The Case for Outlining

Whenever I start a long-term project in earnest—be it a feature film, novel, or bank heist —I begin to embody it in various ways. Or, more specificually, the work reflects existing embodied phenomena in my life—like the werewolf in my most recent film, inspired by the weird hairs and haggardedness of middle age.

Now, I’m headlong into a long-simmering project that I’ve mulled in various incarnations for the past two decades. The Press Club is in many ways the unified field theory of my career as both a journo and filmmaker… (Would you believe that making documentaries never occurred to me until writing this very sentence? Shit.) Thus far, I’ve resisted crossing the streams of journalism and filmmaking because I know, instinctively, that a poorly executed result would destroy any going proposition in either—and likely me in the process. 

This is why I outline.

For me, it starts with genre—I need the broad contours of convention in which to project my weird notions lest they become too unwieldy and abstract. I usually mash in another genre while I’m at it, hence the aforementioned werewolf pic (classic horror tropes-plus-screwball rom-com). In short, I need rules. When I was less seasoned, I used to think there shouldn’t be rules to structure—but try writing a sonnet without ’em and the resulting word salad will hardly entertain a crouton.

Screenplays are much the same. And here, I think we should make a distinction between formula, convention, and the creative subversion of both. When outlining, we know what a screenplay is supposed to look like. We know the conventions, the tropes, and, most specifically, the format that makes a script a screenplay. Outlines help us preserve the internal logic necessary to make all of this work as a satisfying experience for an audience. For me, this is where most of the real labor happens. It doesn’t generate the most pages, but it creates the conditions for a writing experience that’s both expeditious and—crucially, for me—interesting. Flirtations with certain projects never blossomed because I lost interest. The outline helps keep it piqued.

But first, I start with index cards. I jot everything from the tried and true tropes of my genre (with my own spin), to shit I just think would be cool— gags, scenarios that come to mind, vibes. Whatever it is, I give it enough respect to write it down. It’s like Joan Didion’s On Keeping a Notebook but easier to shuffle. Then I pile those into categories: plot, story, tone, theme, and elements, which is a sort of catch-call. 

So this is how I do that: I’ve created a standing document that I call The Hero with a Thousand Script Notes—it’s a sort of personal redux of the mythic hero structure that knocks off everyone from Joseph Campbell to Christopher Vogler who isolated and distilled the archetypes that undergird much of Western storytelling…but infused with my own aesthetic obsessions, points of reference, and cheats, schemes, and twists.

With these beats as guideposts, I start formulating the plot. Here, I want to be clear that plot and story are different creatures. Plot is to fact as story is to truth. Plot is what happens. Story is why it matters. Story, like emotional truth, has an emergent quality—and I interrogate my outline until that begins to occur organically. Then I distill it into the theme and make sure everything thereafter aligns with it.

Then I start the process of filling out the outline. It’s never linear. It’s completely iterative, and I’m constantly bouncing between beats. The outline is where you want to make all of your mistakes and it’s the best place to fix them. One well-imagined, worked over paragraph in an outline can spare you 30 pages of rewrites when you realize your second act sucks. Also, you must promise yourself that no one will ever see it. And never feed it after midnight. To be continued…

In the meantime, peruse and/or use The Hero with a Thousand Script Notes…

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