Thoughts on Transitioning at Work

So, I’m not out to anyone except my fiance and my best friend (who I think didn’t take the confession as seriously as I meant it, but then again, it was a little bumbled as I tried to spit it out. Normally she’s great about gender identity stuff). I still don’t know for sure what category fits best, but the longer I present masculine as my daily default, the more right that presentation feels and the less I want to take up my old feminine presentation again. I’m at least masculine of center, but it’s not certain about timing: is this a newly realized/understood static thing, or is this part of a gender fluid cycle/stage/something? Time, introspection, and recordkeeping-as-journaling will tell.

Back to topic, I’m not out but I’m presenting rather masculine, enough to sometimes pass with strangers. My workplace is a private post-secondary institution, and my masculine-of-center presentation has been there, too. So far, I’ve just preemptively mentioned being a tomboy, which is a very incomplete explanation. However, I haven’t had any issues or comments. I was careful to maintain the same formality of dress (jeans and nice button up) when transitioning from women’s clothes to men’s clothes.

So far no problems, and I live in a state and city where both sexual orientation and gender identity are protected, so theoretically it should be fine. I worry though; especially after a conversation with my boss where she confided in me that she had made a discriminatory decision not to hire or even interview a potential teacher because of the foreign-sounding name. “The students will complain about having a non-native English teacher,” she told me (not quite verbatim, but the idea is there). “They don’t come all the way from their home countries to learn English from someone who isn’t American. I wouldn’t appreciate that if I were in their position.”

That conversation is a huge issue in and of itself. It also makes me nervous about my gender presentation decision. What if students start complaining about my way of dressing and presenting? How many student (customer!) complaints would it take?

I know I’ve already been very lucky. I live in a liberal city in a liberal state with good employment protections. My fiance is incredibly supportive and has made it clear that he and his family will continue to accept me. The direction I’m considering transitioning in (ftm) seems to experience fewer stigma issues compared to the other direction (mtf) or agender.

And yet, I worry so much about the consequences. Would it affect my ability to find a job? Would my proper-to-a-fault, proper-to-the-point-of-superficiality parents accept this sort of decision, given the way they warmed up so much in my high school and college years when I gave in and begin to wear girly clothes? Would I lose my kid to my domestically-violent-but-never-enough-to-prove ex? I have a lot of worries about this, and the choice seems to come down to, simplistically, do I shove myself back in the box that didn’t fit or do I present my gender in a way that the world inevitably will find uncomfortable?