The Zen Metaphor Wanting or trying to think that way or to attain that state of mind may be a sure-fire way to fail. Instead, creative spirit, artistic talent, and a diverse set of non-design interests must be catalyzed by a dedication to the task at hand and a playful sense of humor. The creative state itself is spurred by humor, and perhaps one of the reasons that Millman got such interesting interviews out of her subjects (well, other than her capable and flexible questioning) is that her interviewees were uniformly funny.
Comedy is predicated on the establishment of a set of rules followed by the sudden and unexpected violation of those rules. That sounds suspiciously like what any teacher in the arts will tell aspiring students. Whether it's said about the graphic design grid, Picasso's cubism, or a Zen book of koans, once the student learns the rules, they can throw out the book. The value comes in the contrast of expectation with the arrival of the truly new.
The lateral thinking that makes for a creative designer is akin to that of comedy, so it is not surprising to find a significant wit among these designers. While I'll leave Chip Kidd's comical list of fears to the reader to discover, I can't resist repeating Massimo Vignelli's closing joke. When asked by Millman, "Is there anything that you haven't done that you want to do?" Vignelli replies, "Oversee the redesign of the Vatican. Such a joke! Can you imagine? The pope as a client! That'd be lovely, turning to the pope and saying, 'Well, the symbol is okay. We can live with that, but everything else has to go.'"