Two strategies I’m using to improve my outlining skills

I used to hate outlining. It was frustrating and didn't seem to help my writing at all.

When I'd sit down to write, I'd scribble out a few bullet points that were related to what I wanted to write about. These points were usually a loose collection of thoughts that centered around a single theme that I wanted to convey. I'd shuffle the bullets around on the screen, trying to bring some semblance of order or impose some kind of sequence to them. Usually they included several items that were tightly related to what I wanted to say, plus a few tangential items that I really wanted to squeeze in because they seemed interesting.

After a few minutes, I'd get frustrated trying to herd these cats into an outline, and at that point I'd figure it was time to get writing. The outline could only take me so far, right?

Once I started into the writing, things felt easier. I was on familiar ground now, flying by the seat of my pants, and new thoughts and additional points came to me quickly. My hammering fingers would nail them to the page before they could flit away.

Before long, I'd left my sad little outline in the dust. My writing had moved on, and it no longer resembled the outline that had started its life. No great loss, though, as the outline was just a source of frustration.

But that's changing. Now as I write, I'm finding that my outline is my roadmap and guide. When I'm feeling lost, I consult with my outline and it quickly shows me where I went off course.

What's changed? I'm doing a couple of things differently now, and they're making a big difference.

First, I'm taking outlining a lot more seriously up front. An outline is a prototype of the writing I'm about to plunge into. And if I don't have enough clarity of thought to prototype an article up front, it means I'm going to have trouble later if I try to just start writing now. A sloppy outline that's just a jumble of loosely collected thoughts is a warning sign that I'm not done thinking about the idea—and consequently, I'm not ready to write about it.

When an idea is bouncing around in my head, it's easy to fool myself into thinking that I have a well-formed thought that I want to convey. My brain is pretty good at convincing me of this. The idea starts to write itself while I'm doing other things. I'll get snatches of phraseology and sentence fragments popping into my head. You have to get all of this down before you forget it! it tells me.

But no matter how many clever turns of phrase my subconscious generates, I'm learning that I need to be able to outline the idea clearly before I start to write, or I'm going to run smack into a brick wall later on. I'll start writing, and the article will grow and grow, and then I'll take a slight detour to bring in some related-but-no-quite-relevant secondary point, and that'll lead to another detour and finally a blind ally—and frustration. Now I have hundreds of words in front of me and a vague sense that I'm lost, but no idea how to get back on track.

In addition to devoting more time and thought to outlining up front, I'm also paying more attention to my outline as I work.

I used to see the outline as a disposable tool whose only function was getting me started. Now I'm treating it as the living skeleton of my writing. This has made a huge difference.

Instead of ignoring and neglecting my outline once I start writing, I keep it open on my screen, side by side with my writing. If a new thought occurs to me while I'm writing, I'll add it to my outline first. Or if the words are flowing, I'll finish the thought and then go back and add the new points to the outline.

This iterative approach to outlining, what I call my “living outline,” takes a lot of the upfront pain out of outlining. I've never struggled much with writer's block, but “outliner's block” is definitely a problem for me. On the rare occasions when I'd try to do a serious outline before diving into a writing project, I'd feel pressure to get the outline exactly right before starting. Now I know I'll keep coming back to it later until it's right.

My goal when I finish is to have an outline that mirrors the structure of my finished piece of writing.

I'm finding that there are two benefits to this approach. First, the discipline of fitting new thoughts into an existing outline helps me see when I'm starting to veer off course. It forces me to acknowledge that this interesting side point doesn't really fit into what I'm trying to say. And if I do start to feel lost, a few minutes studying the outline usually makes it clear where I went off track.

Second, it's helping me become a better outliner. When I finish writing this way, I have a completed outline that demonstrates the level of detail and thought I put into my finished article. I can refer to this completed outline in the future when I'm working on a new outline and trying to decide if it's complete enough.

I'm still not very good at outlining before I start writing, but the “living outline” approach is helping me improve my skills while also maxing out the benefits I can get from my current level of outlining skill.