Educators participate in extensive preparation for the role of principal, including teaching and principal licensure. Nevertheless, educators may find a lack of a global framework for the principalship leading to both job dissatisfaction and early exit, as pre-role conceptualizations rely heavily on anecdotal knowledge from supervisors and peers. This paper presents partial findings from a grounded theory study that analyzed role acquisition, conceptualizations, decision making, and exit of former public school principals. Some of the findings suggests three primary themes are present among educators' responses: (1) knowledge constructed during the time as a teacher is critical in conceptualizing the role of principal and committing to the later exit decision, consistent with the role-exit theory; (2) educators rely on informal, anecdotal observations and interactions to drive understanding of the principalship; and (3) there are predictable points of job dissatisfaction.