Sunday Musings #5 – The practical guide to outlining

Posted on Nov 13, 2016 in Blog, Sunday Musings | One Comment

Hey guys,

And finally we’re getting into the nitty-gritty of outlining! How to do it, which tools to use & where to start. Make sure you check out last week’s post on story structure for an overview of the hero’s journey and the arc structure of a story.
And now… let’s outline!

Outlining – creating the map for your writing journey

Your outline is the map for the journey you undertake when you create your book. It helps you keep all major milestones in mind – that they happen, but also when they should happen. This will ensure that you avoid missing vital information or giving away too much too soon.
Besides keeping me on track, outlining has another important function to me: it enables me to write much, much faster. If I know what has to happen in the next scene, I can fill the page so much quicker. A big part of the work has already been done during the outlining, and in the actual writing I can focus on rich description, the right pacing and most importantly, my characters’ actions.
Lastly, outlining makes for a great task when you don’t have the time and place to write (because you’re not on the computer, or your kids are racing around you). I like to always have cards with me that I can use to plan parts of my story wherever I am. You can also use a voice recording app on your cell phone. And the best thoughts really come to me when I take a nice long walk before getting into the next scene.

Where do I start

There are different ways you can approach outlining. I’ve found it most helpful to approach it from two directions:

  1. Big picture to finer detail
  2. Character to plot
Big picture to finer detail

Let’s start with big picture to finer detail. I like to start with an overview of the really big milestones the story should cover. For a romance, there are ten typical ingredients:

  • First meeting
  • Interest / need – what about the main characters in their ordinary environment primes them for the romance
  • Why should they be together
  • Why should they not be together – introduction of internal and external conflict
  • Wooing – Events that lead to the main characters falling in love
  • Sizzle – dialogue that creates tension
  • First kiss
  • Break up – biggest obstacle
  • Make up – Climax / resurrection (mirroring the mid point)
  • Happily ever after (HEA)

These ten ingredients are taken from the book “How to Write a Brilliant Romance“, by Susan May Warren, which I heartily recommend for all aspiring romance writers.
The order of some of the points may vary (e.g., when the first kiss happens), but generally, they are always there.
Depending on the type of conflict, I then add other milestones – the tests the main characters face. This could be a challenge like in “500 Kisses”, the growing apart and getting back together like in “rock” or the chase after Mr. X in “Noticed Me Yet?”.
Finally, milestones of side stories round out the skeleton of the outline.

At this point, I mainly have headlines and possibly a few notes. This all happens at the beginning of a new story, before I really get into the writing.

Once the writing starts, the finer detail planning starts. Now I plan actual scenes for the milestones in my story skeleton, i.e., who’s in the scene, what is their motivation, what is the conflict, and so on. This can get quite detailed.
Additionally, in this phase it becomes clear what additional scenes will be needed, so they are also added to the outline.

Character to plot

When outlining, I like to start with the characters: what are they about? Basically, I try to get a feel for their complete lives. My favorite technique to create these character studies is brainstorming and creating a mind map. A mind map is a technique to structure your thoughts about a certain topic or concept, in this case, a character. You start with the central concept – the character’s name – and branch out into any area you can think of: origin, physical appearance, likes, dislikes, goals, whatever you can think of.
Only when I have an idea of my main characters, I start getting into creating the plot milestones.

The same direction is repeated when doing the finer planning for individual scenes. First, I think about my characters in this scene before creating the story beats.

Tools to create your outline

Outlines can be created in many ways, from simple to sophisticated. Here are the three things that work for me, and their pros and cons:

  1. Cue cards & board. I really like to write my planning thoughts on cue cards and then arrange them on a board (I use a cork board, but could be a white board with magnets). The board is divided into four areas according to the acts of a story (1, 2a/2b, 3). I find this most useful for the “big picture” structure of milestones.
    • Pros: You can create your cards anywhere you have time and don’t need any technology. Also, the tactile process of creating the board and moving the cards around is quite nice.
    • Cons: You’ll have to transfer all the cards into an electronic format at some point. Restructuring can also become a bit cumbersome when you have a lot of details on your board.
  2. Trello. Trello is an awesome free online tool to organize tasks or anything else you want to keep in order. You can create boards for a certain topic, lists within these boards, and then individual cards inside the lists that represent single tasks. I actually organize any tasks with Trello now (from shopping lists to vacations), but I find it particularly great for outlining a story.
    • The story becomes a board in Trello.
    • A list represents an act. Also, each main character gets their own list.
    • Within each list, individual cards represents a story mile stone or scene (within the arcs) or vital character information (within the character lists).
    • Here’s an example of the outline of my WIP “True Colors”, as planned in Trello: outlining
    • A further very handy feature is using checklists within a card. These checklists become the step-by-step outline of an act, or of an individual scene:

    As you can see, Trello covers all our outlining needs discussed above. It’s really become invaluable to me.

    • Pros: Super easy to learn and to manage. Moving, copying and editing cards works like a charm. Also, you can edit you boards on the go with the Android or iOS app.
    • Cons: Your boards are stored online, so you’ll need an internet connection. It’s not integrated within your word processor, so there’s still some going back and forth between e.g., Trello and Word.
  3. Scrivener. An integrated solution of word processor and outlining tool. In Scrivener, you can store of all your notes, but also any assorted other documents or images, and organize them according to your planned story. Then you can flesh out your high-level notes, turn them into scenes and combine them into a final document. Scrivener makes it very easy to keep a good overview of all parts of your story, and to rearrange them if necessary. An interactive tutorial helps you getting up to speed. There’s also a list of books on Scrivener on their website.
    • Pros: Powerful solution to structure and write you novel. No back and forth, everything stored in one place. Available for Mac, Windows and iOS.
    • Cons: Pretty steep learning curve, and quite different from working in Word. You need to be at your computer to do the planning.

All three tools have a place in my process: pen, paper & physical board for the initial story skeleton, Trello for adding more detail and reorganizing, and finally Scrivener for the planning of individual scenes (and the actual writing).

Writing tip of the week

On Jane Friedman’s blog, Stephen Wilbers writes about the power of “less is more” in your writing. The blog post, “A Key to Great Writing: Make Every Word Count“, details the different redundancy traps that authors tend to fall into, and how to spot and avoid them. What really resonated with me and what I want to focus on: redundant modifiers. So check out this post, it is an important essential!

Fiction reads of the week

I recently read the All for the Game trilogy by Nora Sakavic and I loved every minute of this contemporary series. It is gritty and dark and violent in places, but the tension and slow-burn (very, very slow burn MM romance) is off the charts. It is dramatic and perhaps over the top, but also very compelling.

Bits & pieces

I hope I could give you a glimpse into my outlining process! I love plotting, and with the tools I talked about it really becomes a fun part of the writing experience. Enjoy!

Books mentioned in this bulletin:

  • Italian readers, you can now check out my website in Italian:
  • You can get a free e-book by signing up for my newsletter
  • Disclaimer: All links to books in this article are affiliate links, which means I receive a small percentage of the purchase price if you make a purchase using these links. There is no additional cost for you if you purchase the books via these links!

Session #4 – Story structure
Session #6 – The power of perseverance, and how to deal with imperfection

1 Comment

  1. Indie Publishing 2.0: The Power of Collaboration | Self-Publishing Advice Center
    January 16, 2017

    […] Trello is a project management app that was recently acquired by Atlassian for $425m. On Trello, projects are represented by “boards” that are similar to old-fashioned cork boards. These boards contain a series of “lists”, and “lists” contain “cards”. Companies use it to organize their teams’ tasks, but it can also be used for other purposes. For example, here’s how one author uses Trello to outline her novels. […]


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