The recent debate between conceptualists and phenomenologists, epitomized in the exchange between John McDowell and Hubert Dreyfus, has put on the table the age-old philosophical problem of the relationship between concepts and our embodied and embedded existence. The tension between our responsiveness to norms and meanings, on the one hand, and the fact that we are part of the animal kingdom, on the other, engenders difficulties for those committed to strong rationalistic programs along Kantian lines. Sellars, I argue, was better equipped to navigate this conundrum than most of his disciples in what has come to be known as the Pittsburgh School. Indeed, Sellars’s conception of rule-governed behavior, with its peculiar mixture of Kantian conceptualism and pragmatic naturalism, anticipates and successfully solves objections that have been leveled against contemporary neo-Hegelians like John McDowell and Robert Brandom by thinkers influenced by the phenomenological tradition of Heidegger, Merleau-Ponty, and Sartre. More importantly, in tying conceptual abilities with skillful coping, Sellars successfully manages to offer a story of how discursive intentionality enters the lives of creatures like us.