Bestselling Author

HISTORICAL HAPPY HOUR

The Trade Off by Samantha Woodruff

Samantha Woodruff is our guest to talk about her latest novel, The Trade Off. It’s the tale of a young Jewish woman with a gift for math and numbers who wants to become a broker on Wall Street. But, because she is Jewish and female she can’t. She finds a way as the woman behind the man for her twin brother, but when she sees the Great Crash coming, will anyone listen?

Samantha Woodruff

Samantha Woodruff, a Wesleyan University history graduate with an MBA from NYU Stern, spent years in senior leadership roles at MTV Networks and Nickelodeon before transitioning to writing. After teaching yoga and writing humor columns, she discovered her passion for historical fiction at Sarah Lawrence College. Her debut novel, The Lobotomist’s Wife, was an Amazon bestseller, and her upcoming second novel, The Trade Off, releases in October 2024. Sam’s work has appeared in Newsweek, Writer’s Digest, and more. She lives in Connecticut with her family and pets, balancing writing with yoga and concert-going.

In this engaging episode of “Historical Happy Hour,” host Jane Healey sits down with bestselling author Samantha Woodruff to delve into her latest historical fiction novel, “The Trade Off.” Set in the roaring twenties, the novel explores the ambitions and struggles of Bea Abramowitz, a mathematically gifted Jewish woman trying to make her mark on Wall Street despite the era’s gender and ethnic barriers. The discussion spans the inspirations behind the book, including the GameStop short squeeze, as well as the intense research Samantha undertook to authentically depict the period. The episode also touches on broader themes of morality, wealth, and the complexities of the financial market.

Here’s what we covered:

  • 00:00 – Introduction of Samantha Woodruff and her background.
  • 01:46 – Premise of “The Trade Off” and the protagonist’s challenges.
  • 06:58 – Inspiration from contemporary events like the GameStop short squeeze.
  • 11:32 – Research process and historical accuracy.
  • 20:01 – Character development and sibling dynamics.
  • 23:31 – The role of female friendships and the 1920s setting.
  • 29:10 – Writing process and balancing fact and fiction.
  • 32:16 – Advice for aspiring authors and future projects.

EPISODE TRANSCRIPTION

[00:00:00] Jane: Welcome to Historical Happy Hour, the podcast that explores new and exciting historical fiction novels. I’m your host, Jane Healey, and in today’s episode, we welcome my friend, best selling author Samantha Woodruff to discuss her latest novel, The Trade Off. Welcome, Sam. Hi, Jane. Thank you so much for having me.

I’m so excited to be here. I’ve been looking forward to this. Me too. Me too. I’m going to do a quick bio and, a little about you and then I’m going to jump in. But I was just thinking, I’ve been so lucky this month because I’ve had A lot of friends on which is so fun. So I’ve been listening a lot and I’m like,

[00:00:34] Samantha: Oh, it’s good.

It’s a good lineup lately.

[00:00:36] Jane: Yeah, I

[00:00:38] Samantha: know

[00:00:38] Jane: a lot of the ladies. All right. So Samantha Green Woodruff has a BA in history from Wesleyan University and an MBA from NYU Stern School of Business. She spent 15 years at Viacom’s Nickelodeon before leaving to parent her two young children. After studying at the Writing Institute at Sarah Lawrence College, Woodruff completed her first novel, The Lobotomist’s Wife, which was a number one Amazon bestseller and Amazon first reads pick.

She has contributed an essay to the essay collection On Being Jewish, which releases November 8th. All proceeds from the book will go to Artists Against Anti Semitism. A non profit founded in the aftermath of the October 7th attacks in Israel. Welcome, Sam, again. Thank you. So hold up your pretty book, The Trade Off.

Here it is. I love this book. I love the cover. Love the orange. I love the orange. I love the book. Talk about the premise of this novel and what inspired you to write it because I was reading your author’s notes, of course, at the end of the book, and it was actually a more recent event in the news that led to you writing this story.

Yes.

[00:01:46] Samantha: So we could spend the whole podcast with me talking about this. I’m going to try and be as short as I can. So the story of the trade off is It’s about a young Jewish woman named Bea Abramowitz. She’s a twin, and she and her brother are first generation U. S. born immigrants in the 1920s. Her parents were Russian they’re not immigrants.

They’re first generation born in the US and they’ve they’re making their way, but they’re poor Jews on the Lower East Side. And B happens to have this unbelievable aptitude for math and numbers. And she’s the worker of her family. She’s the, she’s the student. She’s the one who’s responsible.

And some of that is also just of the time that there was a lot of caretaking that women did for men in that era. As but she has this idea that she wants to work on Wall Street, because she’s really good at picking stocks, and she’s learned how to do that from a young age.

And so she tries to go to Wall Street to be a stockbroker only to discover that in that, in this era, while there was a lot happening that was liberated for women in the 1920s, it was this like great moment in suffrage that just happened. She can’t do anything because she’s, first of all, female, and there were very few females to begin with.

Second of all, poor, and third of all, Jewish. And so she’s got three huge strikes against her. And she manages to get a job, a back office job, but she really wants to be a broker. And eventually, she hatches a plan for her twin brother. Jake, who is a natural born salesman, super charming and wants to work as little as possible for him to be the broker and the man, the face of the family.

And she does all the stock picking and together they make their family a fortune. But then the tides turn and she sees the crash coming and she wants to do something about it to try and save the family. But her brother doesn’t believe her. And so there’s this whole chicken little she keeps thinking the sky is falling and nobody around her believes that it’s going to happen.

So she, she sees the crash. The inspiration for the story, a very, if we trace it back to the contemporary event, it all started with this event on wall street that was called the GameStop short squeeze. And there was a movie made about it called dumb money and the Seth Rogen character, if you’ve seen the movie.

actually is one of my husband’s best business, like Wall Street friends. Yes. When this GameStop thing was happening, and basically for people who don’t know what it was, it very simply and if you don’t understand long and short selling law, if you sell long, you believe that the market’s going to go, essentially you’re betting that a stock or the market overall is going to go up.

And that means you are a bear, a bull, sorry, bull. And if you sell short, what you’re essentially doing is Assuming that the stock, a stock’s price is going to fall and you’re taking an option to buy it at that lower price. So you make the difference, you buy it and you make the difference of the higher price and the lower price.

But essentially you’re betting that the stock is going to drop. and that it’s overpriced. And those are called bears. And in the GameStop short squeeze, the Seth Rogen character, this hedge fund guy, was short GameStop, which was a bricks and mortar video game retailer in a time, in 2021, like not a growing business.

So it seemed like a natural short sale. However, it was also during the COVID people were still isolated and furloughed and people didn’t have their jobs and there were all these people at home that were investing. And they banded together on Reddit with this one guy as their ringleader.

And they decided that they were going to bet against the hedge fund bad guys and make the stock go up. And for a second they, not a second, for a day they did and it totally disrupted the market. None of that is the part that I thought was interesting, because I think the stock market fundamentally is boring, even though that’s what my husband does for a living.

And I have an MBA, but it’s not, it was never my thing. But what I was fascinated by was that this guy who was our friend, who was the short seller, was vilified by the Reddit people. To the point where he was receiving death threats, and there were, like, evil memes about him every single day.

And. It really was a, it became a personal attack. And I said to myself and then to my husband, I don’t understand how he’s just doing his job here. In this particular instance, he’s not an evil guy. And why is it? That if, that everyone automatically assumes that the, that morality follows wealth. So you’re moral and good if you’re poor, and you are evil and bad if you’re rich.

And I wish I could write about that somehow. And then my husband told me about this guy Jesse Livermore, who shorted The Crash of 29. And I said, Oh, you could, there were short sellers in 1929. And so then I basically built a story around that idea to explore the complex morality of wealth

in

[00:06:58] Samantha: a historical setting.

And then Hernan Diaz came out with a Pulitzer Prize winning book, which totally stole my thunder.

[00:07:06] Jane: But I love this story and I love your take and I remember when the whole GameStop thing happened because the guy who’s, who was the Pied Piper of it all was from Massachusetts and I was like riveted. It was riveting. There was all these characters. It was, and I saw the movie I thought was decent too.

But yeah, fascinating story. And it’s so funny how writers come up with ideas out of things like that. This is historical fiction, but that you came up with it. Yes. I have a few research questions. Yeah. Yeah. So I want to talk, first of all, you were just talking about the stock market.

So this, here’s this bee and she is a genius and mathematically gifted and has an almost instinctive understanding of the stock market. And I, I think I remember us commiserating about research and you did an extraordinary amount of research for this book. And part of what you had to do was know, was learn all of this so that and write about it in an interesting way and also an understandable way.

And talk about that. What was your research and how did you do it? Cause it’s hard. It’s a

[00:08:07] Samantha: great question. Cause it was one of the hardest parts for me, because as I say, my husband is a finance guy, so he actually did some of the legwork for me on this book. He read. all the big economic treaties about the crash.

And some of them actually were more ended up being more social history than true finance economic history, but about the era. And then he was like, read this one. That one’s going to be too boring to you and you won’t understand it. So he did that work for me. And then as I got to understand all the forces of the time, cause it was such a different time than the way we understand finance and the financial markets today.

Even if you understand nothing. It is a lawful to a degree world and back in the 20s it was not, right? I mean you could do anything and the guys, there was a small group of guys who were the big bankers and the richest people in America. who would collude to drive up or down stock prices to, for their own good.

So even if you were someone like B, who could see patterns and predict them and make sense of them, you wouldn’t necessarily win because sometimes things would happen that were totally beyond, anything one could predict. But so I first started there to just understand the market forces a little bit.

And then I had to start putting myself in situations like what would she see that would make her think this? And I literally, I have to be honest, chat GPT was super helpful because I would say what stocks were unusually high in this time? And then they would give me a list and then I’d go check it five other places to make sure it was actually a true list.

I also got the Dow data on a daily. weekly and monthly basis and an annual basis from 1924 through 1930. And they had all these excel charts. I used to do market research. So I like to play with data in Excel. So I would do that too. And I would look at like when I was first writing the story, I would try and.

Yeah. map everything that happened to where the Dow was. So if there’s a moment where there’s a big dip and people are losing money, it’s because that actually happened in the market. That was like one of my, we all have rules in historical fiction for what has to be factual. That was one of the things I made factual.

And then B’s understanding and how she could take her observations and turn them into predictions. I talked it through with my husband. I would say, would this make sense if she saw this and then she thought that and he was like, yeah. And then he read the draft and said, This is so rudimentary, you have to put more stock specific stuff in it.

Huh.

[00:10:45] Samantha: And I said to him, that’s on my audience. I want to write it so that if I read it, I wouldn’t feel like it was a boring stock book. I want it to, I want you to feel the momentum of the stocks and the huh moments, but I didn’t want the reader to be bogged down. And I have gotten a few critical reviews that way.

I’m like, I know a lot about finance and this is not really a finance book. And I’m like, yes, it is not a finance book. Correct. But I spent a lot of time there. And then I got to do the stuff I really like, which is the social history and flappers and speakeasies and early Lower East Side Jewish life and all those other pieces.

So that, that I did that too in my research process, but the hardest part was definitely turning those stock. Concepts into something that could feel narrative and not make someone put the book down.

[00:11:32] Jane: Yeah, and I think you did a really beautiful job with that because it also not historical detail lens and authenticity, you know that you would maybe that’s what your husband meant like you just needed to dig deeper so that people would believe that she was, she was this character, right?

Yeah, totally agree. Talk about how Bea and her family’s story was inspired by your own family history. I thought that was interesting, too.

[00:11:56] Samantha: Yeah, it’s crazy, right? And it’s, I don’t know if you have this in the writing process where sometimes you forget. The origin of things and then you go back and like at this point when you’re reflecting and doing book tours and talking to people You remember how all the pieces came together and some of it I put in my author’s note, but So B’s family history basically, I knew I wanted to write about someone who wanted to short sell the crash and Fundamentally because the crash was such a disastrous moment for the country and the world, this had to be someone who was very likable and empathetic and had to have a good reason for wanting to be in the market and wanting to make money.

And so I started to think about what could be motivations besides greed that would have somebody wanting to be a broker and trying to make as much money as possible. And for B, part of it is because it’s a skill she has and she loves exercising her mind. It’s like doing a puzzle,

but

[00:12:58] Samantha: the other piece of it is I flashed to my grandmother, whose name is Pauline and Pauline is B’s mother in the book, but it’s actually, it was my grandmother, Pauline’s mother, whose name I don’t know.

So my great grandmother had the story that I gave to B’s mom. So she emigrated. from Poland or Russia the borders were very porous to flee early pogroms and had been aristocratically wealthy and lost everything. And so the family lore was that she had several boy children and a girl, and the girl was my grandma, Pauline.

And grandma Pauline was treated like her servant because her mom refused to adjust to the lower to Lower East Side life and do all the things that other women on the Lower East Side were doing. So Pauline had to do everything. And so I thought that was just such a great seed of Developing a lot of relationships about wealth and money and a great way to explore the fact that sometimes you really want to be really rich and it doesn’t make you a bad person.

It’s not for bad reasons. It’s because of family, family trauma, like both Bea and Jake in their own ways. to make money, but it’s because of this family trauma and it’s always better when the family trauma is real. And then there was one other piece of my family history that I stuck in there.

One of my great aunts passed away while I was writing this book. And I went to her funeral down in Baltimore and I got dragged by my mom, kicking and screaming. And then I saw this family and her, one of her kids was talking about her and they talked about, How she always referred to them as the house of whatever.

And I was like, that is so great. Maybe I should call this book, The House of Abramowitz. And then I so I worked that in, that whenever Pauline is referencing like her grandeur, she talks about the house of, so anyway. That’s all family history.

[00:14:55] Jane: You mentioned some of the sources in your research notes in the back of the book.

What, was there anything about in your research that surprised you? And like anything that you were like, Oh, I didn’t see that coming or that helped you like shape the narrative of the story in a different way?

[00:15:11] Samantha: Yeah, so I wrote, I actually wrote a piece about this. Now I can’t, I think for writer’s digest, I can’t remember where I have to look through all the stuff I did, I’ll go out, you like do all that stuff.

I had this, I developed this incredible relationship with a man named George Robb, who is was a professor. He’s retired at William Paterson University in New Jersey. And he wrote a book called Ladies of the Ticker. And it was, he took, he had a very interesting take because he didn’t, it was a lot of he looked at plays and movies and early movies and, early literature.

And he compiled, and then also just history, profiles of women, from the late 1800s through to the 1930s or 40s, women on, who worked in finance in some way. His book was one of three that I was able to find. There was no research, no material available about women on Wall Street in those early years.

And in fact, a book just came out about women on Wall Street, but even that one focuses more post World War II and forward. But that book makes the point that I am about to make to you, which is that there’s a dearth of resources. Thank you And part of the reason is because there were, there was a dearth of women.

So when I learned that, and I, and yes, I should have known it because even today finance is very male. But somehow, when you think of the 1920s, you’re thinking of, this like flappers and liberated women. So you think that in the world of Wall Street, where there’s all this wealth, that there would be the same.

But one of the most fascinating things I learned, which I also alluded to before, is that the only women, the only use they had for women in that era on Wall Street was if they had connections to other women with money who they could then get to invest with the bank. So if you were not a woman who had connections, Meaning you didn’t go to a seven sister school and you didn’t belong to a social club and you weren’t like a daughter of the Mayflower.

There was no use for you in the banking world, really. So that to me was so fascinating and surprising. That, because you would think that those kinds of socialite women wouldn’t be working. So it’s this weird, these women were working, but they were working because they had been volunteering for the Red Cross and at their husband’s side, at the front, and all selling war bonds and doing things that distinguish them in their social echelon.

And then the bank started to say, Oh, you could help us. So as soon as I learned that, and then I learned that if you were not one of those kinds of women, so if you were poor, You were the best you could hope for was to be a secretary and that was a stretch. And then if you were Jewish, that was the other crazy thing.

Some of the big investment banks are Jewish

and

[00:18:07] Samantha: they didn’t hire Jewish women. So there was no place if you were a Jewish woman. to work on Wall Street. And so I took all those things, and that really became Bea’s journey. Because to me, it was like, I was so stunned by it, I wanted the reader to experience it, and I wanted to experience it.

It was big. And George Robb, who I brought up at the beginning, he became the sounding board for me. I reached out to him, which I’ve never done before. I did a lot more of reaching out to people for this book’s research than The Lebotomist’s Wife. Partially because I had no idea what I was doing then.

And I didn’t know you could do that and people might answer you. I didn’t try. This time I did. But he he and I had several conversations. And then I’d get stuck and I’d be like do you think she could do this? And he’d say that would be really unusual. Maybe she would do this. And, all those, even that there was just a women’s lunchroom.

There were things like that. If it weren’t for him, I don’t know if I would have been able to really figure out.

[00:19:03] Jane: Yeah, so interesting. And the fact that they have a dedicated women’s investment group for these wealthy daughters of American revolution type, high society women. I thought that was really interesting.

Yeah.

[00:19:15] Samantha: Yeah. That was

[00:19:15] Jane: basically,

[00:19:16] Samantha: and if you look at the early history, there were a lot of women through the twenties who had like big officer, like jobs. But they were all really manning some aspect of the women’s department. They were women serving women like them. Amazing.

There

[00:19:34] Samantha: was another side to that era, right?

There were, this was also the first time that everyone could get involved in the stock market. And it was a bubble in that way. And so there were women who were like stock brokers, but they were the, they were like going to outer suburbs and, they were in the diaspora. Making house calls and taking mail orders.

So that was, and that wasn’t what I was, I wanted the action. Yeah.

Action.

[00:20:01] Jane: Yeah. So talking about Bea, I want to talk about characters. You have Bea who, as we talked about, brilliant, trying to break into a place that is a poor Jewish girl no one breaks into on Wall Street. And then her brother, who’s like her polar opposite in a lot of ways very handsome.

And he’s the literally the fair haired boy. She’s dark and and small. And she, he’s like tall and blonde. And so why twins? And how did you come up with them? Like, how did you develop them? I thought that was so interesting.

[00:20:29] Samantha: You ask really good questions, by the way. Oh, a good reader and a good question asker and a good writer.

So I, the twin idea, when I started, when I first came up with the twin idea. I wanted them to be identical twin. I see someone in the comments just asked if I’m a twin. I’m not only am I not a twin, I have a half sister from my father’s second marriage who I never lived with. So I’m basically an only child, but I have a girl and a boy who are two years apart.

And so the sibling relationship was foreign to me when I had children. So I think I’m very, I’m extra fascinated by sibling relationships because I don’t totally understand them from my own experience. And originally they were twins because I was gonna have Bea do a reverse Tootsie and dress up as Jake and take on his identity.

That was one of my original ideas. And so I was like then they need to be twins. And then I started to think about all of the twins that I know and people I know who have twins. And there is this connection, it’s like almost psychic connection that twins seem to have. And even if they are polar opposites, which sometimes they are when they’re fraternal but I loved the idea that they could be the yin and yang to one another and still help each other.

And. I’ve had people ask me about feeling like the relationship is toxic, and I think I did not intend for it to be toxic. I intended for it to be real and it and, families are complicated. And so I really wanted, I wanted Jake to have it easier than me, but not, but it only in some ways, right?

Cause he gets pretty screwed cause he just keeps being impulsive. His impulsivity really does him in. But I wanted him to be the one who had, who was the handsome, good, charming, because That would just give him one more thing that would help him fit in a world where, still as a Jewish man, not necessarily easy, but the rules were totally different for men than women in this, in the 20s on Wall Street.

They wanted bodies for men and you didn’t have to have a college degree. You, they were training you on the job, like all that stuff was real. So as I started to think about all the ways they could be yin and yang, I mean it was probably a little trite to make her all dark and make him all blonde, but I, there’s, within Judaism too, there’s this idea of passing a little bit as not Jewish and I liked the idea that he would have this fluidity that she didn’t have.

And that she would have an identity that she couldn’t escape in any way. And that instead she was gonna have to own and embrace and overcome, and make peace.

[00:23:08] Jane: Yeah, I didn’t even think about that, the passing aspect of the story. But yeah, that makes sense too. Interesting. Yeah. This is also a story with strong female friendships and I loved the story, The friendships.

And I also loved cause you got to get into kind of the nightlife and the clothing and the fun and the fashion of the 1920s. How did you come up with Henny and Mildred slash Millie? How did you come up with them?

[00:23:31] Samantha: I have to say they just appeared like I, I decided be needed friends.

And the Lobotomist’s Wife was a very, my first book was very insular in a lot of ways. It was really just this tight relationship and this tight little world of mental illness. And I wanted, I, the 1920s to me just has that, it has a lot of things. There was a lot of darkness, but it has that spirit that you, how can you write about the twenties and not, a young person in the twenties and not have some fun.

And,

[00:24:02] Samantha: And then I, my mom is a therapist and I think I grew up thinking very psychologically about people, so I, my, my characters as they emerge always have backstories and motivations and a whole life story. So Henny. is, she, and I and I, there’s things I wanted to represent that I learned about.

There was a huge divide in the twenties between Jews who had been in, in America for now, like two generations versus Jews who had, who were the first generation born in America. And Henny was the prior. And as a result, she lived a very, a much more upscale life. But she was embracing the twenties and wants to be a modern woman.

And so those things came to be, I thought that was a good, came to be not B E A, but B E A. I thought that was a good counterpoint to who B was because there’s the very, very secular, modern Jewish girl. And then there’s the like more traditional trying to find her way in the world. And then I loved the idea of Henny being this, So she’s this like archetype of who should be successful on Wall Street, but she was gotten her own way, cause she was so awkward.

Like it all just Oh, you mean Mildred? I mean Mildred. Yeah, Millie. And then she has Sophie, who’s part of the melting pot of the Lower East Side diaspora. That is like Italian girl who’s making her way in a whole different avenue. And I don’t know they all just evolved.

Like they just popped in and then they kept going. And then I really, I wanted to have the fun and games and the fashion and the speakeasies and the nightlife. I like, I wanted that for this book. I

[00:25:37] Jane: found a way. Yeah, no, I love that. It balances it out. Exactly. Yeah. I have writing questions as I always do.

And just a reminder after I ask my writing questions, you can put questions for Sam in the chat or in the Q& A. And I’ll take those as well. So I’m always interested in point of view choice. Did you always plan on writing this in first person point of view from B’s perspective?

[00:26:01] Samantha: I tend to I, I’ve been playing with.

other ideas and books. I seem to like Close First Person, but it’s not I. It’s you have to see it through B’s eyes, but you don’t, but you don’t have to. There’s a little bit of room. And and that seems to be where I feel comfortable. I actually, started to play with writing a book in the true first person voice with I did and I saw

and

[00:26:24] Samantha: I got so stuck like immediately somehow saying then she thought makes it so much easier for me than I thought I don’t know why yeah but I like to be again I there’s an I like intimacy there’s like an intimacy that comes with that close first person the first part

[00:26:44] Jane: I guess.

First person close, right? Yeah. I agree. I like it too. I think it puts readers in the story. Yes. Yeah. We talked a little bit about this. How do you strike a balance between fact and fiction in your storytelling and do you have any hard and set rules?

[00:27:02] Samantha: Think that my hard and set rule for this book Bye.

Was about the market. Like I, for some reason I got really stuck on that. They like, she, the investors couldn’t have a good day if the market was actually down that day. And I got to the point where I had to stop looking at daily stuff and pull out and be less granular because it was impacting my story.

Like at one point my editor said to me you can give yourself a little freedom here. Like day by day. So that was one of my big pieces of fact. I wanted. I always like when historical fiction has some real people in it, and you do that too. I pulled people from history and moments and incidents that were real in history, and I put them in the book.

The one place that I did not do that, that I took, artistic license was actually with the opening and this doesn’t give much away because it’s the first three pages but there’s people jumping out windows as the market is crashing and the financial district was an absolute mess and a disaster zone but it’s that is likely just urban legend it’s popular urban legend and I was like this is too dramatic not to put in the But but I, that one I said, I’m not going to care if it actually happened or not.

It’s just, it’s such a visual way to understand the level of panic and despair that was happening in that moment that I used it as a device, whether it was right or not. But so I guess I think I need to know if I’m not writing a fact correctly. Like I want to. the world and I’m a stickler for any, I try not to be anachronistic in any way.

So if someone’s going to a restaurant from downtown to uptown, I want to know, I have subway maps of the time I have, I know what the taxis look like and what, which restaurants people would lunch at. And I try and really keep all of that. Very factual, and then the characters can do whatever they want in that world.

It’s like I build a Lego set with facts, and then I set them out to play. Excellent.

[00:29:02] Jane: I like that. And are you a plotter or a pantser? I feel like we’ve talked about this before and I can’t remember your answer. What’s your writing process like?

[00:29:10] Samantha: I’m like, in general, I’m neurotic and organized. I feel like as I’m getting older, I’m a little bit less that way.

Okay. So I would say I’m definitely a plotter, like I, for this book and for The Lobotomist’s Wife, I outlined, I did, I don’t outline to the scene detail or to the chapter, every scene in a chapter kind of detail. I know the big beats of what’s going to happen all the way through.

But

[00:29:34] Samantha: then in each writing session, I let myself meander.

And there were like a couple moments in this book that really just surprised me as I was writing. And I let that happen. And I love that. And actually right now I’m trying to write Contemporary thriller, just for fun. I’m working on a historical fiction, but it’s really intense and I feel like I want to do something that’s like lighter and fun.

And so I’m trying to write, I live in Greenwich, Connecticut, I’m trying to write like a, social satire suspense novel that takes place in Greenwich, Connecticut. And I know the basic plot, but I haven’t put it down on paper, and I am, so I am pantsing for the first time, and it’s hard. I find it harder.

A lot harder. A

[00:30:21] Jane: lot harder. You mentioned story beats, so do you pay a lot think a lot about story structure up front, too, or you just roughly? I do,

[00:30:31] Samantha: I don’t do it to the point where I’m, like, actually mapping out an arc, but I think, To me, it’s a little bit innate that a story has to have a driving narrative.

A story has to have you turning pages. A story has to have high stakes. A story has to have a protagonist who goes on some kind of journey. I think I’ve got the words to make sense of that when I, in books, in craft books and things. But I know that innately. And because I watch a lot of television and I read a lot of books.

So you I know the point at the book where, in the book where you say, where is this going? And if the author doesn’t tell you, you’re going to put it down. It’s, and it’s, the natural instinct as a writer is I’m going to hold back. I’m going to hold back. I’m going to dance around the subject as much as I can.

So I’m aware of those things as I’m writing, but I don’t do a save the cat like these are the beats and this is what happens where and unless I need to like if I feel like the book is really dragging then I will go back and put it through that structure, but too much of a paradigm and I’m frozen and paralyzed.

So it’s like somewhere in between.

[00:31:41] Jane: That totally makes sense. And Save the Cat, for people who don’t know, it’s a screenwriting structure, but now there’s a novel writing structure book as well. Save the Cat writes a novel, and I have that one on my shelf as well.

[00:31:55] Samantha: It’s a great framework, but I find frameworks are again, like they can be as oppressive as they can be helpful.

So I agree.

[00:32:05] Jane: Yeah. There’s a balance there for sure. We have aspiring authors in the audience and you’ve now published two novels very successfully. What’s the best advice you can give them about writing and getting published?

[00:32:16] Samantha: It is true that you have to, and I think that most people say you got to get your butt in the seat and just write.

And there was no question that’s not true, but I’ve been thinking a lot lately and I really think that one of the most important things, and I’m interested to see what you think of this answer, is to have a community of other people who are writing, whether you do that, whether that is a workshop group or whether it is, whether you find a way to network and.

And it’s in your community center, whether it’s online, like this is a really hard business. And it is so insular to sit and write and you can get so discouraged. And so much of what we go through as aspiring writers and even published writers makes you question yourself and you’re analytical naturally.

And so if you don’t have that group. It makes it so much harder.

[00:33:15] Jane: That is excellent advice, yes. I completely agree. And I’m trying to do more to reach out to my author friends because they’re the only ones that can understand what you go through. With all of these we were just talking before we got on live and Yes.

Yeah you get it. You know what we’re, I’m going through. I know what you’re going through and it’s hard for people who are outside of this world to understand. So yeah, I completely agree with that. Yeah. And

[00:33:39] Samantha: then as far as craft and getting published and all that, I do think the more you write, the more you read and the more you write, the more you learn.

And I had, I have a quote that was up, I moved recently and my pin board’s down and stuff so I don’t have it right now and so I’m gonna butcher it, but it’s from it’s a quote that, from John Steinbeck that basically says, Write freely and as quickly as possible and get it all down and go back later.

And that doesn’t work for everyone. Some, for some people that makes them panic. But for me, I find if I can let myself, if I can just say, I’m going to put my computer on, do not disturb for, I like timed writing. So from a very like structured craft perspective, if you are having a hard time writing and you say, I’m going to sit down and I’m going to put focus on my computer for an hour or for 30 minutes, and I’m just going to see what comes out, what I come up with.

And it can be anything. That is a great way to encourage productivity, I think.

[00:34:37] Jane: Yeah, I do that. I do that too. Yeah, I have to shut everything off and just set a word count and in an hour or two and just, yeah, the world. It’s distracting. Yeah, it’s impossible. Yeah. So I think that’s a real that’s really good advice too.

Okay, I heard this. Question on another podcast, on Ellen Hildebrand’s and Tim Talks Books podcast. And I’m stealing it because I thought it was good. Was there a book that you read growing up that, that made you want to be a writer? That you were like, Ugh, I want to do this someday. I love this book so much.

Was there any books like that? So

[00:35:12] Samantha: It’s funny to ask me that. It’s funny that you ask that. Cause I’ve been thinking about this a lot lately and in this way I am not like most writers. I’ve always been an avid reader, but I recently had to, for some podcast or like blog interview, I had to think back to all these, like the kinds of books I was reading in my childhood.

And I was not the girl reading Jane Austen and the classics and feeling romantic and Anne of Green Gables, like that wasn’t me. I was reading these weird books called Dark Forces when everyone else was reading Sweet Valley High. And there were these like, like kids would go in a cave and there’d be some kind of spirit.

And I was really into Agatha Christie. And so I think always on some level, and I definitely read more intellectually by the time I was in college and in my 20s, and I really appreciated beautifully written books and beautifully crafted books. But, and I think I still write this way. I’m more about the characters and the plot and getting and concise and clear storytelling than I am about the beauty of language.

And

[00:36:30] Samantha: I never thought I was going to be a novelist. I always loved writing, but what I was always best at was argumentative essays. I was a TA in college and I taught people how to write a thesis statement and the backup of it, all of that. And then I worked. in business strategy and I wrote strategic presentations.

That’s where my mind begins. So it doesn’t start with literature for me, which is I feel like it’s an embarrassing I feel like I should go hide it. I was going to throw something at me.

[00:36:58] Jane: No. I think it’s so interesting. And I also think that you might need to write that thriller given your like love of Agatha Christie and like that kind of.

Stuff. This is like

[00:37:06] Samantha: an epiphany I had. I was like, wait, I’ve always liked this. Like I’m a scaredy cat at the same time, but I have always liked the suspense mystery thriller. I was obsessed with Agatha Christie when I was young. Yeah, I think you need

[00:37:20] Jane: to get on

[00:37:20] Samantha: that.

[00:37:21] Jane: Talk a little bit about on being Jewish.

Is it being Jewish now or on being Jewish? On being

[00:37:25] Samantha: Jewish now. And

[00:37:27] Jane: what you had

[00:37:27] Samantha: was like an old press release. And I think they were still toying with the name at that point.

[00:37:32] Jane: Okay, On Being Jewish Now. On Being Jewish

[00:37:35] Samantha: Now.

[00:37:35] Jane: Yeah, so that’s coming out November 8th. Talk about your essay. Talk about how that project came to be.

[00:37:41] Samantha: It’s a crazy story. On Being Jewish Now is an anthology of essays. 75 writers, celebrities, advocates, It’s, I’m like nobody in this scheme of this thing. And I, it’s true, but over the summer, Zibby Owens, who I know you know, Jane, and I don’t know if your listeners probably know as well because she’s got a big podcast that people listen to, if nothing else she reached out, she started with a bunch of, a group of other writers, Lisa Barr, Alison Hammer.

Jackie Friedland, like a bunch of women, started this Artists Against Anti Semitism non profit after October 7th of last year and basically she, Zibi decided that wouldn’t it be great if she could do a book, an anthology, of people musing about their feelings about being Jewish now in the wake of October 7th.

And she sent this email out to a ton of people, a ton of writers and others saying, can you write an essay about this? And can you do it in three weeks? Cause I want to have this book out. This was in July. I want to have the book out by I want to do an audio launch by October 7th or right around October 7th.

And then I want to have a physical book before the end of the year. And so we all did it, and I for, I, maybe I’m talking too long, so stop me, please. No, you’re good. You’re good. No. So for me, I, and the essay I wrote is called Jew ish, and somebody recently, when I was hosting a, like a, I was like, guest hosting a Facebook group and I was talking about this a little bit and someone said, oh, I’m a Christmas tree Jew too.

And I was like, damn, I should’ve called the essay, the Christmas tree Jew. That’s basically what I am. I grew up with like almost no real, like Jewish family tradition, although I was bat mitzvahed. Both of my parents, for their own reasons, were atheists and, or had very distant relationships with their Judaism.

I’m fully Jewish, but and but I didn’t grow up religious. And I grew up with a Christmas tree at both my mom’s house and my dad’s. My dad married His second wife was a lapsed Catholic, so they definitely had a Christmas tree because that’s the piece of Catholicism that even people who don’t go to church like to have.

And my mom was like giving her parents the finger who they were like very religious Jews. And the minute she rebelled and that was part of her rebellion was that she had a Christmas tree. I’ve always loved Christmas and the holidays and all of that. And I never felt a, I’ve always felt a kinship to Jews, but I never felt a connection to my Jewish identity as part of my core.

And that really changed after October 7th, because first of all, I felt, and that’s what my essay is about how it changed. And so I don’t know if I want to get it away, but what happened, what originally I spent a lot of my life and I brought up this idea of passing. I spent a lot of my adult life, my married life passing because my husband is a wasp and I live in Greenwich, Connecticut.

And he, his, and so I’m Sam Woodruff, Samantha Woodruff, like I, and I was always Sam Green and now I’m Samantha Woodruff. And after, in the beginning, after October 7th, I was like, that’s a good thing. It’s going to keep my kids safe. It’s going to, but I was still posting just enough, like just pro Israel, pro like not, and I don’t want to get into the politics of it because it’s so complicated a year and a half later.

But the, I don’t I, the Hamas attack was a terrorist attack in my opinion. And I felt very comfortable with it. That was not political to say this was a terrorist attack and we need to stop the terrorists. And I appeared on blacklists because of it. Like I don’t, and when that happened, I was like, I can’t hide.

And so I’m going to go the other way. And I, it has really I’m, I wear a little tiny Jewish star now. I’ve never worn a Jewish star my entire life. But it really changed my connection to my Judaism.

[00:41:37] Jane: Yeah. Yeah. As it would, I can’t even imagine, Sam. So thank you for sharing that. And that book comes out November 8th.

Pre orders are always important and it’s for a good cause too. But how We make no money. That’s right. It’s not for, yeah, it’s not for the authors, it’s for the cause. To my last, like, How can readers best keep in touch with you, and do you Zoom with book clubs? And then I’ll take any questions from the audience.

We’ve already kept you for a while, though, oh, yes. I’m sorry. I told you that I could talk for

[00:42:06] Samantha: the entire time. No, this is great, though. I love it. This is terrible. Denise, the book’s called On Being Jewish Now. You can find it everywhere, I think, at this point. So you can get in touch with me on my website, samanthawoodriff.

com. It’s waspigirl. You can email me there. You can also, I’m on Instagram at samgwoodriffauthor. I tend to be on Instagram much more than Facebook, but it’s the same handle, samgwoodriffauthor. I’m on threads, but barely so those are my places and I love book clubs and I’m absolutely happy to zoom with book clubs or do them in person if you’re local near, near to Greenwich, Connecticut, but I’m an early bird.

So if you want me to come to your book club and it’s after seven o’clock, I

[00:42:53] Jane: know we’re both in our sweatpants from like here on out. Yeah. Yeah. Exactly. Exactly. Okay, a couple of questions from the audience that I saw. Do you think, Audrey asks, do you think investing in the stock market is like gambling in Vegas?

Would you say that’s a?

[00:43:10] Samantha: That is actually a really loaded question. Like there, this is a huge topic on Wall Street. So yes, I do think it’s gambling to a degree, but I do believe watching somebody who works, who invests for a living. My husband and having gone to business school and studied this a little bit that there are indicators that can help you better predict what might happen in to a stock or in the market overall, but that said there’s a book called a random walk on Wall Street and basically the concept of that is that.

You, that a monkey throwing darts at a board, basically pick to pick stocks will have almost the same results over time as somebody who does like thorough research. My husband doesn’t agree with this. I’m sure. I think it’s hard to not. I think there’s a big gambling element, no matter what, because there’s always outside forces that make things do what you don’t expect them to do.

[00:44:13] Jane: Oh, Denise asks, what are you reading right now? Or do you have a book recommendation, one that we should all read?

[00:44:20] Samantha: Okay I assume you’re all historical fiction lovers, right? I, my most recent historical fiction read was, You know what? I don’t know what, I have to recommend Linda Leugman’s Love Elixir of Augusta Stern, because it is just a fabulous book, and it’s all over the place, I imagine many of you have.

read it already. I really liked Husbands and Lovers by Beatrice Williams. Her and what I liked about it is I also secretly like to read character driven romance. And it was, it felt like an Annabelle Monaghan kind of character driven romance with some history. And I loved that combination. Right now I am listening to, and I’m curious if you read this, Jane, the Paris novel by Ruth Rachel.

Have you read that? I have it on my Kindle. I have not read it yet though. It’s really interesting, like it’s really beautifully and I’m at the point where I’m like, where is this story going to go? Yeah. It’s, I’m really enjoying it. And I’m reading The Whispers by Ashley Audrain because now I’m doing research about structure of suspense.

Nice, nice. Yes, fantastic food, that’s exactly right. She describes food in such a rich way. Oh, she does.

[00:45:35] Jane: I miss her on Twitter because she used to describe food so beautifully on

[00:45:39] Samantha: there. But she she creates this whole world in the same way. It’s like you’re just there. It’s really

[00:45:43] Jane: good. It’s good.

Okay, I’m gonna have to, I’m gonna finally have to read that one. I’m reading The Long March Home by Tosca Lee because she’s coming next week. It’s a World War II novel and and she wrote it actually with Marcus Brotherton. I’m also reading, I missed this one even though I love Ann Patchett, the patron saint of liars.

By Ann Patchett, which is so good because it’s Ann Patchett. It’s just beautiful. Every time I read her, I’m like, Oh, yeah. But I’m so psyched to have you on. I love this book. I hope it soars. It’s the trade off. Hold if you can hold it up again. Here it is again. Thank you. This was a delight and hopefully we’ll see each other in person.

When I’m in New York I’ll text you after this. And And thank you everyone for coming tonight and and sign up for next week. We’ve got another one next week. All right. Thank you guys. Thank you, James. Thank you. Take care. Bye bye.

HISTORICAL HAPPY HOUR

Hosted by Jane Healey, Historical Happy Hour is a live interview and podcast featuring premiere historical fiction authors and their latest novels.

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