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While researchers have studied mobility and turnover of principals generally, few studies provide empirical evidence on charter leaders. This study focuses on how and why leaders in standalone and charter management affiliated schools make their decisions to lead and their intentions to leave or stay in their role. I find that many former teachers took on a leadership role within their organization through a sense of obligation, knowing there were few, if any, potential successors for new schools or departing leaders. The toll of working hours, especially when fueled by repeated interpersonal and internal conflict, were most salient to leaders’ decisions and intentions to leave. By contrast, positive relationships were cited as the most important reasons to stay.