The New Oxford American Dictionary (2001) delineates two definitions for a leader: “1) The person who leads or commands a group, organization, or country; a person followed by others. 2) A short strip of nonfunctioning material at each end of a reel of film or recording tape for connection to the spool.” How often does the latter definition seem more applicable for many of our educational leaders than the former? What are the philosophical foundations of leadership? What does a modern, ethical leader look like? These are just a few questions that will be explored in this article. The challenge beset for the educational leaders of the present and the future is one that will require a bridging and blending of old and new paradigms. A mere paradigm shift may not be sufficient–the term shift is still too mechanistic and linear to adequately describe this new approach. Rather, the modern ethical leader must create a paradigm blend. In the circular way of knowing, akin to the epistemology of the Lakota Sioux (Stolzman, 1986), this article will explore four aspects of modern educational leadership. First, the criticisms and attacks on the educational system will be addressed. Second, the aim of education will be analyzed through three lenses: axiology, epistemology, and ontology. Third, systemic education will be discussed. Fourth, the role of the modern/future educational leader will be explored: specifically regarding the need for him/her to address the concerns of the critics and bridge the divide between two paradigms of education. This essay is a brief exploration that delves into the shortcomings of the modern educational system, the core purposes of education, systemic educational paradigms, and the role of the 21st century ethical leader. The author’s goal is not to provide answers, nor propose a prescription for ethical leadership. Rather, the intent is to aid in focusing the direction which leaders must follow in order to be effective in this millennium. Similar to the manner in which Descartes shared his method of inquiry, the author will share part of his experience in learning and growing as an educational leader. “Thus my purpose here is not to teach the method that everyone should follow in order to conduct his reason correctly, but merely to show how I have tried to conduct mine” (Descartes, 1637/1980, p. 2)