Writing my outline, part two


Reader,

If you want to write a book, you have to get comfortable with two uncomfortable things: uncertainty and the unknown.

Everything about writing is uncertain. Will the right words flow from your fingertips when you crack open your laptop? Will anyone care enough to open the email? Will they make it to the second stanza of your poem? If they dislike what you say, will they leave a scathing remark about your weight? If they like it, will they bother to tell you or will they, like everyone else, assume that some other person is going to do that?

Meanwhile, the unknown is why we write. Contrary to popular opinion, the time to write a book is when you don't know the answer to a question. When a "what if" just won't leave you alone. When you're tired of wondering aimlessly. The times you're sure about what you have to say? You're dead wrong. Hopefully you'll discover that along the way and get a chance to write something worth reading.

This is all to say: I hit my first pivot this week. There I was, minding my own business, reading through my old LinkedIn posts like I promised last week. Suddenly, I realized I was making a mistake. My outline was ballooning, and not in a good way. If I didn't cease and desist, I was going to end up with an unwieldy list of topics. The kind of list that was sure to kill all of the energy behind this project.

So I closed the tab and pulled out my notebook. (As I've learned from Austin Kleon, "analog" tools are just the thing you need when overwhelm rears its ugly head.)

Frederick Buechner inspired the way I've been looking at this project. He wrote three "dictionaries," short books with quick riffs/reflections on a variety of words. Here's a snapshot from the table of contents to Whistling in the Dark:

I'm predisposed to like pretty much anything Buechner writes, but this format especially captured me. The brevity of each piece maximizes Buechner's typical charm. I immediately wondered what it would be like to write something like this.

​When I showed you the start of my outline last week, I was planning to reveal that same format in this week's email. And yet, when I hit that speed bump last week, I realized that it's not going to work for my book. I have snippets that would work like this, but I've also got longer pieces that demand a different kind of format. That's what led me to pull out my notebook for a brainstorming session while my son was at baseball practice.

Here's what happened:

As you can see, I've preserved an element of the dictionary motif. If this outline sticks—a not insubstantial "if"—I'll end up with twenty-six chapters. Yet, as I currently envision it, this book will still have an arc. Like any essay collection, readers can bounce around and read different essays according to their whims. But the best experience will be to read them in order.

I love a lot of things about this outline I've stumbled into. While each chapter represents an "essay" of sorts, I've got freedom to be playful within that format. Some will be a "proper" essay with a beginning, middle, and end. Others will be collections of short musings, tacked together under a general theme. I have an opportunity to have my cake and eat it too.

Some of the chapter titles are obviously about writing (Beginnings, Drafting, Editing, Sentences, Voice). Some hint at some of the mindset stuff I constantly return to and believe is crucial to a strong writing practice (Attention, Fear, Other People, Raw). But others are cryptic (you can identify those on your own).

Those cryptic essays may end up being some of my favorite. I intend for them to be written in the spirit of a Frederick Buechner quote I read this weekend in Telling the Truth. He was writing about the way Jesus talks about the kingdom of God, but I'm stealing his words for all writers, regardless of what they're writing about:

He suggests rather than spells out. He evokes rather than explains. He catches by surprise. He doesn't let the homiletic seams show. He is sometimes cryptic, sometimes obscure, sometimes irreverent, always provocative. He tells stories.

That is precisely the kind of writing and talking I want to be known for. And with this new outline, I think I have a reasonable shot at delivering that kind of book.

This week, I'll be doing some new writing. That's a little nerve-wracking, but I'm nearly a month into my 4-month timeline, so it's time to get some new words down on the page. Stay tuned.

Next week: what's the purpose of writing this book?

Keep your stick on the ice.

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

The Thrill of Writing

I am currently documenting the process of writing my next book. It's a behind-the-scenes look at the beautiful, messy adventure of transforming my short-form writing (emails, social media posts, random notes) into a cohesive, compelling manuscript. If you've ever wondered if you could turn your own short pieces into a full-length book, join my newsletter and learn how.

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