One of the problems of "cool" in the fashion world today is that, with the proliferation of cool-hunters, market research, and commoditized rebellion (think Urban Outfitters, H&M, or other "counterculture" retailers), the cycle from trendsetter to mass consumption is ever shorter and the high-low cultural divide ever narrower. Cool is more quickly copied and mainstreamed these days, which makes the task of being cutting-edge and truly exclusive ever more arduous.
The coolest guy I know is Elmore Leonard, and I doubt if he has ever spent a nanosecond of his life thinking about it.
You've all heard the motto "ABC: Always Be Closing." More importantly I think we should Always Be Reading so we can Always Be Learning. I've never heard anybody regret having more knowledge that helped them build a better business, family, or make themselves a better person.
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