As I’ve gotten older I’ve become a lot more aware and a little bit more comfortable with the fact that I will never be “cool” in the old sense of that word. I’m neither a fashion setter nor even trendy and I’ve gotten comfortable with that too. 
While I associate with quite a few younger people in my day-today life, I also realize that they have completely different tastes and, even if I wanted to, trying to “hang with them” isn’t really going to make me cool either.
It needn’t take a lifetime to realize that trying to emulate someone else or compromising your own values to try to fit in with a different group of people is a waste of your time. You need to become comfortable with who you are and stay true to that, no matter who you choose to hang with from time to time. Steve Jobs put it well when he said,
“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition.”
The funny thing is that most of the people who are living the life that you are trying to emulate are following Steve’s advice. You may see them as leaders or just as cool people, but most of them just see themselves as normal people who are pursuing their dreams.
It’s true that you will hit little cliques of people (usually younger and many times in school) who have all adopted some set of characteristics, like dressing a certain way or talking a certain way; however, they aren’t really cool. Quite the opposite; they are so insecure and unsure of themselves that they have sought refuge in their charade of being cool. The fact that they band together and often make a show of excluding others is actually proof of how insecure they are about themselves. They almost always quickly become caricatures of the cool people that they think they are portraying.
So, if being “one of them” isn’t cool, what is? Maybe you should try “being the only one of me” instead. Like yourself first and
others will like you, too. Be happy with who you are, with your unique talents and outlook on life. Create your own “style”. Wear what appeals to you, not necessarily what “everyone else” is wearing. Do the things that interest you and don’t worry about “what everyone else is doing.” Hang around a variety of people and try to learn from each person or group. Make decisions based upon your own moral compass, not based upon what everybody else is doing.
Finally, don’t try to be cool. Coolness comes from self-confidence not from being a follower. You might be surprised that others are attracted to you, just because you are content just being yourself.
Follow your heart. That’s cool. Have a great day.
NormsMilfordBlog 
[…] Sometimes it’s hard to be happy being with yourself, especially in the formative years when you may not be real sure who that is anyway. Children take cues from all around themselves as they grow and learn and try to find their identities. Sometimes they are not happy with their circumstances and who they think they are, especially as compared to others whom they think they would like to be like. They get hung up on how they look for dress or act in public and who they hang out with (or are not invited to hang out with). It’s hard to be happy with yourself if you don’t see yourself as being “cool” or being a member of the “in-crowd”. I posted here about that in a blog Trying to be Cool Isn’t Cool. […]