This chapter explores how leadership is often fraught with paradoxes. I ground these discussions in historical philosophical, theoretical, and psychological theories of paradox. Drawing from the previous six chapters, I explore the notion of leadership as an exercise in negotiating paradox. I tell my own story of handling leadership paradoxes and relate the stories of the eight participants. I discuss how the leadership identity discourses expressed by the participants differ from those in my earlier works on teacher identity development, as they do not seem to be handling tensions through either borderland discourses or learning to balance contradicting subjectivities. Instead, their leadership identities have developed organically over a lifetime of personal and professional experiences, communications, and reflections. We negotiate the inherent paradoxes of leadership, such as conflicts between personal beliefs and professional obligations or contradictions between follower perceptions of good leadership and authentic leader beliefs, through relationship building, communicating with mentors, and/or building and expressing emotional intelligences.