An outline is not a checklist

My outlines used to be a mess. I'd sit down to write something, and I'd feel like I had to outline first, because that's what writers do, you know?

So I'd throw a few bullet points down on a piece of paper. No, not even bullet points. They were more like a collection of random thoughts with a loose affinity to the topic I planned to write about.

After a few minutes of brainstorming, I'd wind up with a sketchy group of sentence fragments and phrases.

Then I'd start to write, and I'd use my “outline” as a checklist of things I wanted to cover in the blog post or book chapter. I'd start expanding each item into sentences or paragraphs, then poke them around the page until they started to arrange themselves in a logical order. Sometimes this went well; mostly it did not. I'd struggle and fret and fuss until I'd burned a few hours and generated a lot of pent-up frustration. Maybe I'd finish writing the thing, but more often than not I'd abandon it and move on to something else.

After spending the last few weeks learning about outlining and applying some discipline to my writing process, it's obvious what I was doing wrong. I've learned a cardinal rule of outlining.

An outline is a skeleton, not a checklist.

If I want my writing to go smoothly and flow quickly, I have to put a lot of sweat into the outlining process. I've come to think of it as pre-writing rather than outlining. My outline needs to contain all of the bones that my finished piece of writing will contain. But I also need to understand how the pieces relate to each other and support each other. The structure of my book chapter needs to be complete.

One test that I'm starting to apply to determine whether I'm done outlining a section of my book is to ask, “If I were to try to write this section now, do I know what I would say?” If I don't look at a portion of my outline and hear sentences forming in my head, than I'm probably not done outlining yet.

Usually, I'll realize that I've fallen back into the habit of making a high-level checklist of topics that I want to cover. I haven't dug deep and uncovered what I want to say, specifically, only what I want to say things about.

It was hard for me to pick up on this distinction at first because of the bad habits I'd developed. In my old edit-as-I-went style of working, I never felt the pain of not knowing what I was going to say. I would work in non-contiguous chunks, then figure out how to weave them together later.

But now that I'm developing the discipline to write straight through a crappy first draft, it's painfully obvious when I hit a roadblock. I'll come to a section of my outline and just not know what to say. And that's exactly as it should be. I don't know what to say because I haven't yet thought through what I should say in this section. I've tried to cheat on the pre-writing step, to avoid doing my homework.

I'm learning to recognize this feeling of being lost more quickly, and I'm getting better at it.

The remedy is simple: I have to go back and do the work that I was trying to avoid. I have to go back and finish my outline until I can look at each part and know exactly what I will write in each section.

My outlines now look completely different than they used to. Rather than creating a checklist, I'm mapping out exactly what points I'll make in each section, sometimes down to the sentence level.

It's frankly surprising me how detailed they're turning out to be. For my current book project, which has a target length of 20,000 to 30,000 words, I currently have a 20-page outline. That's the length when I convert it from and emacs org mode outline to HTML for viewing.

On one hand that's intimidating. It seems like a lot to cover. But when I look at sections of the outline, I know exactly what I'd say if I sat down to start writing this minute. It's a lot of writing, certainly, but I can see myself flying through it at 1,000 words an hour.

The skeleton is all there, and I just have to flesh it out.