Learning to Love Outlining

I’ve never been a writer who outlines. For anything! Not, of course, for the books I wrote, but not for school papers, not for professional essays, not for presentations or speeches. I wrote, and I discovered, and I revised, and I wrote more. And, somehow, the books got finished. The speeches were made. The presentations were…presented.

It’s probably clear to see that, in some ways, I prided myself on this. It’s hardly that I thought this was the superior choice. As a writer and editor, my biggest belief is that there’s no one-size-fits-all solution for, well, anything. Write every day. Write only when you can. Draft in a weirdly sized font. Write in old-fashioned notepads. Whatever gets the job done. And so not-outlines and me were simply part of that; we were a match that got the job done.

I assumed it would be like this forever. Even when I sold a book on a few chapters and a synopsis, I veered away from that synopsis and found that it held me back instead of helping me. I was secure in my synopsis-hating multi-revising ways.

Then I tackled my most ambitious book, We Used to Be Friends, which is about two best friends growing apart their senior year of high school. Inspired by the musical the Last Five Years, I wrote one character’s POV forward (i.e. in typical chronological order), and one’s backward. Suddenly I was looking at a criss-crossing timeline where I’d need to already know information before it happened, and I realized something shocking.

I needed an outline.

Did it help? Sure. Did I love it? Absolutely not. Did I feel like anything huge had shifted in my writing? Absolutely not. I only had the barest of bones of storytelling in that outline. It just kept me on track and aware of when things would happen. Anyone who’s written a nonlinear storyline knows that being constantly aware of the timeline of events is of crucial importance. But my next ideas didn’t have nonlinear timelines. I saw no idea this would continue.

Then, though, I set out to write a romantic comedy for adults. I’d done it before, in the world of young adult, but I’d spent a lot of time on that first draft, and knowing that romcoms have such steady beats, I wondered if I should think about laying those out ahead of time. Writing in a slightly new genre was a challenge I was excited to take on, and I wanted to take it seriously. After mainlining my way through books that inspired me, made me swoon, and distracted me from the stress of life in 2020, I knew that to honor the genre was to take the genre seriously.

And so I committed to an outline.

In the past, I always saw an outline as a hindrance to the process of discovery. This, I believed, was the true magic of writing, the happy accidents, the scenes that change as you write them, the decisions characters make that seem of their own doing. I was positive that if I committed to scenes and story ahead of time that this joyous process would disappear.

I’m sure those of you reading this who already outline are rolling your eyes, because, guess what? This doesn’t go away. Not only is there plenty of discovery within the outlining process, but once I was writing scenes to accomplish what my outline dictated, I was still finding so many new things. Sometimes this was just a fun bit of banter within a scene. Sometimes this was a new theme that was worth revising the outline to reflect. Sometimes the simple idea dropped into the outline became bigger and more fun once it was drafted.

Anyway, spoiler alert: that draft was very solid and required no structural revisions before it went off to my agent. Did I come up with the perfect story on the first try? No. But whenever I realized I’d veered in the wrong direction, I had an outline to update, not an entire draft. I caught all of those big mistakes when they were just a few words in an Excel spreadsheet. I spent very little time drafting any beats that weren’t already revised.

Obviously, this means that my reputation as a non-outliner is destroyed. I think I can live with that.

It seems as if I’ve already ended this post, but I can practically hear the non-outliners who think they might want to become outliners shouting questions at me, so I’d love to offer some big-picture advice if you’re interested in following my path.

Start with the beats of whatever structure guide is getting you through. I love Billy Mernitt’s Writing the Romantic Comedy, though it’s for screenplays, and Save the Cat Writes a Novel by Jessica Brody.

Next, fill in only a sentence or two of your chosen structure’s required beats. For a romantic comedy, this is as simple as, for example, Meet Cute: Character 1 and 2 run into each other at a fun location. Yeah, you’ll figure it out later. Just get the basics in there.

As you think more about your story, expand your outline. I begin breaking down each beat into chapters, based on my ideal word count. Then I get more specific about what happens in each.

I still don’t know everything, and I won’t until I draft. For some chapters, I may include something as vague as “This subplot needs to heighten, find a way to do so in a scene.” Great. I know what I’m working toward there, and by the time I write it, I’ll figure it out.

And, finally, think of your outline as a living, working document. Once, for example, I fill in how that subplot actually heightens, I should update what builds to it and what its consequences are. The more I know, the bigger the outline gets.

For me, I accomplish this with a spreadsheet; I like listing each beat in a cell and then in the next column filling in what happens, etc. But whatever works for you works for you!