Outlining Like a Boss


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If there is one aspect of writing I feel at all confident about at this stage, it’s outlining. Which might be somewhat unexpected, considering I only learned about the practice a year or so ago. Before that, I was a pantser all the way. And for my troubles, I started a couple hundred stories and finished none of them.

Outlining, when I discovered it, felt like someone had given me a map, when before I’d just been kind of wandering from pretty bush, to interesting tree, before following an exciting river right off a cliff into nothingness. And while I know there are plenty of writers out there who turn there noses up at such structure, for me, flipping that switch felt more natural than the actual writing.

As I’ve probably mentioned a time or two, I’m a planner at heart. So much so, I found myself in a career centered around it. I love making lists, plotting out next steps, and anticipating problems I can then solve before they even come up. It’s the smack-dab center of my comfort zone. And it’s why I have spent so much time since learning about outlining and refining the process.

Gather round, children, and I will share my treasures!

Step 1: The Character Interview

I’ve been doing character interviews for ages, but I recently updated my template upon reading K.M. Weiland’s Outlining Your Novel to incorporate some of her suggestions. Typically, with me, every story starts with the characters. They come first. If I’m lucky, they might wander in with a vague setting, but not usually. Because of this, usually my first step to fleshing out an idea is to flesh out the characters. And the best way to do this is to ask questions about them.

Behold, my gigantor Character Interview Template

It’s massive, I know. And usually, I don’t answer every single question in the process of filling it out. Certain questions are more relevant to certain characters, and by really thinking about those key aspects, it helps to define personality, backstory, etc. Also, it’s super handy for consistency. Say, if I’ve set aside a story for a while and want to come back, and I can’t recall what color eyes I’m supposed to be waxing poetic about.

Step 2: The Character Arc

A lot of times, I start filling this in at the same time I’m doing the Interview, because one tends to feed the other. But this is the tool I use to really narrow the focus of what I want to show in the story. In romance, particularly, a lot of the plots and conflicts are internal, not external. They’re about character growth and relationships. Having a solid character arc is what gives meat to that kind of story.

Compared to the Interview, this is a baby document, but it’s dense: Character Arc Template 

It also might require some general knowledge of writing terms and traditional pieces of a story.

Step 3: The Setting

I don’t spend too much time on this for contemporary (though I know I should, because giving the setting real depth is a weakness of mine). But I do like to work on world building for fantasy stories. In particular, I have one fantasy world I’ve been thinking about for over a year and add information in here and there. I imagine it will be my Big Series whenever I finally feel some semblance of confidence as a writer. I even have a pretty elaborate map of the world, which I spent a ridiculous amount of time drawing.

And speaking of a ridiculous amount of time, I give you Fantasy Worldbuilding Questions, a list created by Patricia C. Wrede. (If you haven’t heard of her, go check out Dealing with Dragons. It’s an incredibly clever, tightly written YA from the glorious Time Before Twilight).

I went through and copied all these questions into a Word doc, and it topped off around 100 pages. If you enjoy worldbuilding, this is your holy grail, my friend. There are questions ranging from climate, to politics, to traditional eating utensils. It. Is. Awesome.

But as for more contemporary settings, alas, I am still lacking. I hope to collect some books and resources on it eventually though. When I do, I’ll be sure to share.

Step 4: The Story Scene List

No template for this one, because it’s basically just a Word doc with a numbered list. At the start of planning, it’s just random thoughts or scenes I think would be fun. Usually I come up with some ideas while creating the character sheets about how to show particular traits or growth points, and I’ll jot those down. More ideas can come as the setting grows more three-dimensional. This is a constantly evolving document for me. It starts sloppy and aimless, but by the end of the outlining process, everything’s been put in order and I’ve highlighted the major plot points and pinch points. At one point, I tried getting super specific and including even the scene parts (Goal, Conflict, and Result). A Little Bit Broken’s outline has this for every scene, and I have to say, it might have been a little bit overkill.

Example below. This is my summary for the very first scene after the prologue in ALBB. Just a little background: JD joined the Army right out of high school, but five-years into his enlistment he gets hurt and discharged for medical reasons.

  1. JD and Perry at Physical Therapy, first session after JD gets home (within a couple weeks)
    1. POV: JD
    2. Setting: PT
    3. Characters: Nihar (PT) and Kitterman (observed from afar)
    4. JD Info: Background of JD’s injury (limit detail about Thibodeaux)
    5. Perry Info: He’s an ass, and mad at JD, but has JD’s back; looks like hell

Goal: Get a clear timeline for recovery, figure out as much as he can do to quicken recovery, do it

Conflict: Nihar hedges and implies full recover is only best-case scenario, and JD should prepare for something less

Result: Hurts himself when he pushes too hard

Emotions: Determined/optimistic to Angry/discouraged

  • Takes place a week after JD is home. He’s been doing in-patient PT in Germany, now starts the out-patient PT. He wants to get a timeline and hear again what the prognosis is, and then pushes beyond that when he thinks he can.
  • Perry has been acting even more like an asshat than usual. He’s pissed every time JD shows weakness, because he’s pissed JD is hurt. JD wasn’t supposed to get hurt.
  • What was it like for JD and Perry, maintaining a friendship almost 5 years long-distance?
  • They might argue and bicker with each other, but against everyone else, they are a unit.
  • JD is clearly the leader, but Perry isn’t a follower. He just deigns to sometimes obey JD (like a cat).
  • Kitterman is there, but mostly they just notice his hot, blonde physical therapist, not him.

This is the second version of the outline, too. The first one was over 40 pages long. This one is the shorter version at just 27 pages. It’s with this document–the scene list–that I’m most struggling to find a balance, because while I like having everything written out, doing so makes it a little trickier when it actually comes to writing. With this detailed an outline, I don’t have as much trouble with writer’s block, but I do have trouble with the natural voice and finding spontaneity, which are the most fun parts of writing. But if I veer too far away from the outline, then I hit a block and am likely to just give up on the story.

Right now, I’m trying something a little different every time I make a scene list in an attempt to find the sweet spot. And every time I read another book about writing, I end up going back to edit and refine my templates.

There are a few other tricks I use sometimes. Like writing all my scenes on note cards and then getting down on the carpet to play with the order (and the cats, though that’s an unintentional side effect). For more elaborate stories, I might add some additional diagrams to show character relationships or timelines for series with overlapping story arcs.

Like I said, I am a planner. I think in an ideal world, I would have a writing partner that would let me outline everything in detail and then he/she would take my notes and turn it into an actual story. But since most writers prefer to write their own stories, I don’t see that happening. And I do still like the writing part. I just don’t feel as capable in that area, and so I get tripped up and discouraged.

Hopefully, in a year or two, that won’t be the case. I’ll feel as comfortable writing as I do outlining, and then all the pieces will come together. Until then, though, more practice!

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