This is new territory for me as I don't work because I'm on disability. I'm looking at volunteering at a local charity, and I'm not sure whether I want to send them an e-mail saying, "Look, I'm trans, I don't pass especially well, but I'd like you to use my preferred name and pronouns." I live in a pretty progressive city, so I don't think they'd "fire" me on the basis of gender identity alone. My other option is to wait until I'm actually in training, and just tell everyone in the room my preferred name, and then politely correct them as they all proceed to misgender me.
To be honest, both options sound fairly mortifying, but I'll be damned if I'll go by my birth name and female pronouns all the time.