Good post, good questions.
I do not know if there is any such thing as a freak flag expert, but I will take a crack at it.
I think that authenticity is actually a relational thing. It is not just about being true to who you are, but rather about being true to who you are while supporting the same in others. Focusing just on your own authenticity just drives a bunch of ignorant, arrogant, selfish and egotistical nonsense…all in the name of “keeping it real.”
Authenticity requires a certain amount of personal awareness and self expression, but it also requires some accommodating. Authenticity is about me taking up all of my space, without taking up some of yours…it is about me being true to who I am, without making it difficult for you to be true to who you are.
“I want to be me without making it difficult for you to be you.”
So there is always some accommodating going on and that varies from situation to situation. Dysfunction creeps in when all of the accommodating is being done by one side of the relationship.
I do have visible tattoos on the insides of my forearms, and my preferred work uniform is jeans and a t-shirt. Not only do I actually like my chosen uniform, but it also gives me a prop to play with in some of the work that I do around challenging labels, assumptions and expectations…as professional speakers are supposed to be well groomed and dressed professionally.
I try to avoid playing it safe, I think that authenticity requires taking some risks, but I do try to be respectful of the audience or organization that I am going to see. For starters I try to make sure that they have accurate expectations of me and I also ask questions about their culture, norms, etc.
I think that clarity of expectations makes authenticity much easier for everyone involved. I have a corporate client that brings me in once a year to spend a half day with their senior leadership team. They love me. They also have a very formal culture that they value. Every year when we are planning our time together they send me a detailed copy of their dress code. Expectations clarified.
Now, I could get all offended by this, and in all honesty, the first time it happened I let loose with a bit of profanity, but this is simply one of the agreements of our relationship. I could walk away from it, if I believed that putting some dress pants and a jacket on was too big of a compromise, but in the context of larger relationship it is just one of many small compromises made by both sides. When we are planning this annual session, I do some accommodating and they do some accommodating.
I appreciate this conversation, because when we do talk about authenticity it is often in the direction of personal awareness and self expression. Those are certainly core aspects, but we should be working towards authenticity for all, not just for ourselves.