Thanks for the replies!
kevlarsjal2--I think you're on to something about my fear of being boring and feeling uncomfortable in the role I play in my life. Although, my life has changed drastically (for the better!) in the last few years, and I need to update the mental image I have of myself.
I work in a creative field, and playing the rebel has actually paid off in the past, and still pays off in terms of getting hired to do work outside of the mainstream. But I'm at a point in my life/career where I have the potential to do things I could only dream of a few years ago--I just can't do them drunk.