Learning How to Outline

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Today I had a thought about writing that I wanted to share with you:

The amount of work I produce is equal to my level of interest in the work. If I am telling compelling stories, I will write those compelling stories. If I’m blocked, it is probably because some deep part of me understands that the story I’m trying to tell is off in some way. Boring, convoluted, perhaps ultimately meaningless.

Imagine you’re talking to a coworker. They ask you how your weekend went. “It was fine,” you say. Now, it might not have been fine, but you’re not really telling them the weekend was fine. You’re brushing the conversation off, because you know that it’ll take about ten minutes to summarize, and ultimately, nothing that happened over the weekend is interesting enough to take up that much life.

Boring weekends can be beautiful. I just had one. But I won’t bore you with the details. It was just nice, for me and my family. It was fine.

Now imagine that your car was attacked by a buffalo. Or your house was broken into. Or your tires all went flat. By varying degrees, you’re going to tell a longer version of those stories. It doesn’t have to be negative, either: you’d probably talk about a big win at the casino, or meeting a celebrity, or completing a major project.

Realistically, you’ll more than likely talk about the stories you watched on TV or read about in books. That’s because all of these things are more interesting than the sublime mundanity of your day-to-day.

So, would it be fair to say that a writer’s block stems from a kind of “fine weekend” of the future? One truncates and waves off a fine weekend for lacking any compelling story, one truncates and waves off a writing project for the same. Except in the case of the latter, we have the opportunity to mold the heavy, pressing lack of story into story. How?

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I became interested in novels for the beauty of their prose, their cleverness, style, and voice. For most of my life I listened almost exclusively to rap music for the same reason, because the best of them can put words together like no one else. I was crazy about language, obsessed with semantics, in love with being carried along by the rhythm of the sentences.

Over time, however, I became bored with these hazy, beautifully written fever dream novels. I found myself finishing fewer and fewer of them. I’d get sucked into their world via the strength of the author’s voice, then lose interest about three chapters in.

What I was missing was a good story.

This week I produced 5,000 words of my new novel. That’s not bad. A little under half of what Stephen King produces during any given week. But I’m not hung up on that so much, anymore. The actual number of words doesn’t matter, because it’s not about words per day. It’s about how many days in a row you can stack. And I wrote every day.

It beats the zero words a day I had suffered through for nearly a decade. That shit is painful. You know you have a story to tell, but you just can’t do it. I needed a solution, and after about a year of research, I found one.

Outlines have taken me a long way from where I was even a year ago, when I was producing one short novella a year. This is because with even a small outline, you have a sense of where the story is going, and that makes it easier (and more fun) to tell. You know that big action, surprising twists, and great characters are waiting for you to spin them into life.

With an outline you know that your book is not boring, because you have arranged every scene into a handful of simple stimulus/response prompts that signal a change in the protagonist. You know your book is not convoluted, because it’s right there on two simple pages. And it has meaning, because you found the meaning once you summarized the book in its totality. That meaning begins to fractal out to the acts, chapters, sequences and sentences.

For those of you who still push against outlines: you still get to improvise. A lot. How are the characters going to talk to each other? What does the building the MC lights on fire look like? What strange creatures will appear? All of these things and more you get to discover for yourself, in the actual writing. Which is why a modest outline is in fact “discover writing” squared. It’s the best of both worlds.

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I’m hosting an outlining workshop over Zoom in about three weeks. During the workshop, I will speak about my theories about the outline, and why I believe it to be one of the most important tools in the writer’s toolkit.

By the end of the workshop, you will have a two-page outline that you can use to get started on the writing. You’ll have a valuable skill that you can carry with you for the rest of your writing journey.

Every outlining course that I’ve taken has been so left-brained that I couldn’t find my way into it until I forced myself to sit down and figure it out. What I found, filtered through who I am as a discovery writer, is decidedly right-brained. I believe we’ve been thinking about this whole thing the wrong way, and I believe this workshop’s method can get some truly creative people, the kind of people we need writing books, to produce those books at a rate that puts them in the conversation.

Come hang out. It’s $100 for four sessions over two weekends. There are ten seats, but I announced it to the Agitator Discord and IG first, so now we’re down to five. DM me for more info on the course and how to sign up. Looking forward to seeing you there!

-JDO