Michael Joseph Oakeshott (1901–1990) was best known during his own lifetime as the author of Rationalism in Politics (1962), a volume of essays which even his critics were forced to acknowledge showed mastery of a flowing literary style. It emphasised the importance of tradition in an era not noted for its friendliness to the established order. But an essay like “On Being Conservative” had no time for traditional foundations of conservative values like natural law or religion. Oakeshott’s alleged conservatism was really scepticism. When read carefully, he did not so much valorise tradition, as recognise it as an inevitability.
Hume, rather than Burke, inspired this position. All societies necessarily had their own established ways of doing things, and altering them would produce unpredictable results, so caution was required. Change was inevitable, but the blank slate, jump to glory, approach that he argued was typical of modern Rationalist politics on both left and right was based on an illusion. This scepticism was at least partly a reaction against his own youthful opinions (meaning that his later works involved considerable implicit self-criticism, something largely missed by his critics).
From a Fabian family (his father Joseph Oakeshott had helped the Webbs to found the LSE in 1895), in his twenties Oakeshott favoured a romantic individualistic variety of socialism which hoped for inner transformation rather than economic redistribution. His Cambridge fellowship dissertation was full of references to Wordsworth and Coleridge; growing up before WW1, the English romantics were still a living presence for him. Oakeshott never abandoned this early romantic commitment to individualism, but he ceased to believe that major spiritual change for the better was imminent.
The mature political philosophy set out in On Human Conduct (1975), written in a far more analytical style, emphasised the difference between the state understood as a civil association in terms of the rule of law, and as an “enterprise association” dedicated to a shared goal or purpose. Since membership of a state was normally involuntary, freedom could only be preserved if people were able to decide for themselves how best to live. Once the state imposed its own agenda, be it the pursuit of salvation, economic growth, or military conquest, the self-determination crucial to freedom was lost. Only civil association provided a framework of agreed rules indifferent to particular interests in terms of which groups and individuals could pursue their own purposes.
Oakeshott acknowledged Aristotle, Hobbes, and Hegel as predecessors, all of whom made law a condition of freedom rather than a limitation on it. But in a modern English context he perhaps stood closest to John Stuart Mill as a defender of liberty, and he was happy for his later work to be described as liberal in its tendencies. In arguing that freedom lay in being able to make choices, however, he paid little attention to market choice. Unlike Friedrich von Hayek, with whom he corresponded, he had almost nothing to say on political economy. His conservatism, insofar as it was not just a reflection of his philosophical scepticism, rested on an increasingly deep dislike of modern mass culture. The Beatles were awful, and so too were the student protestors who took over the LSE just after he retired in 1969.
Striking a Nietzschean note, Oakeshott warned of the danger that “the masses” posed to representative democracy: the majority of people were unused to choosing for themselves, and would become prey to demagogues. But even though he wrote several essays on the ideal of liberal education, he never seriously engaged with the question of how it could help to address this problem. Nor, given his own recognition of the problems involved in shaping society to a deliberate design, would it have been easy for him to do so.
Oakeshott’s concern with liberal education nevertheless stemmed from a deep philosophical conviction that the world could be grasped in more than one way. He spent his pre-WW2 career as an historian at Cambridge, but while he taught the history of political thought, he wrote only philosophy, coming under the influence of the Hegelian Idealist John Ellis McTaggart as an undergraduate. His use of Hobbes’s metaphor of 2the conversation of mankind” in Rationalism in Politics was a poetic reformulation of the argument of his first book, Experience and its Modes (1933), that life was an encounter between different “modes of experience”.
The different genres of thought and action identified in Experience and its Modes all had different presuppositions associated with them. For example, the master-category of practical life was will; of science, quantity; of history, pastness; and of philosophy, timelessness. This youthful conviction that philosophy was able to escape altogether from temporality reflected Oakeshott’s own early attachments to Idealism and Rationalism. Later on, in On Human Conduct, he replaced it with a less ambitious conception of philosophy as an activity of ceaseless questioning in which an answer is a fresh problem.
As a historian-turned-philosopher, Oakeshott had a particular interest in the assumptions underpinning historical enquiry. He was in effect an English continuator of the neo-Kantian tradition that included figures such as Heinrich Rickert and Wilhelm Dilthey. His importance here was recognised by his older contemporary R.G.C. Collingwood, whose Idea of History hailed the theory of historical knowledge set out in Experience and its Modes as a milestone in contributions to the subject. Oakeshott returned to it in his final work, On History (1983), which argued that the critical study of the past offers a unique form of insight, different from our ordinary practical orientation to it.
In the practical mode in which we live most of our lives, the past is meaningful insofar as it is useful or otherwise valuable for us. For the individual, memory supplies an orientation towards the present and the future. By analogy, any society must have what Oakeshott called a “useful past” (which may be heavily contested) which plays a similar role. One could say that Oakeshott, like Orwell, saw all political debates about the past as necessarily part of a struggle for control over the future. Historical understanding was important precisely because it offered a view of the past indifferent to contemporary moral and political issues.
The past seen from the historical point of view, Oakeshott argued, had to be understood exclusively in terms of its own past. After all, unless one wants to defend backwards causation, one cannot explain why an event in the past happened as it did in terms of what came after it. The space between past events and ourselves is the dimension of their significance or relevance, not explanation. Of course, that is not to say our understanding of the past does not change. Oakeshott thought it must do so, as each generation of historians finds fresh questions to ask. But even if the questions were originally motivated by contemporary concerns, the answers cannot be responses to them, because they are in the form of a relation of past events.
Oakeshott was thus diametrically at odds with Lord Acton, who exhorted historians “to suffer no man and no cause to escape the undying penalty which history has the power to inflict on wrong”. Passing moral judgement on the past was appropriate in practical life, where the past was treated as a source of moral guidance, but for historians to do so was superfluous and irrelevant. It was superfluous because in political and ethical life the past was already moralised, and irrelevant because judging that something was wrong told us nothing about why it had happened.
This firm distinction between practical and historical views of the past was in keeping with Oakeshott’s general belief that contemplation and action were fundamentally different activities. He explicitly rejected Marx’s thesis that the point of philosophy is to change the world; like Wittgenstein, he thought that philosophy left everything as it was. There was no straightforward way to translate philosophical ideas into action. The aim of the political philosopher was to identify the conditions of the possibility of political life, not to make policy recommendations.
Oakeshott joked in his retirement speech that “I have tried to be a philosopher, but happiness kept breaking through.” In fact, it is not clear that he was really happy at all; he lived a chaotic bohemian private life that included three marriages and numerous affairs (including a brief liaison with Iris Murdoch). As he remarked in his private notebooks, “Few, in these days, have a simple identity: mostly it is complex, made up of tensions.”