How a Cartoon Caption Contest Can Make You a Better Writer

On the first day of my undergraduate marketing strategy course, I show my students one of my favorite New Yorker cartoons. It is an image of a familiar red-and-white-shirted man with matching cap and wooden cane. He sits at a bar. The caption states, “Nobody ever asks ‘How’s Waldo?’” It’s sharp. It mixes familiar and clever. It’s classic New Yorker humor.

While a good number of my students chuckle to themselves, few if any are regular readers of the New Yorker. Many have not...

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