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The quest for authentic existence is at the root of every man’s craving. But the how to achieve it remains a philosophical enquiry. Kierkegaard postulated that subjective existence is a pathway to authentic life. His notion of subjectivity is embedded in his conviction about the being of man and his own personal life experiences. Together with many other existentialists, he holds that man was thrown into the raw world without being consulted. This thrownness of man naturally disposes him to freely and subjectively define his essence in relation to the existing world in which he finds himself. Again, his personal world-view which involves solitary actions that were seasoned in conscious choices realized in freedom of decisions and responsibility taught him that greater developmental feats are achieved from the inward (subjective) to the outward (objective). This paper investigates Kierkegaard’s subjectivity as authentic way of being and a challenge to contemporary African communitarianism. Scanning through the history of human development, it reveals that subjectivity of life permits individual development as well as that of the larger society for the fact that subjective existence avails conscious self-creation and innovations that do not disrupt social peace rather it respects individual freedom, self-expression and responsible control of one’s destiny. The paper also noted that heightened scientific advancement and civilization are connected with subjective life of individuals which manifested during the 20th century when existentialism exhibited its influence on the people. Further, it demonstrated how contemporary African communitarianism is challenged by Kierkegaard’s subjectivity considering the level of her collective development. The paper, concluded that a certain degree of healthy patriotic individual existence is needed to take significant leaps towards authentic existence. It therefore recommends that a healthy balance of objective-subjective existence is necessary for wholesome human development and that of the society at large.