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The focus of this chapter lies with women middle-level leaders. It reports on themes from women in leadership programmes designed and delivered by Barbara Watterston, through the lens of a programme especially developed for the Association of Independent Schools of South Australia (AISSA). This chapter begins by profiling a description of the programme. The main aim was providing women leaders with an opportunity to take stock of their careers, consider ongoing challenges impeding their work as school leaders, and identify options for the future. After the programme finished, volunteers were invited to write a narrative encapsulating their career journey. Three women leaders volunteered, and their insightful reflections regarding their career trajectories constitute a significant portion of this chapter. The final part of this chapter identifies three common themes that emerged from their stories, resonating with ideas which are frequently illuminated in similar programmes and research. These include the importance of ongoing professional learning to be a successful leader, gender-based barriers that caused the women to doubt their abilities and readiness for leadership, and the deep appreciation the women expressed from learning with and from like-minded other women leaders.