For March (2006) prevailing models of intelligence, supported by technologies of rationality, are often inadequate, misguided and disastrous. In light of this, March has put forward the idea of sensible foolishness as a means to combat the dominance of procedural rationality. However, this crucial interplay between play and reason remains largely overlooked in practice scholarship. This paper employs a sociomaterial lens to explore how serious challenges can be navigated through playful means. Our qualitative analysis of video ethnographic data revealed how sensible foolishness and procedural rationality unfold during strategy-making episodes. Our analysis identified a process of evolving fluidity, which underpins the dynamic interplay between play and reason and the transition from intentional discomfort to unintentional comfort. The evolving fluidity comprised three phases: deliberate, dialectical and dwelling interplay. This unique evolutionary process also gives rise to unintended process affordances to emerge as the dynamic between play and reason provides a springboard for strategy to manifest in unanticipated directions. Our findings offer three theoretical contributions. First, findings advance strategy-as-practice scholarship by explaining how sensible foolishness is performed with materials, bodies and spaces. Second, they extend studies of the dynamic between sensible foolishness and procedural rationality by explaining how this interplay unfolds during strategy-making. Third, we provide new insight into the consequentiality of sensible foolishness beyond strategy workshops.