Up to 50 percent of principals exit their role in fewer than five years, depending on geographic region. 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 examines the decision-making process that leads to early exit from the principalship 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.