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Widely considered a conservative British philosopher, this article presents Michael Oakeshott as, in fact, a critic of conservatism — in particular of the German conservative tradition, represented, among other thinkers, by Ferdinand Tönnies. This tradition was characterised by the rejection of modern individualistic society considered as an embodiment of alienating purpose-oriented rationalism. At a certain phase of his intellectual development Oakeshott himself came under the influence of this conservative critique, with ideas strikingly similar to those of Tönnies. Yet, unlike Tönnies, Oakeshott later rejected the premises of this tradition. Instead, he formulated the notion of rationalistic non-purposive association, which allowed him to become reconciled to modern liberal society.

Two ideas lie at the heart of Oakeshott's philosophy: the notion of the inherent plurality of modern experience and the notion of a modern state as a purposeless civil association. These ideas signify Oakeshott's rejection of the intellectual tradition of British Idealism by which he was influenced in his twenties. The breaking point was the publication of Experience and its Modes, although, with regard to social philosophy, the process of the abandonment of holistic Idealism lasted longer and was completed only with the publication of On Human Conduct. The main difference between Oakeshott and other British Idealists lies in his radical rejection of methodological holism. It is suggested that this rejection might be an outcome of influences of continental philosophical traditions, and that Oakeshott's philosophy is especially indebted to the ideas of the fragmentation of experience prevalent in Central European Idealism, and particularly in neo-Kantianism.

This article argues that Oakeshott's theory of freedom possesses a greater degree of coherence than is often perceived. Freedom in Oakeshott's philosophy may be defined as `recognized contingency', combining the notions of a genuine choice of action and of an agent's awareness of having such a choice. Oakeshott employs his notion of freedom in two different contexts. One is the context in which freedom is understood as a concept distinguishing what is conceived as `human' from what is conceived as `non-human'. The other context is that of membership in societies, which under certain circumstances can be characterized either by the presence or the lack of freedom. The article argues that, while at first glance Oakeshott's ideas look counter-intuitive, at a deeper level this understanding of freedom is akin to that prevalent in the consciousness of modern liberal societies.