This study examined the career stability (career choices assistant principals intend to make over the next five to ten years) in a large, urban school district in the southeastern region of the United States in order to identify factors significantly related to their career aspirations. The study invited a purposive sample (n=177) of assistant principals (N = 286, elementary, middle, and high) to respond to questions on the electronically administered Assistant Principal Career Stability Survey (Modified). The career stability selections were: become a principal, take another administrative position, remain in the position, return to the classroom, leave education altogether, or other (self-reported career alternatives). The researcher used logistic regression in order to predict a model of the respondent's career stability. The current study revealed 84.57% of the respondents possess upwardly mobile career stability: 77.4% of respondents showed interest in actively pursuing the principalship, 6.5% would take another administrative position, 2.4% preferred to remain in the assistant principalship, 0.0% would return to the classroom, 2.9% indicated leaving education completely and 13.7% indicated other career stability with retirement being the predominant response. Four variables yielded a statistically significant relationship to the prevailing career stability orientation of the sample (i.e., upwardly mobile). The fewer years an assistant principal served as an administrator, the more likely his/her career stability inclination was to be upwardly mobile. The fewer years an assistant principal has served in the school district, the more likely his/her career stability inclination was to be upwardly mobile. The more an assistant principal agreed with the role conflict tenet "I receive an assignment without the manpower to complete it" the greater his/her career stability inclination was to be upwardly mobile. Lastly, the more an assistant principal disagreed with the role conflict tenet "I have to buck a rule or policy in order to carry out an assignment" the greater his/her career stability inclination was to be upwardly mobile. No other variables met the .05 significance level.