Oakeshott described himself as a “skeptic.” He meant, following St. Augustine and Montaigne, skepticism about human pretensions to succeed in “the pursuit of perfection as the crow flies,” to build towers into a putative heavenly kingdom, or to control and manage the contingencies of human existence. Such aspirations he admired in individuals, for he applauded individuals seeking their fortunes as they defined them for themselves, but he deplored such aspirations in governments. He did so because he saw the state as a basically involuntary but necessary arrangement presiding over diverse people and interests. To invest in a single ideal would necessarily impose on some for the sake of others, suppressing the natural diversity which is the ground of human freedom. What is preferable is a “civil association” in which diverse people with diverse interests acknowledge and subscribe to a rule of law to insure the basic order they must have, with a view to affording the greatest freedom to live according to their own self-understandings.

In brief, Oakeshott's conservatism is a disposition to be skeptical about private dreams which seek to become a compulsory public manner of living, and to be reserved toward the impatient who pursue perfection as the crow flies. Such a disposition takes its bearings from the current condition of life, learning to enjoy and explore the possibilities of what is present, and to find the resources for this venture within ourselves. Its accomplishment is a settled manner of living that resists frenzied anticipation of the future, believing the present an unfortunate barrier against "real life." Nothing can be required that cannot be confirmed in the experience of selves. There is no unifying interpretation of the meaning of life. There is only the possibility that the conduct of the affairs of selves in relation to each other can be rendered intelligible and regular without having to answer questions about the summum bonum or finis ultimus. Men cannot raise themselves above themselves. A man can see only with his own eyes, and seize only with his own grasp.

There is a theme here: the recognition of friendship and affection as always desirable even though not all of human experience can be contained in them. It is the finding of a way for different kinds of men to delight in each other, not by eliminating differences but by exploring them; not by calculating the advantages of alliance, but by defending each other's idiosyncracies; not by rooting out variety in human motives for the sake of an ideal type; not by judging how well each plays his role, but by encouraging each to introduce a character to the stage.
Timothy Fuller, The Achievement of Michael Oakeshott