Most research focuses on principal mobility generally, but little assesses charter leadership specifically. This exploratory study examines how leaders in stand-alone and charter management affiliated schools in New York and New Jersey made their decisions to lead, stay, and transition to different roles. Leaders cited excitement about autonomy and the mission of their schools as reasons for entering the role. In part because of their connection to the mission and students, many former teachers took on a leadership role or transitioned within their organization through a sense of obligation, knowing there were few, if any, potential successors. The toll of working hours, specifically when compounded by repeated interpersonal and internal conflict, was most salient to leaders' decisions to leave leadership. By contrast, positive relationships were cited as the most important reasons to stay. Finally, leaders discussed consulting, turnaround, central office, or educator training opportunities largely within the charter sector as potentially pulling them out of their current roles.