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Purpose: The purpose of this study is chiefly to interpret and clarify a traditionally notion of the conservative disposition concealed in liberal education by reviewing three basic concepts—familiarity, freedom and learning— from the perspective of Michael Oakeshott. Method: Firstly, we discover that there are two intractable crises in education on account of the observation of history and current situations. The first relates to the sustainability of the conservative disposition and the second to the invitation of liberal learning. They are organically interconnected in that the realisation of the latter, in a way, relies on a response to the acquisition of the former. Secondly, we define familiarity as a characteristic of the conservative disposition that derives from the enjoyment of “the present” through an examination of complex social conditions. Familiarity is the basis of a conservative disposition that runs through the whole tradition of behaviour, or rather the tradition of morality derives its inheritance as a way of understanding education. Thirdly, we systematically expound that the conservative disposition as an essential component of education activities is supposed not only to provide the basis for educational enterprise but to play a role that involves a relationship between teachers and students. Fourthly, we emphasize the pivotal role of the conservative disposition not only in restraining the hegemony of the pragmatic modes of education but in providing a strong guarantee for realizating the invitation of liberal education by criticizing ‘vocational education’. Results: Finally, we put forward the conservative disposition of freedom as a reflective consciousness that plays an irreplaceable role in supervising and advancing the development of liberal learning by virtue of Oakeshott’s perception of freedom. Conclusion: The discussion of Oakeshott’s concept of the conservative disposition, which deepens the importance and necessity of liberal education, can furtherly make a contribution to the re-establishment for the orientation of educational activities, as well as for the trusting relationship between learners and teachers in modern education.

To Be Conservative as a Disposition of Education: Familiarity, Freedom and Learning from the Perspective of Michael Oakeshott