Reader,

In a past life, I worked as an estimator for a painting company.

Our focus was repainting large multi-family properties—townhouse complexes, apartment buildings, and hi-rises. As an estimator, a big part of my job was traveling to those properties and assessing what would be required to deliver a successful repainting project.

It wasn't just a quantity survey, though. Yes, I was responsible to measure up the buildings, primarily to ensure we allowed for enough paint. However, the success of my role depending on more imaginative questions. What was the access like: could we get a boom lift around the buildings or did we need ladders and scaffolding? How much would trees and vegetation impact on our work? (Pertinent because we were often sizing up these buildings in the winter.) What was the owners' greatest concern about this project? And what ought to be the owners' greatest concern about this project?

Though I did this work for several years, I found myself daunted every time I stepped foot on a new large property. A sprawling apartment building with several twists and turns. A 150+-unit townhouse complex with three-storey buildings decked out in four colors and countless architectural details. Where on earth should I begin?

Here's a secret about estimating large properties: your job is to identify patterns. The developers who construct these buildings thrive on repetition. It's how they build efficiency and eke out a profit, since every trade that comes through is essentially asked to do the same thing over and over. I would inevitably locate differences throughout the property, but they would be the exception. My job was to identify and then calculate the norms.

That's still an overwhelming task when you're standing at the front of the property—usually featuring the fanciest buildings, to impress everyone when they first drive up. Which is why I learned to go further in, find the simplest side I could, and start from there.

Estimating, like many things, is all about adjusting your eyesight. Few people can stare at something complex and immediately parse out its discrete parts. But if you begin with a simple version, you start getting a sense of what you're working with. For me in those days, it often started with window trims, gutter fascias, and belly boards. Once I had those substrates clear in my mind, I could expand my vision enough to comprehend the dormers, the corbels, and the board-and-batten accents that had initially overwhelmed me.

Writing is no different.

When you have the spark of a new idea—whether it's a short story or an essay, a memoir or a novel—the possibilities pile up all too quickly. Even if you know where you're starting and how you want to end, the stuff in the middle is overwhelming. How can you possible get from A to Z without losing the plot?

Find the simplest thing, the part you know you can manageably write, and start there. Once that's done, move on to the next simplest thing. Etc, etc.

Of course, this is not a certain path forward. (That's why some of you felt my last paragraph was rather glib.) Working this way requires faith. Faith that your idea has legs. Faith that things will get clearer the further in you go. Faith that you can actually pull this off.

But who ever said the work of writing ought to be something certain anyway?

Keep your stick on the ice.

Frank Ewert
Book Coach, Editor, and Student of Uncertainty
Author of Embrace Your Writer's Block and Blue Ice​