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As the rapid rate of our society's technological advances increases, how can autonomous, authentic learning develop in the secondary school environment through self-directed learning? This dissertation explores the history, present, and future of self-directed learning and develops a theory that addresses the research question. A review of the literature revealed few documented attempts to provide self-direction in secondary institutions, perhaps because educators do not grasp the potential of self-directed learning to individualize learning at the high school level. Without a significant number of working models from which to draw qualitative data, this dissertation explores self-directed learning for high school students from a theoretical perspective within an arts-based research methodology. Utilizing fiction writing to explore an imagined school-wide self- directed learning program, the research considers the characters—students, parents, teachers, and administrators—and how each experiences various aspects of self-directed learning. This narrative explores the advantages and possible disadvantages of this framework of learning. Through storytelling and connected metacognitive reflections, this dissertation explores the impact of recent research on the changing learning needs and styles of the Millennial, "digital native," and "digital resource conductor" generations. The research reflects that these learners seek more authenticity, autonomy, relevancy, purpose, and meaning in their learning than did previous generations (Margaryan, Littlejohn, & Vojt, 2011; D. G. Oblinger & Oblinger, 2005; Palfrey & Gasner, 2008; Prensky, 2001). The theoretical lens of radical constructivism is utilized, which maintains that individuals learn by comparing new, direct experiences with prior knowledge and understanding (von Glasersfeld, 1995). The research investigates how self- directed learning may support increased individualized, autonomous, and authentic learning for high school students as cognitive needs, learning, and training continue to advance.