This did not mean, of course, that the pursuit of perfection is wrong. To repeat what I quoted in the entry yesterday: "the individual must be allowed to bet according to his inclination [but] society should always back the field". The individual can pursue perfection as the crow flies, and he will fail because perfection is unattainable, but when he does society will be there waiting for him. Society, on the other hand, when it reaches its inevitable failure, will have nothing to fall back on because it will have already destroyed its precious customs and traditions in its quest for ideals.
What is the result of a society's pursuit of perfection in the moral sphere? It is one in which everybody is required to undergo intellectual training. We need to be trained to know what the moral ideals are. We need to be trained in the intellectual management of those ideals. And we need to be trained in how to apply them to real-world situations. This gives us (if it is successful) the utmost confidence in those moral ideals, and moreover allows us to know at all times exactly what we are doing and why. But this, to Oakeshott, was its downfall, and it is this which he is referring to when he bemoans the way we see the dominance of the pursuit of ideals as "a benefit for which we should be grateful or an achievement of which we should be proud". Because far from being helpful, the pursuit of perfection as the crow flies inhibits us:
[A] morality that takes the form of the self-conscious pursuit of moral ideals is one which, at every moment, calls upon those who practice it to determine their behaviour by reference to a vision of perfection...[W]hen the guide of conduct is a moral ideal we are never suffered to escape from perfection. Constantly, indeed on all occasions, the society is called upon to seek virtue as the crow flies....And the unhappy society, with an ear for every call, certain always about what to think...in action shies and plunges like a distracted animal.
This is because, according to Oakeshott, moral rules are not the products of reflective thought. Rather, they emerge from activity. Setting in place an ideal and then striving for it in activity is putting the cart before the horse; it is the wrong way round. In fact, the correct order is that human beings first engage in action in society and from their action emerge customary rules and norms; these are then reflected upon and made abstractas rules. In Oakeshott's vision, society generates moral rules in an emergent, evolutionary, unconscious fashion, and subsequently people note that moral rules have been created and reflect upon them. So while morality without reflection is "defective", reflection ought to be subservient to habit; reflection is just the matter of "giving verbal expression to [already existing] principles of behaviour". It is supposed to protect us from degeneration into superstition. Out mistake is that we have given "that which has the power to rescue from superstition...the task of generating human behaviour" in privileging idealism over habit.
You can over-egg the pudding in drawing too direct a comparison between what Oakeshott was saying about moral rules and game rules. The two things are not the same: rules in games require a much greater element of his technical knowledge than do moral rules, for obvious reasons. Games require some rules to make them work as games at all.
Yet there is something to the notion that the pursuit of perfectionism and idealism in a set of game rules also falls victim to this category error that Oakeshott identifies: putting the vision of perfection first and then developing the rules with that vision in mind seems (if it is successful) to be likely to give us confidence in those rules and know all the time what rule we are supposed to refer to, how to apply it, and why we are applying it. The rationale would be clear at all times. Yet this, in itself, will be paralysing. The need to be perfect, to be impervious to criticism, to stand up to reflection, to be "naively coherent", will get in the way of free action. It will leave us certain about how to think but uncertain about how to act.
It seems to me that the project of the Old School Renaissance, by contrast, has been an embodiment of Oakeshottian thought - though naturally and entirely appropriately, it has done so in an entirely unconscious and emergent fashion! This is because the entire process, especially in its early years (around 2007-2009) was almost totally a matter of reflection on, and abstraction of, pre-existing habitual/customary rules and norms. That is, there existed a habit of play which had developed over the course of the decades from 1974 onwards; and though the pursuit of as-the-crow-flies perfectionism had intervened in the meantime to a large extent, it had not quite resulted in the absolute destruction of those customs and traditions. So that when OD&D, B/X etc. came to be "rediscovered" during this period, people were able to look at a wide array of pre-existing intuitive, often unwritten, often implicit, modes of conduct and ways of making rulings - a huge body of practical knowledge - and make them comprehensive and abstract (in projects like Philotomy's Musings, for instance). We might say that, in the OSR, reflection gave "verbal expression to principles of behaviour", in other words. Everything is the right way round.
What this means is that, when one uses the OSR play style, one is rarely if ever concerned about "naive coherence" and is, by contrast, primarily concerned with appropriateness of action: let's say with making rulings, not rules. This we know.
But perhaps more importantly, thanks to the manner of its creation - the fact that the internet allows the sharing of the habit of play between players (the verbal expression of the principles of behaviour) - it means that, in effect, those of us using that play style act as a society which retains its customs and traditions and can be confident in them as non-reflective, habit-producing, largely implicit guides of behaviour. This means that we are always able to pursue individual eccentricities safe in the knowledge that our society is backing the field. Whatever lunatic schemes we might come up with as ways to improve our games, the principles of behaviour - the habits of play - remain. No one individual project will result in a Tower of Babel which "disrupts our common life".
It would be going too far to suggest that this play style which we sometimes refer to as the 'OSR' or 'traditional games' is the best, but I certainly think the case can be made that we have the balance between habit and reflection right: habit dominates; reflection gives verbal expression to it and makes it knowable, teachable, and restrained from blind superstition.