Gabe, I did the very same thing to myself growing up. By judging myself constantly, I became more and more reserved and isolated. As you said, take small steps and move forward slowly. For me, I still don't like being in crowds where I don't know people well. And, I will never be an extrovert, but that's okay. This book really helped me:
Quiet: The Power of Introverts in a World That Can't Stop Talking
by Susan Cain