There continues to be a discrepancy in the number of females occupying the superintendent position in the United States. In Illinois, 24% of superintendents are female while 75% educators are female. This study examined the perceived barriers of aspiring superintendents in achieving the top position in education as well as the differences between genders regarding these perceptions. Data for this study was collected through a survey of the perceptions of barriers. The 85 participants for this study either completed the survey online or on paper. Based on frequency distribution analysis, twelve barriers were perceived as high impediments to pursuing the superintendency by women compared to four by men. In addition, statistically significant differences indicating higher levels of impediments among women in pursuing the superintendency were found in ten barriers. The ten barriers include: the predominance of male candidates for administrative positions, existence of the "buddy system" in which men refer other men to jobs, doubt by those in hiring position of women's long term career commitment, gender bias in the screening and selection process, exclusion from informal socialization process of "Good Old Boy Network," lack of acceptance by male administrators and staff, lack of acceptance by female administrators and staff, the belief that women must be better qualified than men in order to obtain top level administrative positions, lack of strong women's network similar to the "Good Old Boy Network," and covert sex discrimination. The findings from this study have implications for both male and female aspirants to the superintendency. Both men and women respondents in this study acknowledged that barriers do exist for those aspiring to be a superintendent although female respondents perceived the barriers more intensely and in greater quantity. The greatest barrier for both men and women in the study addressed networking. Aspiring superintendents should seek opportunities to network and to be visible in the professional arena in order to break into informal social networks. Future studies comparing barriers perceived by both men and women should be considered. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]