This dissertation is a study of the works of Michael Oakeshott, citing in particular his understandings of the way we learn to interpret the world around us, his views on the aesthetic and the moral, and his arguments against what he perceives as an overemphasis on rationalism. Central to this dissertation is the overlooked portion of the works of Oakeshott, his view of a human life as something to be enjoyed, a predicament in which we ought as much as possible to delight. The paper begins with Oakeshott’s critique of the Post-Enlightenment celebration of and subsequent reliance on rationalism. It then discusses Oakeshott’s ideas on how we come to understand this world of ideas, and examines his argument for the pre-eminence of a liberal education. It turns next to a consideration of Oakeshott’s ideas on the aesthetic and the moral, and the kind of life he finds most admirable, one in which play and Poetry supersede the serious and the ideological. This latter concept is one that has so far been ignored. Oakeshott is discussed not as a conservative, elitist, or anachronism, but as a man who saw life as a brief adventure, a chance to enjoy the trivial, the poetic, the humorous, the serious and the absurd, accepting above all that we should wear our lives lightly.This study concludes that Oakeshott’s preference for a liberal education flows naturally from his predilection for a life that values the individual over the ideological.
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