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So what gives rise to such baffling questions? In a word, self-reflection.
How is philosophy learned? A better question is: how can thinking skills be acquired? The thinking in question involves attending to basic structures of thought. This can be done well or badly, intelligently or ineptly. But doing it well is not primarily a matter of acquiring a body of knowledge. It is more like playing the piano well. It is a ‘knowing how’ as much as a ‘knowing that’.
To process thoughts well is a matter of being able to avoid confusion, detect ambiguities, keep things in mind one at a time, make reliable arguments, become aware of alternatives, and so on.
To sum up: our ideas and concepts can be compared with the lenses through which we see the world. In philosophy the lens is itself the topic of study. Success will be a matter not of how much you know at the end, but of what you can do when the going gets tough: when the seas of argument rise, and confusion breaks out. Success will mean taking seriously the implications of ideas.
How you think about what you are doing affects how you do it, or whether you do it at all.
So the middle-ground answer reminds us that reflection is continuous with practice, and our practice can go worse or better according to the value of our reflections.
When these beliefs involve the sleep of reason, critical awakening is the antidote.
Reflection enables us to step back, to see our perspective on a situation as perhaps distorted or blind, at the very least to see if there is argument for preferring our ways, or whether it is just subjective.
Reflection opens the avenue to criticism, and the folkways may not like criticism. In this way, ideologies become closed circles, primed to feel outraged by the questioning mind.