Outlining a Long Essay in One Afternoon

I used to treat outlining as a warm-up I could skip. Then a 4,000-word piece ate three weeks of my life because it kept turning into a different piece every time I sat down. Now a long essay gets one afternoon, a stack of index cards and a rule: when the afternoon ends, the outlining ends, even if it feels unfinished.

Here's how the hours go.

Two o'clock: the dump

Phone in another room. Index cards, and a pen that doesn't skip. I write one thought per card until I've run dry. Not sentences. Handles. "The night the kitchen radio died." "Why the second draft is always louder." "What the editor said on the phone."

I aim for thirty cards. Usually I get twenty-two, give up, and then ten more arrive in a rush. Those last ones tend to be the interesting ones, which is annoying and also reliable.

Three o'clock: the floor

The cards go on the floor, because the table is never big enough. I move them into piles by feel, then name each pile with a few words on a sticky note. If a pile won't take a name, it's probably two piles. Or it's something I like that the essay doesn't need.

This is where the argument starts to show. Piles that want to sit next to each other are telling me about the order. Piles that keep drifting to the edge of the rug are telling me something too, and I try to listen before I get precious about them.

My sister Joss once watched me do this and asked why I was rearranging a carpet of tiny paper. I said I was finding out what I thought. She said that sounded like a long way to go for an opinion. She isn't wrong, but I've never found a shorter way.

Four o'clock: the spine

Now I write one sentence for each pile and put the sentences in a row on a fresh sheet. Then I read the row aloud. If it sounds like a person making a case, I have a spine. If it sounds like a list of topics, I'm not finished, and I go back to the piles and ask what they're actually claiming.

Four questions get me through this hour:

1. If I cut the pile I'm proudest of, does the essay still stand? (Often it does. Sad, but useful.)

2. Which one pile carries the weight? That one gets twice the room.

3. Can I write a rough first sentence and a rough last sentence, and do they seem to know each other?

4. Which section would I be happiest to write first? That's where the drafting starts, not the introduction.

The introduction is a letter I write to myself last, once I know who's been talking.

I keep that line above my desk, though I'll admit I break it about once a month.

Half past five: stop

This is the hard part. By now the outline has holes, and every hole feels like an emergency. It isn't. A hole in an outline is cheap to fix while drafting and expensive to fix in my head at nine at night. So I photograph the floor, copy the row of sentences into a plain document, and put the cards in an envelope with the date on it.

Then I leave the house for a walk, because the piles keep rearranging themselves behind my eyes and I'd rather they did it outdoors.

The next morning I read the row of sentences cold. Two will look wrong. One will look brilliant and slightly terrifying. I start there.