I work at a bookstore chain cafe and we had a trans mtf regular. She went from Robert to Barbara and we got to watch the transformation. At first she started as robert the regular, who was quite talkative but very nice, and slowly started opening up about how she felt. We were all very supportive of her and we would compliment when she would wear more feminine clothing or nail polish. I remember vividly the day she told me her name was officially legally changed and she was so excited because it had been a hassle. On a weekend night when most of us who had been close with Barbara were working, she came in in a beautiful Cinderella style dress and a giant cupcake from a famous bakery in New York. She told us that she was moving away and wanted to thank is for being so kind and understanding and accepting of her as the person she was and how much we and our kindness meant to her. I haven't seen her since but I think about her from time to time and hope she is still happy.
Edit: I realize the title says emotionally difficult jobs. While retail can be that way, it doesn't compare to things like police work or doctors or therapists. My apologies.