The first step to having more of a fruitful life is to start being content with yourself, be happy about what you have and use it as your strength. We all are different, which means that we all have something to bring to the table every day. It is not the easiest to look at yourself and be happy about everything you have, and if there is something that HAS to be changed, you work hard for it if it will make you happy and actually lead to you being more comfortable with yourself. Reason why I wrote HAS is because today we believe that we have to look and act like others, else we will not be accepted as a human being quiet frankly.
If you can convince yourself that you do not need to change anything with you and be perfectly content with yourself you should have no problem stepping out of your comfort zone. As long as you do not let yourself think about how others will perceive you, there is no reason for you not to be yourself all of the time.
Tomorrow, I want you to dress up in the clothes you are most comfortable in and walk around downtown with it. It could be bed clothes, the ugliest hoodie or the brightest shoes. I started wearing my pajama-pants to school just because that was the most comfortable clothing I had and I really did not bother dressing up for class. I would never have done that three years ago, now I do it on a daily just because it is "me".
"Most shy people wish they were more confident, because shyness is ultimately a symptom of you being uncomfortable with who you are. You judge yourself based on other people's standards and spend too much time in your own head, thinking of how best to act and react in any given situation. This is nothing more than a bad habit, and it's the sort of thing you can break with regular practice." - Adam Dachis (http://lifehacker.com/)