Early Thoughts on Intensive Outlining

If you’ve been around here much, or follow me elsewhere, you’re probably already aware that I’m working on Book Three of the Black Wolf Series. Since I like to reevaluate my writing process at the end of each book and make changes for the next time, I did some serious thinking when I finished Book Two.

The reason for this constant reevaluation is simple. I want to become a better writer all the time. If, along the way, I also streamline my methods and become more thoroughly acquainted with my characters and story, then I win BIG. I always want to know more and feel more so I can do more to communicate the heart of the story. After all, I love my characters and their world, and I want to do them justice.

I’ve mentioned before that one of the first books I read when I started getting serious about writing was Outlining Your Novel: Map Your Way to Success by K.M. Weiland. I put it on my reading list to re-read since I’ve been doing the writing thing for a while. I thought I’d get extra benefit from it now.

Image by Khürt Williams via StockSnap

I ended up deciding to undertake a major project over the last few months as I added this book to my repertoire of writing pre-work. I’ve worked from several excellent resources in the past, and find that I like to start on a HUGE scale with every possible idea and general story concept. Then, as I go through each of my resources, the story spirals closer and closer to home. Adding Outlining Your Novel to that lineup taught me some things, and since this blog is all about documenting my own growth and process, as well as dispensing (hopefully helpful) tips for other writers who are just getting started, I wanted to share a few thoughts.

This is By. No. Means. an exhaustive review of Outlining Your Novel. This is simply a (very, VERY) preliminary list of things I learned or concepts I’d never tried in the way Weiland suggests. That being said, here we go:

First: While I do usually work through quite a lot of resources, I do not consider myself a plotter. I’m most comfortable living in Plantser Land. I like to have a general idea of where my story is going and kinda how it gets there, but I prefer the scenes to write themselves.

With that in mind, you can understand how working through a whole book devoted to heavy outlining made me sweat a little. The good thing is that Weiland gets that fear, and offers kind reminders along the way: outlining isn’t about forcing you into a box. If you need to free yourself up, you can. The methods she presents are a way of getting you to think differently. I can handle that.

Now, this being my first time working through this book, I took the most intensive route. I notebooked up and scribbled by hand in pen. Yeah, buddy. I was committed.

The “What If” Question

As a writer, you have to establish a pretty early love (or hate, but at least a knowledge) of the “what if” question. When I was deeply embedded in theatre life, my improv troupe played a game called *Top That*. The MC for the game used a bell or buzzer or even just an obnoxious mouth sound to get the actor who was currently speaking to change–on command–the last words that were spoken. I always loved *Top That*, because it put me in a brainspace where the pressure of needing to top the last thing I’d said sent my inhibitions packing. I said some of the craziest things in those moments. That’s how I like to approach the “What If” question. Keep asking yourself “what if” about your story–you’ll learn things you didn’t already know. It’s as simple as that.

Scene Lists

Early on the Weiland’s process, she recommends creating your first scene list. This doesn’t have to be exact–it’s just a way to record the things you’ve already learned. I enjoyed this part immensely because have I mentioned I’m Type A? Hello, you had me at LIST. Plus: A) I’m a huge sucker for a new notebook because B) I make notes constantly. It’s an obsession. By the time I sit down to do pre-work for a book, I already have a notebook crammed with Post-Its and scribbles about ideas. This scene list concept gave me a way to organize those thoughts. You guessed it: you also had me at ORGANIZE. End of speech.

See this? This is what I mean by obsessive note taking.
This is the rest of the Black Wolf series in scribble and Post-It note form
(Image by me and obviously taken with a potato.)


I found the theme section to be particularly useful, but not necessarily in the way I expected. I’ve never looked at theme exploration with the approach Weiland offers. I’ll leave it to her to point you in the right direction, of course, but I’ll note that I personally discovered quite a bit more about my characters than I knew before I put them under the theme spotlight.

Creating a Story

Which characters have the most to lose? Does your story have a solid structure? Where are the remaining holes? You review all these things and more as you work your way to the end with Chapter Ten where you set yourself up for the actual writing. The breakdown on this book is super-helpful. There are plenty of reminders to check every aspect of your story and because I love making sure my bases are covered, I enjoyed this short-form approach. Weiland offers handy lists throughout to make it even easier and more comprehensive.

Now, I’ll be honest: for the books I’m working on right now, I don’t have the time, energy, or patience to take the potential years of outlining set-up that’s discussed along the way. It’s not that I don’t love my readers or characters or what I’m doing. But I’m on a very personal mission that doesn’t afford me that kind of space. So, I crammed all my outlining into a two-month period. Even that was longer than I would liked to have taken.

I think it was worth it, though. So far, I’m seeing a pretty clear path from Point A to Point B. I will note, however, that I’m a little concerned that what I’ve written so far is…not terribly free. I think I still bear a little of that *outlining is boxing me in* fear. I’ve had to constantly encourage myself to sling words for Draft One, and I’ve had to stay hyper-focused on the fact that those words aren’t forever. My stories always gain more life and depth after the first draft is done and the words are there. It’s like I need to prove to myself, every time, that I’m still capable of putting 100,000+ words down. Then I feel comfortable messing with them–adding new ones, taking old ones away, you know how it goes.

All in all, I am glad I added this resource to my process. I think, though, that I’ll probably start using it much earlier in my next process. I already have dozens of notes for Book Four, and I’m planning to implement the Scene List concept from Weiland on Book Four as soon as I’ve completed the first draft of Book Three. I’m looking forward to seeing how that changes things.

As always, my process is a work in progress. I still like it that way.

What about you? Do you have any excellent outlining resources?

3 thoughts on “Early Thoughts on Intensive Outlining

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