Modern scholarship has struggled to come to terms with the meaning of wisdom and its significance in the field of education. This book examines the importance of pursuing wisdom in schools by turning to ancient and medieval sources for clarification concerning the nature of wisdom. Sean Steel argues that our current emphasis on the development of rigorous critical-analytic thinking skills, on assessment, and on accountability in education has negatively impacted the ability of schools to foster an environment in which both students and teachers might pursue wisdom. Although in recent times efforts have been made to incorporate the pursuit of wisdom into schools through Philosophy for Children (P4C) and contemplative education programming, such initiatives have missed their mark. Steel therefore recommends not more accountability in education for the purpose of ensuring global competitiveness, but rather the institutional promotion of periods of leisure or schole in the school day.Drawing upon his own experiences as a teacher who has tried to encourage students to search for wisdom, the author discusses some of the challenges and pitfalls of wisdom seeking. He also offers examples of various wisdom-seeking activities that might bear fruit in the classroom.