On drafting and finding the heart of the story

In a comedy writing class at The Second City—a standby in the world of Chicago improv whose classes I would absolutely urge the comedically-interested to check out—a teacher looked at my scene sketch and made a face. She often made that face.

Up for critique was my piece. The story: In the middle of a party celebrating their launch, a pair of startup entrepreneurs get into a steadily escalating blowout debate about their business concept. The sketch started out with a few one-liners about the pickled okra that these guys were serving, and next they regaled their old college glory days, and then they started out-competing each other in some fart jokes, I believe—and then, my teacher made that face. 

“Here’s something I like to tell people,” she said, unimpressed. “Imagine you enter a room full of things. You could take all of the things and put them in your story, or you could take just one of them, and really see just that one thing. Which story would you rather read?”

That little parable might have gifted me with the single most important takeaway of my earliest (and most embarrassing) plowings-away at writing fiction.

I think the metaphor of plowing is actually a useful one. When we plow, we turn over familiar ground. A week later, totally unexpected plants might be growing. Ancient seeds, long dormant in that soil, are sprouting. We discover things we could have never anticipated—and that’s a very exciting process of writing.

One of the toughest disciplines I had to learn, especially in the beginning, is the art of settling on just one main story idea that comes up in the process of drafting discovery. The art of finding the heart of your story. 

For instance, looking back at the entrepreneur scene, I can take a glance at that messy draft and think, ah-ha! How hilarious and satisfying it would be to explore just one core emotional element: the demands of the commitment.

Whether we’re entrepreneurs or not, many of us can relate to this challenge. We might have a dream, but we might never be able to settle on how that dream should take shape. By placing this concept at the center of the story, I could have explored all the hurdles and blockages that most people can relate to, like perfectionism, vulnerability, and self-doubt. 

In my teacher’s words, then, I can now see that I would not choose to explore all the semi-related items I found in the room. I would zero-in on just that one core aspect of their emotional situation—inability to launch—and explore that one thing for all it’s worth.

Within these entrepreneurs, I know that this particular core emotional element is the most interesting, fruitful aspect of their relationship because that element was the initial inspiration for the story: it was an observation that came from life.

I once worked at an Internet company and would join lots of conversations that featured deep pining to start the next big app, online food truck, sustainable grocery delivery service, etc. With relish, I joined in my coworker’s daydreams about Steve Jobs and Zuckerberg, imagining our own startup careers founding multi-billion dollar efficiencies that solved the world’s inconveniences—but we never moved forward with any of these business ideas, big or small. It touched me. I was interested in this moment where Silicon Valley and young entrepreneurship was burning people up with dreams that seemed so challenging to turn into reality.

Do you struggle with focusing on the core emotional place of your story? I now readily embrace the possibilities of the second draft in coaxing this element to life and reshaping the work around its heart. Of all the material you’ve generated in your first draft, of all the ground you’ve churned up and of all those discovered seeds that are growing, what do you have to trim away so that those one or two central story elements, the most vital focus areas, can thrive?