How to Write Cunning, Clever, and Crafty Characters

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My NaNoWriMo novels are full of clever characters, which has baldly reminded me just how difficult it is to write crafty people. I can just see my character acting like Tom Sawyer, but I sometimes struggle to envision the actual behaviors that he or she would use to pull off his or her wiles. It’s great to think my character is tricky, but the number one rule in writing is to show, not to tell. I have to give examples of my character being cunning, not just tell the reader he or she is.

As a reader and a writer, I’m drawn to devilishly shrewd characters. There is something compelling about a brain that works two steps, five steps, or even ten steps ahead of its opponents, and you can find such brilliance represented in all sorts of stories: Coyote and Loki the trickster gods; Sherlock Holmes the master of disguise (and his devious, master-of-the-web archnemesis, Moriarty); Nancy Drew, sleuth extraordinaire; Locke Lamora the penultimate thief.

If you’re anything like me, you have an idea of what you want your mischievous character to be like. You can imagine him one-upping his adversaries, laughing at their stupidity in juxtaposition to his or her intelligence—or respecting an evil but equally sharp counterpart. You can even feel the surprise the reader will feel when he or she reads about the trick. But, if you’re anything like me, you have trouble figuring out ways to pull that off.

My struggles have led me to outline eleven different ideas you can use to brainstorm ways to make your character cunning.

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