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There is growing evidence of a worldwide shortage of persons willing to apply for vacant principal positions in schools. Reports a study about why more persons are not applying for principal positions in Catholic schools in New South Wales, Australia. An analysis of the career aspirations of those eligible and likely to apply at some stage for a principal position revealed a high level of “unwilling” respondents. Ranks and discusses ten factors identified from a study of their perceptions of issues that would discourage or encourage them to apply. The most significant negative factor is the impact on family and personal life. Others include gender issues and the nature of the selection and interview process. The significant positive factor is that principals have the opportunity to make a difference in the lives of others. Reflections on the findings include addressing the changing nature of school culture, the implications for the principalship and the need to develop a culture of leadership in schools.