Living Outlines

I’ve written a fair amount of fiction. 160 free weekly mini-stories, amounting to more than 200,000 words, and four novels (here’s my latest book, JINX!) totalling over 380,000 words. And that’s just the contemporary, published stuff.

Outlines are my planning tool of choice, at least for the phase immediately before starting to write. I’ve spoken about outlining on my podcast, but I’ve found that my approach has evolved a bit since then, and I want to talk about that here.

It’s important to realise that I’m not claiming my new approach is better, per se; I think it’s actually just a consequence of being at a different point in my development as a writer. As we learn, our needs change, and we should always be ready to re-assess our approach.

I write in scenes, not in chapters, only arranging scenes into chapters once I have a full draft. That’s a personal choice, and while I can highly recommend it to you, I know that some people prefer to plan in terms of larger story units like chapters from the start. That’s fine; it’s just not for me. I think it makes more sense to work out what the story is, write it, and then see where the chapter (and part) breaks naturally lie.

My prior novel outlines have been long, detailed things. JINX has an outline that’s five thousand words long, or about five percent of the book’s own final length. That’s a detailed plan for the whole story, arranged as a stream of scenes, each of which has a breakdown of each significant thing that happens — usually with notes attached. It’s a comfort during the writing process, but it’s also highly prescriptive. That approach works really well when you’re still learning to write long-form fiction, and learning which parts of the art of novel writing you can trust your instincts on.

The thing with outlines is that they’re a static representation of something that doesn’t end up being static, in most cases. Books change as you write them. Often, you don’t know what the book really is until you’ve written it, and you’ll always be changing things as you go, which will have knock-on effects. Outlines are living things, because books take on a life of their own.

My previous style of hyper-detailed outlining isn’t well suited for me anymore. I know how to write a hundred-thousand-word novel. I know what the challenges are, and how story arcs work, and how craft meets art, and how to feel out a scene, and all that stuff. I have more instincts now, and I’ve learned a lot. Deep outlining no longer appeals to me, for several reasons.

First, it’s a burden during the planning process, which is the time when you want to capitalise on enthusiasm and energy and raw creativity. Big-picture thinking doesn’t sit well with thrashing out minutiae. But that’s a minor drawback. More importantly, it doesn’t gel with how I write these days. I go with my instincts, because there’s a part of me that knows how to write a book much better than I think I can. Every author has a subconscious co-author, and it’s the real artist. I meet it half-way, or just trust its judgement entirely, because I’ve put in the work to sharpen it by doing things the hard way first. I’m not going to slavishly follow an overly-detailed outline.

My previous outlines go down to about six levels of hierarchical bullet points at their deepest, though that’s an extreme case, but I’d routinely use three or four levels of nested points. Now, my approach is different:

1. Make a top-level point for each scene. It can either be a summary of the scene (if I even know what that is yet), or the first thing that happens in the scene (my usual choice), or just the word “scene”.

2. Add sub-points for each other major thing that happens in the scene. Just one additional level of nesting; all as direct children of the top-level scene point. It’s fine if there’s just one sub-point for a scene, or even none at all.

What this gives me is a narrative skeleton, rather than a full story breakdown. If I need to add more detail to a given sub-point, I’ll let it run into a few sentences — but all within that point. I now outline to just two levels: the top level, and first-level children. If you trust your instincts, that’s more than enough to get started with. Just scenes with bullets.

This allows for a much more free-form approach when I’m writing the first draft. I begin a scene by copying its chunk of the outline into the manuscript (I keep each scene in a separate sheet in my writing app, which has numerous advantages including re-ordering, tagging with keywords to track the flow of conflict or point-of-view, and so on), then I take a couple of blank lines before it, and that’s where I’ll start writing.

What the simplified outlines allow me to do is defer adding detail until I’m already writing the scene itself. That’s the disconnect with an exhaustive outline when you’re more experienced; you either feel strictured by it, or you start to ignore the points that no longer fit. With the simplified outline, I can just take a quick look at a scene’s bullet points immediately before I’m going to write that scene, and add any detail I feel might be helpful at the time. No more problems with whether it’s up to date based on what’s already been written, in most cases.

Novels can change more when you’re writing them than when you’re planning them, believe it or not, and one of the big lessons of experience is learning to embrace that fluidity. I’m comfortable enough with it now, and so my outlining strategy has evolved to accommodate and enhance that inevitability.

In closing, a note on tools. Use whatever suits you best, but my current position is that I do my best brainstorming in a completely unstructured way, using (digital versions of) pen and paper. I use an e-ink tablet for most of my thinking now, but an iPad and an Apple Pencil with Notability is excellent too. I find structured tools like diagramming or mind-mapping apps too frictional.

For outlining, you can do it right there in your text editor or word processor if it’s brief (I only use one or two bullet points in total for each mini-story), but for novel-length works you should consider a good outliner with robust keyboard-shortcut support. I use Zavala these days, which is free and syncs between all the Apple platforms.

For writing and revising, whether it’s novels, short stories, blog articles like this, or anything else, I do it all in Ulysses. The most important thing, though, is just to get started writing.

Thanks for reading. If you enjoyed this, maybe you’d enjoy some of my books too.