The dangers of faking your outline

Writer’s block isn’t something I usually struggle with, but I ran smack into a wall yesterday. It was pretty unexpected, and working around it taught me a valuable lesson about outlining.

I’d cranked through my daily practice writing session in record time, and when I cracked open Scrivener to work on my book, I had high expectations.

I pulled up my book outline in one of Scrivener’s split-screen panes and my current section in the other. I deleted the bright red PICK UP HERE placeholder comment I leave at the end of every writing session, took a sip of coffee, and studied my outline to see what to write next.

The outline clearly mapped out the next few paragraphs. Everything seemed to be in order.

I put my hands on the keyboard and … nothing. I stared at the outline. I sipped more coffee. I fidgeted. For 10 or 15 minutes this went on.

Just write what’s in the outline! I kept telling myself.

But something inside me was stuck. I couldn’t move forward. I was starting to feel cranky.

I sighed and leaned back in my chair to get some distance from the problem. What was going on? This didn’t feel like regular “I don’t want to write today” resistance.

It reminded me of a feeling I used to get when I was a freelance journalist. When I was writing newpaper stories, sometimes the writing just flowed, and other times it didn’t. I almost always found that “writer’s block” meant that I wasn’t finished reporting on the story—I needed to do more research.

Was that what was going on here? I started to look more closely at the neatly typed bullets in my outline. I looked at each item, trying to think specifically about it and what I wanted to say about it.

And for many of the items, I just didn’t have anything specific to say. Taken as a whole, the list looked perfectly reasonable, but I was coming up empty when considering them individually.

How did these bullets end up in my outline, then?

Unlike previous projects, I’m taking a very systematic approach to this book. It’s a technical topic—how to write plugins for Sublime Text—that I didn’t know much about when I started working on the project. So I spent about four weeks doing pure research. I read all the blog posts I could find about creating Sublime plugins. Then I wrote my own plugin, start to finish, taking notes on the entire process.

I waited until I finished this research before I started outlining the book. I spent several days on the outline because I didn’t want to shortchange the process. I really struggled with the outline initially, but eventually I realized that I could look at other well-organized books and courses and borrow the structure that their authors had chosen.

I wound up basing my outline on a course that my buddy, John Sonmez, shared with me. He’d created a PluralSight course about building Chrome plugins, so the structure was a great fit for what I was doing. I took the skeleton of his course outline and plugged in my research—it worked brilliantly. No more outliner’s block!

Once I finished the first draft of the outline, I shifted into the writing phase, which brings me full circle and back to stuck.

But that little review of how I got here contains a clue to my current predicament. I did all of my research first, then plugged my research into someone else’s outline. And while the outline template I used was a great fit for my project, it wasn’t a structure I had in mind as I was conducting my research.

And what did I do during the outlining process when I hit a section of the template that called for information I hadn’t explored in my research?

Why, I made stuff up, of course. Perfectly reasonable sounding stuff. Things I thought I should cover. Conjecture about how I thought things would work.

I faked it.

And my outline looked solid and complete and ready to go, but it was giving me a false sense of security.

Once I realized what the problem was, I took a break from trying to write and went back into research mode. I spent 30 minutes researching and reworking the weak section of my outline, then shifted back into writing mode and quickly pounded out several paragraphs.

My word count for the day looked pretty anemic, but that’s the price I had to pay for cheating on my outline.

Achievement unlocked.