Using outlines to prevent writer’s block - Authors A.I.

Alessandra Torre
November 3, 2022

In a recent Draft Friday, I was joined by Scott Bartlett, a military sci-fi and space opera author. (The prolific Atlantic Canada resident is one of the founding authors of Authors A.I.) We delve into the power of outlining to accelerate your writing process.

Here are some key takeaways from my conversation with Scott:

  1. Scott’s writing journey: Scott, who recently completed a 10-book series titled “Spacers,” discusses his evolution from being a pantser (or discovery writer) to becoming an outliner, emphasizing the importance of having a clear direction for his stories.
  2. The evolution of outlining: Scott shares insights into his journey of outlining from his initial experience of writing without a plan to gradually incorporating outlines into his process. He discusses the influence of renowned authors like Chris Fox, Libby Hawker, John Truby, and Larry Brooks on his approach to outlining.
  3. Benefits of outlining: Scott emphasizes the time-saving benefits of outlining, especially for indie authors who face the pressure of producing content in a competitive market. He explains how outlining provides clarity, direction and purpose to each scene, enabling writers to maintain quality while increasing their output speed.
  4. Understanding plot points: Scott breaks down the essential plot points in a story, including the setup, inciting incident, first doorway, midpoint, crisis point, second doorway, and final battle. He discusses their significance in driving the narrative forward and keeping readers engaged.
  5. Flexibility in outlining: While Scott follows a structured outline, he highlights the importance of flexibility. He advises writers to pivot and adjust their outlines if needed, allowing room for creativity and spontaneity in the writing process.
  6. Character development and flaws: Scott explains how evolving circumstances in a series can bring out different character flaws and challenges for the protagonist. He emphasizes the importance of flawed characters and their growth throughout the story arc.

By following these steps, Bartlett says he’s able to be prolific and rarely encounters writer’s block. It was a great discussion, one you won’t want to miss! Click below to watch our 30-minute recording and hear the questions we answered from the live audience. Keep scrolling if you’d prefer to read the transcript.

More info:

Try out Marlowe, our A.I., for a critique of your novel: authors.ai/marlowe/

Check out Scott Bartlett’s books on BingeBooks.

Enjoy the show? Check out our past First Draft Friday episodes.

TRANSCRIPT:

Alessandra: Hello everyone, and welcome to First Draft Friday. I am your host Alessandra Torre with Authors AI, and I am joined today by Scott Bartlett, who is a military sci-fi author, as well as space opera. And today we’re going to be talking all about beating writer’s block through outlining. That’s my quick and fast summary. We’ll jump into it much deeper, but welcome, Scott. It’s so great to have you on First Draft Friday. Do you want to introduce yourself? Just tell us a little bit about you and what you write.

Scott: Sure. It’s great to be here. Thank you, Alessandra. I write space opera/military sci-fi. I just wrapped up a 10-book series, “Spacers.” And the last two books are done and edited. They’re about to come out and it’s time to see how the readers feel about how I wrapped up a 10-book series. I hope they’re happy because it’s a big investment, a big time investment to read. But until it comes out a little bit on tenterhooks, as they say.

Alessandra: I can’t even imagine the pressure to come up with a finale, you know, that you’ve spent 10 books leading up to.

Scott: I tried not to think about it too much, but luckily with the power of outlining, I wasn’t totally blindsided about how to end it.

Alessandra: So let’s talk about outlining for a minute. So you just finished a 10-book series. How many books have you written in total, roughly?

Scott: I’ve written, that was my 30th. The 10th Spacers book was the 30th that I’ve written.

Alessandra: And were you an outliner from the very beginning?

Scott: I wasn’t. It’s been a bit of an evolution. Well, actually funnily enough, my first book, which I didn’t end up doing much with until at least 10 or 15 books into my career I rewrote it. But anyway, the first book that I published was basically completely pantsed, as they say, you know, a plotter versus a pantser, writing by the seat of your pants. And that one, funnily enough, I wrote it for a contest deadline in 18 days, which seems insane. But a friend of mine who writes to my genre, Craig Falconer, just told me that he wrote an even longer book, in an even shorter time. So, I mean, the output that some people are capable of is really impressive. That was a lot for me. I don’t think I’ve repeated it since. So it was a 60,000-word book in 18 days, and I just flew and it was, you know, it was very fun. It was, you know, very creative. I don’t know if I would call it the most structurally sound book from a story structure perspective, but it was a medieval comedy novel, very absurdist. So maybe that kind of went with that.

Alessandra: Real quickly. That is super impressive also because you are pantsing. Because a lot of times the authors that we hear with these like crazy outputs, they are outliners and we’ll talk about that today, is how that speeds it up. But it was interesting that that first book, it was pantsed and you wrote it in 16 days, 18 days, whatever. Yeah.

Scott: Yeah. I feel like I was going back to my university days, you know, the night before trying to write the essay at midnight the night before the deadline. So the pressure, I feel, it was a really good environment for being creative and kind of having, you know, the connection from idea to idea. But I never want to do it again. So I’m glad I had the experience. Don’t want to repeat it. For the next book, I think I had like a 200 page — I wouldn’t even call it an outline. It was just like a brain dump of ideas that I eventually ordered and kind of wrote the novel around that. So not an intentional outline at all, but I liked having, you know, points to visit as I went through. And I liked having an idea of where I was going, and it’s kind of evolved from there. You know, I’ve read a lot about story structure and, you know, watched videos and things from people like Chris Fox and Libby Hawker. John Truby has been a big influence on my approach. And Larry Brooks’ story engineering has been another one. So my approach is sort of a simplified, boiled-down amalgamation of those four and maybe some others that I’m forgetting.

Alessandra: So let’s then jump into your, and for everyone joining us on, I’m already seeing comments pop up on YouTube and Facebook, don’t be shy. Please share your questions and comments and if we can answer them as we go, we’re going to answer as many as we can. But without kind of diverting too far from what you’re going to talk about today, can you talk just about outlining and how you use it to, you know, to speed up your output?

Scott: So really, it’s like I said, just having an idea of where you’re going. I feel like having an end goal is really important. And the first time I realized that, I was like, okay, well, I need to know how I end the book, and that’s going to give me a sense of direction. And while that’s true, there’s a lot that happens as, you know, Alessandra, from, you know, word one to the end. It’s not really quite as simple as knowing your final destination because, you know, in a good book, one that hooks you and keeps you turning the pages, there are a lot of twists and turns along the way, a lot of reversals and things like that. So as I delved more into learning about story structure, I realized the value of having a lot of little endings along the way.

You know, and it’s really an ending that kind of flips into, or, you know, turns the momentum into a new section of the story. And by having those little mini endings or plot points as they’re often called it gives you a lot of clarity, even on a granular scene-by-scene level. You know, you know where the scene fits in the puzzle of the story. You know exactly what you’re working toward, whether that’s, you know, 15% into the story, 30%, 50%, or you know, what have you. And knowing that is really clarifying. And if you can tie that in to say, like, I want the scene to a) advance the plot, b) build character, c) set up a mystery, then that’s going to be a pretty dense chapter from an entertainment perspective. There’s going to be a lot of meat for a reader to dig in there. And it’s all because you have that clarity from the outset because of your overarching story’s structure that you figured out before even writing a single word.

Alessandra: This is so great what you just shared, and I know we’re going; Scott and I had discussed prior to this kind of the progression of how this chat would go, but what you’re saying is really interesting, and I do want to dive a little deeper into your process. So when you sit down and you say, I’m going to write a book, or I’m going to, well, first of all, you write in series. So do you have to do a series outline first or how far forward are you outlining in your series?

Scott: In terms of heavy outlining, it’s usually book by book. I do like to think about, you know, what are some plot twists that I’m going to have at the end of the series, you know, where generally am I going? What do I need to set up in terms of characteristics and mysteries and so on? But in terms of heavy outlining, I do allow a little bit of a pantser element to work its way in when doing a series. I like to keep myself open if I’ve accidentally written myself into a corner that I don’t have to slavishly stick to that broad series outline, I can kind of pivot and bring it in a new direction if that’s where the story wants to go.

Alessandra: Yeah, that makes perfect sense. And so you have a general sense of where the series is going to go, but when you sit down to outline book two or book three, let’s say you’re writing book three, right then. Do you start with the ending and work backward or do you kind of work chronologically and create those kind of major plot points along the story?

Scott: Yeah. Well, I mean, if it’s a book two or a three or any kind of sequel, you already sort of have the beginning point just because it’s ending off. I mean, maybe you have a time jump, so that’s not necessarily true, but you do have a much clearer idea of where you’re going to be starting in the story. If it’s a book one, then that’s a real question of whether you’re going to start with what I’d call the setup or the ending. What do I feel like I’ve alternated, but I feel like I favor starting with the ending. Now either one can help, because, you know, when you’re doing the setup in the beginning of the story, you’re establishing the character’s world. And a lot of that, for me anyway, naturally comes from the research that I’ve been doing.

And even before outlining I’ll research, especially from, and in my genre, a science and a military perspective. And that gives me a good sense of the sort of world I want to build. So here’s the character’s normal world, and he’s, you know, he is soon going to be drawn into this journey, which is going to be not his normal world, you know, most often, in one sense or another, depending on the genre or the type of story you’re telling. And then the end, the result that’s like the result of having been pulled into this other world and this major conflict. So, I think I favor ending because it does give you that direction even when you’re sitting down and outlining. But I feel like I’ve done it both ways too.

Alessandra: And Chris from YouTube said, “Are these like bullet points or are you really using, how deep into your outline are you going when you’re creating what you’re going to write?”

Scott: You could call it bullet points and I have done chapter-by-chapter outlines too. One of the reasons we touched on for outlining is time saving, especially as indie authors. And I feel like the market in general as we have more and more media to place demands on our attention, there’s more and more competition, more and more books coming out every year. And so the market really does reward speed of output. And I find that outlining is a great way to, you know, retain the quality of your story while giving you that clear direction that’s going to allow you to sit down every day and know what you’re writing that day and what it’s supposed to do, where it’s leading, what its purpose is. In terms of bullet points versus an outline or a more in-depth outline. You could call them bullet points, I would call them plot points. And that is essentially what it is.

These days my outlines are really just a page or two. And like I said, I have done the chapter-by-chapter outline, but I just find that more time consuming. And now I relegate that to each day’s writing. I’ll sit down and think about what chapters am I writing that day. What purpose are they serving? And that kind of keeps it fresher too, because if I’ve outlined these chapters months ago, I’m no longer in that head space. Maybe I’ve forgotten why I’m doing a certain thing with a given chapter. And so this process lends itself more to speed and also a more natural way of writing, if that makes sense.

Alessandra: It also gives you some flexibility in your creativity, because that’s, I know, I’m a pantser who tries really, really hard to be an outliner. And the more I’ve outlined the more bored I am, you know, it’s just like, oh, you know, I know everything’s going to happen. So I like the idea of just having bullet points because also then if my characters kind of take a right turn, I haven’t done weeks and weeks of work in these detailed outlines. I could just maybe create a new set of bullet points and then like at the beginning of each session, sit down. So when you were talking about making sure that the scenes had a purpose and all of the different meat and that you had described being in that scene, you’re doing that the day of writing typically. Is that correct?

Scott: That’s right, yeah. And like you say, it does retain that flexibility and a lot of the fun of writing is the improvisation, seeing where the characters are going to lead you. And sometimes things don’t unfold even from a logical standpoint, the way that you thought they’re going to unfold. So I think not having a super rigid, super detailed outline can be a huge benefit, but by having a more of a bare-bones outline, you get a lot of the benefits of outlining from a direction and a purpose standpoint. But like you say, you do leave a lot of room for that creative spark to bring it where it wants to bring it.

Alessandra: And one of our questions from the audience David on YouTube said, “How do you know when to stop outlining?” So, it sounds like for you, you don’t do like a really in-depth outline in advance. Is that correct?

Scott: Yeah, I think this’ll probably get clear as I get into the nitty-gritty details of my outline. I have a set number of plot points that I identify and then that’s about it. Each one is a paragraph of about that long. You know, maybe I’ll include a few events or a few, you know, notes about the flavor or the tone or whatever that I want to set in that part of the book. And yeah, so this is going to vary author to author, you know, maybe for David, he finds that a chapter-by-chapter outline is what he needs to sort of structure things on the day of writing. And he likes having that more defined outline. And you know, someone like yourself, Alessandra, is more of a pantser and, you know, maybe some outlining elements would work for you, but you really seem to value that creator freedom, you know, in the moment. And an outline is too constrictive and takes the joy out of it and, you know, kind of what’s the point? We need to enjoy just as much as the readers are enjoying it, I feel.

Alessandra: And that kind of leads well to this next question from Terry, which is, “What points do you find most important in your outline, like, goals, stakes, symbols?” So do you have kind of a checklist or do you want to walk us through kind of your process and how? I know we’ve touched on this and I’m sorry for jumping around so much, but is there any part of your process that you want to dive into deeper and explain?

Scott: Sure. Yeah. Well, maybe this is a good time to go through my process and talk about the plot points that I do like to cover.

Alessandra: Absolutely.

Scott: So I think Larry Brooks talks about, he kind of divides things into percentages in story engineering. And I do like to think of you know, what percentage through the story does each plot point tend to land? And I don’t like to get too formulaic with this, and, you know, that is one, I guess danger or one criticism that’s leveled against outlining that it can get too formulaic. But in fact, you know, just to sort of do a little sidebar on that, I find that in fact, placing those, you know, constraints or guide rails, or you could even say limitations on the story, helps to spark my creativity even more, and helps me to order my ideas. And rather than just kind of staring at a blank page on day one with, with no direction, I know exactly what I need to do.

And it feels like a pretty natural process to come up with ideas to fit into the framework that I’ve established for a given part of the book or a given chapter or whatever. So the beginning is, like I said, what’s called the setup, and this is where you’re establishing the character’s normal world, what does his or her day-to-day life look like? Which is important because in one sense or another, the character’s going to be yanked out of that by the momentum of the story. And you know, the story question. So the setup is important and there you want to get in, you know, some character-building details, some world-building details while starting to hint that, you know, maybe trouble might be brewing in the background that’s soon going to yank the character out of this. Then you have the inciting incident and the first doorway, there are a few different names for that. These can coincide, but I think sometimes it’s better for them not to. It’s better to space them out and sort of you know, ease the reader into the plot or you know, sort of space out the tension and the action a little more. So the inciting incident is where the story begins. It’s what kind of kicks off the story. Think Luke Skywalker discovering the hidden message in R2D2. I don’t know if you’re a “Star Wars” fan, Alessandra, fair enough.

Alessandra: But I’m familiar enough with it. I’m with you. Go ahead.

Scott: Okay. So, he discovers the message from Princess Leia and that causes him to go seek out Obiwan Kenobi. But the first doorway also, you might call the Point of No Return is when he returns to the farm and finds his aunt and uncle dead. So, you know, home is now destroyed. There’s no going back to his old life because it just doesn’t exist anymore. And so now he has to, you know, go defeat Darth Vader and blow up the death stars–spoilers.

Alessandra: So what is the difference between the inciting incident and the doorway? Those are two different things, is that correct?

Scott: They can be the same thing. They can coincide with it. The story can start with the point of no return. You know, it can start with something that just blows up the character’s life, and now they have to go solve this, you know, the main problem of the story or answer the story question. But the inciting incident can be separate too. I like to put it at about 15%. That will vary and I do like to have that flexibility even, you know, where I position the plot points. But to keep things rolling, you want to stick to roughly, I would say these percentages. But yeah, the inciting incident, basically, it incites things. It kicks things off and it starts the journey and it starts the process of answering the story question, we’re grappling with the story problem. So, it doesn’t quite lay it all out. You know, when Luke sees that message, he doesn’t know that he’s going up to defeat Darth Vader, but when he sees his aunt and uncle dead, well he knows that someone did this most likely the Empire and that he’s going to have to go contend with them because that’s really what he has left.

Alessandra: So is the doorway pointing him and the character in the direction that they’re going to go next?

Scott: Exactly, yeah. And it’s a door that once you go through it, that door is closed to you forever. So basically, you’re not going back to your old life, at least not until the story question is solved. Like, you know, Billbo did eventually go back to the Shire at the end of “The Hobbit,” but not until he had his adventure and confronted Smaug and so on.

Alessandra: Yeah. All right. So we’re like 15%, 20% in, at this point?

Scott: 30% for the first doorway is around where I like to position that, you know, you could go 25%, you could go 35%. I like 30%. And then we come to the middle of the story, and this is in total around 50% of the story. So now I like to put what’s called the midpoint or the crisis point, about halfway between that, how’s your math Alessandra? 55% is where that’s going to go. So normally I often define that and then kind of work backwards. So this might be getting a little bit confusing for people to follow, but there’s what’s called a first pinch point between the first doorway and the crisis point. So you got your first doorway, the character is on this journey, the antagonist has been defined, the story problem is apparent, you know, he knows now what he’s going to have to grapple with going forward.

The pinch point is some sort of action or appearance by the antagonist. So maybe that’s the villain, you know, cackling in his lair or just a glimpse of, you know, his evil plans coming to fruition. But it’s something to ratchet up the tension to tell the reader that you know, that the antagonist is operating in the background and you know, he is going to come get the main character, and so he better be ready. And yeah, so I mean, that can be an actual confrontation between the antagonist and the protagonist, but just a glimpse to ratch up tension, will do too. Then you get to the crisis point, which is some sort of crisis. You know, things seem really bad and this kind of gives you the momentum to move into the latter half of the story. It helps combat saggy middle syndrome.

So kind of provides that fuel to keep both the writer and the reader, you know, going with excitement into the end of the story. A good way to think about the midpoint of the crisis point is that before the crisis point, the character was reacting to the antagonist. So generally they’re just like reacting to whatever is being done. After the crisis point, the character’s going to gird his or her loins as they say, and really start taking the fight to the antagonist. Start, you know, being proactive about answering the story problem or grappling with the story question. So between. How are we doing?

Alessandra: Yeah, we’re like 55%, 60% in when we reach the crisis point. Yeah.

Scott: Okay. Yes.

Alessandra: I’m keeping up. I think everybody else is keeping up.

Scott: Good. So 55% roughly, and then around 12.5% after the math is getting really complicated. Let’s say 13%. So 68% ish is the second pinch point. And this is, again, another defined action from the antagonist. This will probably be some sort of confrontation. And this can lead into an optional plot point, which is sometimes called the false defeat. So this is between the second pinch point and what’s called the second doorway. And the false defeat can make it seem like all is lost. You see this in movies and in stories a lot. You know, the character just feels totally defeated and sees no way to possibly solve the story problem. But then, you know, right before the second doorway, there’s some revelation, maybe a new ally shows up, some new information comes to light. They just have a training montage. Something that’s going to give them the confidence and or the ability to move into the final battle, which is waiting for us on the other side of the second doorway. And this is often going to coincide with the character contending with his or her major flaw, the thing that’s been causing a lot of the problems throughout the story.

So now we’re at the second doorway, and I like to define the final battle as taking about 20% of the novel of the writing. And here the character will either literally die, not usually because people don’t usually like their characters to literally die in fiction. But he or she will at least die a symbolic death. And that often means they’ve overcome the character flaw that’s been holding them back for so long. So they’re kind of dying to the self and being reborn as a new person who’s overcome this major flaw and is now equipped to confront the antagonist and finally answer the story question and win the day.

Alessandra: But now, if you have a 10-book series and you have the main character throughout the 10 books, are you keeping the main character throughout the 10 books, or do you have different characters in every book?

Scott: I do, yeah. And there’s a number of ways you can go about that. Like in “Star Wars,” obviously Darth Vader is the villain throughout the three books. So yes, while there is a major victory over the antagonist at the end of the first movie, spoiler alert, the Death Star gets blown up. Darth Vader is still out there in the background doing bad stuff and gets really bad and Empire Strikes Back, which is, you know, fairly popular formula. And you could call that sort of the crisis point of that trilogy. And then, you know, Luke comes back in the third story and defeats Darth Vader.

Alessandra: I guess I’m asking like, how is your character having these fatal flaws? Like, are you giving your character new flaws in every single book, or his flaw could just be trust in a friend or, you know, an old grudge that he’s overcoming, or an adversary?

Scott: Yeah, I like to write really flawed characters, Alessandra.

Alessandra: Okay. So they’ve got a lot of baggage they can work through.

Scott: Exactly. And you know, different twists and turns of the plot can bring new problems to light too. So a character trait that wasn’t necessarily holding the character back in book one under new circumstances in book four say of a 10-book series, can suddenly be a major thing and as the circumstances change too. So to give an example from my 10-book series, and I should say about the antagonist too, there’s an overarching alien antagonist in this space opera. So they’re lurking in the background, but also there’s a lot of inter-corporate warfare in this series. So there’s a bunch of characters that are antagonists, you know, for maybe two or three books or even sometimes just one book that kind of, you know, take up the main action of that given book while the major antagonist is, you know, lurking in the background.

In terms of character flaws like I said, circumstances can bring different things to light. So first my character was way too strict with his crew. He is a Starship captain, way too strict, just expected perfection all the time, ran his crew ragged and there were major consequences for that in terms of the functioning of the ship and how well the crew was able to uphold, you know, hold up under that kind of pressure. So now he’s become this, you know, well-known captain who is being given all this responsibility, and now he has to contend with his reputation and how that’s affecting how he commands, how it’s affecting how much others are willing to trust in him. Sometimes it’s too much, you know, sometimes the load is too much and he is being given too much responsibility. It leads him to overestimate his abilities and overextend himself. So you can kind of see how the evolution of circumstances can draw different things out of character and make things into major obstructive flaws that weren’t beforehand.

Alessandra: Thinking about an outline and how much time we have, we’re down to our last few minutes. We do have a lot of questions, so I’m going to try to rapid fire them at you and we’ll see how many we can knock out. Kit said. “So this sounds like basically, Save the Cat.” And this is a tried and true structure that’s in a lot of different books, right? Not just the ones that you mentioned?

Scott: I would say so, yeah, I mean you know, I don’t think anyone has really tried to reinvent the wheel with the story structure. These are pretty ancient structures that seem to keep stories moving at a good pace while being pleasing to our brains. So I haven’t read “Save the Cat” personally, but I imagine, you know, there’s definitely a lot of similarities between the books that I did mention.

Alessandra: Is this a set plot formula for you or do you occasionally move it around or do something different or is this pretty consistently what you stick to when you write?

Scott: Really, it depends on what’s working in the moment of the story. So if my outline is working and everything is logical and it’s what makes sense for the character, then I’ll stick to the outline. If it’s not, well, it’s time to pivot and change things up and I’m not afraid to do that and I would encourage people not to be afraid to do that. You know, an outline should be a tool, not a straight jacket.

Alessandra: A Facebook user said, “I find thrillers take me longer to write because of the complexity. Alessandra, do you find an outline that speeds up your process? I have a loose outline and I don’t find it’s helping my speed. I am trying and trying to be better about outlining because I think it would speed me up if I knew what I was writing every time I sat down or at least had an idea. I have basically just, I know what’s happening at 15, you know, 25, 50, but it’s just a jotted note and then I kind of just find my way through there. And I am not a quick writer. I am a little faster than you because I see your follow-up comment to that Facebook user. But I do think that a more organized outline would help me write faster. And that was really kind of what we were here to talk about today is that outlining and we got so excited about the outlining process. We didn’t really touch on it much, but your point really coming on, Scott, was that you can write faster and produce faster if you outlined. Do you want to share any final thoughts about that in the last minute?

Scott: Sure, yeah. Basically, it’s really just that knowing where you’re going and rather than sitting down with each chapter and trying to figure out where it fits into a story you know, what you need to do. Because you already have a lot to think about when you’re sitting down on the day of, in terms of what you’re going to do with the chapter, how it’s going to develop character and so on. So having certain pieces figured out, you know, the plot’s development, establishing mysteries and hooks and things. I do find that it’s just less mental bandwidth the day that you sit down to write and therefore you can write more on the day of, for having figured a lot of that stuff out.

Alessandra: That makes perfect sense. And for any of those who have trouble or who would like to start reading one of your books that they can see your outline in action, where would you suggest that they start, if they want to read your books?

Scott: Probably book one of “Spacers.” I have a box set out now. “First Command” is the first of six books and very affordable in ebook and audio. So that’s what I am, you know, most ready to recommend these days.

Alessandra: I understand that wholeheartedly. And thank you all for joining us for First Draft Friday. We’ll be back in two weeks with another First Draft Friday. Thank you so much, Scott, for joining us today and thank you for everyone in your comments and questions.  

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