The Coming Out process can be a minefield, but I think if done with conscious thought often the potential negative aspects can be minimized. One way to do that is to work with a therapist who is experienced in gender issues. It isn’t unusual to be very fearful about major life-altering decisions. That makes it very hard to focus on and work through what we need to figure out. A therapist can help with the process.
You will need to come out sooner or later. If later, that’s a lot of time for stress to build. On the other hand, haste is not your friend, so some reasonable balance needs to be struck. The essence of coming out is that you get to tell YOUR story YOUR way. If you get outed by someone else, it becomes very difficult to tell your story. You are placed on the defensive and it is hard to get the narrative back. When you do come out, it needs to be on your terms.
Ordinarily when someone talks about transitioning in place, I would recommend that they look up Dr. Margaret Stumpp and Stephanie Battaglino. However, they both transitioned while working for large insurance companies (Stump for Prudential and Battaglino for New York Life). However, I don’t know if a lot would translate to your situation, but check them out.
In any event, Good Luck and keep us updated. I think there could be a lot for others to learn…
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