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Isaac Asimov is without argument, one of the most prolific writers of all time. At the time of his passing in 1992, he'd penned way over five hundred (Wikipedia credits Asimov with 506) books and racked up virtually all of the awards a writer could hope to win.
While Asimov himself wasn't a big fan of writing outlines before commencement (or even towards the completion) of a book, he gave three invaluable pieces of advice that should settle every manner of issue within the individual writer.
When Asimov wrote his first novel, his publisher (Doubleday) had him write 70, 000 words. He managed to do it without an writing an outline. The time came around for him to do his second novel and he thought such an amazing coincidence (writing without an outline) was not likely to happen twice in a row, so he drew up an outline.
Asimov discovered two things:
One, an outline constricted him;
Two, he couldn't force his characters to adhere to the outline.
He never tried an outline again.
These 3 rules that follow are really going to help you make up your mind as far as outlines go. So do your best to keep them at your fingertips when you pick up your pen to write or when you pound on the keyboard of your computer.
I. If you are a structured and rigid person who likes everything under control, you will be uneasy without an outline.
II. If you are an undisciplined person with a tendency to wander all over the landscape, you will be better off with an outline even if you feel you wouldn't like one.
III. If you are quick-thinking and ingenious, but with a strong sense of the whole, you will be better off without an outline.
And Asimov explains something I feel would be on the edge of everyone reading these mind; "How would I know if an outline is right for me or not?"
To this question, Asimov replies:
"Well, try an outline, or try writing without one, and find out for yourself."
Always keep in mind that rules all have one thing in common; they can be broken. And this is especially so when it relates to the individual and his creativity.
And as Asimov said, "Stick to that which makes you comfortable."
That's the bottom line; let the guy on the inside decide.
Keep your pen bleeding.