Self Discovery Insecurities?

I keep hearing and being told that being open and honest is a big part of this voyage, that the only way to remain on the right path is to be open and honest with yourself and that is the key along with acceptance in allowing another's guidance to lead you to the places where some of these answers are that will ease those fears, doubts, and insecurities. And while i do not deny this to be true? I still am questioning my place? Even when I know where I belong? I still doubt. Even when i am sure of who i am. I still question, even when sometimes i may already know the answer. I am open, because i do not fear myself.
I understand that internal battles are within us all and i understand that acceptance, true acceptance, is the key to remaining on coarse through this voyage. And that the answers we may seek along this voyage may only be found from deep inside. I understand that judgment comes from all walks of life and that not everyone in the world is going to accept me. I understand all of this but i still question.
Is there a point where being too open is 'too open'? Where absolute honesty about yourself can be seen as ridiculous or childish and deemed unworthy because your willingness to share is viewed as not being serious? Is it weird that while upon this path of self discover it is not myself that i fear but the exchange of power that is needed to be properly led? Is it weird to have this need to give up that power but still at the thought instinctively want to stand and fight against it?