The joy and chore of outlining fiction

In terms of writing these days I am mired, knee-deep, in the squelching, quaggy plot of my novel. I’m trying to make sure that the story is fun to read, makes sense, and is historically plausible — or, at least, not blatantly inconceivable.

Every time I sit to work on the outline I sense my brain grasp more firmly how stories are composed. But, at the same time, I feel like I might be wasting my time. I’ve heard people spend weeks or months on an outline, but most of those testimonials come from writing manuals which try to peddle this or that super secret, totally guaranteed™ method of writing.

For a long time I shied away from outlining, precisely because it is promoted by a lot of writing books. It’s easier to explain how to write a novel from top to bottom — from broad concept, to outline, to individual scenes — than to capture the messy process of writing a novel through, one sentence at a time, followed by multiple revisions1. My hunch was that the authors of writing manuals recommend the top-down approach because it’s easier to fill a book with such a method, in much the same way that literary critics opt to analyse books that lend themselves to lengthy exegesis.

But when I tried to write a story of any substantial length without a plan, I got hopelessly frustrated. A few years back I wrote a fifty-thousand word novel in a month2. The hardest part wasn’t writing the scenes. It was dreaming up what would happen next. That month I walked around in a daze, striving to think up plot ideas before I had to write them. When I had a sense of what was going to happen, the writing went briskly. It was far from effortless, but the effort was focused. When I didn’t know where the story was going, the effort was diffuse. I wrote slowly, badly, feeling miserable.

I finished the novel, such as it was, and the result was, mildly put, a mess. I finished it because I thought it might teach me something about finishing. It did. It taught me that I would never write a book without a plan.

I’ve had three or four false starts since then, partly because I didn’t take outlining seriously enough. Outlining is hard work, and not to be dispensed with over a few late nights, in a brief montage in which the writer stares at his screen by the hazy light of a single lamp. He paces the room, rubbing his hands because he can’t afford heating. He acts out a scene while walking the dog. He talks out a plot problem to his partner in bed only to find out that she has fallen asleep in his arms… It is not like that at all. Well, not the heating part.

Writing manuals are quick to offer structural remedies, such as the three-act structure. While these are useful in diagnosing an ailing story, I haven’t found them so useful in developing one to begin with. To do that you first need to figure out a story’s internal logic and then to make sure that the story is appealing to the reader. To a reader who, like myself, wants to be swept up in the story, but is ready, with cheerful malice, to mock its foibles.

I’ve been nurturing this outline since the end of the summer. But only started working on it more regularly since December. I’m trying to organise my life so that I can write more, and more frequently and it’s slowly happening. But all the while, I’ve had a nagging doubt in the back of my mind. Is this the right path? I kept that doubt quiet by telling myself that if it isn’t, the only way to find out is to try it out.

Outlining a story, I’m discovering, is not something you do before you start writing. It is writing. In my outliner application I sketch out scenes, move them around, develop characters, all within a few thousand words — instead of trying to tackle this work on a 90,000 word manuscript. It feels workable. And it feels like the right approach.

I was pleased when I came across Joss Whedon say this about structure:

Structure means knowing where you’re going; making sure you don’t meander about. Some great films have been made by meandering people, like Terrence Malick and Robert Altman, but it’s not as well done today and I don’t recommend it. I’m a structure nut. I actually make charts. Where are the jokes? The thrills? The romance? Who knows what, and when? You need these things to happen at the right times, and that’s what you build your structure around: the way you want your audience to feel. Charts, graphs, coloured pens, anything that means you don’t go in blind is useful.

I find that the advice of writers is often not practically useful. And this isn’t useful, except in this: to confirm that maybe I’m in good company, though I haven’t gotten to the point of color-coding anything yet.

A lot of Joss Whedon’s work clicks for me. Along with Aaron Sorkin, he is one of a handful of writers with whose work I feel a deep kinship. Their work is often dark, but marked by an essential goodwill, and peppered with dazzling verbal wit. I don’t aspire to write exactly like either of them. I don’t even work in the same medium. But maybe, finally, I’m on the right track to figure out how to write like me.

  1. The only writing manual that recommends writing in this piecemeal way, bottom-up, is Sol Stein’s Stein on Writing (1995). ↩︎

  2. I wrote that story in August of 2013. So it wasn’t a strict NaNoWriMo, which takes places annually in November. But the principle was the same: write a complete story from beginning to end, that is at least 50,000 words in 30 days. Since I was working at an academic library at the time, I happened to have more free time in August than November. No sense in picking the battles you don’t stand a chance to win. ↩︎

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