This paper outlines a semester-long, 28-session class, titled ‘Dive In: A Self-Awareness and Personal Development Journey’ for college students. Dive In is geared towards ‘emerging adults;’ students between the ages of 18-25. Through modules on self-exploration, emotional intelligence and personal growth, students will learn how to deepen their self-awareness, manage their emotions, and take charge of their lives. The sessions are highly experiential and use several positive psychology concepts and interventions. The course is built on the theoretical frameworks posited by prominent well-being scholar Carol Ryff and leading adult development theorist Robert Kegan. Dive In is predicated on the premise that self-understanding, a positive relationship with oneself, and development of the self are crucial to flourishing, which are key components of Ryff’s (1989) theory of well-being. Robert Kegan (1994) postulates that a certain level of mental complexity is necessary for modern life; by helping students develop meta-cognition of their psychological and emotional functioning, Dive In also aims to increase their level of mental complexity. The course is just a start; it is designed to function as a catalyst for students’ lifelong personal development journey. This paper recommends that, in order to build 21st century readiness in young people, university and school systems create a variety of programs like Dive In for students of all ages.