The purpose of this presentation is to describe the journey of Janet who was appointed as a first time principal in her 50s. The study is relevant to the field of educational leadership as although girls outpace boys at schools and universities and are currently entering the work force at higher salaries than ever before, there have been minimal changes in the proportion of females in top executive positions in the last decade. For example, in 2012, around 60% of the total number of high school teachers in New Zealand were women but they held less than 33% of all principal positions. This being the case it is useful to reflect on the stories of women who have achieved school principal positions, in order to discover what helped and hindered them on their journey. In 2015, Janet shared her story about her journey to principalship using a guided interview framework characterised by the creation of themes with open ended questions. Her unique lived experience and the significance of her everyday life to becoming a first time principal was documented and explored by drawing out patterns through coding the transcript and identifying themes through a process of careful reading and reviewing. Janet described her journey, identifying the enablers and barriers 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. She also identified enablers, the people and the processes that helped her to succeed in her career including, her strong belief in social justice which arose from her parents, her support systems including the mentors who guided her throughout her career path to the present day, and the professional development opportunities she was able to enjoy. She talked about a gestalt shift her identity and its collision with circumstances which gave her the confidence to apply for her current job as a school principal. Janet showed she was capable of making workable, manageable and balanced judgments in relation to her work and life including finding people and activities that could support her. Building on the work of Mamood (2015) a visual metaphor that encapsulates Janet’s journey is proposed. This provides a rich view of a woman’s road to principalship and demonstrates the complexity of Janet’s educational leadership journey.