This paper examined teachers' decisions to pursue graduate programs and their career choices following completion of their studies. Based on document analysis and statistical examination of teacher questionnaire responses, this study determined that teachers choose graduate studies for different reasons, their program choice influences future career options, the impact varies across programs, and barriers preventing teachers from advancing to leadership positions exist. These findings also show that females are underrepresented in the most senior leadership positions and there are significant gender differences in career goals and program selection. Policy makers need to address issues like the work-life balance, increased workload, gender imbalance, and increased opportunities for aspiring leaders.