it’s not easy being cool.

Charlie has always been a poser : Charlie is kind of a poser.  He’s confident.  Self assured.  Comfy in his own skin.  He kind of just came that way.  Check out Elvis here and superman here and cool dude Charlie guy here.
We’re trying to figure out ways to teach him to wield his awesomeness for good.  Yes, we want him to be cool and confident, but mostly we want him to be good and kind.  We want to teach him to be a leader for the right, to watch out for the underdog.
So far, I’m not sure we’ve figured out how to do that.   It probably doesn’t help that I bought him a t-shirt that says “it’s not easy being cool” in Spanish, seems like a surefire way to plant him on the path to becoming a cocky frat boy. (It was only $2 at the children’s place and we’re trying to teach our kids more Spanish). When Jeff tried to translate the shirt for him he was very confused.  Here’s how the conversation went:
C: What do all these words mean on my shirt?
J: (translating word for word) “No is easy to be cool.”
C: I don’t get it.
J: Well it’s saying “it’s not easy being cool”
C: I still don’t get it.
J: You know, it’s saying that it’s not always easy to be a cool dude.
C: (exacerbated) Dad, I don’t get it!  It IS easy being cool.

Then, the other day I overheard Charlie talking to a younger friend.   Here’s the conversation:
C: Do you know how to ride a bike without training wheels?
F: No.
C: Do you know how to ride a bike with training wheels?
F: No.
C: Do you even know what a bike is?
Charlie is cool, no doubt, and he’s pretty confident.  And mostly he is kind and good and chooses the right.  Having a baby brother has especially drawn out his sweet, protective side.  But how do we make sure he heads down the right path and doesn’t turn into what Jeff calls a “frat boy”? 
I thank my lucky stars that he has so many uncles and uncles in law (9 to be exact) who are paving the way.  They are all confident and kind, successful and smart and good.  Plus he has two pretty incredible grandpas and one remarkable dad.  That’s all got to count for a lot.  
So, this is what is on my mind lately.  Boys are hard to raise and boy does the world need good boys.
Any ideas?  Anything that has worked for you?