"The only references I have encountered by Oakeshott to Hayek’s work are his somewhat dismissive summary of The Road to Serfdom, and a very sympathetic review of The Constitution of Liberty. Hayek praised Oakeshott, for example, in the introduction to Law, Legislation and Liberty, but Hayek never, to my knowledge, produced any in-depth commentary on the views of his purported counterpart."
"It has not been generally recognized that Oakeshott’s most famous work, on rationalism in politics and in conduct, flows directly from the philosophical ideas put forward in Experience and Its Modes. The rationalist misapplies the standards of one mode (theoretical science) in another mode (practice) where they are categorically irrelevant. As Oakeshott saw it, the rationalist believes that every essential aspect of any human practice can be conveyed adequately by means of a “technical manual.” The rationalist view is that arriving at the correct theory on some subject is all that is required to achieve successful performances in its domain; indeed, attending to any anything else, such as long-standing traditions, is a positive barrier to success in a field. What is necessary to be “rational” is to approach any activity with a tabula rasa upon which the correct technique for that activity can be cleanly inscribed; as Oakeshott put it, in this view, rational conduct involves “a certain emptying of the mind, a conscious effort to get rid of preconceptions” (1991: 101).
Quite to the contrary of that understanding of the relationship between technical guidelines and tacit knowledge, Oakeshott argues that the rationalist, in awarding theory primacy over practice, has gotten things exactly backwards. Theoretical understanding is always a by-product of practical skill: we come to understand the general and abstract only through understanding the concrete and particular. In fact, Oakeshott sees the dependence of theory upon practice as being so unavoidable that not only is the rationalist incapable of successful performances guided solely by a theoretical model of the activity to be performed, he is not able to stick to his purported guidelines at all: instead, he will fall back on some existing practice instead of actually following the abstraction that supposedly guides his conduct. Oakeshott’s point here is close to Wittgenstein’s on “following a rule”: at some point we have to go without rules and just know what we are doing as part of a way of life, since otherwise we need an infinite regress of rules: meta-rules to tell us how to follow the first level rules, and meta-meta-rules to tell us how to follow them, and so on. (See Wittgenstein, 1953: 85-86.)
However, Oakeshott‘s assertion that the rationalist never really can proceed according to her avowed principles does not mean that her attempt to adhere to them will be inconsequential, but only that it will not succeed."
-Gene Callahan, "Hayek and Oakeshott on Rationalism", June 26, 2017: https://voegelinview.com/hayek-oakeshott-rationalism/