Revision with unchanged content. Do today’s men and women pursue leadership positions for the same reasons? Do the career paths of men and women differ in duration and types of positions held? What personal and professional variables affect the aspiration to leadership? The purpose of the this study was to investigate differences between males and females who were actively pursuing or not pursuing the superintendent’s position with respects to personal and professional variables. Gender, personal characteristics, career path, career barriers and career facilitators were examined in relationship with aspiration level to the school superintendency. Findings showed the interaction between gender and career path was significant. More males tended to have linear career paths, while more females had non-linear career paths. In addition, the analysis of the career path interactions showed that male respondents in a linear career path were significantly larger than those in a non-linear career path. Female respondents were divided evenly between linear and non-linear paths. This study also found a majority of women to be firstborn as in previous research.