How do I rid myself of the insecurities that are preventing me from becoming confident and outgoing?

Fake it until you make it! If you act like your really interested in people 9 out of 10 will blah, blah, blah! The one 1 is not someone you need or want anyway. It is a two way street. You just throw in a few words here and there, really? Great? Good idea! That sounds fun! Too bad, I am sorry to hear that. People love the sound (or most) of their own voices. You have outgrown a lot of it, and you will continue to do so, and personality has very little to do with how happy/successful you will be. In fact I have known a lot of highly successful people, who are happy, and are NOT outgoing. I was always terribly shy and still am, but was literally forced by my parents to be a "kiss up", and I resent it to this day, because I was brought up to put others needs/thoughts/feelings before my own. Concentrate on yourself, and if you feel social, do it otherwise, do your own thing. Everybody else seems to.