How to Illustrate a Book
In the world of book illustration, a lot of the specific techniques illustrators use are carefully guarded by that secretive guild. However, there are some basic ideas most illustrators follow when they pick up the pen. Illustrating a book has always been a somewhat open endeavor but with its own standards and conventions. Here are some ways to successfully get your pictures combined with a book's narrative.
Instructions
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Find critical "climactic action points" in the book that warrant illustrations. You'll see in classic literature that the illustrations are very carefully tied to specific points in the book, even to specific lines, either quotes by a character or a line describing a specific action. In newer books, this isn't always the case, but getting your action points gives you a clear map to getting your illustrations on paper.
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Match your illustrating ideas to the tone and audience of the book. Before you draw, think of your characters and how to depict them on the page according to the age of the readers and the style of the book. Cartoons may be great for a younger audience but not so good for an older one. Take these issues into account when planning your overall style.
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Think about space and prepare to draw somewhat to scale. Otherwise, detail may be lost. Know whether your illustrations will be full-page or combined with text, so that you can fill what you need to fill on paper. Also anticipate other limitations of the publisher. Ask if your illustrations will appear in color or only in black and white.
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Do studies. Lots of really good illustrators work up to full illustrations starting with playful character sketches that they call "studies" because they draw them while studying the form of an original item or photograph. These help you develop your characters and hone your drawing style before you go to create the actual item that will go into print. The sketches can also come in handy later if you're doing gallery shows or other demos of your work. You can also include mock-ups or other souvenirs of work in progress.
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Develop extras. When you're ready to meet with the author, publisher or other involved people, arrange your portfolio and include multiple options such as different poses for a character, different compositions for a scene, or heavier and lighter line drawings, considering that there might be some illustrations your collaborators will want to pass on. Having a couple of surplus offerings can come in handy when sealing the deal.
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Tips & Warnings
Try to resist the temptation to "avant-garde" slash-type drawings that may appear sloppy to readers. It might be really cool to you, but unless your book is really out in left field, readers will likely be turned off by abstracted, highly stylized illustrating. Think about what you as a reader would like to see on the page, and don't turn characters into caricatures unless that's what everybody really wants.