Oakeshott argues that the rationalist, in awarding theory primacy over practice, has gotten things exactly backwards: The theoretical understanding of some activity is always the child of practical know-how, and never its parent. In fact, he sees the dependence of theory on practice as being so unavoidable that not only is the rationalist incapable of skillful performances guided solely by theory, he is not even able to stick to his purported guidelines while performing poorly. Instead he inevitably will fall back on some tradition of how to proceed in order to give context to his abstract instructions. (This is similar to Wittgenstein’s insight that every attempt to follow a set of formalized rules necessarily is grounded on informal customs and practices that determine what it means to follow a rule “correctly”—the formal rules cannot also embody their own, “correct” inter-pretation because any effort to incorporate that interpretation into the first-level rules would create a set of “meta-rules” themselves requiring meta-meta-rules to guide the interpretation of the meta-rules, and so on, in an infinite regress.)
This also brings to mind Gödel's incompleteness theorems.
Oakeshott contends that the essence of an accomplished practitioner’s skill cannot be conveyed to a neophyte through explicit technical instructions, but instead must be learned tacitly, during a period of intimate apprenticeship. The formal rules purported to underlie success in an activity merely present an abstraction from the concrete and formally unspecifiable knowledge possessed by the true master, who may offer such an explicit set of precepts as a rough surface map of his deep sea of experience-born proficiency, useful so that the beginner does not feel lost when first venturing into those waters, but hopelessly inadequate as a guide to their depths.
I think anyone who has practiced any art know this is so, which is why those who can do, while those who can't theorize.