Many adult educators utilise literature to facilitate transformative learning, with an interest in exercising the imaginations of students and so offering an alternative to functional, economy-driven learning. I explore how literature, informed by a sociological imagination, fosters critical reflection and empathy. Drawing on the works of C. Wright Mills, Alfred Schutz, and John Dewey, alongside insights from critical theorist Oskar Negt, the paper outlines a rationale for literature’s role in supporting the sociological imagination and transformative learning. It argues that imagination is crucial for critical reflection and envisioning alternative realities, thus making transformative learning possible. The paper addresses critiques of transformative learning’s individualistic bias by emphasising the dialectical connection between the personal and broader societal issues, rooted in theories of sociological imaginations of Mills, Schutz and Negt. The importance of including a dialectical understanding of the relationship between the person and the social is highlighted as an important iteration for transformative learning thereby advancing transformation theory towards a critical theory of adult learning. The paper concludes with practical implications for educators, advocating for learning environments that are supportive challenging, and utilising creative materials to promote emotional engagement and critical transformative conversations.