A few years ago while serving as a professor and academic administrator at a private university, I was charged with the task of creating curriculum for a leadership studies program for selective undergraduate students. Since this occurred during my final year of coursework for my doctoral degree, I was consumed with a myriad of abstractions. However, my years of experience in leadership within the academy and nearly fifteen years of working as an entrepreneur, compelled me to design a foundational course that examined the inner life of the leader. In fact, that actually became the name of the course that was first introduced to the students in the Fall of 2004. I began my first lecture sharing a modified version of Plato’s Allegory of the Cave. Though a discourse on the origins of epistemology (knowledge), I believe that Plato’s illustration has much broader, relevant implications for individuals that span 2,500 years. Plato likens the journey out of the cave to the process of becoming. As we orient ourselves towards the penetrating and illuminating properties of the Sun, our awareness of reality or truth for that matter is more easily accessible. Often, we spend large amounts of our lives residing deep within the damp, dimly lit cave. As we contemplate our surroundings, we notice that but for the shadows, very little activity informs our understanding of reality. Shadows are nothing more than distortions of an object. They are limited in scope and function as they possess neither color, nor depth, nor autonomous movement. For many people who become leaders, the ascent out of the cavernous existence that represents human limitation, ignorance and disjointed reality is a slow one. For some, the ascent never begins at all. Consequently, leaders cling to their shadows (untruths) and make mistake after mistake within their organizations and hurt others. Until we confirm and confront our own shadows, our leadership is severely compromised. This blog will examine the deeper issues that inform our leadership practices. Transforming Organizations from the Inside means two things. First, tremendous organizational change can be initiated from within an organization. While it is desirable for a CEO to be the catalyst behind the activities, other individuals, can acomplish a great deal regardless of their position provided wisdom, strategy, and risk are appropriately balanced. Second, a dialectic exists between our being and our behavior. However, our being should inform our behavior. Who we are and what we value should order our steps. This cannot occur unless we recognize the incalculable importance of self-awareness. The baggage that we carry to the workplace, to the gym, to church, and to our families may be very, very heavy and have the capacity to cause great harm. The last thing that most people want to do is to hurt others. Unfortunately, this happens frequently without the slightest inclination on our part. Leadership that transforms organizations requires not perfect people, but rather, people who acknowledge their strengths as well as their shadows and have initiated the climb out of the cave toward the sun. As the leader is transformed, the organization can flourish.