How to write something long and complicated

I find myself in the new and delightful position of writing for money. So I needed to step up my game in terms of workflow and file management. The last time I tried to write something long, I was in college, using Windows 3.1 and good old Wordperfect 6. Then the Microsoft hegemony set in and I switched to Word, along with the rest of the industrialized world.

Word started off pretty useful, but each successive version was a bigger and bigger drag. There were more toolbars and menus and animated characters giving unwanted advice. Finally, I couldn’t take it anymore. I followed the geek example and switched over to plain text editors and HTML.

But this year I wrote a book proposal and some other long-form, complicated stuff. It got to be difficult keeping track of which thoughts were in which text file. Then I read a blog post by Steven Poole called “Goodbye, Cruel Word” that hipped me to Scrivener, and I’ve never looked back.

Scrivener costs $39.95 to Word’s $229.00. Instead of Word’s awkward metaphor of sheets of paper in a typewriter, Scrivener is based around the idea of index cards on a corkboard. Here’s part of my book proposal’s sample chapter.

You can reorder the cards by dragging and dropping. Cards can contain groups of other cards, or even folders of folders of folders of other cards. You can also drag and drop in and out of the outline on the left. You can drag and drop stuff from the Finder too.

Having to come up with little titles for your index cards forces me to think on the meta-level. This has been valuable, because I need all the help I can get to come up with a point and stick to it. You can write your own summaries on your index cards, or you can have the computer generate them automatically from the cards’ content.

In its basic word-processing capacities, Scrivener is really just a dashboard for TextEdit. This is a good thing. Scrivener has its own particular file format, but it conveniently exports to Rich Text, Word documents, HTML and myriad other formats.

The only way for me to have fully-formed thoughts is to write them out of order in nonlinear chunks that I rearrange later. I don’t have the attention span to write from top to bottom. I admire people who do. One of my literary heros is Philip Pullman, the author of the “His Dark Materials” trilogy. Pullman says on his web site that he writes for three hours a day longhand on a legal pad in his tool shed. I don’t even approach having that kind of discipline. I’m a child of TV and the internet. I grew up in a fragmented family in a fragmented city in a fragmented country. If I can’t even think in linear streams, it’s not realistic to expect myself to write that way.

The index card format also helps with anxiety and writer’s block. There’s nothing worse than a blinking cursor in the upper left corner of a blank screen. I prefer to copy and paste in some text from wikipedia or my Delicious bookmarks and then start organizing it into index cards.

I appear to have two writing behaviors. There’s the efflorescence stage, where I start with my notes and source text and let things flow outwards from there, doing my best to not judge or criticize, just banging stuff out. Then comes the pruning stage, cutting the unwanted branches off, letting the inner critic do its job. Pruning mode is also where I have to come up with all the metadata. If I can’t find a home for something, it can always go to the blog or the odds and ends folder.

Scrivener is a good outliner, but my Mac came free with an even better one called OmniOutliner. It’s all too rare for the name of a program to explain what it does, but OmniOutliner describes itself well. It makes outlines, in an omnipotent and omniscient way. In fact, that’s all it does, which is a refreshing change of pace when you’re used to Microsoft bloatware. Scrivener has a lot of OmniOutliner’s core functionality, like drag and drop ordering and metadata and expanding/collapsing sections. But OmniOutliner does automatic section numbering, which Scrivener doesn’t. More importantly, OmniOutliner renumbers your sections and subsections as you move stuff around. Once you’re done you can just export your neatly numbered outline as Rich Text and drop it into Scrivener. Bring on the writing jobs!

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