Hardest Stuff First

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When I was in my twenties one of the ways I kept body and soul together was moving furniture. The first thing that experienced movers will tell a rookie is Take the Heaviest Stuff First. Why? Because if you wait till mid-afternoon before tackling that grand piano, you’ll be so tired you won’t be able to handle the weight and the cumbersomeness.

Move this first.

I have the same rule for writing.

Attack the hardest parts first.

What that means is that I don’t work on a story in sequence. I don’t start on Page One and push straight through to The End.

Here’s how I do it:

I’ll start with a Foolscap (a one-page snapshot of the whole work) and a broad-strokes outline (I usually name the file “Three Act Structure”) and I’ll add a more detailed Scene by Scene (sorta) outline. So I know where I’m going and the general contour of how I intend to get there.

But from there, I’ll work wildly out of order.

For instance, if I were writing Moby Dick, I might start with the climactic battle between the White Whale and the Pequod, just because it’s the hardest.

Why do it that way?

Because once I’ve broken the back of that daunting sequence, I feel tremendously relieved knowing that that make-or-break part of the story can be done, even if I haven’t got it exactly the way I want it yet.
Serendipity and happy accidents. I often find that when I tackle the hardest stuff first, really interesting ideas or plot twists or character notions will “pop out” spontaneously in the heat of the writing. This makes sense, because the toughest scenes will naturally hold the most difficult moments, story-wise and character-wise. (That’s why they’re tough.)
The third reason for working this way is it’s the strongest posture to take against Resistance. Resistance wants us to piddle around on the margins and take on the easy stuff first. We get soft that way. Our resolve is not fortified by the way we’re working but attenuated by it. Always hanging over our head is the knowledge that we have to confront that Big Tough Scene sooner or later—and that we’ve allowed ourselves to be daunted by it so far.
Setups and Payoffs. In a way, tackling the hardest stuff first is a subset of the principle, used all the time by screenwriters, of Start At The End.

The climax is likely to be the most difficult part of the story. Our own laziness and Resistance will make us want to put off facing it. “I’ll get to it when I get to it.”

But if we can lick it first, we can see (or discover spontaneously as we write it) what all, or most of, the payoffs of the story are.

If we know, for example, that Ishmael is going to be the sole survivor of the final battle (payoff), we can work backward and built into the story the instrument of his salvation— Queequeg’s airtight coffin, fabricated earlier by the ship’s carpenter, which bobs to the surface after the sinking of the Pequod (setup.)

But how will Ishmael survive (payoff), clinging in the middle of the Pacific to that fragile little ark? Ah, let’s have the Pequod encounter another whaling vessel, the Rachel, just before the final battle with Moby Dick (setup). And we’ll have the Rachel searching for a man overboard, the captain’s son (setup). That’s how she happens to be prowling the waters when she comes upon Ishmael (payoff.)

In terms of fatigue, the writing of a long-form project may not seem to be an exact analogy to moving furniture. On a writing job you’re working over a period of months or years, not a single day. But as anyone who’s done it can attest, you can get pretty damn tired working on a book. Six months in, or sixteen months, you can be weary to the bone.

Move that Steinway grand first, while you’ve still got the strength.

And use a dolly!