Hi Jay, I am also a retired teacher. Mostly I taught elementary school and middle school except for my last four years in which I substituted for just about every grade imaginable. In my experience in the small rural communities and urban neighbor where I taught it would have been impossible to come out as a transgender female. Most of the other teachers I taught with were female. I did everything I could not to be "the male" in almost every situation that I could. Personally being "the male" was never me.
However in almost all of the communities I felt that I could not stray very much from what a man should look like, and how one should act. The same was true for woman. If anyone in the communities where I taught had strong feelings that your absences was more desirable than your presence then it was time to move along down the road.
Yes, there were always some teachers who seemed to have divine protection and could stray from the norm and still keep their jobs, I was never one of them. About six years was the longest time I ever worked in anyone community.
However presently on Facebook, I have befriended several of my past students, some of which were friends of my adult children. I have outed myself as a transgender female and have outed myself in pictures and the reaction has been pretty much muted with no wild reactions.
I have gone to my children's schools pretty much dressed as you see in my picture even wearing more makeup and found lots of polite silence but no openly negative reactions from their teachers or other parents or children. Most of my opinions are not accepted with any real validity, but then again they rarely have been, even though they are based upon years of experience and I have a Masters Degree in elementary education though I don't dress or act like it. Which may mean that I have always been viewed as being more female than male.
I am not really sure if you should out yourself at work or not. No one may say anything or you might run into that one outspoken parent the administration feels that they must bow down to and you might find yourself in deep do do. My experiences in teaching have lead me to believe that the teacher's world is more of a soap opera than most people would admit and that the difference between between a good teacher and a bad teacher is in the wild imagination of the administrator.
Really bad teachers don't last long because of all of the stresses of the profession. But teaching can transform your personality and this transformation can be sorted into the good, the bad, and the ugly.
Administrator's can also hire and keep a lot of the Ken's and the Barbi's who can turn out to be some real perverts and duds because they are lost in their own egos and in feeding their own personal desires caring more about maintaining their self image then they do about the children they teach.
Take care, it might be best to go through with retirement. Then go through transition and then see if you are one of the lucky ones who can get hired as who you really are and then inspire your students to be who they really are.
As for me I have found myself in the dust bins of life. And the best I can do is reflect back at my struggles and hopefully shed a little insight into what might or might not be relevant to whomever finds it so. And so I ponder on while a dim light still shines in the attic of my mind.
