My Advice: A Great Way to Outline a Novel

For National Novel Writing Month (NaNoWriMo), I am doing my part on The Memory Tourist to try and be more celebratory of the writing process. While it will not be a total shift, every week I hope to have content that will encourage writers to get out their pen and notebooks and start scribbling down ideas. If you prefer, open a Word document on your computer and start getting ideas out. Frankly, I don’t know how anyone could write a successful novel in a month. For me, this is more of a period of getting your creative juices flowing, inspiring you to try and write something meaningful, if just to you.

Personally, I am approaching the editing stage of my second novel and am spending the month starting to fine-tune the details. It’s too early for me to share what my intent with it will be, so I will be sharing all of my advice that I’ve acquired from personal experience writing my first full-length story “Apples & Chainsaws,” which came out in 2019 and started my career down the path to writing something more ambitious. If you’re still at the stage where you prefer to write short stories, I feel you. It’s a great way to play with the form without having to worry about an overbearing structure that is more likely to dissuade you than inspire the next poet laureate.

What I’m about to share is something more reminiscent of novel writing, though I think that it works just as well for short stories. I personally think that any story that has an outline, or at least an idea of trajectory, will be far more successful than a blank page free-write. I’ve found myself several times trying to tackle bigger stories (30+ pages) and finding myself coming up short. Without a clear path, you’re more likely to make mistakes and feel like nothing at all makes sense. Don’t worry. If you get to this point, you can do one of two things. You can see it as a learning curve, or find opportunities to use the next draft to edit, changing massive amounts of the story to better fit whatever vision you have in your head. After all, that in itself is like an outline and the hardest part (conception) is done.

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But how do we get to the point where writing a novel becomes easier? Mind you, novel writing is rarely easy. Easier, yes, but unless you have the utmost confidence in your vision, the words pouring out of you may sometimes take days, months, and years to perfect. Sometimes you’ll need to use placeholders just to keep the vision from coming to a crashing halt. I’ll confess that sometimes the obsession for that specificity has caused me to take unnaturally long pauses in writing, but that only speaks to why outlines are crucial. Every good writer has the novel in their head, but like water behind a dam, it needs to come out in a moderated fashion. Otherwise, you risk runoff and it disappears altogether. 

So let’s begin. 

I can only speak to how I’ve personally written a novel. While I may have taken advice from the literary greats who have shared their personal tips online, you ultimately need to find ways that make sense to you personally. My work schedule may be different from yours. The intention could be entirely different and thus you could require more time to research and have accuracy. Others, like when William Faulkner wrote “As I Lay Dying,” will only have time between 12 AM and 4 AM to create a manuscript. Everyone has their own way and sometimes it’s a matter of what hour strikes you better, such as when you’re a morning or night person. I wish that you take this in perspective when applying your own schedule.

No matter where you go, it all starts with the inciting incident. There has to be something that latches onto your brain, growing in your mind into something more provocative. It’s an idea that you want to spend more time with, writing out these characters that symbolize some deeper desire. You’ll know what they are when they strike you. I ask that if one excites you enough, don’t forget about it. Hold onto it until you can write it down and determine if there’s anything there.

For me, “Apples & Chainsaws” came two years into my self-publishing career. I felt the need to begin writing short stories in 2014 and have been slowly gaining my passion back for English. However, the idea of writing a novel was always daunting. I’ve experimented with form but found myself always stalling out before Page 100. I feared that I would never have a good enough idea to expand upon, resorting to a career in short stories. This is not a bad thing, but I knew deep down that I would personally regret not at least trying once in my life.

My idea came not from random ideas, but a moment in my life that felt special. Sometime in 2016, finding that novel-writing regret surfacing again, I began to explore ideas again. Then it came to me. I was 27 and preparing to enter another phase of my life. What I concluded was not a story, but a theme. My goal was to self-publish “Apples & Chainsaws” by the time that I was 30, proving that I was capable of doing this. As a result, I chose to view the whole project as a eulogy for my 20s.

For me personally, my 20s have been a formative time with as much triumph as it was regret. I began to wonder how do I encapsulate all of these ideas into one story. It was a time when I began to lose my high school friends, experience burnout at work, drop out (then reenlist) in community college, have weight issues, and overall feel like my place in the world was inadequate. There was so much on my mind that I wanted to draw from personal experiences (again, your level of comfort with this is up to you) and I wanted them all in there. It would be a novel that was as much a picture of me as the world I observed, such as mass shootings and women’s marches. To me, these were all substantial to whatever eulogy I would write.

First and foremost, I wrote “Apples & Chainsaws” for myself, as a time stamp of what my life was like. I wanted to approach further decades and have this door into my past. I want to understand what I was thinking back then. I was going to allow myself to be self-indulgent, maybe making mistakes that a better writer wouldn’t. It was designed to be every idea that I ever wanted packed into one book. So long as I promised myself that the next novel would be more streamlined, I could be as messy as I wanted.

Another thing that helped guide my vision was finding examples of how I imagined writing the novel. For me, I wanted four protagonists with interweaving stories though everyone’s journey is ultimately independent. It is why I chose to initially center the story around a high school reunion before slowly molding it into something else. I began to wonder what would these people say when they got to the reunion and had to fill in people on those 10 years. As one can assume based on what I’ve said, I personally feel insecure answering that question. I didn’t have a wife and kid. I didn’t have a glamorous job. Frankly, I still was doing the same career (writing) that I did in 2008. If nothing makes you feel stalled out, then nothing will. 

Some of my biggest influences for the structure were ensemble stories. Among the more obvious was Victor Hugo’s “Les Miserables,” which would center on a variety of characters for any given chapter. They all informed each other in this subconscious way. I am also someone who was obsessive about HBO dramas like The Wire, where a whole community is understood in these miniature narratives. Finally, in something that feels more fun and creative, I looked at the work of authors like Stephen King and Kurt Vonnegut. The former’s series “The Dark Tower” is an impressive story that seeks to combine every book he’s ever written with subtle references that forced readers to perform literary hunts, dedicating all of their energy to understand the depth to a single moment.

Gotta catch 'em all!

I recognize that I’m not going to be the deepest writer, though it’s the place where I started the paths. For me personally, the next step is best done with handwriting in a notebook. Form your own superstitions around this process, but for me, all of the writing needs to be done legibly with a black pen. Even if you don’t use the idea, write it down. Preferably organize your notebook into various sections so that you can use them as a more effective resource. To me, this will help the story feel more personal, like it’s drawn more from your body. Also, I tend to remember what I handwrite more often than type.

No matter what you do, I suggest opening with your personal pitch. What do you want the novel to be? You can come back later and expand on this section, but first, you need to commit to an idea. If you open this notebook, the first page should give you some assumptions about what lies ahead. They don’t have to be detailed, but saying something like “A story of four people approaching their high school reunion while looking at the various struggles in their lives.” That makes it more permanent. Given that I also wanted to explore duality within this concept, i.e. the different ways we struggle with depression or validation, I wrote it down on the page knowing that I would combine it with later sections.

What comes next is up to you, though I would make a concerted effort to write a page of brief character bios. Even if they’re as simple as relating to other characters, that will give you guidance for when you need to quickly pull a reference. My experience is that I always plan too small and end up having later glossaries added to the notebook of characters I created when I saw areas that needed help. Still, if you have the characters first, you can reference what follows a whole lot easier.

Next, you’ll want to write down a page full of your ideas. This is designed as my least formed section, where I will write down how I perceive the characters or understanding what I want to put into the plot. Given that I wanted certain areas to have more subtext and specific references, I put them down just so that I would remember them later. It’s also where you can begin to assume what your characters are like. For me personally, a novel is difficult to write if you don’t have a strong idea of who your characters are. To put it in another way: think of a context outside of your story. How would your characters act going to the grocery store, buying gas, or watching a movie? If you can figure that out instinctually, it will be easier to bring them to life when the chapters are in motion.

Finally, outline chapters. Don’t be afraid to write as few or many chapters as you want. Frankly, the more the merrier. Having too many forces you to later compromise what you feel is fat and what was secretly lean this whole time. I don’t have any advice on this, as my story (while linear trajectories) played more like a series of short stories. What you should know is that having a start and/or finish is valuable. If not, just write your idea and determine how you got there or where you’re going from. If you’ve done your homework on the other sections, this should be easier. 

All you’ll have to determine by this point is how things will play out. For me, “Apples & Chainsaws” was a three-act structure that started with the introduction of the issue, the middle where everyone is struggling (it’s also where the high school reunion plot was introduced), and a metaphoric third act that symbolized growth in the shortest section. Combined, I feel like it was an exploration of its themes in the most rational way imaginable. Some could say that it was messy, but I’m proud to say that it taught me a lot about how to write a book. 

Composition notebook is
also my brand of choice


I was always turning back to the notebook. Sometimes it was just for a quick reference. Other times I found myself hitting a wall and needing to write my way out. I did so by consulting the chapter order and determining where things went wrong and how I could fix it. That’s something important to remember. A successful outline is one that’s constantly evolving until the novel is eventually done. In order to get started and have success, I suggest preparing with as much information as possible. Put it down someplace where you can quick access so that you’re not struggling to recall various character dynamics just to please half a sentence.

I hope that this finds you well and that it will guide you as you write your novel. Remember first and foremost that you should write for yourself, finding something substantial that you’ll want to spend a lot of time working on. Just because you don’t have your laptop available doesn’t mean that the writing comes to an end. Grab a notebook, organize it however ideas come to you. Once you achieve this, the novel will look a lot clearer, producing a picture that should make you feel aspirational. If you do this, everything else will be a lot easier. You can add or remove anything you want, but first, you’ll need something to work with. Good luck. 

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