Purpose: The purpose of this study was to explore the experiences of former teachers who transitioned into self-directed education (SDE), a K-12 educational paradigm where learning is authentically student-led. Design/methodology/approach: Drawing on Ivan Illich's Deschooling Society and qualitative thematic analysis of interviews with educators who have left conventional teaching, the research delves into understanding the modern concept of deschooling, critique of conventional schooling's limitations and the implications of both for the future of educational practice. Findings: The study highlights the themes that emerged from a cross-analysis of text and lived experience, emphasizing the need for childhood autonomy and agency in approaches to education. This study reveals a reimagined relationship and new profession for educators as they reemerge on the other side of the deschooling process. This study offers insights into the transformative potential of deschooling and SDE's alignment with Illich's vision for a lifelong learning society that transcends institutional constraints, thereby contributing to the discourse on educational reform and the empowerment of authentic learner-directed education. Originality/value: Research on SDE as a field is quite limited, with no known prior empirical studies on SDE mentors or their process of deschooling. This work also provides theoretical novelty in using Deschooling Society as a lens for understanding the phenomenon of deschooling through lived experience as a critique of modern society and creating a real, re-envisioned future.