At 29, Abby Stein occupies a unique position: She is the first publicly transgender woman to have grown up in the ultra-Orthodox Hasidic Jewish community. Today, the Columbia graduate is a speaker, activist and the author of Becoming Eve: My Journey From Ultra-Orthodox Rabbi to Transgender Woman. But getting to this point has taken incalculable grit. Stein grew up in a prestigious, rabbinical family in an enclave of Williamsburg that felt more like a 19th-century Eastern European shtetl than Brooklyn, New York. She spoke no English until she was 20, had no access to the internet, and was confined to male roles in a society with some of the most rigid gender segregation policies in the world. 

When Stein left the community in 2012, one of the first books she read was Deborah Feldman’s...