Reverse outlining

I was writing this thing, the details are boring, let me just say I was allowed about 3,000 words, maybe a few more. I wrote 2,000 and felt good about that. The content was okay and I was on track to not have the piece be either too short or too long. Life distracted me - groceries, bills, childcare, preparing for holiday travel - and to be completely honest I procrastinated out of fear, because that piece might be seen by some very smart people who I’m intimidated by. The combination of distraction and procrastination created a delay in the middle of writing this piece. I had a lot of ideas in that delay, but did no writing. A few days later I got back at it. I started from the new ideas, and I wrote another 3,000 words. That put me way over acceptable length, and with two incomplete drafts of different documents that needed to become one.

I went for a lot of long walks and started at the ceiling a lot and I learned a lot about New Order - did you know Bernard Sumner built the synthesizer he played when they first started up? Pretty neat! - and I read a few years of Peanuts comics… Everything except get back to work on this piece of writing. I mean, I jotted a little, and I stared at the words, and I reread bits of what I’d written, but I was making no forward motion. The answer hit me suddenly: reverse outline. Duh. That’s always the answer. I always find that answer late, because it’s quite painful.

Here’s what reverse outlining is as I do it. The point is to create a map of what I’ve actually done, then use that map to identify the immediate next steps I need to take. Here’s what I do.

First I number every paragraph in the draft I’m working on. Then I write a one sentence summary for each paragraph, in another file. This is boring but it’s very fast because I don’t need to read closely to write the summary. This is also comforting in the face of fear because it’s very finite. All I’m doing is reading one paragraph and summarizing it. That’s not hard, even if I’m doing it over and over again.

Once I’ve summarized all my paragraphs, I read the summary I wrote, without looking at the document summarized. I make notes on the summary to indicate where paragraphs are out of order. I often have new ideas during all of this too, so I write those down in another file. Then I copy the summary of the paragraphs into a new file and I move the bullet points around to make the piece flow more logically. Then I copy my draft for backup purposes and I move the paragraphs in the draft to match the new outline. That’s the end of the reverse outline, at least for now.

The next thing I do is read the re-organized document. Usually what has happened by now is that I’ve got all the paragraphs in the right sections, but they may be out of order within a section, and there may be issues inside some of the paragraphs. What I do next is fix the sections, starting with the order of the paragraphs again. The order is the logical skeleton of the argument and flow of the document. Once I get the order right, it’s much easier to fix the prose. In order to get the order right within a section I sometimes needs to reverse outline a second time, outlining the section I’m working on.

After everything in a section is in the right order, I read it and find material I can cut or condense, and identify things that are missing. I try to not fill in those missing parts while I’m cutting or while I’m re-ordering. I’ve figured out that I can really only do one thing at a time. I can come up with ideas, organize ideas into a logical sequence, and make my sentences more concise. I can’t do more than one at the same time. Moving quickly from one to the other is very tiring and distracting. I do best if I go over a piece of writing thinking about structure of the piece as a whole (the order of the larger units, the sections and paragraphs), then go over it again thinking about structure at a smaller scale (the order of paragraphs within sections and the order of sentences within paragraphs), then go over it again thinking about the prose, and then at the end I will write out any remaining ideas I wanted to flesh out. The order may vary - I may have an idea that I jot down and the jotting turns into generating new prose that’s not just bullet points but full sentences - but the point is to do focus for longer work sessions on one activity and way of thinking, rather than changing quickly and repeatedly from structure to prose to big ideas and back. For me, every transition in thought, every shift of my mental gears, costs me some energy, so the fewer gear shifts I do the better.

I will also say, sometimes I need one section to make sense in detail before I know what subsequent sections are going to do. When that happens, I just finish an early section as well as I can, knowing that I may have to revise it again after I write the parts after it. That can be hard but sometimes I need an earlier section to serve as a building block or foundation to rest later sections on.

Part of why I do all of this is to focus efficiently on one kind of thinking at a time, as I said. Another part of why I do this is to manage the fear and other negative emotions that come up for me in doing writing. I doubt my work a lot, if I think much about what I’m doing. I like writing when I’m in the middle of it. In the middle of doing writing when I’m really going, my fingers are moving on the keyboard, I often experience what some psychologists call ‘flow’, where I’m not really thinking about what I’m doing so much as I’m just doing it, I’m partially dissolved in the experience as opposed to judging my performance and my output. That’s enjoyable. The judging is not, and the judging rushes back at any break in the flow of writing. When the judgment returns, I doubt my abilities and myself and I assume the piece won’t turn out and I berate myself for even starting or trying and I just want to quit. A friend summarized this well, he said “I hate myself until the fourth draft.” The early stages of writing are a time when my inner voices betray me and try to stop me.

With all that berating going on, there’s a lot of mental noise in my head and it gets confusing and it gets tiring. Reverse outlining and the progression from large structure to small structure to prose, that means the tasks are clear and broken down. I know what I’m doing now and next. I can push through to that activity without having to deliberate much - deliberating gets harder what with the Society For The Prevention Of Nate’s Writing hosting its convention in my mind. And as I push through rather than dither, the more the attendees at that convention start to lose interest and drift away, making the activity less difficult and more enjoyable. The doing makes the doing easier, and reverse outlining is partly the practical plan - the order in which I will do the task - and partly a motivational and emotional management strategy. Having a finite simple task in front of me (number these paragraphs, summarize this paragraph, read these bullet points) means I can always do something. It’s comforting.

Of course, it’s also terrible. The reverse outline itself isn’t terrible but the fundamental thing it requires is, namely that I have to read my own writing and then write more. This is why I always am late to remember to reverse outline. I don’t want to read my work. Reading my work is emotionally difficult. It’s scary. My impulse is to procrastinate and spread the writing out over a longer period of time - write a little, dither a lot, write a little dither a lot. The result if I do that is that I do little over long periods but I feel tired as if I have done a lot, and I feel afraid and uncomfortable for a longer time. If I push through the rereading and the new writing faster it concentrates all that unpleasant emotion in a much shorter time frame, which is scarier to think about before doing it, but is ultimately for the best. It saves me a lot of time and the writing that results is much better organized and thought out.