This transcript has been edited for clarity.
Caroline: Hi everybody, I am Caroline Leavitt, the New York Times bestselling author of thirteen traditionally published novels, including Is This Tomorrow, Pictures of You, and Cruel Beautiful World. My latest novel, With or Without You, is now in paperback from Algonquin books.
Moreover, I just sold an outline (and the first 70 pages) of a novel provisionally titled Days of Wonder, which follows the adult lives of a teenage couple charged with attempted murder when they were fifteen.
Gina and I are going to be talking about whether you should outline before or after writing and whether it’s the right thing for you.
Intro to Outlining
Gina: I feel like I'm the lucky one here to be talking with you. You’re my inspiration about all things writing, and the evolution from being a pantser to now becoming more of a plotter.
I know that a lot of people talk about whether they fall into one camp or the other. At the beginning of my writing journey, I was somebody who wrote completely in the dark: I just had an inspiration and I followed it through. I didn't actually map out until many drafts later.
There's nothing wrong with people who write that way, and today we're going to talk about how different books require different things from you. There's nothing wrong with writing both ways.
And then we are going to talk about how outlining and blocking out all the beats can really help you with deadlines, when you need to make sure that every time you sit down at your desk you've got something that you're focused on.
Caroline: Yeah. Gina’s approach to plot is driven by the work she did to create characters as an actress, which many of you might find helpful. As a novelist, I'm really in favor of structure, mostly because every once in a while I will get a lot of novels that have near-miss rejections. I get a lot of novels from Reedsy and the problem is always structure. Either the character arcs are not strong enough or things aren't building as they should.
Outlining could give you a map, an early map before you start drowning. So I always begin with an outline, and I always begin with what's haunting me. I don't think about the market and you shouldn't either. Not yet. And I don't think about my readers, not yet. And you shouldn't either. Instead, I think about what is the thing that I want to know that I care about? Because if I go deep there and figure it out, the deeply personal is going to become universal.
The first thing you need is an idea that's going to grab you for the year (or years) it might take you to write this novel, and usually it's a question. For my novel With or Without You, the question was: what happens in a long-term relationship of a couple in their 40s, when one of the partners falls into a coma, and when she wakes she’s a stranger, both to herself and to her partner? And she has a startling new talent that gives her the fame her partner's desperate for, and she's not so sure that she wants.
But first, Gina, I want you to talk about your evolution, from someone who never outlined with their first book, to outlining partly through your second book, to now outlining your current book and writing a synopsis as well.
Free Writing vs. Outlining
Gina: There are a couple of things to mention. With your first book, you have a lot of time because maybe you haven't sold it yet, or you don't have an agent yet. You've been working on it for years, or at least that was my situation. I worked on it for a very long time.
I just had an idea, the first line of dialogue, and I went with that. I wanted to explore who this woman was, and I started putting the story together. I sort of built it out character-wise, exploring the themes and relationships between them. And don’t get me wrong, it was wonderful - but it took many, many drafts to get to the end of that book.
This was years long, and I remember having a conversation with you Caroline, saying that I really didn't want to take that many years to write the next book! And so we talked about the benefits of outlining, which is something that I resisted for a long time. I kept thinking that I would not have any fun with it, or discover things as I write.
But I learned that it’s not true. The next book I wrote, I still started with those big questions:
- What is this book about?
- What are the main themes?
- Why are these characters here now?
It’s a creative brainstorm, just to see what I'm thinking about. And then I still like to write a couple of pages that are in the character's voice, where I blindly follow one character. Cause for me, character informs the plot. If I know the character, I can follow them. I know where they're going. I'm going to trust them. They're going to take me on their journey and I'm going to be able to follow them.
Then I look back and I see what I have, and early on I start to map out those arcs and really get a sense of what their trajectory is, what their journeys are going to be. Then I look at who the secondary characters are, and how they inform that journey. To sum it up:
- I start with a high-level outline
- I break it down a bit more
- I write a narrative synopsis for it
- I break it down into the first, second, and third act
- Sometimes I break it down beat by beat (like I did for The Wise Woman)
What about you?
Caroline: My writing journey started when I won a young writer’s contest in my twenties. I thought it was going to be a short story writer, but then all of a sudden some editors wanted to buy my story as a novel. I had no idea how to write a novel. I thought the story was already complete.
I instantly got an agent, and the agent said: “Well, you have to outline it and then we'll have a book sale.” Oftentimes traditional publishers ask to see a synopsis, which is a fancy word for an outline, so it's always good to be able to write one, whether you hate it or not.
So I had to write a novel about this idea and it was really hard, but the book sold and it did really well! You would think that I'd continue outlining my stories, but I didn’t. I had this misconception that I was losing the muse and the source of creativity. So I went back to freewriting, and I ended up with these 800-page books that had no story.
I wrote seven of them like that, but eventually, I discovered structure. I began to realize that you can outline a book and still have many surprises as you write it because everything changes all the time.
So, Gina, you were talking about detailing your characters’ motivations, their moral arcs, and their trajectories. That’s what I do too when I outline. I'm thinking about the character arc: they started wanting this, and at the end, they should be sort of different, having learned something.
I call this The Rolling Stones method of plotting a book, because the character can't always get what they want, but if they try really hard (like in a novel with high stakes) they can get what they need, which is different.
So anyway, I wanted to know if you can talk about that about character motivation and moral arcs. What is a moral arc?
What is a moral arc?
Gina: You said it beautifully: the character doesn't always get what they want, but they get what they need. There's growth, the character is placed in a situation there's a catalyst that has changed their world. As readers, we have to watch them grow, get new information, and be transformed by that new experience of the world.
It's about growth and evolution: starting in one place with an idea of who they are and how the world works, then things don't work out for them, but they grow from the experience and it enriches who they are. Finally, they face the future quite differently, with an altered worldview. Hopefully, they've grown as a person.
Caroline: It's really about how to live in the world, I think. But I'd like you to talk a little bit about your process of writing and outlining at the same time. What does that look like?
How to write and outline at the same time
Gina: I like to have a general idea of what the book is about. For example, for my latest book, I was thinking about the concept of betrayal. Usually, when we think of betrayal we think of infidelity. But what if you were betrayed in a different way? Maybe somebody had lied to you, or you were betrayed because the job that you had devoted so much to didn't work out. Or maybe you’re aging and you've got pushed out of your industry. You were betrayed by your own ideals, as they ended up working against you.
So I wanted to really explore this theme, and I had this character's voice in my head. I knew she was a mother who had suffered a betrayal in her marriage. I started writing from her voice and I just put her in a situation where she discovers the betrayal right away. I wrote about 50-80 pages just answering a few questions: Where is she? What does it look like? What is the environment? This allows me to know the character very well.
I feel really comfortable starting with the people and then filling out the world around them. I think it comes from my background as an actress, where I spent so much time developing character, understanding their backstory, and what motivates them.
With Clementine, that's what I did. It became very clear to me who she was, what kind of mother she was, and what her relationship with her husband was. All the other characters started coming into the story and I start to discover the tone, the voice. I realized that there was a lot of humor in this book. All of this comes from writing the character at the beginning, it really drives my story.
Then I pause. This is all fun, but you got to have structure at some point!
I ask myself: what am I looking at here? Well, I'm looking at a woman who is now facing a future that doesn't look anything like what she anticipated. That future has changed. There's a catalyst that happens in the beginning.
From there I’m able to map out the story, adjusting the outline as I write the story. About midway through I usually have the outline. I haven't written all the pages, but I have the structure.
To learn more, check out Reedsy's Guide to Story Structure.
I use the writing as the engine and inspiration to figure things out, and then I'm able to logically go: “Oh yeah, this could happen next. And this could happen next.” And I allow myself to change it as I go. There are always new threads that happen, and other characters you want to give space to, and it’s easier to do when you have the story mapped out.
Outlining the Wants and Needs
Caroline: I wanted to talk about my Wants & Needs Bible, something I talked about it during a previous Reedsy live and that I give to every single one of my Reedsy clients.
I discovered it when writing my ninth novel when one of my students at UCLA said “I want you to read this book about structure” and I said, “Oh no, I want the muse! I want to just free write and discover!” And she said, “Okay, well, why don't you just read it?”
Eventually, I read it, it was a book by John Truby, The Anatomy of Story, where he talks about moral choices and character arcs. The book blew my mind and since then I began to develop steps in my approach to writing. Once I have the basic kernel of what the book is about, I fill out my Bible of Wants and Needs.
These are the questions I answer:
1. What is it that the character wants desperately or something terrible will happen? What's at stake? For example, a poor man needs to be rich in order to survive and win the person he loves.
2. What is the character's misconception that keeps him from getting what he needs? He grew up really poor and he once visited a friend who was wealthy, his main feeling was that in order to be happy and loved you have to be rich.
3. What is his plan and how does it fail? Usually, the plan feels because of The Misconception. Our hero probably works really hard, gets a scholarship at Yale, goes into banking, something he doesn't really like but that's part of his plan. He gets a job as the Head of a bank, has a trophy wife, but he's not happy.
4. What is the “all is lost” moment? Some people call this The Big Doom. This comes about three-quarters of the way through your outline. It’s when the hero comes home to find that his trophy wife has left him because he's working a thousand hours a day. He realizes that what he thought he wanted (lots of money) didn't make him feel happy, but it ruined everything in his life. Now he has to figure out what to do next. He has to take action.
5. What's he going to do next? He quits his soul-crushing job, and he starts doing something he loves, like painting, which he used to like. He is surprised because he's actually doing it. He starts selling paintings and people like his work. And because of that, he starts to interact with all kinds of people, with all kinds of finances. He changes as a person.
6. What did he learn? At the end of the book, you can call this “the new equilibrium.” This tells how the character has changed in living his life. Our hero has quit banking, he's painting. He takes a job teaching art to elementary school kids. He loves it. The pay might be crap, but he doesn't care because now he's realized money is not as important as happiness.
Once I have this outline, I usually write the first chapter. I do that because editors and agents won't read past the first three pages if they're not great. The first three pages are a microcosm. They have to show:
- Who's the main character?
- What do they want?
- What is the question?
The first chapter is asking a question that your last chapter is going to answer. In the example I gave the question is: “Does money bring happiness?” Other questions that agents and editors consider are:
Does the world of your story change as the character changes? Hint: it should.
Is the ending satisfying? You should not tie up every single loose end, but given you give readers what I call “a never-ending story”.
So Gina, what do you start with when you're outlining?
Outlining Best Practices
Gina: I developed a method that works best for me and goes as follows:
I start by asking myself: what is this novel about? For my last work, the answer was: “This is a novel about facing a future that looks different than the one you expect.”
Then I list a bunch of other themes.
- This is a novel about women rallying together to help each other.
- This is a novel about family.
- This is a novel about change.
- This is a novel about getting back to what matters to you.
- This is a novel about what's important
The list goes on and on and on. That’s how I start every time, the themes I want to explore start to emerge and I write with those in mind. I care to know why is this story important to me right now.
Then I look at the characters: what's happening in their life right now? I'm not running their whole backstory. I want to come at the moment where things are happening to them. That's my style. I want to set them up and have a catalyst that happens.
Since I'm also a copywriter and I've worked in marketing and branding, I like to write the elevator pitch, which is basically what it would say on the back of the book. So if somebody asked me: “Hey, what's this book about?” I would know how to answer.
I find that when I'm forced to get succinct with what the book is about, I realize quickly where the holes in the plot are. If I can’t explain it clearly, I need to improve it. But plot holes are normal, it’s ok if it’s unclear for a while!
Wants and Needs
Finally, I also have the Wants and Needs checklist to map it all out. I write about each of the characters to know who they are, what they want, and what they need. I continue to map their moral arc as I go.
Caroline: I want to stress that writing a synopsis (or you can call it an outline) it's really difficult. I mean, I know how to do it, and it still takes me six months. Along the way you keep making discoveries, for instance, one time I didn't realize that one of my novels had a strong theme about fame until my 10th draft.
So Gina, now you're working on a new book. What do you know now, as opposed to what you might know after a few drafts and you're adding things to that?
The Benefits of Outlining
Gina: What I know now is that outlining is fluid. I was really thinking that if I was going to outline, I was going to lose all the fun, that I wasn't going to make any discoveries, but that’s not true.
Moreover, I want to make the most of my time. Strangely I'm not getting younger, I'm not aging in reverse (how rude!), and I want to be able to write more books. I'm a working mom and when I sit down I want to make the most of that time.
I love that feeling of writing. I think we all do. That’s why I've resisted outlining. I thought it was going to eat into my writing time and hamper me. But instead, I found it kind of freeing because I have something to work on that day, you know? I can always take a section of the book, a chapter, a beat, a scene.. and I can work on it.
Right now I have a pretty tight timeline, I wrote up a proposal for the book, a really high-level summary of what it’s about. Then I wrote and revised three chapters that I felt were really good, just to make sure the style and tone were working. Then I did that big brainstorm document I mentioned, covering themes, secondary themes, the main characters' conflicts, and the catalyst. Then I broke down the first, second, and third acts, and I felt really good about it. I thought it was enough and I showed it to my agent and to my editor, and they like it. But they asked me to break it down even more.
Outlining by Beats and Three Acts
Outlining by beats was new for me. I created a 22-page outline that has about 80 different beats: some of those beats will be scenes, some will get put together, and some will become chapters. Right now it's almost like a point form of things I need to know happen, but I still have the freedom to play with them.
I used to do cue cards, which I love, but my writing is terrible and I can never get enough detail on them. I always need to go back and add something else! So this time I wrote copious notes and I typed them all up, then I cut them all into strips which I put on my wall to visualize them better.
In act one I have my setup, the world that the character lived in before. It's the reality where we're meeting them in their current circumstances and where the catalyst happens and changes their world. The protagonist makes a decision of whether or not they’re going to change. For instance, the catalyst makes the character say: you know what? There have always been problems in this marriage. I got to really face things that I'm not dealing with. And so they move into the new world. That's that first act for me. I break it into A and B, the setup and the call to adventure.
This is what I like to call “the new world” or “the new world rules”. (By the way, this structure comes from the Hero's Journey, Truby, Save the Cat — all these movie structures that I personally find really helpful.) In Act 2a we have the new world rules, this new environment that the person is in, and then we have all these complicating actions, the things that go along with this new world that make it difficult to live in and to navigate.
That brings us up to the midpoint, which can be a couple of things. It can be where the character's world has really changed, or they're either really thriving in it, or they're failing in it, but it's all these new realities.
Then we go into Act 2b, with all of the complicated reactions, developments, more storylines, and B characters coming into play. We start to see all these different crises and battles that happen within the character as has they're adjusting to that new world. This is moment is also called the “all is lost moment'' or “the dark night of the soul”, or a big crisis that tests this character in this new world.
What are they going to do with all of that information? Are they actually gonna grow? Is it actually going to set their world on a different course? Are they going to have that aha moment? Is there really going to be an evolution for them?
These questions are answered in Act Three, where there is the resolution, which hopefully ties into the themes that you've been establishing the whole way through.
To learn more, take a look at Reedsy's Guide to Three-Act Structure
What is a beat?
Caroline: There is a question that flashed up: what is a beat? Each beat is an action and tells the main story of the main character. My agent used to make me do something she called Eight Beats.
For example, let’s look at Little Red Riding Hood:
- Beat one: She has to go visit her grandmother who's sick and dying, and she's afraid of the woods.
- Beat two: She gets the basket all set up and enters the woods, terrified.
- Beat three: Red sees the Wolf and something happens between them, she realizes that maybe he’s not so scary.
- Beat four: She finally makes it to grandma's house.
- Beat five: Red comes into the house and something's wrong with grandma, she doesn't look like grandma and she discovers it’s the Wolf.
- Beat six: Red has a choice: she can flee to safety and let her grandma be harmed, or she can stand her ground and fight back, knowing it can be the end of her.
- Beat seven: Red overcomes her fear and she vanquishes the Wolf to rescue her grandma.
- Beat eight: There is a self-realization: Red realizes she is brave.
This is just an example, you can experiment with different ways of outlining and figure out what is going to make this book work for you.
Gina: Yeah, absolutely. Some people like to break it down into just eight beats, some into 15 different points, and some expand even more. I think it is important to play around with all of those different versions and as you go along, you find out what level of specificity you need for yourself.
Final Thoughts on Outlining
Gina: I don't think that anybody is just a pantser or a plotter. You will find that there are sections where things work really organically. For me, the opening of the book comes much more naturally than in the middle of the book. All of these tools allow you to get unstuck and have something to return to so that you won’t stare at a blank screen or experience the infamous writer's block.
Outlining gives you something to focus on, a map to work things out. I know people who still like don't do any outlining, or some who just want to know the beginning, middle, and end. The more you work with it, the more you'll discover the best strategy for you.
The following is the editorial synopsis for With or Without You by Caroline Leavitt. Text in [square brackets] indicates Caroline's commentary and annotations.
Synopsis for With or Without You
[This is the question the novel is asking] What happens when we or the people in our lives become people we don’t recognize anymore?
[What do they WANT? What do they think they NEED?] After almost twenty years together, Stella and Simon are starting to run into problems. An up-and-coming rock musician when they first met, Simon has been clinging to dreams of fame even as the possibility of it has grown dimmer, and now that his band might finally be on the brink again, he wants to go on the road, leaving Stella behind. But she wants him to grow up, to finally commit to her, buy their apartment, have a child. They’re drinking, arguing, and when Simon finds a recreational pill in his pocket, both a reminder of their early reckless days of love and a possible antidote to calm themselves down, they both take it. [Inciting incident that spins things around.] They pass out, but in the morning Simon wakes. Stella doesn’t.
Rushing to the hospital, Simon realizes he’s lost his chance at fame, but he can’t lose Stella. Stella’s in a coma, and Simon’s become a caged animal, having to juggle bills by driving a Lyft, watching his band cut him out and then go on to the fame he’s always been desperate for. [He made the right, albeit for him, a terrible moral choice. He chose her over fame but he is paying for it.] Libby, who never thought much of Simon’s posturing, begins to realize how devoted he seems to Stella, and the two of them grow closer, and to both their shock, fall in love—something neither one wants to act upon because of Stella’s possibility of waking up. Libby tries to help Simon, promising to send a demo he’s made, and then deciding last minute, not to, because she believes Stella needs him present—and so does she. [Enter another character, Stella’s best friend who wants the best for her friend, but she is also falling for Simon, which gives her a terrible moral choice. Does she betray her best friend—or herself.]
[Now the stakes rise. Simon stayed for Stella, but this is no longer the Stella she knows. Libby, too, has her stakes rising. Before she was betraying her friend—but who is Stella now?] But when Stella wakes months later, she wakes a radically different person, with a radically different personality, one that disrupts both their lives, and the lives of Libby, Stella’s best friend and the doctor taking care of her. Stella and Simon are strangers to each other.
Stella is so restless that she cannot concentrate. Going back home is a nightmare. She doesn't recognize anything about it. She notices that Simon is now taking care of the things she used to do, the bills, the cleaning, and when she tries to get back control, she screws up. She wants closeness and Simon isn’t sleeping with her anymore. She begins to run at night, to get the energy out, and one night, when she is running on a long dark road, she gets a thrill of adrenaline. It’s the first time she’s felt alive. And she wants more of it. She almost died in coma, and now all these risks seem like a way to live for her. She begins to choose the more risky routes to run, each time feeling happier and more alive. [I am arcing her transformation from the wrong thing (running, picking up guys) to the RIGHT thing, her painting.]
But after a while, running isn’t enough of a rush. Stella is science-minded, and she knows that adrenaline is addictive and she craves it now. She begins picking up men and sleeping with them, and as soon as she does, she’s horrified with herself. She comes home and begins, inexplicably to draw—her new addiction. As Stella draws in the park, she realizes she has this extraordinary talent. She can see the inner lives of her subjects. To Simon’s astonishment, Stella becomes incredibly famous, the way he had yearned to be, but unlike,e Simon, Stella doesn’t want the fame. She just wants to draw.
As these three people—Stella, Simon, and Libby—get closer and closer, it leads to an incredible betrayal, which sends Stella vanishing, and Simon and Libby fracturing. [Yep, here is the BIG DOOM, all is lost moment, which allows characters to realize their misconceptions and find what they truly need.]
[Here is our friend, the new equilibrium.] But in the end, all become someone new. Simon learns that the love of one person is far more important than the love of many as a rock star. Libby realizes that the control she’s had over her life and over people as a doctor doesn’t work in real life, and Stella will become something she never expected or thought she would want—a single mother, working as an artist in a small town. And who knows what other lives she might have.