In the following I show that Hubert Dreyfus’ account of skill rests on a misguided interpretation of Martin Heidegger’s work on understanding in Being and Time. Dreyfus separates understanding according to the analytic philosophical concept pair, so called ‘know-how’ and ‘knowledge-that’, that corresponds for him to the pragmatist differentiation between skillful acting and theoretical conceptual thinking. Contrary to that, Heidegger argues that only one form of understanding exists that is neither captured by ‘know-how’, ‘knowledge-that’ or a combination of both. Instead of presupposing two radically different ways to engage with the world, one practical-agential, the other theoretical-conceptual, Heidegger shows that all genuine forms of comportments rest on the same form of understanding that exhibits the highest degree of intelligibility when we deal with the world ordinarily. The Heideggerian account therefore comes without the many dichotomies so often criticized in the literature on skill and understanding, and offers a radically different view of world disclosure and of what we do when we ‘theorize’.