The arts and cultural sectors are increasingly seen as holding out potential for new models of leaders and leadership. The discipline of leadership has thus become alive to the notion of drawing upon and learning from arts-based methodologies to improve practice and development. However, there remains a paucity of emphasis on leadership from and within the arts. This chapter provides an empirical account of how that can take place. Using a narrative inquiry approach, the chapter explores the journey of a select cohort of arts practitioners from Southeast Asia and shows an emerging rich framework for leadership capacity building. In commenting on how the study evolved, the chapter provides insight into gaps in the theory and practice of leadership development within the arts.