This study investigates the career trajectories of elementary school principals in Chile between 2015 and 2022 and identifies seven trajectory groups through a multi-trajectory modeling approach. Thirty-three percent of our sample remained working as principals at the same school throughout the period, while seven percent did so in different schools. Among those departing from this role, we found highly heterogeneous pathways regarding their subsequent roles, tenure within the school system, and the probability of returning to the principal role. Our findings reveal that younger individuals, females, and those with full-time contracts are likelier to stay in the principal role. Additionally, the type of school administration emerged as a pivotal predictor of principals’ career trajectories, with private schools (state-subsidized and privately paid) showing higher principal retention. High-performing schools were more likely to retain their principals, with no significant disparities observed among schools serving students of different socioeconomic backgrounds. These findings illuminate the intricate career paths of school principals, identifying the factors associated with transitions to non-principal positions and exit from the education system, thus offering valuable input for this workforce development.