In this chapter, we discuss the basic elements of heroic leadership, showing how heroism and exemplary leadership are deeply intertwined. We then describe six paradoxical truths about heroic leadership that are often unrecognized and unappreciated. We believe that ignorance of these counterintuitive truths and paradoxes about heroic leadership can lead to misunderstandings about leaders, leadership, and leadership development. Most of these paradoxes are a central part of the hero’s journey as described by comparative mythologist Joseph Campbell (1949). We will discuss the genesis of these paradoxical truths, and we will suggest ways that an awareness of these principles can engender better leadership and more effective leadership development.