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Research has established that women superintendents encounter challenges in both achieving the superintendency/directorship as well as retaining the position. These barriers ultimately may also have an effect on how these women address the various challenges or perhaps even why women choose to leave the position. The stories behind these different challenges and struggles has not received an adequate and focused exploration. The purpose of this study was to examine the stories and experiences of women who have held the position of superintendent of schools (in the US) or Director of Education (in Canada) and help to make sense of how they deal with the challenges that are so prevalent.