I dress pretty hip these days.  I rarely wear a suit any more and even though I have a fancy Juris Doctorate and the big 40 is now less than 365 days away, I have a pair of Vans and I wear them often. I must admit that my wife buys all my clothes that people don’t give me on my birthday, but family and friends have done a pretty good job of making me look respectable.  Nothing represents what we think is cool more than what we are willing to wear on our bodies.  And this got me thinking.

As I put on my walking billboard this morning, I thought, “How in the world did Old Navy convince me to wear their name across my chest?”  Well, first of all my brother in law, Philip (who dresses pretty snazzy), bought me the shirt and if he buys it, it must be cool.  Second of all, I too think it looks pretty cool in a laid back non assuming way. But I wanted to see if there was more to being cool than just how a couple of dudes feel about a shirt.  I started to do some reading today and found out that according to the 2010 Coolest & Gaps Branding Survey, the top 20 nominated brands represent 60% of the respondents’ “coolest experience”.  Wow, a small minority of the nominations account for a huge portion of the public’s opinion of a cool brand.

What the survey really taught me is that we know cool right when we see it.

Yesterday I left the Apple store in Salt Lake while I was waiting for my flight back home.  The mall was a ghost town, but the Apple Store was filled to capacity.  Tall people, short people, stinky people, old people, young people and some dude from Idaho packed the store.  As I left the store I heard a mother pushing her baby in a stroller say to her friend, “That is so coooool, I wanted it the moment I saw it. I must have it.”  I bet this mother did not know the technical difference between the Apple and an Acer.  I bet she doesn’t know the difference between megahertz and a caramel macchiato, but she knew cool when she saw it. Most of us do.

I am finding that part of my job each day is to help people build their company and personal brands.  Everybody says they want to be like the great brands but don’t want to take any chances or make any mistakes.  Well good luck. Companies like Apple, Diesel, Nike and Adidas take chances all the time.  Some of their ideas are terrible. (Check out this article about the train wreck Apple Pippen). We forgive Apple’s debacle with the Newton Pad, because we love our iPads.  Great brands take their lumps and are not afraid to take chances. Apple knows that hardly anybody knows about the dismal failure of the iPod U2 Special Edition, and probably don’t care now because they are still making a bizzilion dollars selling U2 music on iTunes.

The secret to life (yes I said life) is not to avoid making mistakes, but be willing to make enough mistakes on the path towards your successes to make people forget about your mistakes. (That was pretty deep, I know, you can’t make this stuff up) We all know cool when we see it.  Don’t be afraid to take some chances that make you happy.  Don’t be afraid to improve the human experience of your brand and products.  What makes things cool is not massive calculations, but massive feelings.  Take the cautious blinders off and have some fun. Live a little. Laugh a lot more. Loosen up and let your brand be cool.