This study uses an event history analytical approach to explore the career paths of elementary school principals in Taiwan. Existing research divides elementary school teacher career routes into two categories: teaching and administration. Statistics indicate that the number of women who achieve positions as elementary school principals is disproportionate to the number of women employed in elementary schools. Accordingly, this study focuses on two issues: (a) the potential for gender bias in promotions from teacher to administrative positions in Taiwanese elementary schools, and (b) whether domestic factors such as marital status, reproduction, and family caregiving affect teacher career development. Results from an event history analysis indicate significant gender differences in elementary school principals' career development over time-that is, it takes longer for female elementary school teachers to make the transition to administration, with marital and caregiving factors being the strongest mitigating factors. The authors hope that these empirical findings prove useful in illuminating the current situations in which female leaders find themselves in terms of achieving educational management positions.