Zibby speaks with debut author Jessie Rosen about THE HEIRLOOM, a cinematic and utterly charming novel centered on a deeply superstitious woman and the international adventure she sets out on to uncover the story behind her vintage engagement ring. Jessie reveals this superstition comes from her own Italian family (who think vintage rings carry the karma of previous relationships), and Zibby shares the story behind her own engagement ring. Then, Jessie talks about her career trajectory—from blogger to screenwriting to fiction.

Transcript:

Zibby: Welcome, Jessie. Thank you so much for coming on Moms Don't Have Time to Read Books to discuss The Heirloom.

Jessie: Oh, thank you so much. 

Zibby: Old, someone new. 

Jessie: Yes! Thank you so much for having me. I'm a fan, and I'm just excited to get the chance to talk about it. 

Zibby: Oh my gosh. I have to tell you. So my, well, you know what? You tell what the book's about, and then I want to share this with you. Okay, 

Jessie: so the book is about a woman who has a very strong superstition around vintage engagement rings, meaning they hold the karma of the relationships in which they have been worn in the past.

And I should confess, this is a family superstition for my Italian relatives. So of course she gets proposed to with a vintage ring and she insists on knowing everyone that's ever worn it before. So, so begins a whirlwind adventure around the world and throughout time to discover the origin of the ring, but really to uncover her feelings about why she's so anxious to be married and what that really means for her.

Zibby: So cool. I have thought about this so much because I originally found my ring to my wedding to Kyle in a vintage store in Charleston, South Carolina. And I saw it and was like, but what about the person? What's the story? Right. And I couldn't get it out of my head. And we ended up bringing the ring to New York to have it, you know, looked at or whatever.

Turns out it was totally cracked. So I copied it. So this isn't the original. We sent the original back to the store. But, in the store, and in every vintage store I've been in, I'm just like, surrounded by ghosts. Like, what is the story? And your book is like, It's like what my brain wanted to know the answers to.

You just like went ahead and did and I'm like, thank you very much. I love this. 

Jessie: Me too. Well, you got the best of both worlds, but I feel like I have to promise to readers because of course readers are going to fall in the spectrum in terms of superstitions. That's why I felt like I had an idea in this book because when I was pre engaged and I had this superstition and it came up.

people wanted to debate me non stop about it. And so I just, it felt like, you know, fodder, but I promise to readers, no matter where you fall on the spectrum, you will feel comfortable with the choice of your ring at the end of the novel. Do you think that's fair to say? I think that's fair to say. 

Zibby: I love it.

Yes. It is with everything vintage though. Don't you feel like, like, I feel like a great writing assignment is just like go to a vintage store and make, like, look at a piece and just like tell the backstory of the piece. Go. 

Jessie: Yeah. And that's, I think that's the beauty of it, especially when you feel like, I love that you went into the store in Charleston, you saw the ring and you felt what sounds like deeply connected to it.

Yes. Yeah. I mean, you can't deny that. And there's a bit of that in the book too, really. This idea that, hold on, this feels meant to be, how do I resolve this other feeling I'm having? Yes. And yeah, I'm there all the time. I'm a huge vintage collector. I also come from this very superstitious Italian family.

So there's, you know, resolving those things has been, continues to be a lifelong battle as I sit here. wearing a vintage scarf. 

Zibby: And as I said, you're wearing vintage nothing, but that's okay. But you, uh, in the book, not you, your character in the book, uh, it's very clear that there are things, right? You, this is like how you come out of the gate strong with your character being like you're, I mean, essentially it's like the, her fiance is just not listening to her.

Like that alone would be a warning bell. She outlines very early on that there are four non negotiables. And the fourth one is that you can't. Like, I will not, which is a random thing to have as one of your non negotiables, but like no vintage wedding rings, geisha rings. Yeah. So, even though he has this great reason and it's romantic, you know, blah, blah, blah, it's still a complete, completely defying what she wanted, which is never a good thing.

Shoe to start the right foot. What's that expression? That's the right foot to start on or whatever. 

Jessie: Yeah. And that was one of the huge things that when writing this, I had this idea and of course I had to, you know, have this premise going in that I had to figure out how to resolve. So I had like this story that I wanted to tell as a writer, but then of course it had to follow logic.

So earning that decision from the fiance, whose name is John, but then also using it as a red flag for my main character. That's kind of what I wanted. You know, what is she, what's going to be the thing that kicks off her idea that this really beautiful and perhaps quote unquote the one relationship might not be.

Zibby: Yeah. 

Jessie: Which is terrifying. 

Zibby: It's never good when you have to drag your sister into the bathroom two minutes later. 

Jessie: Yes. Another real life example. Yes. We'll have a bathroom confessional in my family. 

Zibby: Your family sounds awesome. Like, I don't know, what you've said so far in two minutes is like, this is a party I want to go to.

Jessie: Oh, I love it. I love it. Yes. Good food. Very good food. 

Zibby: Great. Kyle, my husband is Italian, so. 

Jessie: Yeah. The best. 

Zibby: It's the best. Yeah. He's such a good cook. Anyway. Okay. You've had the most interesting career to date. I am obsessed with the whole thing. Tell listeners about it, how you started the 20 nothings, how you've transitioned this to this massive thing career and screenwriting and pretty like all the stuff. It's so cool. 

Jessie: Thank you. Yeah. I mean, like many things, there have been these really interesting nudges, both kind of intuition nudges and then really helpful nudges and guidance from people along the way. So my blog, 20 enough things, which was started and listeners probably remember there was like a blog boom around 2004, 2005.

I was against it. Meanwhile, I was writing about my experience of having moved to Manhattan and struggling to be a 20 something as emails and sending them to my friends, who were sending them to friends of friends of friends until someone finally said, really now, this should be a blog. So I think that that fear of kind of exposure and the exposure of writing has always been with me as a confidence issue.

And so again, it took a friend saying, when I read your blog, it's so dialogue heavy. Have you ever considered? So, um, you know, when you grow up on the East Coast, as I did, we didn't have friends in the film and television industry. It was a huge dream. And I was a huge lover of that form of writing. I just never thought it was possible for me.

So all these steps required me to kind of. Take a class at the new school when I lived in Manhattan and buy that book on screenwriting and really very slowly build to the point where I was ready to move to Los Angeles and secured a manager who left the business, secured a second manager who left the business.

Oh no. So, you know, these, there've been these long, these long steps and processes and finally landing with reps that helped guide me to some original content in film and TV, some staffing, but. I think it was five years in Los Angeles before that really started to churn for me. And again, I was really lucky to be with reps that said, we think you should try your hand at prose.

You know, we think that it's an interesting, expansionary voice and very wisely, as I'm sure you appreciate the IP of it all. Owning your content, having that book turn into a film or a television show is just a business model that's become, you know, who knows if it will happen with this novel, but at the same time, just the idea of ownership at all of your property, it's very different in the book world and not.

So with that support, I, I expanded into that kind of work and yeah, it's been, I mean, really, when I look at it, it's been, Almost 18 full years of pursuing different things along the way and never not also dabbling in a little freelance writing to support myself, also doing a little writing coaching, speaking at retreats to support myself.

So it's such a, um. It has to be diverse, I think, to maintain it and your energy around it. I like my brain getting to go between different formats. 

Zibby: That's so cool. So you went to L. A. and then when did you do the Bratz? Right. 

Jessie: Yeah. Yeah. 

Zibby: Tell me more about that. That's so cool. 

Jessie: I was probably about five or six years into really turning on the television writing front and I got approached by, uh, Studio that was looking to almost in the old studio system of we hire a team of writers and this full team is going to be creating content in house for young adult audiences.

And it was so interesting because I am an oldest sister. I have three younger sisters and I think that one of the reasons that I got that job is because they were looking for a showrunner, but really this auntie big sister mentor energy that could come into the room and say, okay, team, this is how we're going to get this done.

And yes, it was about the writing and it was about churning the content, but it was really about setting up systems and about. leadership and about figuring out how to really get a ton of work out of a young cadre of writers and make sure everyone felt okay doing it. And I have to say the one thing I miss in these years I've now gotten to spend writing novels is that dynamic.

I love it. I love being in the mix of this was a group of young women, which is especially, you know, important to me and getting to figure out how we make writing productive. And it's fun how we are nice to each other in the process inside a system in, in Hollywood and Los Angeles that can be very cutthroat.

So I really love that time. 

Zibby: So you're the big sister of Los Angeles, essentially. 

Jessie: A grand title. I don't know. 

Zibby: I don't know. No one else has it. So you might as well grab it. 

Jessie: I'll take it. I love it. 

Zibby: So when you went from, sorry, I'm in New York, so you're hearing lots of sirens. When you went to pros. Like, it doesn't seem like you're just testing it out, like you're really good at it and you have voice obviously down, dialogue down, but that's, you, there's so much else to making a book a good book, right?

Like, so how did you, did you learn that or was it just, did it feel instinctive to you? How to structure it? How did you go about it? 

Jessie: I think three things. First, I had first envisioned the heirloom as a film. So I used that classic beat sheet, save the cat book structure. And I think that helped because I had really clear structure.

Of course I had to expand upon it. So like all that teaching in that style of plot and story development, I think really helped me. But then two things, I have amazing guidance from my literary manager. And then Um, we brought in a book agent for this project and really, truly excellent notes, even direction in terms of, okay, I know you're a reader of this and this, you need to go read this, this and this to hear this and see this, you know, I chose to write this in first person.

That was a huge learning curve for me. So the journey from zero to a manuscript that we sent for submission on heirloom was over two and a half years of really me. really honing the pros of it all and hearing that and getting that right because it was, it is such a different thing. I can't believe how many words you have to put on a single page in the book.

They just, they just go down the middle when it's a screenplay and then, and then it's done. So yeah, such a different thing. So I think it's a testament to people believing in me and giving me really good notes and then me kind of resourcing from it. Absolutely everything I could find to just learn the, learn the craft and to say like to begin to learn the craft, you know, I hope that this is something that becomes a lifetime of, of work for me and I am a beginner.

Zibby: Well, I mean, beginner's luck. I don't know. It works. When you were working on The Heirloom, were there books you looked to that you were like, oh, I want it kind of to feel like this, or these are the comps, or sorry, there's even more sirens out here. There's probably, my, my building is probably, something's probably happening, but it's fine.

I'm not going to stop the podcast no matter what. Were there books you looked to or voices you love that guided you along the way? 

Jessie: Yeah, I feel like I have these three biggest influences, which may seem like such a weird combination of people, but it's always for me, Jane Austen, Judy Blume, Nora Ephron.

And it's, it's, I think that that does make sense. Maybe when you read my writing, there's always like a little social commentary, a little culture commentary like Jane Austen. And then there is some. Yeah. Personal journey stuff, like confronting a big thing like Judy Blume always gave us. And then Nora, I mean, for the rom com of it all.

And for, and you know, I think of Nora's films a little bit more than her books, but Heartburn is a beautiful book. And I of course read it before getting ready for this. So those are kind of the, the elder influences. And then I would read my Rebecca Searle, you know, those kinds of voices that I think had a little bit of what I was trying to achieve in a lot of romance.

and always comedy, but really giving readers an in depth look at this relationship between a woman and herself. Her love for herself and how is she going to tap into that and honor that. So that was something I was always looking to find influence on. 

Zibby: That's a great answer. I also love Judy Blume and Nora Ephron.

I should give those as answers myself. You're welcome to them. I posted recently about Irma Bombeck, who I love. 

Jessie: Oh, yes. And I saw that you were at one of her, um, conferences. They're so good. I've got to get there someday.

Zibby: I also love Anna Quinlan. Yeah. Anyway. But yes, I love the humor that, and just that real, you know, no artifice, right?

Of Judy Blume and Dora Ephron. They, it's their interpretation of the way things are and the funny in the everyday, which you obviously do in the heirloom as well. So that's great. 

Jessie: Thank you. 

Zibby: I love that. 

Jessie: Thank you. 

Zibby: Did you have a cover in mind, and was this it? 

Jessie: Well, I had a dream for what the cover wouldn't look like.

Zibby: Okay. Okay. 

Jessie: Which may be a strange answer, but I really wanted this book to have a chance to differentiate a little bit from the visuals that I think are very strongly rom com oriented, which are of course, and rightly so, images that contain a couple. In any way, shape or form. And of course, that is such a huge part of the book.

But I wanted a cover that made you say, I want to get inside that book. Yeah. I want to go there. I want to feel that. And when we talked about the originally with my publisher Putnam, they were so in support of that. I was thrilled. No, of course, this is a book about an engagement ring. I envisioned a pitch that was.

an engagement ring on the cover. Yeah. But I think we all felt like we wanted to give readers a chance to understand that this was more than that. And that like vibes are going to be heavy. I think that's it. And it's so funny. I gasped when I saw the first draft of the book, because those are the colors of the book, which is this sunset ombre is, is like the colors of my entire closet.

Zibby: Really? 

Jessie: It's like the colors of my soul to me. 

Zibby: Wow. It is absolutely gorgeous. 

Jessie: Yeah. Such a lovely thing. And we need, we need a few, uh, adjustments along the way. So there's a little image of a woman that you'll see gazing out across a distance. And that was something that we decided to add in like a little characterization just to say, you're about to go on this journey to this, take me their place with this woman.

Zibby: I did not even notice the woman. 

Jessie: Yes. Okay, good. She's a, she's an Easter egg. 

Zibby: I had to just put on my glasses to see that, but now I see her and that's awesome. Yeah. Very cool. Oh my gosh. We have like a section. Well, you'll see because you're doing an event at the bookstore, but we have a section on rom coms abroad.

So many people come in wanting that. 

Jessie: Yeah. Yeah. You want that. And I think you want to be transported. I wrote this partly during the pandemic and some of the locations I chose just because I wanted, I wish I was there instead up in my house. Relatable. 

Zibby: Are you working on another book and will it take people lots of other places as well?

Jessie: Yes, I am and it will. So I was really lucky with this sale for it to be part of a two book deal. And the second book we decided not to be a true sequel, but we're calling it A Spiritual Sister, which is you know, you're going to get journey, you're going to get a confronting question that a woman is going through and yeah, we're going to hit the road.

I feel like right now that's just a vibe that I really enjoy of. I know, I think I like a woman and a character that just says, well, If it takes going, I'm going to go, I'm going to get on the plane. I'm going to take the journey. I think that's fun. And I think that it's aspirational. So yeah, we're going, there's some tonal returns to some places and then there's some totally new stuff in the mix.

Zibby: Very cool. I feel like you need to do a trip around these books for other people, like retreats and stuff. You working on any. 

Jessie: Funny you should say that. I mean, it's a very big dream. I'm so focused on this right now. But yeah, I mean, your retreats are a really good example of just when you bring bring people together in.

Beautiful. The beauty of the place and the vibe of the place and the energy. That's why you go on retreats to places instead of having them, you know, in your hometown. Every retreat is worth it but yeah, location. 

Zibby: Yeah. Okay. Maybe we team up for an internet. We'll talk. We'll talk. We'll talk later. Okay.

We'll talk later. I would love to do that. I know I'm like 2025. It's going to be my international year. We can move things. 

Jessie: Yeah, yeah. I love it. 

Zibby: Do you still do? I'm sorry, and I should know this, but are you doing stuff still in the TV screenwriting studio world at the same time?

Jessie: So for the past year, I've been totally focused on getting book one and now developing book two ready.

There is a plan to pitch book one, the heirloom. So that will happen and I'll be out in that world in that capacity, but no, in terms of. Writing in a writer's room or show running a show. It's been about three years since that. And yeah, I miss the people, you know, I miss the connection. Writing is so solitary.

I'm constantly trying to find ways to just bring people into my physical space. Like, do you want to write in my living room and I'll write in my office or vice versa? Just because the social nature of film and television work is great, the collaboration. And so I've been, I really want to stay with prose and stay with novels for a bit and really try to grow this piece of, of my life.

But I also need to find ways. I think that's where the retreats come in. See? This is sounding better and better. 

Zibby: Okay. I'm with you. I'm with you. 

Jessie: Yeah. Yeah. So that's the plan. 

Zibby: That's so exciting. Well, having just taught yourself how to write fiction easily, as it turns out, what kind of advice would you have for somebody who's embarking on a novel?

Jessie: Yeah, I think you have to be a reader to be a writer. I think it's the very first thing is just to consume it. It's almost like you have to get the rhythm. This is, I think, why I struggled because I had a rhythm of television and film writing in my bones and in the way that I approach things, the rhythm of the structure of what it sounds like and how like single paragraphs or chapters flow is so important.

But then I think the other thing you have to do Go like almost like do that and then erase it from your mind because the idea is what it's about You'll figure out the structure. Someone will help you. There are so many people between one more time retreats coaches and You know amazing places where you can go to learn the craft I am often so frustrated for writers when I hear that they think they can't do the prose Oh, I can't I write this, I could never do that because I think that's important, but also forget about it.

You will, you will learn it and consider yourself a beginner because then the pressure is off for it to, it to be perfect. Go with the idea, find the character, start to let it flow, and then you'll fix all the rest. I mean, that's how I did it, certainly. 

Zibby: So why would you not just take the heirloom and write the script yourself?

Jessie: Yeah. So when we pitch it, I am, it is my dream to attach myself as the, uh, to do the adaptation and that process, we'll just kind of see how the cookie crumbles. If there is interest in, you know, someone, a producer or a studio kind of taking that on, or if it turns out that I need to spec it or write it on spec, we'll see what happens.

Zibby: So you wouldn't just do it on spec to have it to pitch. 

Jessie: Not at this juncture. And a little bit of that is just, I wrote the manuscript, the book manuscript on stack instead of trying to sell off proposal. And that was kind of that process. And now I think it may be just the way that, and all writers should know this.

The. The market for interest in books and IP is just huge. It's bigger than ever. And I think that allows writers, you know, my goal for every writer is to get paid to write the work and that's not always possible. And it has not always been possible for me. And so there are moments when you say to yourself, the wisest investment is one of my own time in writing this on spec and not getting paid.

And then there are these moments when you say, I wonder if we could take this out and we could sell this and I could be paid to write the first draft of the script. And, you know, it's a, it's, it's always an in and out with that. It's hard to know, but yeah, that's the goal. 

Zibby: Excellent. Wow. Okay. So what are other superstitions of your family that might be?

Might or might not make appearances in fiction. 

Jessie: Right. We have this very weird one that you cannot enter from a door and exit from a different door. So it's this huge superstition around houses. And entering a home and being in a home and then exiting a home. So that is one that always comes to mind. I don't know if it's fodder for a whole book, but that's a big one.

And then there are a lot of superstitions that aren't so much don't do something, but do do something. So like, Line up the plastic statues of the saints and each one of them has a special if you bury this one in the backyard upside down you sell your house. If you wear this one around a necklace while you're pregnant, you have a beautiful pregnancy like all these sorts of things.

So I think it would be fun to play with one of those almost like an inverse of the heirloom. The heirloom is kind of a don't do this or else superstition. And I think it would be fun to play with the superstition that's like, Oh, If you do this, this will happen. 

Zibby: Wow. I love it. So what part of Italy is, are all your family members from?

Jessie: They're all from kind of, if you go like down to Naples and then go a little bit, I guess that would be east into the countryside. So some really small towns, the biggest town is Salerno, which is actually on the coast, but then there's some teeny towns in the, in the middle towns. I have not been to, which is.

potentially even more fodder for some future work because I'd love to get there. Yeah. And just see if there's any of the last names of the family still in the mix. I don't, I think I strayed, if I remember correctly, I don't think any of the last names in the book are exactly the last names of my family, which was also kind of a different version of a superstition, you know?

Let's just take a one vowel step away from this. 

Zibby: Interesting. But close. Close? 

Jessie: Yeah, exactly. 

Zibby: Not exactly. 

Jessie: Honoring, but not, uh, yeah, exactly not easy. 

Zibby: And when you're not writing, and in LA and all that, what are some of your go to things to do? Are there restaurants you love? 

Jessie: Yeah. Yeah. Yeah. My husband and I are big, both big restaurant foodies and also just people that like to cook for others.

So having dinner parties and having people over in our, in our little house, I'm a dog mama, so I've got, you know, dog hikes and fun things like that. And then we love to travel. One of the things, as much as I miss living in New York and on the East coast, one of the nice things about Los Angeles is you can hop in your car and get up to, you know, a wine country in two hours, you can get east to Palm Springs, you can get down to San Diego.

So we like to kind of pop in the car and go up and discover somewhere. Our current favorite is the San Ynez Valley. And I feel like, I feel like you may have done a retreat there. There's like the Los Olivos area and just discovering new wines and food there. 

Zibby: Oh, uh, California is great.

Jessie: I mean, I go two hours.

Zibby: Where am I like Philly or something? Anyway. 

Jessie: Yeah. Yeah, yeah, yeah. 

Zibby: No, no, nothing, nothing wrong with Philly. In fact, I'm doing that drive soon, but it's not the wine country. Let's put it. Yeah. Yeah. Natural beauty.

Jessie: Exactly. 

Zibby: And I know you have your favorite authors, but are you reading anything that you can't put down?

Or has there been something lately? 

Jessie: Yeah. So I'm writing fiction. So I'm writing book two right now. And so it's really hard. It's hard for me to read fiction in the middle of writing fiction. That is to say, I do have Rebecca Storr's expiration dates on my bedside right now because I just, I couldn't resist.

But I'm actually reading something so interesting. It's called Burnout by Emily and Amelia Nagoski. I think it may have been about like a year or two ago. It's fascinating about the process of like unloading stress, how you do it, what it looks like physically, why you do it and you know, what better time than when I'm launching a book and trying to write a second one.

I just felt like I needed tools and this book is fascinating, so I highly recommend. 

Zibby: Interesting. Okay. Amazing. Well, Jessie, this has been so much fun. I really hope I get to meet you perhaps this weekend, perhaps another time, but this has been great. 

Jessie: I appreciate it. 

Zibby: Yeah. 

Jessie: Thank you. 

Zibby: Thank you.