Twenty Drafts, Three Books, One Character: Sherilyn Dector on Writing The Promise Trilogy – The Writing Coach Ep. 241

Kevin Johns: Today on the podcast, I have Sherilyn Dector. Sherilyn, welcome to the show.

Sherilyn Dector: Hey, thanks for having me.

Kevin Johns: Congratulations on the release of not just one book, but a trilogy of books. How does it feel to have the giant project out and completed?

Sherilyn Dector: Oh, it’s been amazing, both for the milestone, the celebration, and being able to see all of those words out in print and in front of readers. I’m getting lots of great feedback, and that’s always exciting when you’re an author. You’ve lived with that work all by yourself, alone, for so long, and then suddenly people are seeing your words and feeling your words and understanding the story. It’s a fabulous moment.

The other thing, of course, is that as an author it’s just really great to have that project done. By the end of three books, you’re so darn sick of it, and you’re just dying to move on to the next story that’s been living in your brain for so long.

Kevin Johns: Take me back to the beginning of the trilogy, because I know the lead character is a character in your other series. Tell us a little bit about the moment where you said, “I think I’m going to take this character and tell her origin story.”

Sherilyn Dector: I’ve always been fascinated by the stories of women, especially women whom society and their families were trying to keep small. There was a character in one of my series, the Moonshiner Mysteries, and she was the direct opposite of the main character. The main character was this feisty broad who was a moonshiner, rough and tumble. Lucy was a teacher, and she was very correct, very polished. She was Italian. She was the sidekick. She never broke the rules, and she was well respected in the community. Everything that Dolores wasn’t.

I wrote a couple of the Moonshiner books, and I got more and more curious about why this woman, who was so traditional, would wind up in a backwoods gold mining town in Montana. It went against everything a good Italian girl in the 1920s would do. So I started kicking around different ideas, and then finally I thought, I’ve got to write this story. I started writing and kept writing, and I went through about 20 drafts and never found Lucy. I thought, this is crazy. I couldn’t figure out how that girl became the woman I’d met in the Moonshiner books.

It was a real journey for me, both as a writer, because it challenged all of my assumptions about craft, and because it was such a fascinating story. It was like so many women of that time, where the need to break the rules was a slow process until it couldn’t be denied anymore. That’s what happened to Lucy.

Kevin Johns: I was trying to recall when the project first came to me. Was it originally one book? I feel like at one point it was four books. Talk through how you ultimately ended up on a trilogy, because I think it had several constructions along the way.

Sherilyn Dector: Well, as you know, I like to write lots of words. Unlike a lot of people, I don’t have a problem describing setting. I write historical fiction, and that’s a huge element of what draws both me and readers into the genre. So I started writing Lucy. I knew she had to be about 17 so that she would arrive in Montana at the correct age. I got thinking about what a 17-year-old girl in 1918, in this specific case, would be dealing with. I thought, well, for sure her Italian family would want her to get married. Then I said, yeah, but that doesn’t fit my story. So what else could she be doing? And I thought, maybe she’s graduating high school. That was really unusual for an immigrant girl in New York in 1918, so I had to create a story around it.

But it’s an Italian family, and we needed conflict, as every good writer knows. So she had a fiancé, an understood fiancé, one the family approved of. It wasn’t formal, because she hadn’t graduated yet. But graduation became the doorway where she was going to have to leave the life she thought she was going to have. She wanted to be a teacher. She had this whole vision of what that life was going to be, and then when she graduated, that whole life went poof, and Mama took over. Mama Santoro had other plans for her, as did the rest of the family.

You joined the story when we were well into how she was dealing with Carlo. There was the bad boy, because there’s always a bad boy who catches her eye, but we didn’t quite know how to deal with him. There were lots of other great subplots going off in different directions that have eventually become all kinds of interesting short stories that are part of the series. So it was this mammoth thing, two stories squished into one.

The first time we sat together, we asked: okay, what story have we got? Where’s the beginning? Where’s the midpoint? Where’s the inciting incident? Where’s the climax? And we found multiple, because of course it was this giant, almost stream-of-consciousness story. That’s when we decided to split it into two books. That was great, because book one was now a manageable length, and, tickety-boo, we revised it. Then we started revising book two, and I thought, no, I’ve got an idea. I know what we need to do with Dante, the bad boy. And book two blew up into a book two and a book three.

Then there was a complication where maybe Lucy would get pregnant, and so there was a book four, and it was a whole thing. That’s the flaw of any historical fiction writer: you go down into these research rabbit holes. I looked at homes for unwed mothers, and I was amazed at the situation a lot of those girls were dealing with, and how they had to abandon their babies. I thought, oh wow, this is great, so that became book four. It became a whole other book.

Finally some very wise writing coach said, “Sherry, you’ve got to rein this puppy in. You’re going to spend your whole life writing this book, and we’ve drifted so far away from that 17-year-old high school graduate who wanted to be a teacher.” So we started again and got rid of book four. That meant we needed a different climax, which meant we needed a different storyline for Dante, which meant we had to change a lot of the character arc for Lucy. So it went back to book one, and we started again, and then books two and three.

Then we had the writing retreat. In the middle of the retreat, on the way home, I had this giant brain wave. Oh, don’t you hate those?

Kevin Johns: It happened on the airplane, didn’t it? I think you landed. It happened on the airplane.

Sherilyn Dector: I took out my notebook and started writing and writing and writing, and we landed. The very first thing I did was send you an email to say we’re starting again, because now I know who Lucy becomes and how she gets there. I’m telling you, Kevin, that was such a journey, with so many starts and stops and redirections.

It was interesting, because one of the things I realized, and I think we realized together, was that Lucy’s journey was also reflecting the process of discovering who she was. We were asking her at the beginning to be something she couldn’t be. She tried to fit into that mold and failed miserably. Eventually she had to push through all of the plots and subplots and versions, in books three and four and draft 12 and draft 17, et cetera, until finally the person Lucy was became real. That allowed us to go back and write toward that question of who Lucy Santoro was, and then the process went very smoothly.

Kevin Johns: Oh, of course. Not a hiccup anywhere along the way.

Let’s say you’re a Canadian author, but this trilogy really grew into an American epic. When I think of it, I think of The Godfather or these sorts of defining American tales, even fairy tales. How does it feel to be a Canadian author writing about how America became America, and what it was to be a woman in the 20th century in America?

Sherilyn Dector: Well, certainly the experience of a woman in the 20th century is pretty similar to anyone’s in the Western world. Whether you lived in England and you were a suffragette, like in Mary Poppins, fighting for votes for women, or whether you were a Canadian, and we had our gang of five, who were championing a lot of the social justice issues at that time. That part of the story really resonated with me.

I’ve always written in the 1920s because I’m fascinated with how women were dealing with those crossroads in society. My books have all been set in the United States, partly because there are a lot of readers there, and a lot of popular movies are set there, so even Canadians have an understanding of that world. What was missing for me was the story of the women from that world. We had Boardwalk Empire with Nucky, and we’ve had The Godfather, and we’ve had lots of stories about the men of that time, but few about the women.

What was also happening in parallel, and I’m a huge current-events news junkie, was what was happening down in the States politically. The parallels have been recognized by many deep thinkers, not just me: social justice, governments withdrawing rights, the destruction of political infrastructure and justice systems, corruption, all that kind of stuff. I found that those themes were being integrated into the story as I wrote, because they were of the time.

When we were writing about the labor issues that surface at the end of book two and drive the story in book three, that was happening both in our current times and in 1918 and 1919. There was the Red Scare, and the roots of McCarthyism were being established and grown. A lot of very similar things were happening. So it was a story that formed as a reaction to what I was going through as a person, and all of those feelings were showing up on the page, which is what a lot of authors do. You write what you know.

Kevin Johns: That’s one of my favorite aspects of the story. I think it started as this coming-of-age historical women’s fiction novel, and then you mentioned the retreat, and shortly after the retreat, Trump announced he was going to take over our country and turn it into a state. Now the trilogy’s out, and he’s renamed Lake Ontario, right? Throughout the entire writing process of this book, these things were happening, and I felt like every time Trump did something horrible in the United States, your book got better. When I look back at the horrors of the last couple of years in America, I do say, at least Sherilyn got a career-defining trilogy out of it.

But tell me about that. Were you conscious of this more personal story becoming a much bigger, politically infused narrative, or did it evolve more organically?

Sherilyn Dector: I think it was very organic. My own background has very strong labor roots. There’s a scene where immigrants are being harassed and rounded up, and then there’s the Great Strike. In Winnipeg during the Great Strike, there were unionized streetcar drivers who overturned streetcars and set them on fire, and my great-great-grandfather was part of that. He was chased through the streets by mounted police officers and hit with truncheons. That story was part of my family history.

When Lucy starts teaching immigrants to pass the citizenship tests, that came out of the rent strikes, where the mounted police showed up to break them up. But at the same time, in our current world, there were all the ICE raids happening down in the States, with immigrants being dragged off the street and people being shot and children being terrified. That overlay was there: I would spend the day writing Lucy’s world, and then in my downtime I’d watch the news and see it play out again in real time. The fear in those immigrant stories in Minnesota and in Michigan was in my brain when I went back to my computer, writing about my immigrants’ fears and their anger and their resistance, and the people around them and how they were trying to support them. It became an interwoven process.

My challenge as a writer was not to make a diatribe about authority. We had to make sure there was an understandable rationale, one you may or may not agree with, for why the government in 1919 was dealing with it that way, and frankly, why the government in 2024, 2025 and 2026 is also dealing with it that way. You can see how they got there. And the challenge in both our societies, and I’m now speaking as the author and not as Lucy’s mentor, is that society recognized the intrinsic evil of it and yet let it happen. It certainly did in the United States through the ’20s and the ’30s and right through McCarthy. It was systemic. So I’m hoping readers read this with two eyes, one on Lucy’s world and one on what’s happening around them, and that they can make the connection and see how it’s affecting the other side.

Kevin Johns: I think there’s a core point of view that you bring to the narrative as well. It’s not that we forget Lucy’s story and the trilogy grows beyond it. It’s that Lucy’s story is every minority’s story. The opposition Lucy comes up against, whether it’s what career she wants, or who she wants to marry, or how society is going to treat her, we see her struggle through that. But then we see there’s a nation filled with Lucys in New York at that time.

Sherilyn Dector: Yeah, it was something I was very conscious of: creating a balance. The reader had to see Lucy torn, wanting to be the person her parents wanted her to be, the person society wanted her to be, because that world was so attractive and appealing and safe. And it also had to have that tension, being torn enough that it would be strong enough to push her out of that safe world and give her the courage to defy it.

A lot of book two is her trying to find that balance and that compromise. Book three is very much her saying, “I’m not going to compromise. It’s too important. When I compromise, I’m compromising my students, and I’m compromising who I am as a person and the values I’ve struggled to create.” It’s not an easy decision, and it’s not an obvious decision. Many times I hear from readers, “Oh, I wish Lucy had chosen Carlo,” which was the safe choice and the traditional life, or “Oh, I wish Lucy had stayed as a teacher at Henry Street and helped generations, because she was so good at it.” So readers are seeing those inflection points in their own lives as well.

There’s a cost to Lucy. It’s a cost she struggles with, that she realizes she’s going to pay and is paying, but it was not an easy decision, and it didn’t arrive without a lot of scars. Those are a lot of the scars that show up in the Montana series, where I first met her as a teacher.

Kevin Johns: I have a lot of experience in leadership roles, whether it’s leading half a dozen writers at a retreat or the 30 writers who are part of my programs at any given time. You have even more leadership experience. Did you see book three as your opportunity to dig into the complexity of what it means to stand and represent a group of people, or the sacrifices that have to be made to achieve goals for a group?

Sherilyn Dector: I think good leaders are always at the back of the parade, pushing, versus at the front. It’s easy to stand at the front and inspire, but then there’s a gap between the leader and the followers. I found that the best way is not to lecture, and that was a danger in these three books that I was very aware of. I realize there are other points of view, and I would hope that someone who believes in tradition and in listening to your parents can read these three books and not be angry at me as the writer, and not be unable to understand Lucy’s journey. Lucy was part of that process of pushing forward.

It shouldn’t be held up as a morality tale. It should be read as a young Italian girl in East Harlem in 1918 trying to figure out what she’s going to do for the rest of her life, with all of the blinders and the lack of awareness that anyone in that period would have going into that world. Of course she couldn’t foresee what was going to happen. She was swept along by events, and those events continued to shape her as a person. So the Lucy at the end of the trilogy, while very different from the Lucy at the beginning, is at her core the same person who believed in herself. She believes in her community, but the definition of who she is and who her community is changes.

Kevin Johns: We’ve been talking a lot about the politics of the book, because I find that aspect of it so interesting. But this is also a historical family drama, as well as a bit of an epic love story. Maybe this is my own bias, as a man who loves Byronic heroes, but Dante just sizzles off the page for me. He’s probably my favorite character in the series. I don’t know if we can call it a love story, but tell me about the Dante and Lucy relationship over the course of the three books.

Sherilyn Dector: Well, I love symbolism, and I love looking at how characters can carry a theme. We had the traditional good boy, Carlo, the parents’ approved model, and then we had the bad boy, Dante, a gangster and a troublemaker who’s on the wrong side of the tracks, probably a lot of the tracks. They very much symbolized the duality Lucy was trying to face.

Carlo couldn’t be a wimp. He had to be a real man who believed in Lucy and loved Lucy. Within his own mindset, he was trying to give her what she wanted, because he loved her and wanted to make her happy. But he was trying to reconcile it within his world. When she said she wanted to be a teacher, he said, “Well, yes, all good mothers are teachers.” She said, “No, I want to teach others.” And he said, “Great, you can teach Sunday school at the church.” He was really trying, and readers admired that because he was growing as a person, but he couldn’t let go of the traditional world he lived in.

Then there was Dante, and Dante saw her from an entirely different perspective. He didn’t see the teacher. In fact, Dante despised teachers: a bunch of rule makers standing at the front of the room trying to enforce artificially seized authority. What he saw was someone strong enough to defy the rules and make new rules, and he really encouraged that side of her. She was always torn through book one between the power Dante represented and the safety of Carlo’s world, and book two very much has them at loggerheads.

She decides she’s not going to marry Dante. Spoiler alert: turn off the sound now if you’re in the middle of the book. She chooses to be the person Dante sees, but then she realizes, like many women, certainly now but even then, that you don’t need to be defined by the man you love. You can find your own self, and hopefully those two pieces fit together. When Lucy found herself, she realized that that wasn’t going to fit with Dante’s world, or with Dante. She had to make the decision that Dante wasn’t going to be in her life. Her life was going to be her. And whether she ever finds that fit, her other half, you’d have to read the Moonshiner series.

Kevin Johns: Let’s talk about the family aspect, because, as would likely have been the case for an immigrant family at the turn of the century, Lucy has a lot of brothers and sisters. How did you go about crafting a mother and a father and then a whole handful of brothers and sisters? And as an author, how did you juggle all of these different characters across those books?

Sherilyn Dector: Well, it was a huge undertaking. First of all, there’s Mama Santoro, and she’s one of my favorite characters in the book, because I can hear my grandmother in her. I can hear that generation of women. I could recognize her on the street if I met her today. She’s always got a story, always got a moral parable to share, always has the rules that can’t be broken. Then her husband: how did he fit in? We needed someone who played a traditional role but would still permit the daughter to go to high school.

Then all the brothers and sisters arrived. The boys were easy. There was the older brother, who in Italian culture is almost a substitute for the parent. He sets the rules for the siblings, unless he’s vetoed by a parent, usually the father. We had the bad-boy brother, Zoro, who was raw energy. We had the solid, massive, quiet, still-waters-run-deep brother, Bruno, who sees everything and was the protector. We had the simpatico brother who recognized Lucy and was closest to her growing up. We had to take a few brothers out because the cast became too big to keep track of. The brother who was going to be a priest doesn’t exist in the trilogy now. And there’s a little brother who’s an imp and a scamp, because everybody needs a little brother.

But we needed some sisters too. There had to be a sister who was the role model Lucy was supposed to aspire to, so Maria became the married daughter, with her husband and the baby, living on the third floor, everything Mama Santoro wants for the rest of her daughters. We needed a younger sister who wants to be Lucy, who’s jealous of Lucy, kind of mean and spiteful and nasty because she’s jealous, but who becomes Lucy’s greatest ally because she’s got that 1920s independent spirit as well. And then we needed a third sister who could be the dreamer, who was still very much the child that could be molded.

At the end of the day it was a large cast, which is brutally difficult to write because of dialogue tags and different voices and different mannerisms. Eventually you can get rid of the dialogue tags because you recognize Zoro’s voice as being different from Tony’s, and how they handle things. They’ve got to have different motivations and different backstories, and one was a war hero. It became another reason why the books are so big.

Kevin Johns: Everything you’re describing there is what you would expect from a novel with a lot of characters. But for this project, it was very important to you to write the entire thing at once.

Sherilyn Dector: Yeah.

Kevin Johns: So take all of that complexity and multiply it by three. This is by far the most ambitious project I’ve ever been a part of. You were literally working on all three books at the same time. I don’t know what the word count ended up at, but I’m sure you wrote a million words over the course of the different drafts of the three books. I feel like I’m still in recovery. Tell me what it was like from your end. I only had to deal with it a couple of hours a week. You were living it. What was it like juggling three big, complex novels all at once?

Sherilyn Dector: Well, keeping the story in your head was critically important, and so it was important to understand timelines: January 1918, January 1919, and a lot happens in those 12 months. Overlaying that was what was happening in real life at the time. Who was the mayor of New York? What was happening with the government? And layering that over what was happening in the Catholic calendar for religious observances.

One of the reasons we had to do the books at the same time was that things had to be organic and adaptable, both in terms of the setting and the plot and the environment. Halfway through book two, you realize there was a flu pandemic that was really important to the story. So we had to go back and introduce the pandemic, the Spanish flu, which of course was our COVID, into book one, and then change book three as well, because by then it was a full-blown pandemic.

Lucy’s character arc had to be consistent. Where she left book one had to be where she started in book two, so that took a lot of massaging back and forth. The trilogy is also rich in symbolism. The color red shows up in multiple ways, and then there are the questions of where we can introduce that symbolism in book one, where we can introduce the bells, where we can introduce the silver flask, and where the silver flask in book two winds up in book three. So it was about keeping each book open, so you could go back and make sure the plots and subplots and settings and character details and nuances all stayed continuous through all of the rewrites, through all of the drafts.

It was one of the reasons I was so glad to be able to close it and write “The End” and release it to the world. I thought, that’s it, I’m done with you.

Kevin Johns: You mentioned symbolism, and maybe it touched on theme a little bit there. It was one of the first pieces I saw from you. I don’t even remember whether it was an outline or an act, but I just recall looking at your work, and after every scene you had written a little paragraph about how that scene ties into the theme of the book. I thought, okay, this is a thoughtful writer. Tell me a little bit about that. How did you, again and again, for hundreds of scenes, come back and ask yourself, “What does this scene do to emphasize what this book is really all about?”

Sherilyn Dector: Part of that came as a result of so many false starts. When we finally landed on who Lucy was and was going to be and how she was going to get there, it became my safety rails to keep me from going off track, because I get fascinated with story. I get swept up in a subplot, and before you know it I’m down the road and on book four. So that was my touchstone at the end of every chapter, because I draft in chapters. At the end of every chapter, I would pause and think, how does this relate to where I need to go? If it didn’t, I started again. If it was beginning to get heavy with theme, I started again, because it didn’t need to be a moral tale. It needed to be the story of a young woman. So it really was a reminder to stay true to the story.

Then, as I was going back and doing the revisions, I could see where my head was going, both in the development of the character arc and in how we needed to adjust what was happening around Lucy to give her a platform where she could grow with the theme, so we would all wind up at the same place at the end of the day.

Kevin Johns: I have a client who’s fantastic at writing opening lines to scenes. In one coaching call, we were talking about writing great opening lines, and I asked her, “What’s the secret? Your opening lines are always so great.” And she said, “The secret is I write them like 20 times.”

Sherilyn Dector: Her secret: hard work.

Kevin Johns: Hard work. I know you’re a very prolific author, but I also know you work harder than any other writer I know. I know people who spend 10 years on a book, and you just released 300,000-word-plus books in one year. But if you took the hours that author spent over 10 years, it’s probably less than the hours you put in over the last two years on this trilogy. So give people some insight into how you’re able to write so much. Maybe we’d like to be magicians and just say, “It’s magic, and the muse breathes on me,” but I know the reality is you work harder than anyone I know. Tell me a bit about your work ethic.

Sherilyn Dector: Well, I have the advantage. I’m retired, and my kids are all grown and moved away. As long as I keep my husband fed and my dogs happy… I should probably have reversed that. I can sit at my desk for as long as I can, and I love writing, and I love getting into it. Writers often talk about flow, and my flow is almost every day that I write intensively. I also have a lot of words. You can tell by how much I talk. A lot of those words are on the page.

What I do is start with dialogue, because that’s the most comfortable for me. Maybe I start even before that. Usually I start with an outline, with the exception of the trilogy, because I see the story as a whole. My outlines are binders of characters and details and plots and subplots and story arcs and plot structure and how everything’s going to fit together, so I have a good roadmap when I start. Then I start drafting, and I start with the dialogue, because I know what I want the characters to say. The dialogue usually doesn’t have a distinct voice. It’s usually my voice. Lucy will sound like me. Dante will sound like me. Mama sounds like me. Everybody sounds like me.

Then, excuse me, I go back, in draft one or draft zero, and put in the settings that I want. Hoarse again.

Kevin Johns: I’m taking you up on the opportunity. Yeah, yeah.

Sherilyn Dector: And then, when I’ve got that, I start looking at those questions of theme, and that’s usually the first time that little note shows up: is this chapter working? I know what the other chapters are going to be. I know where I’m going. By the time I move from draft zero to draft one, I’ve got far more words on the page, because I find it easier to take out than to put in. I’ve got a rough sense of what the emerging symbolism is going to be, and an image that’s really strong in my mind. So I go through the whole book. I pause at Act One. I pause at Act Two. I pause at Act Three. I pause at Act Four to look at the acts and how they’re working. I do a little mini developmental edit to see what plot holes I’ve got. Am I leaving them open on purpose? Am I closing them? I write a lot of mysteries, so I like red herrings and misdirection.

I start looking at the voices in greater detail, and the mannerisms that go with the dialogue. Would Lucy be an expressive person? Probably, being Italian. Would some of the characters around her be clipped and reserved? We’ve got Sergey, who has that edge to him, that he’s always fighting, whether he’s buying bread or leading a demonstration. He’s always angry, so is that showing up? I keep working back and forth in the story until I’m happy with it. That’s when, in the trilogy, we began to discover that we had two books in this story. We had two climaxes and two midpoints, et cetera.

By then I’ve already put a ton of work into it, so I find I want to keep winnowing as I go, because I know I’m going to be making substantive changes, and I don’t want to lose those beloved words. Those are my darlings, right? So I also keep large files of cuts. If I’m deleting a chapter, I cut it into a file. I work in Word, and I sometimes envy the people who use Scrivener and those kinds of writing aids, because I have to manually cut and paste chapters, which is a nightmare in Word. I keep an eye on my page counts. When I’ve got an 8,000-word chapter, I know I’ve probably got too many words, so my first question is: lose the words or split the chapter?

But the story isn’t really done until copy edit, and I don’t think I’ve written a book where the copy edit showed up earlier than maybe draft 10 or 11, simply because I’m constantly revising and searching for the best book, that jewel that’s in there.

Kevin Johns: So many authors, especially beginner authors, hate the idea of revisions. They think they’re going to get it perfect on the first try, or maybe the second draft. When they ask me how many drafts, I’ve always hunted for whether someone has ever said something officially. Steven Pressfield said, kind of casually, in one of his books, not The War of Art but one of his other ones, that you’re probably going to do about 10 drafts of a book. So 10 has always been the number I think of. As a professional author who takes your writing seriously, how many drafts of this book are you probably going to do? Probably 10, right? So the fact that you’re saying 10 or 11 is spot-on with what I would expect from a real writer like yourself. This isn’t your first rodeo. You know what you’re doing, and you understand that writing is rewriting.

So maybe, for beginner writers, or writers early in their career who are resistant to the idea of doing 10 drafts of something, what’s your advice? How can they come to terms with that reality?

Sherilyn Dector: Well, I think there are phases to any story. There’s that initial fall-in-love burst of enthusiasm the first time you start putting words down on the page. Those words are brilliant, and you cherish them, and they’re exactly how you think they should be. Before you rush to the printer, or to share your book, put it in a drawer and do something else, whether it’s write a short story or watch a bunch of videos or a movie, whatever. Get your head out of that story. When you come back and reread it to make sure it’s still shining as brightly as you thought it was, you will see it in a very different way. You can’t believe you wrote that, or you think, oh no, that doesn’t belong there, or holy cow, is this ever boring, or what happened to that great idea I had, that there was going to be a gnome appearing under the drawbridge? That’s your second draft, when you go back. And then you think, yes, this is the story I want to tell.

Put it away in the drawer again, because every time you bring fresh eyes to it, you see a different side of the story. You hear the words differently. Some people read their stories aloud. I really like Word’s feature where it reads the story to me, and I can hear how the words are working together, and when the sentences are going too long. That’s draft four. Then you begin to think, I really think she should have a limp, and that’s draft five. Before you know it, the story you started out with is still there. That gold nugget is still there, but you’re polishing it and polishing it and polishing it.

If you give up on the story too soon, yes, you’ll have a good story, and stories are great, and you can share them with others. But if you want the story to really shine, you’ve got to keep polishing it until a beta reader, or a coach, or a trusted advisor, or a mentor, or a book partner says, “This is as good as you need to get it. I understand what you’re saying. I can see it in my mind. I can feel it in my heart. Let’s get it out there.” That’s usually about draft 10. With the trilogy, it was over draft 20. It took a while and a lot of polishing. We had a pearl necklace.

Kevin Johns: One of the benefits of having so much to say and working so hard is that, in addition to this trilogy, you’ve written a ton of short stories over the last few years, many of which you’ve shared with your newsletter subscribers. Tell me what it’s like being one of your newsletter subscribers, because I imagine it’s pretty delightful to be a fan of an author and get a new novella on a monthly basis. Tell me about your short stories and how you use them to build out the world of the trilogy.

Sherilyn Dector: Well, as you say, I’ve written a lot of books, and I have a fairly established newsletter subscriber base. As I was flailing away writing the Lucy trilogy, time was passing. Normally readers and subscribers are patient. You give them a little update: I’m halfway through the next book, or here’s the cover, or here’s the first chapter. But time was passing, and my readers weren’t restless, exactly, but they wanted more story. They liked my stories, that’s why they’re subscribers, and I needed a way to keep them engaged. In the middle of the Lucy story I knew it was going to be even longer than I’d expected, and I needed to reward my subscribers for their patience.

So, exclusive to subscribers, I started writing short stories. I’d never written a short story before. And again, a lot of words. I’m still not sure I’ve written a short story.

Kevin Johns: Well, my short stories are…

Sherilyn Dector: My short stories are short novellas.

Kevin Johns: Novellas.

Sherilyn Dector: Yeah. My short stories are 16,000 words. My novellas are 50,000 words. It’s a different scale. But I would take a character and think, we don’t want to talk about Lucy specifically, because that could introduce a rip in the time continuum, so let’s talk about the other characters. What would Mama’s backstory be? What’s an aspect of Mama that we could share with the readers? So I started writing the short stories, and they were a little clumsy, because it was a new style and a new craft, and I was learning it as I went. But I have patient readers. They started off getting one every couple of months, and I got great feedback: “Oh, I love this! I’m really excited to start reading Lucy’s story.” I always ended with a note that this is part of Lucy’s world, and a light bulb went on. I thought, let’s rebuild this enthusiasm for the trilogy. So I started writing the stories deliberately, one a month.

Then I started thinking, I love writing. Short stories are a great way to experiment with different writing styles that you can’t try in a novel, because you don’t want to commit a couple of hundred thousand words to a style that doesn’t work for you. So I wrote a noir mystery set in the 1920s, with a gumshoe and heaters, and “heater” as a description for a gun, and it was so much fun. Then I thought, I’m lousy at comedy, so I should try to write a comedic short story. I put a couple of characters from the book, way back earlier than the book is set, when they were kids, and they find a lucky penny. What does that lucky penny do? It grants wishes. Are the wishes real? They go through the short story believing their wishes, and of course the reader sees that they’re not, but the kids are bright-eyed, and the comedy was a lot of fun to write.

So I did a whole year of writing different genres and different styles, which was great as a writer because it gave me a different ear. Dante’s voice got a little more gangsterish, not Cagney cartoonish, but Jimmy Cagney, you know, how he probably would have spoken, because I’d written that noir mystery. Then I started thinking about bundling, and reader magnets, and all of these short stories kind of grew and grew. I started writing different points of view of scenes. I’ve now got 28 short stories that belong with the trilogy, and at some point they’re going to be something I’ll market and sell as a product.

It also inspired me. I’ve got another series on the go, about Christmas mysteries in the Jazz Age, because I’ve always wanted to write one, and they’re a nice seasonal thing to have. I thought, we need some short stories here, so I wrote four of them even before I started writing the novel, because I wanted to get a feel for what that world was going to be like and who the characters were. From those short stories, I picked my main character. So it helped the writer, and it will start entertaining the readers. The first one will drop in September, because we’re now into the world of that next series.

Kevin Johns: Fantastic. If folks want to get on your mailing list or learn more about you and your writing, where should we send them?

Sherilyn Dector: Have them drop me an email at [email protected]. I hope you can put it in the show notes or whatever you do, and I would love to add them to my email list. Or frankly, you can go to my website, which is sherilyndector.com, and click on a link to pick up some of those short stories, and you’ll automatically be on the list.

Kevin Johns: Fantastic. I want everyone to check out The Promise Trilogy. I know how much work I put into it, so I can only imagine how much work you put into it, and I think it all paid off. At the end of the day, no one cares how much work we put into it. They care whether it’s a great read, and I truly believe it is. I think people are going to love it so much. Where do you want them to go to pick up the book?

Sherilyn Dector: It’s on Amazon, on all the Amazon platforms. I really hope they read it, and if they do, I’d love to hear from them. They don’t have to leave a review on Amazon, although that’s always great. But send me an email and let me know what you think. Did Lucy make the right decision, to be a teacher and not to marry Carlo and, frankly, to leave Dante behind? Were you scared when they were fleeing the raids? Were you crying when she said goodbye to her family? These are all moments that any writer works so hard to give you that emotion in, and to be able to hear that you felt that is just so rewarding.

Kevin Johns: Well, I’m sure more than once you and I got on a call on a Saturday and I said, “You had me in tears last night while I was reading everything at prep.” It was such a pleasure to work with you, Sherry. This was truly, as I said, one of the most challenging and complex projects I’ve been a part of, and getting to see you juggle it and conceive it and put it all together and now finally release it has really been an honor. You should feel so proud of this trilogy. I think it’s a real accomplishment for your writing career. Thank you for letting me see behind the scenes and be a small part of it.

Sherilyn Dector: No, thank you very much, Kevin. You really did pull it from the ashes and breathe life into it. And it is our book, I guess. The role of a coach, especially when the author needs to talk to someone and get out of their head, is critical, whether you’re starting out, or in a new genre, or frankly dealing with a project that’s overwhelming, and you certainly played that role for me. Thank you.

Kevin Johns: Well, it was an honor. Thank you for being on the Writing Coach Podcast. It’s so great to finally get you on the show. Thanks for spending some time with us today.

Sherilyn Dector: You bet. Thank you very much for inviting me.