Writing the detailed outline, part 2

Yesterday, I spoke about how whenever I start work on a novel or short story, I begin by drafting a detailed outline that often approaches the length of the final manuscript itself. This may sound like a huge “outline,” but it seems marginally less insane when you realize that it’s actually my second or third outline, depending on how you define it. The first outline, at least for a novel, comes in the form of a five- to six-page synopsis to my publisher, in which I briefly summarize what I see as the plot, based on a few weeks of mulling it over. The second outline, which I develop concurrently with the first, is a more detailed breakdown that aims to lay out the action chapter by chapter, at least for the first big section of story. (For reasons that I’ve mentioned before, I try not to outline an entire novel at once, but to save some unanswered questions for later in the process.) And it’s this second outline, which is basically just a list of chapters with a few brief notes, that I need to turn into something more substantial.

And I do it a chapter at a time, usually a chapter a day, for however long it takes. (My novels, incidentally, tend to have between fifty or sixty chapters for a manuscript of 100,000 words.) For City of Exiles, I did two detailed chapter outlines per day, which I’ve since decided is too intense a routine: I could keep it up for one book, but not for much longer, at least not without burning out entirely. A chapter a day is a much more manageable pace, and it also dovetails nicely with how my brain works. In outlining, as in everything else, it’s often best to focus on one thing at a time: one beat, one scene, one chapter, as if the rest of the novel didn’t exist, even if it’s always at the back of your mind. Devoting one day to outlining an entire chapter allows you to give it the attention that it deserves, without worrying about the second chapter that you have scheduled for later that afternoon. And it allows you to ruminate on that one chapter during those moments of daily downtime that are so crucial to the creative process: washing dishes, running errands, taking a walk in the park.

So how does a typical day look? When it begins, I generally have some general notes on the chapter in a text file, an additional set of more detailed research notes on any technical matters that I expect to encounter, and a stack of index cards with miscellaneous ideas. (For more information on the index card system, see here, or Kenneth Atchity’s useful book A Writer’s Time.) I try to review my notes as early as possible, ideally before my morning shower—which is the best thinking time in the world—or, increasingly, at bedtime the night before. And my first goal is to come up with the most basic possible structure for the overall chapter, with David Mamet’s three questions as a guide:

1. What is the scene about?
2. What is the protagonist’s objective?
3. How do we know when we’re done?

These questions are so helpful for guiding my thinking that I include them as a footer in my outline document in Word, along with a fourth question, which I added after reading Mamet’s famous memo to the writers of The Unit: Why now? And my first order of business is to structure the chapter around these questions, in a chunk of narrative that has a beginning, middle, and end. (Later, of course, I may seek to cut the beginning and end of each scene, and jump from middle to middle, but I’ve found that it’s useful to think in these terms at the outline stage.)

Once I have what seems like a workable narrative shape, I begin to flesh it out, putting myself into the scene as much as possible, writing it from one beat to the next, orienting myself with the structure I’ve mentally developed, and thinking whenever I can in terms of actual paragraphs. The result, as you can see in these pictures of the outline for my story “Kawataro,” is a series of sentence fragments, telegraphic, joined with dashes, a series of reminders to jog my memory when I actually start to write. Once I’ve finished a draft of the outline, I break for lunch, take an hour off, and often do a mind map to generate one last round of ideas, after which I polish the entire thing one last time. In the end, I’ll have a comprehensive outline of a single chapter, which I copy and paste into my general outline for the entire book. The next day, I do it again. And if all goes well, weeks or months later, when I start writing the chapter itself, I’ll open the file, look at my outline, and still remember what the hell I was talking about.