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Up to 50 percent of principals exit their role in fewer than five years. Thus, understanding undesired turnover may provide school systems leverage points in preventing undesired attrition by maximizing limited resources. Utilizing a grounded theory methodology, this study was to examine the decision-making process that leads to early exit from the principalship through firsthand experiences of first-time principals. Data include interviews and biographies of 10 former principals. Findings indicate that there is a predictable, linear decision making process in acquiring and exiting the principalship, regardless of the school setting or principal background, including: (a) anticipatory socialization; (b) first doubts in role; (c) role burnout; (d) considering alternatives; and (e) turning points and final decisions.