Authentic leadership has been a long sought goal of many leaders over the course of time. It is not without pause that we recognize the basis of whence it springs and how best to move it forward when it presents. In this qualitative research study, the notion of authenticity and hope in leadership were explored through life-stories shared in interviews, by five leaders in a New England school district. The data collected in these life-stories, as told by the five leaders, suggested that authentic leadership and hope may be a product of life-story experiences as told, whereby one identified major life events and turning points and reflected upon them in this process. This process served to uncover the essence of self, and how one has developed over time. The development of authentic leadership requires assembly, in that it requires development of the individual and the context in which one is embedded over time (George, 2003; Luthans & Avolio, 2003; Johnson, 2019). It may be that assisting leaders in this guided process of reflection may help them to identify and define one's convictions, gain greater self-clarity, and come to view life with hope and an opportunity for finding one's authentic self. Elements of this study suggested that one may develop authenticity as a product of examination of self. The research focused on one small set of leaders in one school district. Findings may inform practices in this school district as well as other schools. Also, one hopes that this study may contribute to the development and application of this process for all school leaders and perhaps teachers in this district to realize our full authenticity potential. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]