To answer this question you have to decide what it takes to be the "coolest person" in your own mind. Then imagine that person has had the same life experiences you have had and has until now made all the same decisions. (Yes the coolest people can make mistakes to, so don't get hung up there.)
You have to ask what are the values this person holds?
What are they spending their time doing?
What are their goals?
What is that person doing to achieve those goals?
And how do they act day to day?
After you have figured these things out ask yourself why are you not doing them?
You may come up with reasons, or as some poeple like to call them excuses. Because think again of that cool person, the reason they are cool is because they didn't let things hold them back. They didn't get overwhelmed. They took a bite out of life and swallowed.
So how do YOU become that person?
Well you wake up and you do what that person would do. You listen to your heart, not your fear. You go for it! And even if your story doesn't go exactly how that cool person in your head is, you will never know if you don't try and some of the coolest people are the ones with stories to tell of how they took chances.
So whats cool to you? and how will you be cooler today?