Can philosophical understandings of power and care illuminate roadblocks that disrupt the potential of women in leadership? This book examines leadership challenges by drawing upon debates that pulse through the history of philosophy and into present-day philosophical conversations and larger social concerns. Its in-depth engagement with Nietzsche’s power theory, and its historically grounded discussion of debates in feminist ethics around sexual dualism and care, offer essential lessons for contemporary leadership studies. The book provides compelling examples from literature, film, and art history, as well as short case studies of contemporary lives, that productively demonstrate tensions between concepts and embodiments of caring and power. Its analysis of related notions of ressentiment, desire, disobedience, and resistance creates novel dimensions for addressing barriers that undermine successful female leadership, such as the “glass cliff.” As such, the book reveals how philosophical investigations add to understandings in leadership, business ethics, and organization studies.