This paper contributes an autoethnographic account of how Paulo Freire's work shapes understandings of education, social change and the possibilities and practices of social research. Drawing on connections between anthropology and education (Schultz, 2014) that underpin "Pedagogy of the Oppressed" (McKenna, 2013), I explore spaces and practices through which Freire's seminal text provided me with the critical consciousness to interrogate the human experience of education and learning, and to question my practice as I transitioned from teacher to researcher, paying particular attention to learning through discomfort (Boler, 1999). The paper therefore contributes an applied contemporary reading of "Pedagogy of the Oppressed" to demonstrate its continued significance for theory and practice in formal and nonformal education, and its relevance for reimagining research practice. As a form of critically engaged reflective scholarship, the autoethnographic enquiry asks educators and researchers to question their own conceptualisations and practices of knowledge and research to consider a significant and urgent proposition: how we do the work to understand education and our imaginations of what and how it might become.