‘“Individualism” claims G.K. Chesterton, “kills individuality.” While perhaps formulating a subjectivist paradise devoid of “pure” objective rationality, Nietzsche opened the door to a form of individualism that led to a new extreme of impotence and feebleness that the Enlightenment might never have reached. Peterson’s dour temperament, juxtaposed with the well-adjusted temperaments of the jovial Chesterton and the vivacious [Slavoj] Zizek . . . testifies to the death of individuality under the tyranny of individualism.
To base one’s moral compass on lived relationships with real people outside of one’s head, rather than on abstractions of their selfhood or of “humanity” broadly speaking, seems to be both a necessary and perplexing conundrum. The self, for Chesterton, was perpetually caught in a tension whose dynamic was relational. Existence and freedom are not to be harnessed and regulated, nor outsourced and relieved of responsibility. They are gifts…and at times curses, but always given, implying a relationship between a gift-giver and the self as receiver. “Most modern freedom is at root fear,” writes Chesterton, “It is not so much that we are too bold to endure rules; it is rather that we are too timid to endure responsibilities.” Responsibility for Chesterton is not so much a matter of lifting oneself up by one’s bootstraps, but a response to the One who gives one his existence. Thus, we are faced with Chesterton’s ability to hold together the paradox of the power of free will, but also its fragility and limitations.’
— Stephen G. Adubato: “Beyond the Cult of Self-Reliant Bootstrapping”