The post-positivist corpus of planning theory is replete with myriad theoretical interpretations of planning practice. Yet the theory–practice gap remains. This article seeks to explain this theory–practice gap as a systemically inscribed outcome of the very desire to theorise planning in the first place. It is argued that this theoretical disposition to the subject combined with a related preference for a methodological approach that rests on epistemic phenomenology is the reason we have collectively struggled to provide convincing accounts of practice. In an attempt to think again about how we understand planning practice, the philosophy of Ludwig Wittgenstein is introduced to suggest an analytically investigative approach.