Outlines: Necessary Tools that Sometimes Feel like Tight Sweaters

I’m working on second draft revisions for a memoir I’m writing. I feel like half of my life is spent exploring a specific time in my life and the other half is spent exploring how time works, as in how things should be sequenced together. There are a lot of issues I could discuss related to time: the use of the near flashback, vertical versus horizontal time, structures that create suspense. In the coming weeks, I plan to talk about all of these things. But, for today, I’ll talk about the most basic tool for managing time: the outline.

I’ll be the first to admit I hate outlines. The word conjures images of an eleventh grade research report I had to complete in the years before Google. A complete outline filled with roman numerated topics, followed by supporting lettered arguments was required before we could begin even a single sentence. I was writing about abolitionist John Brown, a man who believed armed insurrection was the key to ending slavery, and reasoned he wouldn’t do this part of the assignment. I rebelled and procrastinated. I barely got the project done.

Every time I think of outlining, I conjure those roman numerals like a too-tight wool sweater. I feel cramped and sweaty. But I know they are essential.

Plenty of highly productive writers swear by them. Author Katie Rose Guest Pryal won’t even start writing until she’s outlined her entire novel—every chapter and scene. Brett Anthony Johnston is just a meticulous, only he outlines everything in reverse.

But, outlining before you write isn’t for everyone.

I know several authors who carefully outlined everything before they wrote their first sentence only to feel like their book was missing some essential piece at the end of the first draft. It’s not that outlining as an activity was wrong, but the time for outlining was off. They didn’t give themselves room for exploration.

In his book Writing Life Stories, Bill Roorbach suggests that writers outline their entire books after they finish their first drafts. He believes that the self-discovery that happens during free writing is essential to finding meaning in work that may seem all summed up. You have to crack open sections that haven’t been explored. And then there’s that chapter (or two) you didn’t add to the outline because it felt too uncomfortable to write about. The entire story may hinge on what comes out of those writing sessions.

But don’t just consider the organizational process when it comes to outlining. Think about the pleasure your writing brings you. I derive a lot of pleasure from the surprises that arise in stream of consciousness writing. In fact, some of my best writing comes from those messy experimental places. Outlining early in a project would hamper my creativity. When starting a new project, I do some free writing and when something feels like an actual piece I outline it, often starting in reverse because as Brett Anthony Johnston said at the 2015 Virginia Quarterly Review Conference, “If you work backwards, you will ensure that the plot is logical and that everything must’ve happened.”