<p>This capstone project serves as the culmination of my inquiry throughout the Critical and Creative Thinking (CCT) program, a graduate program at the University of Massachusetts Boston. It focuses in the area of adolescent education, relying primarily on relevant research and personal narrative reflection. The more pedagogical lines of inquiry draw from my experience as a school administrator in addition to my work in the CCT program. The central thesis is that an ideal aim of adolescent education is to help students develop and articulate a clear statement of purpose. That by doing so, students may leverage the powerful intrinsic motivation that is characteristic of purpose and use it to maximize the chances that their learning experiences bring them closer to a state of meaningfulness, defined in this paper as a deep sense of personal wholeness and fulfillment, similar to Mihaly Csikszentmihalyi’s concept of flow. The paper’s audience is adolescent educators - teachers, administrators, school leaders - who seek to make more immersive, effective, and holistic learning experiences for students. The paper is subdivided into two parts and a significant set of appendices. <em>Part I: Adolescent Education And Meaningfulness </em>examines three main concepts and articulates the relationships between them; meaningfulness, purpose, and adolescence. The concept of adolescence is presented in two subdivided sections; neurological and psychological perspectives. <em>Part II: Envisioning The School Guided By Meaningfulness </em>provides a closer look at adolescent education in practice and posits some pedagogical applications of the concepts advanced in Part I. <em>Appendices A-E</em> includes five example lesson plans taken from a more comprehensive curriculum that teaches reflection skills and is influenced by the concept of meaningfulness. <em>Keywords:</em> meaningfulness, purpose, adolescence.</p>