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With a focus on Ethiopia, this study examines educators’ role conception and socialization as they choose to become principals. Collecting data from 237 principals through surveys, we conducted logistic regression analysis assessing how personal, organizational and professional factors influence the desire for principalship. Our findings suggest that individual level, organizational and professional factors contribute to the desire for principalship both positively and adversely, including earning a degree in a field other than educational administration, working at metropolitan centers, and wanting more decision latitude by becoming a principal. Encouragingly, even after accounting for all demographic and personal factors, the factor “reasons for becoming a principal” was still statistically significantly associated with a person self-applying to the principalship.