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This theoretical paper develops a pedagogy of doubt that positions questioning as central to transformative learning (TL) by synthesizing Rorty's pragmatic irony, Hollis' depth psychology, and Freire's critical pedagogy. Using hermeneutic analysis of primary texts through Klafki's methodological principles, we challenge Mezirow's emphasis on disorienting dilemmas, arguing that doubt and self-doubt can initiate profound reflection without crisis. Through a conversation between a philosophical text (Rorty) and a psychological (Hollis) text integrated with TLT, three themes emerged: doubt as catalyst, redescription as method, and unfinished becoming. A pedagogy of doubt allows us to reimagine transformative learning, breaking the silence among philosophy, psychology, and education.