Oppression, so we agree, is a social injustice, which, by nature of its being unjust (whatever “unjust” means in today’s cultural, philosophical, and historical sociopolitical context) is something we ought strive to eliminate. At the very least, the elimination of oppression as a manifestation of injustice gives us an ever-evolving project with which to occupy ourselves. From Plato to Rawls, I think we’re well due to admit that defining injustice, much less eliminating it, is a delightfully Sisyphean task. Yet we must imagine Sisyphus happy, remember, and be content in engaging the problem of injustice, despite its likely intractability, because pondering the philosophical dimensions of our existence is simply something that we human animals cannot help but do. Philosophy is, or is part of, our nature. To affirm or deny the truth of this is itself a philosophical endeavor, and so quite literally, paradoxically, we cannot help ourselves from being philosophical. Moreover, any prolonged attempt to deny or step out of the cycle verges on infinite regress, insanity, and the despair of futility. So, preferring affirmation to denial, I choose to roll the boulder up the mountain rather than lose my mind to it.
With that preface, I’ll briefly engage the problem of oppression as a form of injustice. First, then, I must explain what exactly I mean when I say “oppression.” More accurately, because oppression inherently involves an oppressor and an oppressed, what I mean when I say “I must explain exactly what I mean when I say ‘oppression'” is that I must explain what fundamentally drives the oppressor to oppress. That is, the paradigmatic origins of oppression as it stems from the oppressor.
In the oppressor I see (among other less seemingly pertinent qualities) intolerance, closed mindedness, judgment, and arrogance. Intolerance of diversity and difference. Closed minded to alternative ways of living and thinking. Judgment about value, purpose, meaning, importance, the good and the bad, wrongness and rightness, propriety, hierarchy, and intrinsicity. Arrogance about the ultimate significance and objectivity of his or her own judgments. Therefore, one might take it upon his or her self to expose and vanquish intolerance, closed mindedness, judgment, and arrogance.
Montessori education and training in the history of philosophy, are, I believe, at least partial remedies for intolerance and closed mindedness. Montessori schooling encourages the flourishing of diversity in talents, interests, and values in children. It creates an environment that enables young minds to take on the world as Socrates without the threat of hemlock (suppression being one sort of oppression with which I am concerned). Montessori education, contrasted to dogmatic, standardizing, and normalizing pedagogy, allows children to naturally arrive at and explore the salient questions of life as unique individuals, encouraging and appreciative of diversity. Tolerance is implicit in Montessori education, making permanent, instead of stifling, the natural open mindedness of children so that it extends into adulthood.
Training in the history of philosophy is important to cultivating tolerance and open mindedness in people for a similar yet distinct reason. If undertaken transparently, the history of philosophy exposes the philosopher to ideas, values, and worldviews different from, and perhaps inconsistent with, his or her own. In exploring the history, complexity, and evolution of human thought, one becomes witness to the paradigmatic diversity and multiplicity that being human naturally involves. So much so that one must inevitably admit that intolerance of and closed mindedness about diversity are fundamentally in conflict with the possibility of amiable participation in human social life, and indeed, ecologically speaking, incompatible with the preconditions for natural selection and evolution.
In confronting judgment about value, purpose, meaning, the good, and the rest, I’ve found the distinction between arbitrariness and non-arbitrariness to be helpful. Non-arbitrary judgments are those that pertain to the objective biological conditions of being human, namely, involving the fulfillment of our non-arbitrary needs. Exhaustively, our non-arbitrary needs include foraging for food and drink, seeking out mates, searching for shelter, and sleeping. Thus, judgments about anything beyond this short list, which certainly means the myriad of normative, existential, and teleological judgments for which one might be oppressed, are arbitrary. That is, made on the basis of one’s own personal inclination, however capricious it may be.
The line of argument is then that the normative, existential, and teleological judgment that an oppressor believes justify his or her oppression are entirely arbitrary. The arbitrariness of oppressive judgment undermines the self-proclaimed legitimacy of the oppressor, for such a proclamation reveals his or her motive for oppressing to be a function primarily of an unwarranted arrogance about the importance, significance, or objectivity of his or her judgment. Arrogance, then, must be overcome.
Arrogance about the importance, significance, and objectivity of one’s own judgment reflects one’s more fundamental conviction about his or her place in nature and the universe. This includes notions of hierarchy, dualism, centricism, propriety, cosmic significance and importance, purpose, divinity, intrinsicity, and progress. For undermining such arrogance, deconstructive postmodernism is quite apt. Yet deconstruction comes up short when faced with concrete political questions, for in deconstructing the metaphysical ground works of all universalistic judgments and distinctions, deconstruction renders itself unable to put forth any positivistic claims of its own. In effect, deconstruction can reveal the contingent cultural and historical contexts upon which the oppressor derives his sense of objective legitimacy in oppressing, but deconstruction, by nature of its being a negativistic methodology, cannot suggest an alternative, inherently value-latent interpretation of justice or injustice of its own to fill the void it leaves behind without contradicting its philosophical presuppositions. Deconstruction can show why arrogance about one’s judgment is ultimately unfounded, revealing the cultural and historical contingency of such judgment’s origin, but in doing so prevents itself from recommending a virtue of its own. This is the challenge of overcoming arrogance on any scale, individual, national, or international, in a sociopolitical environment that so often demands strict relativistic pluralism and pluralistic relativism. How might we defeat “arrogance” without ourselves becoming arrogant about our own worldview about overcoming arrogance?
Confidence and humility are compatible in my opinion, but any judgment, construction, or distinction I could offer would be, to a significant degree, a product of my own cultural and historical environment, which therefore axiomatically precludes me from developing any universalist or absolute moralism without contradicting myself. Indeed, the modern progressive liberal paradigm that determines oppression to be a categorical, absolute injustice is historically and culturally situated — a position with which I most certainly agree. But oppression was considered both just and necessary in ancient Spartan society, and up until the 1960s in the United States, de jure discrimination and other vestiges of slavery were understood as the natural order of things. These social conditions are easily detestable from where we sit today, but in their own times such inequities were seen as normal, not objectionable. So where does one begin, left flailing in utter contingency, to find solid, non-arbitrary ground from which to contest oppressive arrogance? When does insisting on the virtue of diversity and demanding universal toleration itself become oppressive and dogmatic?
 For more on the arbitrary v. non-arbitrary distinction, see The problems of society – Part one: The normative question.