Behind every school leader is an individual with experiences. These experiences, personal and professional, shape how an educator conceptualizes leadership. This study examines the types of experiences that leaders, enrolled in a Master of Educational Leadership degree in Australia, draw on to inform their leadership. The findings reveal four key experiences that influence the way school leaders view and practice leadership: experiential; educative; vicarious; and personal. We discuss how the medium of digital story supports school leaders to develop their personalized educational leadership theory (PELT) as part of educational leadership development.