Discrepancies in the number of females occupying superintendent positions in the United States continue to exist; therefore, this study utilized a survey design to examine the perceived barriers to achieving the top positions in education as well as differences by gender among aspiring superintendents in K-12 in Illinois. Statistical analyses (Mann-Whitney U test and factor analysis) were performed on the results from the Aspiring Superintendents Perceived Barriers Questionnaire developed by Dulac, and its underlying constructs were used to investigate the extent to which aspiring female and male administrators perceived barriers to the superintendency position. Eighty-four participants completed the survey either online or on paper. The study found significant differences between male and female aspiring superintendents in 10 of the 21 perceived barriers. Factor analysis yielded two factors (societal issues and workplace expectations) as barriers identified by females, and three concepts (societal issues, workplace expectations, and masculinity in leadership) as barriers identified by males.