Women face a unique challenge as they enter jobs that have been traditionally held by men. Their stories can light the way for other women. The lessons that they have learned can be applied to all leaders who seek to move their organization forward. This book tells the stories of three women who have entered the male dominated world of school leadership. The research for this book gives a firm foundation for 21st Century leadership. There are roads not yet travelled by women in school leadership. This book serves as a guide for women to succeed in the work and on their own terms. Mentoring and supporting other leaders is key to the success of school principals. This book spans the bridge between what is and what can be. The stories will allow women to enter leadership roles with more confidence in their abilities and a road map to guide them.