The path to becoming a school principal is characterized by a variety of trajectories that reflect the diverse experiences and backgrounds of aspiring leaders. While ideally the road to the principalship would result in a proportional and representative body of principals, research has shown this is rarely the case. To gain a better understanding of where sorting mechanisms may occur along the principal pipeline, this paper longitudinally analyzes the full, start-to-finish career trajectories of over 1.6 million educators in Texas for 30 years. Using social sequence analysis and discrete-time hazard modeling, we find that (1) emergent principals tend to stay in their first teaching position longer than other educators and most often take a direct pathway towards the principalship; (2) proportionally, more principals emerge from elementary, ELA, Social Studies, or STEM fields, while fewer come from Special Education; (3) holding other features constant, male and Black educators are more likely to become a principal while female and Hispanic educators are less likely; and (4) educators are more likely to first become principals when transitioning to a smaller school with more Black and/or Hispanic students. While the pipeline does result in a balanced principal market in some areas, increasing efforts to encourage a more diverse content area representation as well as representation for Hispanic educators in Texas will be particularly important.