This chapter describes the journey to school principalship of a New Zealand woman committed to making a difference for the students with whom she worked. Janet described her journey into and through leadership. She identified the enablers and barriers she experienced along the way and the identity work that enabled her to gain her first position as a school principal. Janet acknowledged the impact of gender, being a wife, and being a mother to a school-aged child, and the gender-specific expectations others have of principals, as barriers in her journey.