This study analyzed the historical and theoretical roots of self-directed learning. Self-directed learning (SDL) is a philosophy of education in which the learner initiates the learning process, identifies the resources to be utilized, sets their own goals, and is involved in the evaluation of their work (Knowles, 1975). The COVID-19 pandemic caused renewed interest in SDL as educators looked for ways to motivate students to direct their own learning in remote settings. However, SDL pedagogies are far from a passing trend. There is a rich history of education philosophers, theorists, and practitioners who have advocated for a view of education that empowers the learner to be the agentic center (Rousseau, 1762; Dewey, 1916; Neil, 1960; Holt, 1964; Freire, 1970; Illich, 1970; Greenberg, 1987). The aim of this philosophical study was to analyze the deep historical and theoretical roots of self-directed learning models, explore exemplars from different cultural and historical settings, and put forward a new conceptual understanding of SDL to inform post-pandemic pedagogies and policies. This study utilized philosophical methods to present arguments, historical and contemporary, in favor of shifting education toward self-directed models and away from a view of education that places teachers, administration, curriculum, and standards at the center of the learning endeavor.