That's part of the problem, living an authentic life is an entirely internal process. People end up paying attention to the external things of what this "seems

That's part of the problem, living an authentic life is an entirely internal process. People end up paying attention to the external things of what this "seems" to mean, and how people got there. But an authentic life is doing things that accomplish your values in life. A lot of living like this is wanting to communicate in a clear and "authentic" way so you end up with little communities of this stuff. As for your problem - the problem is you don't really know what your values are in life. You are letting external requirements drive what you are doing, and you aren't thinking strategically, or agent-y. I'd suggest checking out the book "Focusing". You will be able to help yourself a lot better after you learn how to what the book describes. Also consider http://rationality.org http://rationality.org as well