Author's Notes on: Outlines

Wait... I need a framework?

My entire life, I’ve HATED doing outlines.

English was always my best subject. With a pen, paper, a source, and about an hour or two, I could write an essay about anything. Writing essays about literary metaphors and themes were my specialty — I had a knack for weaving the source evidence together to make a compelling case for any theme I picked. You’d be surprised the number of poems you can argue are about time, death, or the human experience if you know where to pull your evidence from.

I had a shark mentality when it came to essays though: if I stopped writing at any point, I’d instantly lose all momentum, shrivel up, and die. It led to my essays being extremely wordy, so, obviously, instead of actually addressing that, I brought more paper and learned to write faster.

(Sincere apologies to all of my English teachers that were forced to read that handwriting.)

Even when there wasn’t a timer, this was my exact process for typing up essays. I’d sit down for an hour or two, write it in a literary haze, then be done with it. And all throughout middle school, high school, and college, I got amazing grades on those essays.

I got the occasional note about my ideas being less organized than they could’ve been, but it hadn’t affected my grade, so I didn’t care all that much. To me, outlines were lots of extra work for little to no return on investment. Furthermore, they were an additional step in the process that made getting the assignment done take much longer, so I just cut it out whenever I could. The only time I ever did outlines was when the assignment specifically required proof of an outline, and honestly, there were several times where I just wrote the whole essay first and then outlined the essay from what I’d already written.

This was my process, and it worked for me.

…all the way up until the point where it didn’t.

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I should preface by including the fact that I’m still very new to outlining in general, especially for books.

The Cold Breath of Autumn was a wild child that had no outline or plan until about halfway through and I have no idea how it got that far without one. Beneath Still Waters and People of the Anthill had plans but no official outlines — I knew sorta what was going to happen and was able to fill in the connective tissue by just writing and seeing where the characters would take me. I occasionally attempted outlines, but they never went anywhere.

Sleepless is the first book where I have made a plan and specifically mapped out an outline. I have roughly 27-30 chapters planned out in a loosely color-coded spreadsheet, the chapter variation being largely dependent on the fact that I’m still not entirely happy with the current outline and may break up certain chapters that have too much content in them.

I did it in a spreadsheet because differentiating the outline from other bits of writing helped it feel unique and helped me concentrate and parse out what I wanted to happen in each chapter. It’s by no means the best way to make an outline, but it works for me.

I came into Sleepless already having a ton of content but no idea how to organize it. I decided to start simple: The three-act structure is fairly common and I liked the sound of it as a base. For anyone that doesn’t know what it is, the three-act structure is one of many structures and is widely used in literature, film, theater etc. In basic terms:

• Act I is the setup, introducing the characters and giving us a reason to root for them. It typically contains the “inciting incident”, which is the plot point that leads to the events of the rest of the book. It’s the call to action, so to speak, though it may take many forms.

• Act II is where you build up the tension and stakes of the story. You show the obstacles that stand between the character and what they want, and how the characters succeed or fail at overcoming them.

• Act III is the payoff. It contains both the climactic resolution to all that tension you’ve built up in Act I and II, as well as any aftermath you want to include.

From there, I took each act and broke it into its own smaller three-act structure. I wanted the book to have a sort of ebb and flow for the same reason songs have a bridge — if a story stays at one constant energy, it gets boring.

Stories need their stakes and can get extremely tense depending on what it’s about, but characters also need moments of respite and relative calm. They need proof that things could be okay if only X wasn’t happening, “X” being shorthand for whatever is stressing your character(s) out the most, and is most likely synonymous with or parallel to whatever antagonistic force is at play in your book.

Having these quiet scenes grounds not only your story, but your characters.

So, we have a three-act structure, with each act broken into a smaller three-act mini-structure. For each of these mini-acts, I set out three chapters.

If you’re already confused, I don’t blame you. I’ve said “three” so much it doesn’t look like a real word anymore.

An exhaustive breakdown of how this works is admittedly less helpful than you might imagine, but I think it’s worth it to at least outline my general flow and rhythm for Act I.

ACT I — Chapters 1-9

Act I’s job is to set the scene for the rest of the book, so it’s important to get a good grasp of who our characters are, why we’re rooting for them, and what they’re striving towards. A lot of the book’s tone can be set with how we introduce characters and how we introduce the reader to the setting. I break it down like this:

1. Chapters 1-3: Essentially the act I of act I, most likely to carry a lot of exposition weaved in. I use it to focus on who my characters are, what they want on a basic level, and what’s keeping them from it. Many of my older books had the philosophy of having one chapter of setup, then making everything go to chaos by chapter two. I’ve more recently opted to give myself more time to set up characters, pushing back the inciting incident to chapter three, but this isn’t to say that one way is better than the other. Some stories benefit heavily from a quick start.
   The initial inciting incident is often a point of no return, or a point at which return is possible but only if the protagonist acts quickly. This does not mean plot-relevant stuff isn’t happening in chapters one and two, just that chapter three contains one of the most important decisions that lead to the rest of the book happening the way it does. I’ll get back to why I call it the “initial” inciting incident in a second.

2. Chapters 4-6: This is still the setup phase, but it’s the act II of your act I, also known as the confrontation phase. I take this opportunity to develop characters further by their reactions to the initial inciting incident. I start to raise the stakes and give the reader a broader scope of what characters want. I also tend to start introducing larger obstacles here to set the tone with how my characters respond to them. These problems can take many forms — sometimes it’s a conflict that becomes small in the scope of the rest of the book, while other times it’s something too big for the character(s) to handle so early into the story.

3. Chapters 7-9: Once again, this is still part of the setup phase, but it’s the act III of your act I, also known as the resolution phase. I use these chapters to pay off the starting tension I’ve built with a small resolution that leads to larger consequences. Whatever they’ve done in the setup chapters resolves the current danger/conflict, but inevitably leads to infinitely worse circumstances or larger stakes in general. They’re far from being out of the woods yet.
   Remember that initial inciting incident? Well, this is where I get to a secondary inciting incident — something I call the “Snowball Incident”. Generally, this is an important plot point around chapter nine that’s often directly caused by the compounding effects of whatever my initial incident was in chapter three. This marks the official threshold beyond which there is no return.

Act II and III will obviously look different than this for many reasons. For example, the Act I of your Act III should NOT be exposition that late into the story — I generally think of it more as time for reorienting the protagonist(s) and their goals, or setting up the final confrontation.

The beauty, I suppose, of breaking my outline up in this manner, was that in doing so I realized I had actually already been writing in threes. I went back to my other books and was surprised to find the three-chapter pattern littered all over them. It wasn’t always perfectly precise and, of course, a lot of other important and plot-relevant things were happening, but roughly every three chapters there would be a major plot point.

Moreover, the pieces of Sleepless that I had already written fit the same structure. Armed with this knowledge, I made a spreadsheet with space for 27 chapters, a prologue, and an epilogue, as this is the projected amount of chapters I would need with this outline.

I slotted my currently-written plot points into the outline, and quickly discovered three things:

1. I was trying to fit two books worth of content into the final act.

2. Some plot points in Act I and II were definitely third-chapter beats and needed space to separate themselves from the other important plot points happening around them.

3. One of the book’s primary antagonists suddenly stopped being relevant somewhere in the middle of act II.

So, I took out nearly the entire third act of Sleepless, expanded it into two additional plans for sequels, and used the extra space that left me with in book one to elaborate on the plot points I already had. The third-chapter beats were moved to multiples of three and the connective tissue of the chapters in-between was filled with character building and setup for those third chapter payoffs. Additionally, the antagonist was developed further and tied much more cleanly into the overall plot of the book and the series as a whole.

Untangling the messy web of a story allowed me to recognize what had been holding me back and grow from it. I was able to give my plot points the breathing room they needed to be fully realized, and I’m very hopeful for utilizing this process again with the next project I take on.

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But why the change? Why did writing without an outline stop working for me?

The most truthful answer is that I don’t know. I don’t know what changed between then and now. I’ve entertained many thoughts, but none of them ever seems to explain it in its entirety.

Taking a stab in the dark, I wouldn’t be surprised if outlines didn’t work for me with essays because I just wasn’t as invested in them as I am in these posts and my books. Of course, I wanted my essays to be good — I cared a lot about getting good grades — but I didn’t care what I was writing. It didn’t matter to me if what I was arguing was actually what I thought. It didn’t matter to me whether or not I believed what I was writing.

The only thing that mattered was what I could convincingly prove in an hour.

Author’s Notes and my books are different. They both feel so much more like extensions of myself, and it’s important to me that they’re well-written and thought through. Whether intended or not, everything I put out for the world to see will have a message and I want to do what I can to make sure those messages mean something.

I didn’t outline the older books much either, but I think the move to outlines and structure is my way of getting serious about my writing career as I got older. To be clear, there is something really nice about writing without a plan and I do encourage anyone reading this to try it sometime. And, if you are the kind of person that can write without an outline, this is not meant to discourage you or suggest that your way is wrong! This is just my assessment of where my head’s been in moving to create order of my own chaos.

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Finally, I felt I should wrap this article up by circling back to something I said earlier. I mentioned briefly that I don’t believe a super in-depth breakdown of how I write each chapter in each act would be helpful — this is for several reasons.

First off, I don’t want to give the impression that writing is formulaic. There is a general structure that many books follow, but that doesn’t make an outline a perfect template. Your inciting incident could be in chapter three, or it could be the first line of your book — there’s no cookie-cutter way to do it. And speaking of structures, while the Three Act Structure is very popular it’s far from the only structure out there — the Seven Act Structure and Nine Act Structure are both variants that come to mind, and using them (or any other version) is perfectly valid.

Really, how you write is very much a personal preference. You’ll find a style and voice that works best for you the more you write, like an athlete training a muscle. I could talk for hours about how I do it (what is Author’s Notes if not that in text form?), but I can’t help you find your own voice.

A core concept of biology is that structure dictates function, and function dictates structure. How you function best should be reflective of how you structure your writing, and in turn your structure will determine how your writing functions. At its most basic, your ideal system should be a manner of structuring that works for you to produce literature that functions the way you intend.

Second, even I don’t always follow the 3x3x3 method. It’s a general spacing guideline, but some events can and should happen faster or slower depending on how you feel the book should be paced. In Beneath Still Waters, for example, the major plot beats in the first act happen in chapters 3, 7, and 9, which is close enough to the usual 3x3x3 method, but Act II and III speed up considerably, with major plot points happening roughly every 2-3 chapters instead of 3-4. You could argue that several important plot points happen rapid-fire one chapter after another — this was by design*, as feeling overwhelmed and helpless are big themes of the book.

*Admittedly not a perfect or advisable design, mind you.

And finally, perhaps most importantly, I don’t believe a super in depth breakdown would be helpful because I’m still not great at making outlines, much less sticking to them. And sometimes? That’s actually better.

Outlining is still a very new medium for me. I value the structure it brings and it has helped me get a good handle on how I want my story to flow, but I can’t TELL you how often I’ve written up a chapter outline, stared directly at it while writing the chapter, and somehow still managed to end up somewhere I didn’t originally intend. Sometimes these tangeants don’t fit with how I want the story to go or get to a plotpoint too quickly, and I have to go back and delete them. But other times, these unexpected turns make a lot more sense and flow a lot better than what I had in my outline.

Structure is great, and gathering my ideas really helped me pin down exactly what I was trying to get at with my books and articles, but it isn’t the end-all be-all of writing. Personally, I’m an advocate for a healthy mix of structure and freedom. For me, spending too much time trying to plot out what’s going to happen often leaves me less motivated to go back and write the actual segment of the book. Just like me and essays before, it feels like double the work and becomes boring and not worth it. Allowing myself the freedom to take a creative liberty with my own train of thought isn’t always the best move, but it keeps me moving and engaged with the material.

Sometimes these alternate drafts are absolute trainwrecks, and that’s okay. Being creative often means leaving a big mess in your wake that you’ll have to clean up later. They were still fun to write, though. They allow me to run wild with an idea for a short time and just see how it feels. What if we suddenly found out a character had magic? What if this heartfelt moment at the dinner table was suddenly interrupted by something crazy going on outside? What if in the middle of a major war, characters had a chance to bond over the small comforts they brought to the battlefield with them?

Writing is about creation. If being creative isn’t part of that, why do it?

So, if you’re like me and hated doing outlines for school, maybe give it a shot for something you genuinely care about. You might like it more than you realize! And if you’re the kind of person that’s already very versed in how to structure your writing, try writing without an outline for a little while and just see where it takes you!

Ultimately, just don’t be afraid to experiment with your writing. There’s tips all over the internet that you can try out or be inspired by! Keep the things that work and try variations of the ones that don’t. Explore your options for programs online, but also consider making something you can physically hold or touch! Do art and doodles for characters and scenes like a storyboard!

Start a new document and just run with the first idea that comes to you! Take a part of your story you’re having trouble with and suddenly make a drastic change! Take old story ideas and reimagine them as told from a different perspective, or with different environments, time periods, and character dynamics! Start a timer and just write until it runs out!

Try structure! Try freedom! Get outside your comfort zone!

Try happy middles of all shapes and sizes!

Be creative!

Be creative, and most of all, have fun.