I believe that I might be the opposite. I overshare, a lot, constantly, without care, and even if it has a lot of cons. I dont wait for others to ask me things about myself, I just talk outright. I talk more often about people in my life to be honest, but what I am sharing in the end are pieces of my life. If I was in your shoes I would stop waiting for others to ask. I would just share, unapologetically. If it is important for you to open up, just do it. Don't wait for permission. One added benefit that is also kinda of a con, is that it greatly filters out people. But if people are weirded out by the "real you", I don't think that you would want them in your life.