This Think Piece critiques the prevailing focus on predefined learning outcomes in adult education, arguing that such frameworks can restrict authentic dialogue and diminish the transformative potential of learning. Drawing on principles of critical pedagogy and practitioner experience, it uses a Freirean dialogic framework within which experiential learning as proposed by Wilfred Bion is given precedence. It eschews the stifling role of tick box learning outcomes in favour of a Winnicottian emphasis on play as central to the transformative learning encounter. In an age of Artificial Intelligence the piece invites educators and policymakers alike to reconsider how we define and value learning.