How Jasmine Guillory Plots Out Her Best-Selling Books
From messy first drafts to revision spreadsheets, the author shares tips and insights from her own writing life.
Previously in my author conversation series: Alejandro Varela, Ingrid Rojas Contreras, Megha Majumdar, Ada Limón, Chanda Prescod-Weinstein, Crystal Hana Kim and R. O. Kwon, Lydia Kiesling, and Bryan Washington.
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This month, one week before her publication day—a time when many writers would be hard-pressed managing a million promotional tasks and trying not to crumble under the weight of pre-pub anxiety—the romance novelist Jasmine Guillory asked her Instagram followers: “Have a question for me? Need a pep talk?” One person turned to her for career advice, another for writing motivation, a third for insights into the publishing process. Others shared more personal stories and struggles, and I followed along as she responded to each one with her typical care and candor.
This is one of many reasons why I wanted to chat with Guillory for my newsletter. She is the New York Times best-selling author of eight books—including her debut, The Wedding Date; the Reese’s Book Club pick The Proposal; and her latest, the effervescent Drunk on Love, out tomorrow—and can frequently be seen recommending books on the Today Show. She is, in other words, one of the busiest and hardest-working authors I know—and I can think of no one who gives better advice or offers more generous encouragement to their fellow writers.
Guillory wrote her first couple of books in her scant free time, while working 60+ hours a week as a lawyer. “I had writer friends and I knew how hard it was to make a living at this. I thought I’d be juggling both jobs for a long time,” she said. She writes full-time now, and speaks honestly about the way inspiration can flag and then flare; the stress of deadlines and messy first drafts; and the cycles of brainstorming and hard work, frustration and epiphanies that make up a writing life. She doesn’t pretend that it’s easy. At the same time, it’s clear that she is doing what she chose to do, and what she loves: writing books that are a source of joy to her and her many readers.
“I think the time before you’re published is the best time for you to experiment,” she told me. “Listen to different types of writing advice, try it one way and then try it another way, and see what works for you.”
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Nicole Chung: Jasmine, can you start by sharing a little about how you first started writing, and how you made time for it in the margins of a full-time working life?
Jasmine Guillory: A lot of people decide they want to be writers when they’re little, but that wasn’t me. I started writing relatively late, when I was in my 30s. I was a lawyer and realized that I needed a creative outlet in my life—I’d been out of school for a while and I missed the experience of learning something new. I’ve always loved reading, and I had some writer friends and had some tentative conversations with them and they were very encouraging, and I had a novel idea—so I just kind of dove in.
It helps to know what kind of a writer you are. I knew I was not going to be one of those writers who got up early to write. I’d bring my laptop to the Starbucks across the street from my job and write for 30 minutes at lunchtime, write for an hour at night after I got home from work, and write for longer stretches on the weekends. I don’t think you have to write every day if your life does not support that or it doesn’t work for you—but for me, it worked. If I don’t write every day, the next day it just feels a lot harder. Even if I only write a few hundred words, working on the draft every day keeps it alive in my brain; it helps me get new ideas and problem-solve and figure out how to fix things. I also track my word count every day, because it helps me to be able to look at the spreadsheet and see it add up—like, Oh, it’s been two weeks, and look at how much I’ve gotten done, even though it felt so slow and impossible at the time.
Chung: Do you think working as a lawyer had any impact on how you approached having a creative career?
Guillory: In some ways, it made me think about it as a business earlier than I might have otherwise. Early on, it was relatively easy for me to learn to separate the writing and publishing parts of the job. My background in law, I think, made me more organized and detail-oriented in terms of my approach to the publishing side—I remember being very analytical when I was trying to figure that out.
Chung: So, unlike me, you probably knew how to read your first book contract.
Guillory: Oh, absolutely not! That’s the thing: Publishing is an entirely different language you have to learn. I remember when I got my first book contract, I was like, I know what these words mean, but I don’t know what they mean in this context. I think because I’m familiar with the law, that meant I knew exactly how much I didn’t understand.
Chung: Tell me about your first drafts. You just said that they’re messy—what do you mean by that, and then how do you build on them?
Guillory: I always have an outline. I will have at least the first third or so in my mind, a general middle, and an ending. As I write and learn more about the story, I’ll keep going back and adding to the outline. For my last book, By the Book, I had a very detailed outline—and then I started writing and got a third of the way in and was like, Nope. I need to start over. I’d never had to start over on a book before, but I had figured out who the main character needed to be and knew what was wrong. For this new book, Drunk on Love, I had a looser outline. I knew the beginning, I knew the first third of the story, but didn’t quite know the rest. With this book, which is set in Napa, I knew the setting would be a family-owned winery, and that at least one of the main characters would work there. Since I live an hour away, I can go there often, and I started doing some research on those trips, asking more questions. I had to get a first draft done before I knew which questions to ask, though—to some degree, I don’t always know what I don’t know until I have the story down.
I usually start writing a book by hand, because I think a blank Word document is so intimidating, and then type it up and keep going on my laptop. With this book, I wrote the entire first draft by hand. In the process of typing up what I’d written, there was a lot I discovered about the book—I saw that one of the subplots wasn’t right, and how to fix it. When I figure something out midway through a draft, I never go back, I just keep writing as if I had already known that. So anyone who read my first drafts would be very lost, and that’s what I meant when I told you that they’re messy!
I have a big revision spreadsheet, an idea I got from my friend, author Amy Spalding. Each draft is in a different tab. I create a column for each chapter, and add notes about things I want to cut and change. By the time I get to the end of the first draft, I can visualize the entire book in the spreadsheet, and I have a record of a lot of the changes I want to make in the next one.
Chung: We can count on a happy ending in your books. Within that frame, you make room for a lot of nuance and evolution and surprise—I feel like one thing you consistently do so well is let your characters figure out what’s best for themselves, and often it’s not what they thought it would be. What are some things that help you figure out your characters and their arcs, and what are some of the themes you’re always trying to explore in your books?
Guillory: I love thinking about and developing the characters, figuring out what makes them who they are and how they reached a point where it is right for them to share this story. Family, including chosen family, is a huge theme for me—I’ve said that all of my romance novels are secretly family and friendship stories, because so often these are the relationships that shape you and make you who you are. And the relationship with work is always a big question for my characters—how do we think about our work, how does it make other people think of us, and what misperceptions might we have about work and our connection to it?
Chung: It’s true that your characters’ perspectives on their careers nearly always change, too, even if the jobs don’t.
Guillory: I think that’s something that is really hard for many of us—changing our perspective on or our relationship to our work, and finding new ways to do what we want to do. And as we’ve seen over the past few years, caring for ourselves is both very important and very difficult. We think of our responsibilities to other people and institutions as more important than our responsibilities to ourselves.
Chung: What responsibilities do you have to yourself and your writing—what have you learned about your own relationship to it, and what you need?
Guillory: I’m a people pleaser and would always say yes to things automatically. Last year, I made a decision matrix for myself. The first question is: “Do you want to do this? Be honest with yourself.” Sometimes the answer is yes, but I still might say no in the end, because I’ve gone through everything it would mean if I said yes, and I know that I can’t.
Now I don’t have so much regret around missing out on something, because I’ve taken the time to stop and really think about what I need to do. And when I do say yes to things, I can know that I’ve made a good decision—that this is something I want to do that is justified for all these reasons.
Chung: You started giving pep talks to people on Instagram during the pandemic. Why did you start, and why have you kept doing it?
Guillory: I was having one of those bad pandemic days when I felt stuck, like this would never end, and I thought, I need a pep talk. Maybe some other people do too. So I asked in an Instagram story, “Does anyone need a pep talk?” and so many people responded, telling me about the things they were going through. I felt so touched that they would trust me, and it made me feel better to be able to offer some encouragement.
As I’ve kept offering pep talks, people have come back and given me updates—I’ve met some of them at book events, and it really means a lot to me. The pep talks have helped me think more about what we have in common—and the importance of being kind to others, because you never know what they may be going through. It’s also interesting to see many people going through the same things. A few weeks ago, when I offered pep talks, I heard from all these people headed back to school—teachers, students, parents—and when I responded, even more people responded saying they were feeling the same worries. One person recently wrote saying that they felt like they were lagging behind all their friends, and I knew how they felt—most of us know what that feels like, right? And yet we often think that we’re all alone in what we’re going through. It helps to remember that we aren’t alone.
Chung: What’s your go-to advice for writers—especially those just starting out, trying to find a little space for a creative pursuit, the way you did once?
Guillory: Obviously, reading is just as important as writing. I read every single day, and it always helps me think about writing. I pay attention to structure and dialogue, notice beautiful sentences and descriptions that I love, think about what makes a story or characters compelling.
Every time I start a new book, the beginning is scary to me. So I set a deadline, start writing on this day, and make myself begin. After I dive in, it’s always easier. And I think the time before you’re published is the best time for you to experiment. Listen to different types of writing advice, try it one way and then try it another way, and see what works for you. And remember: You can’t compare your drafts to, say, the tenth draft of a book that is published and has been revised and edited and copy edited.
A lot of writers who come to me for pep talks ask questions like, “How do you find the courage to start?” “What if I write something bad?” Sometimes it’ll be bad. I always think my first drafts are bad! There’s going to be some good in there, too—try to figure out what that is, and figure out why the bad isn’t working. You’re the only one who’s going to read your first draft anyway, so give yourself permission to write it. As others have said, you can’t edit a blank page.
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Some of my colleagues will be in conversation with several of today’s biggest names in business, culture, politics, and health this week at The Atlantic Festival. For a limited time, use the code TAFFRIEND for 50 percent off in-person registration. Learn more here.