And recently, it's clicked.
It's not that everything goes away -- it's not that the shyness or intimidation suddenly disappears from my personality -- it's just that the bouncing back and forth quiets down. And quiets down significantly. And quiets down because you see suddenly how you are good enough to be in the conversation and have the job and make a loving relationship work. Maybe not all conversations, jobs and loving relationships, but the ones that are the right match for you.
Finding your life's "right matches" is the pathway to reconciling expectations with reality and destination with journey -- it's the way to actually being happy with yourself. Being at peace with yourself. Loving and accepting of yourself. The more you let yourself explore, the better you are at finding your match because the more criteria you have to check it against your own personality. The thought here: 1) like yourself, 2) let yourself be open to trying a match out and learning it's not a match, and finally, 3) once you discover a match, run don't walk to weave it into every part of your life cause you know how important a discovery you just made.

