In high school and college I would write long assignments using a series of outlines. I’d start with a single sheet where I’d write down the key phrases, connect them with lines, and then write more and more phrases until the page was filled up. Then I’d write a series of outlines, culminating in a sentence-level outline that was roughly one line per sentence of the paper. Then I’d write. It worked pretty well. Or horribly, depending on how you look at it. I was able to produce 10-page papers etc. on time. But I think it crippled my writing style for years. It’s taken me a long time to learn how to write directly–to explain clearly what I’ve done and why. And I’m still working on the “why” part. There’s a thin line between verbosity and terseness.

I went to MIT and my roommate was a computer science major. He wrote me a word processor on his Atari 800, which did the job pretty well. For my senior thesis I broke down and used the computers in campus. I formatted it in troff which worked out just fine.

In grad school I moved toward the Latex approach of starting with the template and an outline (starting with the Introduction and ending with Discussion and References), then putting in paragraphs here and there until the paper was done. I followed the same approach for my first few books.

Blogging was different. When I blog I tend to start at the beginning and just keep writing until I’m done. I’ve learned that it’s best to write an entry all at once–it’s hard to come back a day or a week later to fill in any gaps. I think this has helped my writing style and my writing efficiency. The only trouble is that my entries tend to be story-like rather than article-like. In a story you begin with the motivation and then gradually reveal what’s happening. When I’m blogging I commonly start at one place but then, once I’m halfway through, I realize I want to go somewhere else. In contrast, in a proper article you jump right in and say the key point right away, and everything gets structured from there. I’ve tried to improve my blog-writing by contracting introductory paragraphs into introductory sentences.

I’ve been blogging for over six years, and it’s affected my writing. More and more I write articles from beginning to end. It’s worked for me to use Word rather than Latex. Somehow in Word, as in the blogging window, it’s easy for me to just get started and write, whereas in Latex everything’s just too structured. Really what’s relevant here, though, is the style not the software.

Sometimes, though, I have a complicated argument to make and it helps to outline it first. In that case I’ll write the outline and then use it as the basis for an article.

But recently I came up with a new strategy–the best of both worlds, perhaps. I write the outline but then set it aside and write the article from scratch, from the beginning, not worrying about the outline. The purpose of the outline is to get everything down so I don’t forget any key ideas. Having the outline gives me the freedom to write the article without worrying that I might be missing something–I can always check the outline at the end.