This study investigated assistant principals' motivations to stay in their current position. It identified characteristics, events, and factors that describe why assistant principals choose to stay in their position rather than return to the classroom, transition to a lead principal position, or leave the profession entirely. This was accomplished by identifying the typical responsibilities of established assistant principals, determining how they describe their motivations for staying, and exploring the most influential factors in their choice to stay in the position. Prior research focused on the concept of supply and demand in educational leadership, the attractiveness of the principalship, strategies for recruiting and retaining school leaders, administrator career stages, and career moves (Farley-Ripple, Raffel, & Welch, 2012). This study contributed to the current body of research by providing an in-depth view of assistant principals' career stages through twelve qualitative interviews. The data analysis process revealed that assistant principals have distinct roles and responsibilities. However, the implementation of these roles can vary based on the building they are in and grade-levels they serve; the COVID-19 pandemic has significantly impacted their typical responsibilities as well. Assistant principals described several motivations for why they stay; the most frequent reasons include: the immense pride they have in their position, their strong desire to support those in their building, and their desire to avoid the political landscape associated with the principalship. These concepts expose the participants' moral purpose, which sustains them in their current role. Participants frequently cited their desire to maintain their current job responsibilities as an influential factor in their choice to stay as an assistant principal. Additionally, assistant principals' self-esteem is another factor related to this decision. Collectively, these two factors highlight the importance of an assistant principal's career development. The decision for a well-established assistant principal to stay in their position is not composed of just one factor, but rather, it encompasses a myriad of factors and influences. [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.]