Emotional well-being is gaining importance within educator preparation, supporting how cognitive traits are vital but not adequate for optimal professional success. For this reason, it is imperative that the whole realm of human learning be reinforced by elements of holistic education often neglected. The purpose of this article is to: (1) describe the historical context of institutions of higher education (IHEs) in the United States; (2) illustrate how the sociocultural context influences higher education culture; (3) explain human intelligence theory; (4) present the nature of contemplative practice (CP); and (5) provide practical implications for a contemplative leadership approach that may best serve new generations of educational leaders and their personal and professional development.