I agree that aspirations and ideals are certainly a part of what we are talking about. Authenticity is inherently aspirational in that it is about a more noble delivery on the promises that we make. I think that the questions that we currently use, properly framed, do surface aspirations; though we can certainly be more explicit about that.
Not only is it important to know what you want to become, it is also important to write and read and have adventures to further inform those ideas.
Freak flag flying is rooted in awareness and has a lot to do with authenticity, but there are certainly other things involved, courage, integrity, action, daring, reflection, feedback, etc.
You pose the question:
“What if you are striving to be something more than you are today? Is it still flying your freak flag when you are acting in accordance with who you are trying to become rather than who you are today?”
Each of us is a moving target. This is not a state or a destination that we are talking about, but a practice.
I have no interest in trying to figure out if I am being authentic now or if I have to first become more of who I hope to be…that smells like a big distracting wormhole to me. Are you doing the work? That is what I care about.
Are you asking yourself tough questions?
Are you focused first on holding yourself accountable?
Are you doing things that scare you?
Are you taking risks?
Do you leave the majority, go against the flow on occasion?
You will know that you are flying your freak flag when you experience both the fear of doing something new and unique and the high of having done something new and unique consistently as parts of your life.