to plan her own life and plan the lives of the people that she loves and so she sort of marched in at the head of the queue of the Padavano sisters.

So you’re working, Edward is out in the world, all of the family stuff is happening, the rest of the world has, you know, it is what it is. You start in the 80s with Julia, you’re starting with her in the in 08, and were sort of working backwards. I mean, she’s a great character. But man, when she’s on the page, you know, Julia is there.

I knew one or two things that were going to happen in 2008 when I started. At one point, something that happened in 2008, was the prologue so that you have a sense of the book. So, there was there were things that I knew I was working towards, but there was a lot I did not know before I got there. So I really wrote it in the order is written to try and feel my way through their lives chronologically. All of the interaction between the sisters and their mother, Rose, and their father, Charlie and William, so much that happens in the 1980s is still resonating in them in the 2000s. When I think about when I write, the thing for me, it’s like, it’s all emotions for me. I feel like I write with like an emotional tuning fork where each sentence, I’m like, is this true? Is this true? Is this true? And if it’s not true, I have to go back to it. And they’ll end up being a scene where I’m like, I could tell this is an important scene and I have not yet reached the emotional pain that I’m working for. I’m not sure exactly what it is yet, but that’s what my process of writing is. It’s like a feel for about the emotional truth so that I had to make sure everything was emotionally correct in the first part of their story before I could, you know, build correctly into the latter part.

Basically, you know it when you see it.

It’s like, I feel it. It feels almost like music. I barely listen to music, which I always feel guilty about, but I actually think it’s because language is like music inside me all the time. And so when actual music is playing it’s like too much for me.

No, no, I absolutely, absolutely get that— basketball has its own music. Basketball was a huge part of this book, and I wasn’t expecting that at all. And William, I mean, he’s a really lonely kid. The opening of this book is really wonderful. I think of it as like, sort of, perfect pitch Ann Napolitano. He’s a really lonely kid, basketball is the thing that ultimately saves him, I did not know you were a basketball fan.

Well, when I teach fiction writing, which I do, like erratically, I always talk to my students about paying attention to their obsessions. And I tell them to think about like all of us, not just writers, everyone has like a magnetic board that’s inside them like a refrigerator magnet board, and it fills your fills your torso. And you have to pay attention to listen for what thwacks against your board because it’s going to be something that’s different than like your partner or your best friend or your twin sister. As an artist, you have to listen and pay attention, because it’s very easy to be like, oh, I should be reading that novel, or I should be watching that movie. You have to be like a real weirdo as an artist and really pay attention to the things that are calling to you so that you can draw on them in whatever strange way they want to appear in your work. And so, like for Dear Edward, I became obsessed with this specific plane crash. And I was like, why I have no idea I don’t even I hate— I don’t want to read a book about a plane crash, yet I’m compelled to write one. And like a couple years before I started this book, I became obsessed with the history of basketball. I mean, it was partly an interest in social justice that like reading about the history of social justice that led me into the history of basketball and figures like Bill Russell and Kareem Abdul Jabbar and the Cleveland summit that they held, but there’s all these different athletes in the Vietnam era. It’s like, fascinating to me. And I actually, like wanted way more basketball in this book than was appropriate, unfortunately. There’s just something about that subject that I just became obsessed with. And I still, I read so many books about the history of basketball, so many great books. I listen to lots of basketball podcasts, I played soccer growing up, I’m married to an Englishman who’s like obsessed with soccer, like none of this makes sense, but for whatever reason, like Bill Russell is my hero. There’s just something that pulled me into it, and I knew when I started the book that the main male character was going to be a basketball player, and I interviewed like an NBA physio when I was in Los Angeles, and like, it was so fun. I was like, oh, God, I wish there was more.

It’s a great way for you to though, to talk about men’s friendships. I mean, you write about siblings, in amazing, wonderful, well thought out ways and we’re going to come back to siblings in a second. But the idea that William is surrounded by his former teammates, that he’s surrounded by genuine friendships and lots of love from his peers and that’s not also something that we always get to see. And you write with such an intimacy for all of your characters, whether it’s William interacting with the sisters, the sisters interacting amongst themselves, but also William and his best friend, Kent, and there are some other minor characters. How did you get there? Does this just this go back to you with the tuning fork, and just knowing that this is what needs to happen for your characters in the story?

Yes, I guess so. I mean, I think part of what I loved about writing about a team sport was the team. And I do think for men, particularly, you know, both watching and participating in sports is a way that it is acceptable, and just sort of like comes out of them in a way that they can all deal with, and allow, and it’s a way for them to love each other and a means through which they can love each other. So exploring that through the team was really interesting to me. Because also, like, there’s the idea that a team is alchemy, it’s, you know, like the best team in the NBA, they have to operate as a team. If you have like the six best players, they’re not necessarily going to be great. They have to be all wanting the same thing. And like magic, like a music between them. Right? That was fun for me to write. And then I fell in love with his best friend, Kent. And I also just wanted to write about us, you know, taking care of each other and being kind to each other. And I do think that there’s more of that in front of our eyes than we often see in our stories or in our news, certainly, or in our news reports, there’s almost nothing I find as moving and as people being kind to each other in like a real nuanced, true way. So that’s always something that I sort of hope comes across like the story not necessarily like comes across in my writing, but I hope it appears and I hope it’s natural to that character, etc. And in a way Dear Edward was a boy walking out of a physical wreckage of a plane and William in this book is walking out of an emotional wreckage. And so people do come to see that and see that he needs something and they walk towards that kind people walk towards him in the same way that kind people walked towards Edward.

It’s almost impossibly refreshing in some parts because you’ve got this balance. You do this so well, where it’s just like, in some ways you’re writing about the intimacy of trauma, right? Like, we’re not going to go into huge amounts of detail here, obviously, because this is airing right as the book is pubbing and we want people to experience Hello Beautiful but there is an intimacy to trauma, there is a shared experience, there’s a level of trust and shared experience that builds this really tight, kind of bond. And yet, you’ve created a world where your characters actually have space to move and make mistakes and grow and change and evolve and it’s kind of amazing, because all of it is so organic. Like I believed every single moment of this, and some people do some wild things in this. Then we have Rose, we have mama Padavano, who can be a handful. Oh, wow, she can be a handful. But you can see where her daughters get some of their personality from, I mean, it’s certainly like they have plenty of Charlie, their dad in them too. But Rose, woman of her time, everything else. So for you, though, as the writer, I don’t remember from earlier conversations, if you’re an outliner, I don’t think you are, but I can’t remember.

No. I needed some level of like, thought and planning. And so for Dear Edward and this book for the first year, like, prior to me starting writing, I don’t let myself write what I call pretty sentences because I once I start writing, then I’m in the music of the language and things are happening and but I can’t think anymore. So, for the first year, which in the best-case scenario kind of overlaps the prior book coming out. So, like, you know, while Dear Edward was in production, I was thinking about the next book. I researched— that’s when I met with like the NBA physio, and I read all these books about basketball and thought about who I wanted these people to be in it and I took notes and all this kind of stuff. There ends up being maybe like 40% that I know and then there’s 60% that I have no idea. In this book, because it does span such a long time there were some things that I knew happened in 2008, but I had no idea how we were going to get there. Unfortunately and fortunately, I guess, I can’t outline and the true like Ann Patchett, John Irving way, because that seems very handy. My brain doesn’t work that way. But I do some of it.

I will say there is, and I’m certainly not the only person who’s going to pick up on this, but there’s a bit of Commonwealth, Ann Patchett, there’s a similar feel to Commonwealth— that kind of epic overlay to essentially a domestic story. I mean, this is the story of family figuring out who they are and who they want to be and where they’re going, and I also envy the real estate a little bit. There’s an epic house that ends up happening, 2008 was a really long time ago.

Yeah, for sure, exactly. I did not want to write about the pandemic, etcetera.

Oh, I don’t blame you. I mean, also these characters, when you say, you know, you kind of wrote this, I don’t want to say in a rush, but you know, kind of obsessively, I get it, it never slows down, which I really appreciate. Because even when there are some scenes where you would expect things to slow down and yet, because the characters are coming to grips with their realities, it never slows down. It’s never just sitting in one place, which I found a little unexpected. I just, I knew the basics of the story when I picked up the book, but you cover a lot of ground.

A lot of people write a book in a year, so I can’t act like this is insanely fast, but it is for me, I felt like oh my god, I’m writing a soap opera, like I’m writing something like that has melodrama and like big swings of life choices, etc. The criticism of my works overtime, which I’m I understand, is that nothing happens. Because I am really interested in the emotional interiority of characters like across the board. So, when I was writing this book, I was like sweet heavens, look, there’s a lot happening— maybe too much. But then, you know, hopefully, and then as I got in deeper, I was like, okay, I can deepen it, this is not a soap opera. This is just the notes that I knew I needed to hit and then I have to do the connective tissue to earn it.

Did you surprise yourself? While you’re writing this book, it feels like maybe you did.

Yes. I mean, this was my most personal book. There’s a strange thing to say because like almost nothing that’s happened in the book has happened to me. But my whole heart is in this book and my own heartbreak and grief and the things that I was struggling with, worried about, sad about are all worked through in this book. And that continually surprised me. For Dear Edward. I felt like I walked into that world every day when I wrote and I was so happy to be in it, even though it has a lot of sadness in it. This book felt like it took place in my body, and I had a fever with it. So, I felt insane parts of the time and just feverish with it. And the whole state of it, I was like, I have no idea if this is good at all. I can’t tell, I honestly can’t tell ever all I can tell is this right? Is this right? Is this right? So I was desperately trying to make scene after scene right, so that I could eventually hit some kind of peace. So, I feel like this book is going to be reverberating inside me for a long time in a way that my other books haven’t just because I think it’s very much tied up into, you know, we all go through different phases in our lives. And everyone has had a weird last couple of years. So, yeah, I feel like, that’s part of how I was able to move through it and I feel very grateful that I got to do it with these sisters.

I mean, also, when you say, “right”, you’re talking about the emotional truth of whatever scene you’re writing, right? Not just, you’re not just putting together a puzzle pieces, so you can move the story forward. It’s whether or not it’s true to the character, true story, preferably true to both. And then you sort of move on. So how much of this is rewriting? Because again, you with the pretty sentences and like digging in there but balancing the story you want to tell the research you want to do and also, frankly, the craft. I mean, I don’t feel like I’ve ever see the seams in Hello Beautiful, it just sort of, it feels like here’s someone telling me a story. And I don’t want to put it down.

Well, hopefully, most novels by the time they get to you feel like that. You shouldn’t see the seams.

You shouldn’t, but…

The pretty sentences actually can be helpful because when I’m in a scene and, the language comes out of being this with this musicality that I’m sort of following the music, it pulls together and it just like is it works, and I’m like, okay, I hit truth. Like, that’s true. The lyricism of the language tells me that, but there are parts of the book that I struggled with and rewrote a lot. There’s a very dramatic section, in sort of the first half of the book, and Julia’s role in it, I rewrote many times, because actually finding the emotional truth of her reactions to the things that were happening was really tricky. It was like I was in the mud. And I had to go back in over and over and just be like, is this true, but over many revisions and other parts that just flew out.

You’ve taught writing for a really long time here and there, you’ve been an editor for One Story magazine, which I adore, can we talk about some of the influences that aren’t Little Women? Because I mean, obviously, it’s a great touchstone, you know, yes, the books that we read when we were 8 obviously, we carry around with us for a really long time. But you’ve been doing this for a really long time, you have a couple of readers, Hannah Tinti and Helen Ellis, who are part of your triumvirate, both of whom are fabulous, everyone should read them, too. I mean, so good, so good. But especially The Twelve Lives of Samuel Holly.

23:02

That came out, like right after Trump, and so it disappeared. It’s one of those books that so sadly, like, did not get the readership that it deserves. I wish you all to take it out of the library, buy it from your bookstore, it’s so good.

23:13

Big beating heart in that book, and so, you know, anyway, so sorry to run off on the side for a second. Seriously, who are some of the writers who helped make you Ann Napolitano?

I meant read a million books before the age of like 12, which Little Women fell into, there was like a voracious period of reading where I didn’t know anything about quality or genre or anything like that. So I read like all the Zane Grey westerns and I read all Lois Lowry’s, like, scary hallway books and all, you know, all the series that everybody reads. And that sort of filled me up to here with like this, all these and they’re all still in there, because everything you read, read at that it just stuck and Little Women is in there. When I was in high school, I read Doris Lessing’s, The Golden Notebook, there’s a few books that like blew my mind open and that was one of them where I was like, you can do this because there’s like a diary in it. And I was like, this is the kind of truth telling, like emotional truth telling, like the interior of women. I was not yet a woman. But I was like, this is amazing. That really had a big impact. And then, in college, I read the short stories of Raymond Carver for the first time and actually specifically the story “Cathedral”, about a blind man and this husband and I was just like, oh my god, I again, my brain exploded, and actually Henry James, I also read all of Henry James during college, I went into like a Henry James period. The Ambassadors is my favorite of his books and the main character, Strether, basically, he has gotten to like middle age and he has not made any choices in his own life. He’s just sort of let himself and he’s realizing, looking at this vibrant younger man who is trying to babysit, he realizes that he has no life, like if he he’s empty on the inside. And there’s something about that that still resonates for me where I always find him trying to write about how to live a meaningful life, you know, Ann Patchett, John Irving, Toni Morrison, obviously, like now I just read Demon Copperhead by Barbara Kingsolver, and that is such an important book about sort of the opioid crisis in this specific part of America and it’s so it’s just amazing. It’s a remarkable, amazing book, the books that I love now, it’s interesting because you feel like you get shaped for a while and now I’m just like, now it’s like, which books do I want to like hug to my chest and Deacon King Kong, Hamnet in the last couple of years, The Great Circle by Maggie Shipstead, the newest Emily St. John Mandel, The Sea of Tranquility. Oh, my God is so smart. I just delight in wonderful novels. I don’t know how much they seep inside me anymore. I feel like you get less porous as you get older. Now, I just have this deep, deep gratitude for wonderful books when I read them.

Yeah, but when I hear you rattle off that list, you know, the voice for all of those books is impossibly straight. Like it’s beautiful. It just pulls you in, immediately. And I know you read for language just because other things you’ve said. And I just— how do you balance though? How do you balance all of the things that you want to do as a novelist? The voice in the story and your characters and the emotional truth? Because sometimes they don’t always quite intersect until you pick at them a little bit and then you get them closer. So how do you balance all of that? Because ultimately, the voice is the thing. I mean, the voice in this book is so good. It’s so good.

Thank you. I don’t think about voice at all, as you said, I teach. So, I do teach craft that’s breaking everything apart, which is really interesting to do, for me, looking at other works, that I cannot do it to my own work at all. It really for me, it’s very dumb. It’s like, it is a place where like, this is right, this is right. The most upsetting thing to me in any kind of fiction is when a character does something that I don’t think that character would do. Like, that makes me so upset. That kind of is like the core value for me. So, the thing that I’m following through the book is the story is going to take me wherever the story takes me. I’m going to hope that that’s entertaining. And I am going to follow the emotional truth of those characters wherever it takes me. And I’m often you know, I am often surprised or confused by where it goes. Sometimes I’ll know that what just happened was right, but it won’t make any sense to me. That will be like two drafts later and I’ll be like, okay, now I understand because I have a deeper understanding of like, what happened with Charlie or you know, like, I think of that, like Q-bert video game, am I aging myself? The little guy Hopster? Mario Brothers works too, where you have those little like, islands that you’re jumping to. So, I’ll have like seven islands that I know. And then all the other ones will end up getting filled in. And I’ll know that those were right. They were right the whole time. But they didn’t fully make sense. They weren’t any good. I always say like, what I’m writing is pretty terrible for like, the first 50% of whatever the time is, like anyone who read it would be like, well, there’s, you know, potential. And then it’s in the second half where the stitching together happens, because I think that’s my interest and that is what I’m writing towards. Like, I’m not writing thrillers, or horror stories, or, you know, I so admire, like, outrageous twist endings. Like, that’s the kind of books where I’m like, I could never do that. I wish I could, but I can’t. But I can write you know, an emotional wallop.

When do you know it’s time to hand it over to your agent and your editor? I mean, are you doing it as you go? Or is it finally sort of, here’s X number of words and I’m ready to say okay.

This book was different than everything else that I’ve written in that I actually went to go so Kevin Wilson, the writer of many wonderful novels, who I love, he has the same agent as me, Julie Barer and I went to go see Kevin at a reading of his actually for… the exploding book.

I can see the jacket in my head, the children set themselves on fire.

Exactly. It’s so good. The book prior to the one that just came out in the fall. I went to go see him do a reading and in his reading, in the q&a, he said every the first 100 pages I write of my book, I give it to my agent so she could give me a thumbs up or thumbs down to be like, is this worth proceeding with or whatever? And I was like, oh, I want to do that. And I so with this book after I wrote 100 pages, I gave it to Julie, and she was like, I think we could sell this to my editor of Dear Edward and I was like what, like that had never occurred to me as a thing. And never was a thing, like I couldn’t have done that earlier in my career. And so we did. I essentially wrote the rest of the book where every 60 pages that I wrote, I gave them to Julie and my editor Whitney, which was very efficient. It’s part of why this took two years to write instead of, because I like to go off on like, 50-page tangents. And I’ll often follow a character, you know, I, I had characters that I mean chapters that I wrote, from the mother Rose’s point of view, I really liked to go into different people’s heads. So actually, they reigned me in in a number of ways that I would not have reigned myself in and that was really helpful.

I knew we were going to see a lot of Julia and I knew we were going to see a lot of William. But there are some other supporting characters who show up and they sort of get their big moments. And I was wondering if it was going to be a larger cast, but I love the way that it’s so tight, and you get everything you need, emotionally without giving everyone sort of their turn at the mic, if we’re going to extend this music metaphor. They need, story-wise like, you don’t miss a beat. And I was kind of amazed at how quickly I read it the first time. I’m just I’m kind of trying to do the muscle memory of what the read was. And I remember flying through it. And then obviously, the second time you go back and reading more for detail and rhythm and all of the things that you need to walk into an interview. I remember thinking, holy cow, this is amazing. This is amazing, because it flies. And again, I love the fact that part of it is set in the 80s. I love the fact that, you know, there aren’t a lot of cell phones unless we’re in you know, 08. And even then it’s not everyone, like it’s just there’s much more serendipity, there’s much more discovery, there’s much more being in a place and in a time and I just I really liked being centered with these characters in a way that I hadn’t necessarily felt. I’m trying to think of there’s something recently I’m like, now, actually, because you just have this expansive emotional terrain that not every writer can do, which I really appreciate.

That’s very nice. Thank you.

Question, though. Have you started the next one?

I’m thinking about it. I mean, I have an idea and I’m doing research. Yeah, I read The Overstory in the last six months which I had not read before, I felt a call to arms and listened to many, many interviews that Richard Powers did, in one or two of them, he says I feel that it’s a responsibility of our contemporary novelists to take this on, that as we diversify the worlds that we write about more and more, which is necessary and wonderful, that we have to diversify into the world around us too. Because we are all a woven together ecosystem and we’re all there’s so much sentience, and so many beings, etc. Don’t worry, I’m gonna write about people, but there’s gonna be trees too.

I kind of don’t worry about you. But I was, you know, you probably have already found this in your research, but there’s that giant, I don’t know if it’s considered a single tree, or if it’s like a group of trees, but they share a root system, like out in Utah or something. And I should remember the name of this, and I don’t but like, apparently, they live is one kind of, yeah, like, I think it’s a clump of trees, but they share a root system. Yes, they act as if they’re one tree. And I was like, I didn’t even know that was possible.

There’re trees that communicate with each other from like, 200 miles away from each other.

That I did not know.

I mean, it’s a wide, fascinating world. So I feel lucky that I get to read about it.

Okay, but considering also what you pulled out of the history of basketball, and a couple of other things. I mean, there might be a little art history research that happened, there might be a little research into Chicago— they’re like, there’s bits and bobs where I’m like, there was a little research there, but the humanity that you pull out of it, the intimacy that you pull out of it, the emotional truth, it’s just really satisfying, this book. I mean, Hello Beautiful, it’s just really satisfying. It just hits all of the notes that you want from a big domestic drama and these characters, they’re just I really like these women. William’s great, Kent is great, but I really like these women. Do you have a favorite of the sisters?

I think all three of them are me except for Julia. All three of them. Three of them are me. Yeah, I guess I’d have to say, I can’t actually. I really love all three of those women. I love Julia too, but it’s hard for me to choose between Sylvie, Emily and Cecilia.

Yeah. And Julia really is her own person. I mean, there were a couple of moments with Julia where I was like, I’m glad you’re not pissed at me. She’s very intense.

Yeah. But she’s a certain type of woman who in the 1980s, could prove their strength and their feminine power in the way that was burgeoning at that point. So like, she also is of her time. Yeah,

Completely of her time. But at the same time, fun to read. They’re all just really fun to read. And, again, ups and downs, complications that we are dancing around. But yeah, it’s just it’s a really satisfying sit down. Don’t rush the way I did. Just sit down and enjoy it. But I got to read it twice really quickly. What’s next? I mean, you we’re working on the next thing. You’re going on tour? We’re opening up the world again. I mean, you get to go on tour this time, right?

Yes, I’ll go on tour. And then, hopefully, a couple months after that, I’ll start writing with pretty sentences, the next one, that’s, that’s my it is my happy place. Like, the being out of the world is more uncomfortable for me than being alone in the room.

Wait, but you teach?

Well, I like talking, I love talking about books. I do love people. I feel like I have the most purpose when I’m doing the work as opposed to talking about the work. But I love talking to readers and I love you know, talking to you. And I feel very lucky for the whole thing. This is just the slightly less comfortable part of it for me.

I get it. I do get it. Wait. So does this mean you have time to teach or not like that’s kind of when you that’s really sort of haphazard, a little bit.

Very haphazard. I do like, I really love teaching, I find that it’s like because I care so much about what we’re doing. And I feel like in a workshop is such an intimate, vulnerable place for all the students. I just feel like it’s so important that I just do it sparingly because it’s really actually hard for me to do, to write and teach. And they feel like very similar ground in a way but it’s like I’m holding ground for the other writers in the class. And then I don’t have, I can’t hold ground for myself or my work at the same time. But it feels like the same kind of work. I mean, whether you’re nurturing other people’s work or nurturing, you know, my own, it’s still, it’s in service to stories being crafted.

Well, and also nurturing your characters too, that’s not a small thing. Is there anything we missed? I know, we’ve been dancing around. I mean, you and I obviously talked through this a little bit before we hit the record button. But is there anything we missed about the heart of Hello Beautiful that you want to add, before we let the recording go into the world.

The only other thing I think about is I wanted to write about love. And I it’s obviously important to me that it not be like hokey or sentimental, which is like where the tuning fork comes in, and making sure it’s right and not. But one of the things that I found myself writing about in writing about love is how important it is for us as humans to feel seen and what that means and how we take each other in is so important. And if you feel seen, or even worse, if you’re not seeing if someone looks at you and sees either their own pain, or they see a version of you that they wish you were and you’re not, we do that to each other all the time. And I don’t know writing this book and the story made me very sensitive to how we do that to each other. I feel like I learned something from writing about love in that way in this book that I feel like we would all benefit from paying attention to.

And that also just seems like a really great place to end the interview. Hello Beautiful is out. Now if you haven’t somehow read Dear Edward, please go find that as well and go find Helen Ellis’ novels and Hannah Tinti’s novels and go subscribe to One Story as well. It’s a really good magazine. Yes, please. Thank you. Thank you. Thank you.

Thank you so much, Miwa. I really appreciate it.