The predicament of Western morals...is first that our moral life has come to be dominated by the pursuit of ideals, a dominance ruinous to a settled habit of behaviour; and secondly, that we have come to think of this dominance as a benefit for which we should be grateful or an achievement of which we should be proud.
What he meant here was simply that there are two ways to approach moral education: to encourage reflection and "the self-conscious pursuit of moral ideals", or to prefer acting in accordance with a habit of behaviour - an "unreflective following of a tradition of conduct in which we have been brought up". On balance, he preferred the latter of these. He did not argue for a moment that reflection on moral ideals was a bad thing, nor that blind following of tradition was good. But he thought in general society should lean on habit rather than idealism. To quote one of his more memorable lines: "human life is a gamble; but while the individual must be allowed to bet according to his inclination...society should always back the field". If individuals want to be "moral eccentrics" that is their business, and indeed to be encouraged, but society as a whole should not engage in the pursuit of moral ideals or grand moral projects. Rather, we should prefer a situation in which people generally follow moral rules unthinkingly and instantly without reflection, by course of habit. And although this might sound like an argument in favour of hidebound, unflexible tradition, he was keen to make clear that he was not against change; he noted, rather, that customs and traditions change all the time, but not in a self-reflective way and not in pursuit of an ideal - they evolve slowly as circumstances require.
His earlier essay, "Rationalism in Politics", made a similar argument in its separation of technique from practical knowledge. He argued, probably uncontroversially, that mastery of any skill involves both technical and practical knowledge. Learning to cook means learning what is in cookbooks (technical knowledge) but that is only the half of it: cooking is also about practising making dishes and learning intuitively what tastes good with what, how much salt should go in which dish, just how long something should be grilled for, and so on. A really good chef can take a bunch of ingredients and rustle up something tasty that he has never prepared before and has no recipe for, because he has intuitive, practical knowledge about what goes well with what - and it is quite likely he won't even be able to explain why. The analogy holds true for any skill you could name - be it poetry, driving a car, playing a sport, whatever.
Oakeshott then goes on to explain why in his view the privileging of technical knowledge in politics has led to rampant rationalism which has been a negative influence in the British political system in modern times, but we don't need to go into that; this isn't a political post. Oakeshott was a political philosopher but there is much more to his work than that. What I like about the emphasis he placed on habit and practical knowledge, not as the be-all and end-all (a cook still needs to be taught technique through books or from a teacher; a driver still needs to know the Highway Code and which pedal does what) but as where true value lies. A book of recipes is extremely useful, but nobody wants to eat at a restaurant where a beginner chef is just following uncreatively what is in a cookbook. The best chefs create their own dishes using their experience, know-how, and tacit knowledge. You can study iambic pentameter all you like, and knowing techniques of poetry-writing is useful and important, but that isn't going to turn you into Samuel Taylor Coleridge.
Moreover, practical knowledge allows for responsiveness. Oakeshott was not the first person to observe that you can read all the books on a given subject in the world, but all of that technical knowledge will never cover all of the situations that might arise in the real world in that field. The master of technique can never amount to the mastery of the entire art. It doesn't allow you to react to the unexpected - only practical knowledge can provide that. Only experience and intuition.
You can probably see where I am going with this: who is the better DM - the person who has only been trained in the rules or the person who knows the rules but has 10 years' experience at the table? The latter, of course. A banal observation. But an important one: a DM with a high level of practical knowledge is going to be able to do things that one with only technical knowledge simply can't do: he is going to be able to react to the unexpected in a way which makes sense within the context. He is going to be able to make rulings effectively based on his own intuition, and because of his mastery of practice these rulings are going to be fair and reasonable ones. This is not to say for a moment that beginner DMs can't do the same thing. Just that the more they do it and the more they develop their practical knowledge, the better they will get at it.
You may go so far as to say that the aim of a DM should be to develop a habit of play. That is, the aim should be to be in a position wherein one makes rulings not out of reflection but out of instinct - as a matter of course. Why? Because reflective judgement-making is slow and inefficient, but, much more crucially for Oakeshott, reflective judgement is prone to the pursuit of perfection, which prizes what he called "naive coherence", preferring intellectual defensibility over rough-and-ready suitability - which in turn makes it sterile and inflexible. In other words, it will be more important that a decision is impeccable and impervious to criticism than that it is appropriate to the moment. This will give rise to an approach that is perfectionist and paralysing rather than confident in itself as a method of action. Reflection will inhibit sensibility. As he said, "[T]ogether with the certainty about how to think...must be expected to go a proportionate uncertainty about how to act."
As with practical and technical knowledge, Oakeshott was at pains to make clear that he did not believe that habit could or should exist without any reflection, critique or effort to explain. Habit on its own very quickly degenerates into superstition, and has no way of rescuing itself: since it has no reflection, no means of analysing itself, it has no method for escaping a descent into blind, unthinking inflexible copying of ancient ways of doing things. But given the choice of emphasising habit or reflection, in his view, the dominance of habit is to be preferred. (At least in moral matters; though I think the line of thinking holds in other areas.)
So much for that. If anybody has the energy for more of this tomorrow (or even if you don't; I'm going to write the entry anyway so fuck you), I'll be relating what is contained in this post more closely with the OSR and the development of RPG rulesets.