Principals are instrumental in establishing effective schools and positive learning communities. There is only one principal in every school and thus, the position clearly requires a knowledgeable, highly skilled, and well-prepared individual. Principal training programs provide generally effective instruction that seemingly prepares emerging leaders for the expectations and logistical demands of the principalship. Yet the state of the profession is unstable. The research on principals shows that fewer administrators are applying for the position, newly hired principals are younger and less experienced, and longevity is a problem. The position is synonymous with long hours, little appreciation, and high stressful situations. Although principal preparation programs do address logistical problem solving, there is no curriculum for incoming principals that addresses the phenomenon of the unexpected event. Surprise events are stressful, salient, disruptive, and can make or break a career. A principal who is able to control an unexpected event, whether the event is caused by them or not, and foster an appropriate outcome likely feels strongly self-efficacious. On the other hand, principals who are faced with unexpected events and handle their own role in a manner that leads to a negative outcome, likely develop low self-esteem, low feelings of efficacy, and are more likely to leave the position or be ineffective leaders. This research project queried high and middle school principals from a moderate sized urban school district about whether they have experienced an unexpected event and if so, the details of that event were recorded. Specifically, qualitative descriptions were collected to develop an understanding of the variety of events that could and do occur during a principal's career. Using both quantitative and qualitative data collection, the research documented the principal's role, feelings, and self-reflections about the event. The purpose of the study was to evaluate the nature of unexpected events. The project also sought to discover, in depth, the personal experiences of the principal and the views of the principals about the event and outcome, and most importantly, the feelings of the principals about their role in the event and their role in the outcome. The investigation revealed several notable findings that linked event types and outcomes with principals' feelings. In all, principals experienced significant unexpected events that had a high impact on all involved. The principals mostly stated that they were unprepared yet most controlled their own emotions and behaviors well. Theoretical frameworks were used to conceptualize the events and the emotional impact on the principals was characterized. Further, principals were passionate about elucidating the concept of a surprise event as a component of principal training programs, as all felt that if they could expect these events on some level, their ability to handle them would have greatly improved. This important implication was discussed and further research suggested.