In this article, I explore what I find to be the essence of Coburn’s and Maduro’s articles: the tension between thinking of humans as independent selves and as contextually determined. I try to show that this “dialectical core of self psychology,” as problematic as it might seem, is necessary if we are to have an adequate basis for a system of ethics and justice, and that the West’s overemphasis on autonomy has been deeply injurious. I, then, integrate the two papers by proposing, along with Coburn, that the ability to concomitantly “own” one’s contextuality and individual freedom is the basis for a new concept of psychological maturity, and that Maduro’s concepts of courageous knowing, emotional experiencing, and rigorous relationality are the keys to developing this innovative vision of psychological maturity.