Jaded,
You know transitional people are not alone with this whole situation of fearing letting people down. There are people that pick their careers, who they married, what religion they were members of, and so much more, all based on families that decided for them. Or place inappropriate expectations on them, That fear of stepping up and saying,, "no this is not me, this is me" be it issues of indentity or otherwise.
Maybe you know some people in your family or circle of friends that chose to step out of the boundaries of what was "expected" of them, and you may be able to ask them questions on how they got through it and why the decided to make the choices they made. You can do this without even disclosing your own personal struggle. They would probably feel good that someone asked them about their feelings, and they can tell you about their experience.
We are all human and struggle with the same emotions/feelings in life, just that are specifics may be different, but all people can relate. Maybe talking to someone you know that stepped out, would be helpful to you. Just a thought that may be able to allow you find someone you already know that you could listen to , and share "feelings" not specifics, for support.
Peace,
Taylor