This dissertation will explore leadership as a mytho-poetic transformational journey toward self-knowledge, authenticity, and ultimately wisdom; the power to make meaning and give something back to the world in which we live; and the necessity of transformation. I view leadership as a transformative process and a transformational responsibility. As leaders we must undergo our own transformation in order to lead change on a larger scale. The dissertation will be both philosophical and theoretical, exploring how the threads of the hero's journey, transformation, wisdom, and leadership intertwine. It will also examine the role of education in this process. Education does not necessarily mean institutional learning as it is so often taken to mean. A broader understanding of what education is and how it needs to serve us individually and as a society, particularly with the intention of developing wisdom and leadership (or wisdom in leadership) will be explored. The hero's journey, the mytho-poetic journey toward authenticity and self-knowledge, is the golden thread that weaves itself throughout this dissertation. It is both the idea of developing leadership and wisdom as a journey (as opposed to a destination) and the idea that meaning and authenticity is ultimately what drives wisdom and leadership. These concepts manifest themselves in different ways throughout the chapters. In many ways this is a very unorthodox and unusual way to approach leadership. It asks for full engagement, participation, excellence, and mastery--a lifelong dedication. None of these concepts are new, but most of them are often unheeded or not practiced. It also focuses on the common good, an element that research in both wisdom and higher stages of consciousness share. The intent is to explore the transformational process inherent in becoming a leader and consequently leading transformation that ultimately makes the world a better place on a number of different levels--leading deeply. Leading deeply makes a difference through tapping into meaning and purpose. When our lives are about contribution and giving back, growth and wisdom, evolution and making the world in which we live and in which our children will live a better place, the experience of life becomes deeper, richer. Leading deeply connects us back to life, creates meaning, and helps us understand that what we are doing does matter. A leader is one who has gone through his or her own heroic and transformative journey, returning with a gift, and enabling others to do the same. The goal is development. It is directed toward growth, flourishing, higher levels of consciousness, and understanding. It is paradoxically rooted in tradition yet always embracing the change in which we live. Leading deeply takes us deeper to what is ultimately important for all of us.