Matt Statler’s chapter, “How You Wanna Go? Learning from the Unfortunate Rake” introduces folk music as one of the possible media for presenting narrative accounts of wisdom. Focusing on the ‘Ballad of the Unfortunate Rake’, a cycle of songs originating in Ireland and England and continuing in the New Orleans jazz and American folk musical traditions, the chapter considers the question of how we should live when faced with death. Integrating considerations from ancient Greek and Roman philosophy with Montaigne and Nietzsche, the chapter encourages leaders to adopt stoic equanimity in the face of death while cultivating the affirmation of life while it lasts. The implications of this lesson for leaders include re-framing leadership as an aesthetic phenomenon, exploring the potential of aesthetic phenomena to enable collective action, and shifting the ontology of action toward an engaged or active passivity, playing along with the world.