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Sure! Things usually begin by connecting two things that I sense have something in common. For instance—how screens are like plastic: they can be anything, and they are everywhere.
From there, I start looking for supporting evidence or anecdotes or general ideas. Often times I reference diverse topics, and I'm pulling factoids or images from my pool. This is a library of photos and text snippets I've been collecting for years while surfing the web, reading books, etc.
And, this is probably the most important bit: I work in Keynote. Each slide has an image or a short sentence describing the idea. Maybe I'll toss in a movie clip. In the presenter notes, I'm actually writing the full talk/essay. I like Keynote, because it's visual. I can nest slides inside one another like an outline; I can click and drag things around to change the order; I can display all the slides in a grid to get a sense of the pacing of the story. It's really quite wonderful—much closer to how my mind naturally works. I find it's essential for the "rich, media-heavy" stuff you're referencing.
And no, I don't know the end: it's a wild goose chase. I'm a big weirdo and can't start writing in the middle. I have to start at the beginning to make sure the ideas flow in a logical fashion, then take a million walks through the ideas in order to refine and reconfigure.
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Frank, I love your writing style. Can you give a general walk through of how an idea for an essay or book becomes a rich, media heavy, experience? Can you often see the end from the beginning?