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When it comes to clinching a sale, long, detailed outlines are best. There are two reasons for this, one logical and the other human. The logical one is that the more substance and detail you include in an outline, the more the editor is able to know about what you intend to do in the material to come, and thus the better able he is to judge whether the book you will write will be a book he would want to publish.

The other reason is rather less firmly rooted in logic. Editors are people, too — hard as I occasionally find it to admit this. If they are going to commit their firm to the purchase of a novel in progress, and if they are going to lay substantial cash on the table as an advance to bind the deal, they like to feel they are getting something tangible for their money. A fifty-page outline, comprehensive enough to be what the film industry delights in calling a “treatment,” has some heft to it. You don’t even have to read it to know there’s something there; just weighing it in your hand will get that message across. And, by George, you can tell that the author put in some time writing it. It’s infinitely different from a one-page synopsis that he could have batted out in eighteen-and-a-half minutes on a rainy afternoon. Never mind that the one-page synopsis might be as much as he’d need to have a firm grasp on the remainder of the novel — anyone would be more comfortable dealing on the basis of a fifty-page treatment.

Just how long and detailed an “outline-for-submission” must be varies greatly with circumstances. Random House contracted for my third mystery novel about burglar Bernie Rhodenbarr on the basis of a one-page letter to my editor, Barbé Hammer. In the letter I told her the book’s basic premise and some of the general avenues I intended to explore. There was nothing in the letter to show that I knew how to resolve the plot complications I intended to develop, and there was considerable vagueness even in the opening premise — I said, for instance, that Bernie was going to be hired to steal a particular collector’s item, from one enthusiast for another’s benefit, but I didn’t say what the gimcrack would be because I admittedly hadn’t yet decided.

I got by with this rather cavalier approach because of the particular circumstances that were operating. Barbé knew and liked my work. Random House had already published two books about Bernie and folks there were pleased with them aesthetically and commercially. All I really had to do to get a contract was indicate that I had a sound idea for a book, that it was sufficiently “the same only different” to continue the series, and that I at least was confident of my ability to tie everything up neatly by the end of the book.

In contrast, my outline for my World War II novel ran a dozen or so pages and was as detailed as I could comfortably arrange. In this instance I was offering to write a book of a sort with which I had no real prior experience, and a more substantial outline was necessary not only to convince a publisher that I knew what I was setting out to do but to make me similarly confident. Before I began a 500-page monster of a novel, I wanted to assure myself that I wouldn’t wind up somewhere around page 374 having painted myself into some plotting corner. In retrospect, I wish I’d written this particular outline two or three or four times as long; had I done so, I might have had an easier time of writing the book.

To sum up:

An outline is a tool, the equivalent of a painter’s preliminary sketches. Use it to whatever extent it is helpful. Don’t be a slave to it; if the book begins to grow away from the outline, let the book chart its own course.

Above all, remember there’s no one right way to do it. You can sit down with no outline whatsoever and write the whole book from first page to last. Or you can write a one-page synopsis, expand it into a chapter outline, expand that into a detailed chapter outline with each scene sketched in, and even expand that outline into a super-treatment with bits of dialogue included and point-of-view changes indicated. Some writers operate this way, blowing up the balloon of their novel one breath at a time, until the writing of the novel’s actual first draft is just a matter of doubling the length of the final outline. If that’s what works for them, then that’s the right way to do it — for them.

Finally, for anyone interested in the best illustration I can recall of what an outline is and how it all works, I would recommend Donald E. Westlake’s hilarious novel, Adios, Scheherazade. The narrator is a hapless hack who has written a sex novel a month for the past twenty-eight months and who confronts a massive writer’s block when he attempts to write Opus Twenty-Nine. At one point he produces an outline for the book, an outline that’s very instructive to any apprentice novelist while it finds its way to one of the funniest punchlines I ever read. I can’t reproduce it here, but I earnestly commend the book to your attention.

Chapter 7

Using What You Know... and What You Don’t Know

How to put the background you have to work in your novel. Capitalizing on your own experience. Research — how and when to do it, how and when to do without it

Write about what you know.

That’s the conventional wisdom, and it seems as sensible now as it did when I first heard it back around the time when the idea of becoming a writer first occurred to me. Several writers whom I greatly admire — Thomas Wolfe for one, James T. Farrell for another — had written whole series of novels which I recognized as frankly autobiographical. Others wrote books that clearly derived from their own life experience. One dust jacket blurb after another would recount the author’s background, and each of those writers seemed to have the sort of job résumé that would strike terror into the heart of a personnel manager. A writer, I quickly learned, was someone who grew up on an Indian reservation before running off with a circus. Then over a period of years he worked as an itinerant fruit picker, a gandy dancer on the railroads, a fry cook in a lumber camp, and a teacher in ghetto schools. He saw combat in an infantry division and spent a few years as a merchant seaman. He wrestled a grizzly bear and made love to an Eskimo woman — or was it the other way around?

Never mind. In any event, it was evident to me that I had two choices. I could ramble around the world gathering up subject matter for stories and novels or I could probe the depths of my life to date, telling an eager world just what it was like to grow up in Buffalo, New York, in one of those happy families that Tolstoy has assured us are all alike.

I recognized at a very early date that I was not temperamentally equipped to write the conventional autobiographical novel. While I would not argue that my family and childhood contain nothing of the stuff of which novels are wrought, I was neither sufficiently perceptive nor of the right emotional bent to turn that background into fiction, though many writers have done that successfully.

Nor did I seem inclined to stride adventurously into the world, ready to take on whatever grizzly bears and grizzlier women presented themselves. I was in a hell of a hurry — not to amass experience but to get busy with the actual business of writing. As I’ve recounted, I wound up writing for a living at rather a tender age; I couldn’t write out of my own experience because I hadn’t had any, for heaven’s sake.

One way or another, this is the case with a great many of us. While a few of us actually have the adventures first and then learn how to type, that’s not usually the way it goes. In actual practice most real-life adventurers never get around to writing; there’s always another grizzly bear in their future, and they’re too much inclined to pursue fresh experience to bother with emotion recollected in tranquility, as Wordsworth characterized the origin of poetry. Even when we start out with a background of extensive life experience, adventurous or otherwise, we generally tend to use up our past in our fiction and find ourselves stranded like an overzealous general who has outrun his supply lines. It doesn’t take too many books for most of us to exhaust the experiences we’ve piled up before we started writing. And how are we to gather fresh experience after that point? We’ve just been sitting in rooms, staring into space and banging away at typewriter keys, and how are we to fashion that experience into a novel?