This text articulates how and why suffering can be pedagogical in character and how it is often key to authentic and meaningful acts of teaching and learning. This is an ancient idea from the Greek tragedies of Aeschylus (c. 525 BCE) – pathei mathos or «learning through suffering». In our understandable rush to ameliorate suffering at every turn and to consider every instance of it as an error to be avoided at all costs, we explore how the pedagogy that can come from suffering becomes obscured and something vital to a rich and vibrant pedagogy can be lost. This collection threads through education, nursing, psychiatry, ecology, and medicine, through scholarship and intimate breaths, and blends together affinities between hermeneutic conceptions of the cultivation of character and Buddhist meditations on suffering and its locale in our lives. This book will be useful for graduate courses on hermeneutic research in education, educational psychology, counseling, and nursing/medicine.