Identifying and attracting potential school leaders is a challenge for school districts. Whereas teachers represent the group from which the largest number of new principals will be drawn, fewer and fewer of them now seem willing to seek administrative positions. While women are prepared educationally, certified professionally, and waiting in American classrooms to move into administrative positions, there are certain barriers that obstruct them from obtaining educational administrative positions. This study inquired into the factors influencing the application for principalship and further examined the female teachers' perceptions about the incentives and disincentives associated with the principalship. Further, this study compared secondary female teachers who held administrative licensure versus those who did not in their perceptions of the incentives and barriers associated with the principalship. Participants were asked to complete an on-line survey based on a survey developed by Andrianaivo, Howley, and Perry (2005). The survey contained structured and open-ended questions and contained five parts. Part I contained 42 conditions to which the participants were asked to rate their views of the principalship; Part II asked participants to rate the personal importance of nine specific values; Part III contained open-ended questions about the participants' perceptions of their work; Part IV asked participants' demographic information; and Part V asked participants to complete information about their school district. Data were collected from 138 urban, rural, and suburban secondary female teachers in Arkansas, Mississippi, and Tennessee. Descriptive statistics and multiple t-tests were used to analyze the data. Findings suggested: (a) several factors encourage educators to enter the principalship and are considered incentives; (b) factors impacting educators' decisions to not seek the principalship are considered barriers and discourage possible applicants; (c) possible female candidates perceive the principal's job to be very demanding with social, political, and professional expectations; and (d) mentoring and networking opportunities are needed for female teachers considering the principalship.