This paper investigates the reasons and motivations that people pursue administrative licenses. Questions such as who enrolls, why they choose to seek an administrative license, and what are their future goals, are all relevant to address challenges of principal attrition and turnover. With calls for the development of quality, equity-focused leaders, it is important to understand how motivations of entrants align with those of school districts and policy makers. This paper contributes to the research on the so-called “principal pipeline” by analyzing the reflections of candidates from an institutional perspective. This view considers modern schools to be social structures governed by various norms, values, and rules. Official elements like an administrative license, or even simply enrollment in a licensure program, can become more than just a way to develop technical competencies but symbols whose meanings shift based on cultural assumptions. Using a qualitative analysis of interviews with eleven candidates, I argue that these interpretations are influenced by race, gender, and current life circumstances, and contribute to a mismatch in the personal and institutional goals for principal training.