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Many districts experience high rates of leadership instability. This is particularly concerning in systems that educate predominantly children of color or low-income communities, which can experience 50% attrition of new principals in five years or fewer. Understanding factors that contribute to exit can slow attrition and maximize limited resources. This grounded theory study explored the decision making processes and contributing factors surrounding early-career principal attrition. Study findings include: (1) principal knowledge constructed during time as teacher was critical in conceptualizing the role of principal and committing to the exit decision; (2) educators rely on informal observations and interactions to drive understanding of the principalship; and (3) there are predictable points of job dissatisfaction.