This qualitative phenomenological study explores the lived experiences of four purposively selected teachers from the Department of Education (DepEd) and higher education institutions in Davao City, focusing on their implementation of transformative education. Grounded in Jack Mezirow’s Transformative Learning Theory, the research investigates how educators navigate disorienting dilemmas, engage in critical reflection, and utilize rational discourse to foster personal and professional transformation in their teaching practices. Data were collected through semi-structured interviews and analyzed using Colaizzi's (1978) seven-step method to identify significant themes. The findings reveal a modified paradigm illustrating the dynamic and cyclical process of transformative learning among educators. Key themes identified include Disorienting Dilemma, with sub-themes of unexpected student disengagement, self-questioning of effectiveness, and language barriers and generational gaps. Critical Reflection encompasses processing and questioning teaching approaches, seeking feedback, and recognition of the need for flexibility. Lastly, Rational Discourse is characterized by communication and shared understanding, connecting learning to real-life and personal experiences, and the teacher as a listener and facilitator." The study highlights that challenging classroom experiences serve as crucial triggers for teachers to shift from content-heavy instruction to learner-centered, inclusive pedagogies. To sustain this transformation, the study recommends that future research directly link teacher perspective shifts to measurable student outcomes and classroom climate. Additionally, it is recommended that disorienting dilemmas and structured reflective practices be intentionally integrated into pre-service teacher education programs. Finally, the study suggests exploring the role of digital platforms and AI-powered tools to facilitate ongoing rational discourse and professional collaboration among educators.