I recently finished a book called "Chasing Cool ." It’s about the corporate temptation to try to "be cool" rather than allowing coolness to emerge from relevance.
I recently did an interview with a writer for HOW magazine (hi Lisa !) about designing for a specific target and stated that "relevance is proven by action." In other words, the attempt to be relevant immediately proves us other-than-relevant.
How do you handle the coolness factor? How do you avoid the temptation to "chase cool"?
For me, it’s a continual examination of my motives. Am I "positioning" myself? Even the attempt to "not try to be cool" can be a veiled attempt at coolness. (It’s amazing how so many teens who are a part of "counter-culture" look alike, dress alike, listen to the same music, etc.) We all want to connect with others in our expression, but we also can’t allow our unique edges to be smoothed over by the stream of cultural mediocrity. Culture tends toward the middle because it’s the safest place - like a dip in the middle of a sagging bed, we all roll to the middle.
Many of the people we call "cool" never wanted that tag - in fact, if you ask them, they would say they’re "geeks", "nerds" or misfits. It’s their willingness to shed popular opinion that gives them the ability to stare the fear of rejection in the eyes and walk through the heart of it. I’m still working on this one, but it’s definitely a battle worth fighting and winning.
In this interview, 
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