On Outlining


I like to think of fall as the unofficial start of a new year. 

This could be because most of the people who mean the most to me in this world are teachers and September is the official start of theirs, but it’s also true that there’s something about cooling temperatures and seeing the first dusting of color on the tops of trees that makes me think of a fresh start. 

Who doesn’t love a new beginning? 

Which makes now, while I wait for news on my soon-to-be-published first novel (yay) the perfect time to work on my next writing project.

I’m excited about this one. It’s a rewrite of an old piece I dug out of my personal slush pile that’s based on a dream I once had years before I ever knew I wanted to write romance. Even if I still believe the best material comes from our dreams (and nightmares), I learned from finishing my first novel that raw imagination needs to be shaped and molded before it even remotely resembles what we hoped it would be. 

I also learned that I’m a plotter, and that the odds of me writing a coherent book significantly decrease without an outline. It took a while (and more than a little kicking and screaming) to surface this truth about my creative life, but here I am. Like it or not, my muse has plans for me. 

Pun intended.

There are probably 1,001 and one different ways to outline a writing project. I know because I tried 999 of them while working on my first book. Yes – you read that right. I outlined my novel while working on my novel. The path to greatness is never a straight line, my friends.

But, if I hadn’t spent that time experimenting with various plotting techniques, this post might not exist. I wouldn’t have found the method that (I think) works for me and the one I’m about to share with you right now.

Character Sketches

Start here. When I started my first book, I read many articles about getting to know your characters that I promptly ignored. No need, I said. I know who my characters are and, if I don’t, I’ll just figure it out as I go. 

Spoiler alert: I really didn’t, and I really couldn’t. 

This time, I created character sketches for not only my hero and heroine but also any important secondary characters that would shape their story. Googling “Character Sketch Templates” will yield enough results to get you started. My template includes prompts for a character’s physical characteristics, emotional motivations, background and family history, fears, strengths and weaknesses, even their favorite foods, color, and places to visit. I also started a Pinterest board where I save inspiring images – everything from jewelry a character might wear or tattoos they have to what their bedroom or office might look like.

Keeping in mind that I usually get about two hours of writing time per day (more on the weekends), this process took me about a month. For me, this was just enough time to make me feel confident in my characters while still giving me the freedom to explore them further as I write.

Story Free-write

I didn’t plan this step, but once I started, I couldn’t stop. I had a few early plot notes I paired with my character sketches to compile a free-write essay of the story. At this stage, I didn’t focus on story mechanics like hitting the right beats or plot points. I just wrote about my characters taking action and their resulting reactions, and brainstormed potential conflicts. The only difference between this essay and a children’s book was that it didn’t start with Once upon a time, and its self-imposed NC-17 rating.  

Here’s a sample:

Brooke shows her worth right away by helping Nate (a lawyer) win a case against a judge who has disliked him from day one. It was a test that he expected her to fail and he finds it annoying that she passed. He’s annoyed further by Brooke’s easy camaraderie with his brother after they meet following their morning in court.

Brooke has an easy rapport with almost everyone – from the UPS delivery man to all of his clients. Everyone except Nate. She gives him the cold shoulder, and he doesn’t like that her opinion of him matters.

Nate receives his first strange package.

This type of long-form writing really helped me organize my thoughts into some semblance of a story flow. It’s around 4,000 words, and took me about 2 weeks to complete, but I could easily have spent more time here if I wanted to. Instead, I only wanted to use it as a stepping stone to creating a basic plot outline. 

Plot Outline – Short

Once I had a better understanding of where I wanted the story to go, I started drafting a basic Plot Outline. I used Scrivener for this, but you don’t need fancy software. An electronic or on-paper bulleted list will work just fine.

To create this basic outline, I plotted my scenes using my free-write as a reference. Hint – only write a few sentences to describe the action in each. I think of this step as similar to writing stage direction into a screenplay. Short, sweet, to-the-point: 

Nate and Brooke arrive at Nate’s office after their day in court. Brooke meets Brady for the first time. Nate gets jealous and pulls Brooke into his office to discuss job duties and ground rules. They discuss her experience. Nate gives her some notes on a case and a couple of law books and tells her to get to work. 

This was also where I tried to identify the important plot points – Inciting Incident, Key Event, First, Second and Third Plot Point, etc. Even if I didn’t know everything yet, I marked the places in the scene where I knew something major would happen. This process was 50-50 for me: 50% art (gut instinct) and 50% science (understanding of writing craft), but it was definitely 0% final. 

While it was a good starting point, I left myself plenty of room to change the order of scenes in the extended plot outline. 

Plot Outline – Extended

This – for me – is where the magic happens. 

Or where it is happening right now. After getting to know my characters, a long-form free-write and planning out my plot points, I’m using my short outline to expand on each scene. Each scene gets its own page (or several) and I’m digging into the action and drafting snippets of dialog between the characters. I’m also including Goal, Conflict and Disaster notes for each scene to make sure there’s movement in the story and the characters are always working toward something. 

Just so I don’t lose any momentum, I’m marking the places where I need to do more research so I can come back to them later. Even without researching as I go, I expect this will be the longest part of my journey and will take me between 3-6 months (based on my current writing schedule) to complete.

I already know it will be worth it. 

Research

After working through my extended outline, I’ll go back to all the sections I marked and do some further research. Determining, for example, the details of the court case Brooke helps Nate win, or the actual responsibilities of a legal assistant in a law office. Research can also involve adding specific details to the story that I missed, such as determining what kind of package Nate receives or making notes about secondary characters.

I’m not sure yet how long this process will take, but I estimate anywhere from 1 to 3 months. It will probably vary for you depending on several variables, including the genre you’re writing in, and your personal appetite for research. My opinion on research is to spend as much time as you need to get the information that will best serve the story.

***

So far this process is working, but the real test will come when I actually sit down to write. As much faith as I have that all this pre-work will make my words flow easier, it’s my muse who will undoubtedly have the last one.

She always does. 

-K

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