Oakeshott argued that rationalism in politics is the mistaken belief that political problems can be solved by applying abstract, technical principles divorced from the practical knowledge embedded in tradition and experience . He saw rationalists as people who, 'having cut himself off from the traditional knowledge of his society,' succeeds only in undermining the institutions that hold civilized society together . For Oakeshott, politics is not about implementing a rational plan but about navigating the 'boundless and bottomless sea' of human experience using the resources of a traditional manner of behavior .

This is the central distinction in Oakeshott's masterpiece, *On Human Conduct* (1975). A *civil association* (*societas*) is a formal association of individuals bound by a system of laws, without any common substantive purpose; its rules are procedural and formal, akin to a game's rules rather than a plan of action . An *enterprise association* (*universitas*), in contrast, is organized around a common purpose or goal, requiring a managerial class to coordinate efforts toward achieving that goal . Oakeshott saw the modern state as an unstable mixture of these two ideals, with the managerialism of enterprise association posing a threat to the freedom of civil association .

Oakeshott is regarded as a leading conservative thinker because of his profound suspicion of ideological politics and his defense of tradition, experience, and the value of the familiar . In his classic essay 'On Being Conservative,' he describes conservatism as a disposition to enjoy the present and the familiar, preferring the tried over the untried . However, some scholars argue that this labeling obscures the radical, self-critical nature of his philosophy, which challenges all doctrines, including conservatism itself .

Oakeshott associated a specific notion of freedom with the English political tradition, arguing it was distinct from French *liberté* or German *Freiheit*, which were tied to ideological, purpose-oriented politics . For him, English freedom was characterized by the rule of law, which he defined as 'the enforcement by prescribed methods of settled rules binding alike on governors and governed' . This created a procedural, economical approach to government, avoiding overwhelming concentrations of power. He considered the great American charters to be 'abridgements of British political experience' rather than universal blueprints .

A common misconception, especially among earlier commentators like Peter Viereck and Russell Kirk, is that Oakeshott was simply a Burkean traditionalist . In fact, his philosophy is rooted in a form of objective idealism that is relentlessly self-critical and refuses to accept any doctrine on authority . His purpose was to criticize all forms of ideology—including modern conservatism itself—from a philosophical position of radical skepticism about all political projects. His aim was to challenge the 'legend' of his own conservatism rather than to provide a foundation for it .