In this chapter, I make the case for pragmatic readings of social and political life as opposed to those associated with agonism (as developed by Chantal Mouffe and others). Drawing on evidence that demonstrates how the experience of working across difference to re-open a school building in New Orleans both grounded participants’ political commitments and altered them, I argue that agonistic theory is limited by its inattention to the lived experience of negotiating difference and by its assumptions regarding the futility of doing so in non-adversarial ways. In contrast, Deweyan pragmatism offers a useful counterpoint by centralising experience and emphasising the value of learning from engagements across difference. A Deweyan lens trains scholarly attention on the knowledge people create as they work across difference to understand and shape their own circumstances. In so doing, it encourages scholars to grapple with the limitations of their own expertise and points to potentially transformative practices that might otherwise be ignored.