This book is a written account of a qualitative, narrative-based critical autoethnography exploring the development of leadership identities of women leaders, including the author, working in various educational settings, including K-12 schools, universities, politics, research centers, and community non-profit organizations. The author layers key findings from these participant stories with her own experiences, as well as with dominant US cultural ideologies about leadership, to capture the lived experiences of participants. Alsup also understands leadership identity through the lens of the animal-human bond, by integrating personal experience and scholarship about animals and their complex, evolutionary relationships with humans. This book is grounded in interdisciplinary scholarly research and theory exploring leadership, identity, mentoring, empathy, feminist thought, and animal studies. This project aims to better understand the leadership trajectories of women leaders in educational settings and, by extension, inspire and transform young women thinking about leadership.