This chapter branches out to the larger cultural milieu of leadership, primarily in the United States. The goal is to contextualize my leadership reflections to provide both broader connections and deeper understanding. I discuss the irony of differences in perception of effective leadership when ‘micro’ (local) versus ‘macro’ (national/international) contexts are considered. I define toxic leadership and how it might be addressed, as well as the uses of disinformation, emotion, metaphor, and paradox. I consider how contemporary technologies and media representations of reality might lead to a type of identity-splitting, whereby both leaders and followers might lose their authentic selves in the service of powerful, emotionally laden leadership narratives.