NaNoWriMo Preptober

The Ultimate NaNoWriMo Preptober Checkpoints For Pantsers Who Hate To Plot

T. Cole Williams NaNoWriMo 2019, The Outlines, Troubleshoot Valley Leave a Comment

The first time I tried to do NaNoWriMo (aka, National Novel Writing Month), I biffed it.

I hadn’t completed any NaNoWriMo Preptober work (arrogantly believing I’d be able to pants the bish just fine, thank you very much), I was gone for most of the month on vacation in Paris (like, can one even do anything other than eat all the foods whilst in Paris? me thinks not), and I ended up hating everything I managed to write because most of it, if I’m being totally honest, was about my protagonist eating fresh Parisian croissants for the first time in her life…

So this year, I vowed to do all the things that I didn’t do last year. And that all begins with a little diddy called Preptober!

What Is
NaNoWriMo Preptober?

NaNoWriMo Preptober is a month-long swan-dive into planning, researching, and organizing the novel you’ll be writing in November for NaNoWriMo (if that’s something you’re into and all).

It begins on October 1st and continues until Halloween when, the next day, NaNoWriMo begins.

In that time, the goal is to brainstorm, research and organize your novel as much as possible in preparation for the month to come.

Some writers go all out for this, others don’t even bother showing up.

Having previously done the latter to no avail, it’s safe to say you’ll catch me in Preptober-fever this year 😉

Why Bother With Preptober?

Speaking from experience, I can tell you this much: the more you are prepared, the less stressful NaNoWriMo is.

Novels are not conjured from thin air and those that are aren’t always great.

The simple truth is that the best novels are the ones with keen story arc organization, thoroughly analyzed plot possibilities, and deep character connectivity, traits that typically exist in planned and pondered novels.

I think the problem for a lot of budding novelists is that planning an entire novel of content seems overwhelming and they don’t know where to start. So instead of doing any planning in October, they wait until November when it will – hopefully – “flow organically” and then…the plot holes crop up, the characters don’t make sense, the story is a runaround with no end in sight, and some jabroni with two thumbs is wishing they took Preptober a helluva lot more seriously (I see you 2018 TIFFANY).

The Ultimate
NaNoWriMo Preptober
Checkpoint List

Introducing the Ultimate NaNoWriMo Preptober Checkpoint List, a convenient guide to planning, researching and organizing your next NaNoWriMo novel concept.

All you need to get started is a general concept in mind and a few characters up your sleeves.

Head into checkpoint #1 to discover how your characters can sway, enhance, or ruin your plot.


With only a general idea in mind for a story concept, I go straight to character development.


Because I’ve found that my characters will guide the plot forward through their personal experiences.

Getting to know your characters, one at a time, helps to develop dialogue styles, emotional motivations, potential story arcs, and so much more.

I follow three steps for assessing my characters:

Step One: Demographic Chart

Open a new document for each character and answer the following questions to formulate your demographic chart:

  • What is their physical appearance?
  • What is their personality like?
  • What is their occupation?
  • What is their Jung Archetype?
  • What are their habits or mannerisms?
  • Can you find an image to represent your character?

I like to get as specific as possible when making my demographic chart, but I also like to create a new chart every other day or so as I develop my story concept throughout Preptober.

I’ve had characters that start off good and end up evil. Characters that start off female and end up male, and others that went from being adults to being children. Ideas change, storylines shift, and your demographic charts should be updated regularly to reflect those changes.

step two: Character Backstory

Once I have a demographic chart worked up, I like to create backstories for each character.

These typically end up being brief, one-page biographies that detail the underlying motivation to their presence in my story.

But I don’t limit myself to writing only what’s important for my characters’ story arc.

Though some advice will recommend writers stick to bio facts that serve some storyline relevance, I find that subtle, very fascinating details will pop up out of nowhere and up serving a unique purpose in my character’s personality.

If, for whatever reason, one of my characters’ backstory details how she lost her parents at sea when she was nine – even though that fact bears no weight in my novel – I write it down anyway as a personal note to myself.

When developing a character backstory, here are a few key questions you should answer:

  • What is your character’s internal struggle?
  • What is their external struggle?
  • Where do they come from?
  • Where would they like to go?
  • Where are they being pulled toward?

step three: interview questionnaires

Interviewing your characters is – in my opinion – the best part of planning your novel!

The most interesting and authentic character development happens in the thick of interviews and it’s often where my characters go from being one thing to a whole other beast entirely.

You can view my list of The 66 Most Effective Character Interview Questions to get started.


Once I have my primary set of characters brainstormed and interviewed, I begin to play around with plot twists by creating a scene list.

I start by writing down every scene I can think of, starting from wherever I’m inspired in my story.

This is a messy process that I prefer to do on my computer since so much gets cut and altered.

step one: start to finish

Jot down, from beginning to end, how your story plays out using only one-sentence snippets.

Don’t worry if you get stuck along the way, just put a question mark next to that sentence and keep going. Trust me, you’ll figure out the details soon enough…

step two: fill in the holes

You’ve likely got a modge-podge storyline with many a hole to fill.

Start from the beginning of your story and begin to read each sentence. When you find one that begs a deeper question (as far as you’re concerned, not in general for a unique reader), pause and answer them.

How did this character get from point A to point B?
What makes it possible for reindeer to fly?
How was the protagonist able to scale a building so fast?

This can take some time as each question may offer a variety of answers that you need to sift through in order to find the perfect fit.

step three: final round of questions

Now that you’ve organized your story concept and filled in the plot holes, it’s time to ask the difficult questions, questions that could change the course of everything you’ve just created.

Create three lists and jot down various storyline answers to the following questions:

  • What if…?
  • What is expected?
  • What would be unexpected ?

Start by asking yourself the what if’s that any avid reader might ask.

What if this character died in the end?
What if this character’s parents never survived?
What if this character could read minds?

Answering the what if’s opens up a plethora of doors for enhancing your storyline (or at least answering the difficult questions that may crop up later).

Next, create a list of the things you think a reader might expect from your novel.

Do the main characters fall in love?
Does the hero win in the end?
Does the villain get what they deserve?
Does the story take place on Earth the entire time?

Some of these expectations you may want to meet and others you may decide to work against for the sake of a better story.

Finally, ask yourself what your readers would never expect and see if it’s anything you feel could be worth adding. Everyone loves a good twist!

Could your protagonist die in the end?
Could your villain switch sides?
Do aliens show up and put a parking boot on the circumference of the Earth for remaining at an unpaid parking meter for too long?!


It’s around this time that I feel I’ve got a comfortable grip on what my story is all about so that I can now prepare my premise paragraph.

A premise paragraph is a general synopsis of the storyline. It should answer:

  • Who is the protagonist?
  • What situation do they find themselves in?
  • What is their mission?
  • Who is the antagonist?
  • What will push the protagonist to action?
  • What is the primary conflict?

Using those questions as a jumping off point, create a premise paragraph like the one below based on the movie Star Wars: A New Hope:

Luke Skywalker (protagonist), a restless farm boy (situation), wants nothing more than to leave home and become a starfighter pilot, so he can live up to his mysterious father (mission). But when his aunt and uncle are murdered (push) after purchasing renegade droids, Luke must free the droids’ beautiful owner and discover a way to stop (conflict) the evil Empire (opponent) and its apocalyptic Death Star.

Having a premise paragraph will keep you on track with your general storyline while you’re in the thick of the Writer’s Trench.


Plotting isn’t something I like to get too serious about, or make too detailed, in Preptober. I like my story to have the leniency to surprise me at any turn and I find that’s hard for me to allow when I have a formulaic plot map in front of me.

That being said, I do plan out my primary plot points in Preptober to give myself a concise jumping off point.

step one: The First Act

The Hook – 1%

Capture interests and attention with an opening hook that sets the scene. In Harry Potter & The Sorcerer’s Stone, the hook is when Professor Dumbledore leaves Harry on the Dursley’s doorstep.

The Inciting Incident – 12%

This is the moment your protagonist first learns of what’s to come, even if they don’t engage it. In HP&TSS this is when mysterious letters begin showing up to the Dursley’s house on Privet Drive.

The First Plot Point – 25%

The first act ends when the protagonist is forced to join the action. In HP&TSS this is when Hagrid shows up at the shack and asks Harry if he’d like to go to Hogwart’s.

step two: The second Act

First Pinch Point – 37%

Pinch points are when action begins to force the protagonist in a defined direction. In HP&TSS this is when Harry and Ron face a troll set loose in the dungeons. Their conclusions about said troll are completely wrong, but, from this scene forward, the power of the mysterious antagonist is strengthened.

Midpoint – 50%

The midpoint should solidify the direction and beliefs of the protagonist against the antagonist. In HP&TSS this is when Harry’s broom is bewitched by an unknown party (the children believe it’s Snape).

second pinch point – 62%

The second pinch point should further convince the protagonist that they know what’s going on while further clarifying what’s at stake. In HP&TSS, this is when Harry, after sneaking into the restricted section of the library, overhears Snape threatening Quirrel.

step three: The third Act

third plot point – 75%

The third plot point serves to finally show the protagonist what they’re up against. In HP&TSS, this is when Harry is serving his detention in the Forbidden Forest and encounters Voldemort sucking the blood of a unicorn.

climactic action – 88%

The climax is when the protagonist finally moves to stop the antagonist and learns, in the process, their true motives. In HP&TSS, this is when Harry, Ron and Hermione chase the villain – who they expect to be Snape – past fluffy and a barrage of magical booby traps before Harry – alone – finally learns that the antagonist all along has been Quirrel.

climactic moment – 92%

The climax moment is when the protagonist and antagonist – knowing of each other fully – face off. In HP&TSS, this is when Harry defeats Quirrel by placing his hands on Quirrels body, killing the professor with his touch – aka his mother’s love.

resolution – 98%

The resolution is when the dilemma is resolved and the protagonist once again feels safe. In HP&TSS, this is when Dumbledore awards the house cup to Gryffindor as a result of Harry, Ron and Hermione’s actions.


The last thing I like to do in preparation for NaNoWriMo is to map out as many scenes as I can in advance.

This step has been a game-changer for me! Instead of sitting down every morning to a blank slate, I instead cozied up to a few scene outlines that helped guide my writing with action and purpose.

It turns out, scenes can be broken down into two parts: the action and the reaction.

the action


The protagonist wants something, be that something physical (like their birth parents to be alive) or abstract (like escape from the Dudley’s).


The protagonist is blocked by the opposition, either physically or mentally.


Something destructive hinders the protagonists’ success – an injury, danger, or some other setback.

the reaction


The protagonist emotionally responds to the conflict and disaster.


Analysis sets in and the protagonist must find a solution to the conflict.


The protagonist must decide to either take action or not.

a harry potter example:

Harry wants to know what’s in the letter (goal) that his uncle won’t let him open (conflict). When his uncle decides to move the family to a secluded shack to avoid any more letter deliveries (disaster), Harry accepts that he’ll never know what’s in the letter (reaction), but when Hagrid shows up on their doorstep to inform Harry that he’s a wizard and that he’s been accepted into Hogwart’s School for Witchcraft and Wizardry (dilemma), he must decide if he believes in magic and wants to attend or if he wants to remain with the Dursley’s (decision).

And That’s How I

It’s a lot of work to do and for years I avoided doing it because it was so much work, BUT – after two years of avoiding it and one year of actually doing it – I can say this much: this checkpoint list has been a significant help as I work through a storyline that is out of this world.

My story is about the murderous daughter of Santa Claus as she makes her way around the world, wreaking havoc upon the most nefarious scum who inhabit it. Along the way, she picks up a CIA officer, a NOC operative acting as the President of United States’ Secretary, a conspiracy theorist journalist, and an army of bastard children born and raised solely to become elitist bodyguards.

It’s a lot to make work in a short amount of time and I don’t know that I’d be able to do it without this Preptober checkpiont list.

How do you Preptober?

Share in the comments. I’d love to enhance my Preptober game!

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