This case study follows the career of world-renowned orchestra conductor Marin Alsop. As a gay woman in a blatantly male-dominated (and often sexist) field, Alsop faced significant challenges in her rise to the top of the profession. At virtually every turning point on her unconventional path, Alsop received the message that she should not or could not advance – and yet she did, relying on a nuanced mix of perseverance, self-awareness, and willingness to upend the status quo.