In this study, we used survey research methods to examine (1) factors that motivated educators in the state of Iowa who held administrative licensure (125 females, 164 males) to actively pursue secondary principalship positions and (2) aspects that dissuaded them from applying. Respondents rated 10 factors that potentially motivated them to pursue administrative licensure, 36 factors related to perceived barriers to pursuing the principalship, and 5 questions related to perceived quality of leadership preparation. Results revealed that educators were attracted to the principalship for intrinsically motivating reasons. Although perceiving potential barriers as being only minimal-to-moderate obstacles, females identified concerns related to gender discrimination and gender stereotypes, and males were significantly more likely to apply to available positions. Respondents indicated concerns regarding time demands of the position and an emphasis on management over leadership responsibilities. (Contains 5 tables.)