Disciplinary pressures within academia often produce specialised and one-sided accounts of complex social processes. Convincing accounts of popular education regularly acknowledge the importance of social movements but without theorising them adequately–and vice versa. This one-sidedness is compounded by a widespread tendency to generalise from often highly specific institutional and political contexts, as though all movements learned in the same way across space and time and popular education’s role in fostering this learning is simple. Unchecked, this leads to the reification of ‘critical’ theory and the reduction and flattening of emancipatory practices to methods or even predefined goals. This paper constructs a dialogue between the work of Choudry, Freire and other authors in both fields, aimed at both celebrating and problematising their contribution to learning from our struggles. By developing a conversation between them, we want to explore how their insights might be usefully integrated for contemporary social movements.