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This paper examines the motivation of teachers who pursue graduate degrees in education and whether it leads to a career path that will alleviate the impending demand for senior positions in curriculum and school leadership at the school, district and department levels. This mixed methods study provides statistical analysis based on questionnaire responses from graduates and also seeks an in depth understanding of the findings through comprehensive interviews of a representative sample of participants. Preliminary findings indicate that teachers choose graduate studies for different reasons, their program choice influences future career paths, and the impact varies across programs. These findings also show significant gender differences in career goals and the barriers, which prevent teachers from advancing to leadership positions.