The Present paper deals with an inward quest for liberation from materialistic possession. ‘The Winter of Our Discontent’ is the work we have selected in which the main character, Ethan Hawley as a common man in modern American society experiences an epiphany realizing the importance of love and freedom. He demonstrates great power of introspection, self-analysis and psychological probing as the darkness in human soul is complete. As the protagonist, he is a character of discipline and ambition, but with a mixture of desire and disgust, he proceeds to achieve prosperity through evil ways in already social, moral, political and economic decadent order of the world. Ethan takes to the path of darkness (materialism) goaded by his family which leads to sinful life as selflessness and spiritual light departs from his soul. As the story unfolds where his acquaintance with employer, land owner, banker and councilor propels him to search contentment, but he reaches the point of death which fails to bring him redemption. As Ethan chocks in between light and darkness, his conscious mind seeks spiritual discipline and selfness-ness. This turning point signifies his inward quest for liberation from materialistic possession. It partakes moral awakening as the prerequisite of spiritual awakening, the truth behind ‘light’ leaving his life. The paradox of spiritual heavenly joy as the conquest of selfless-ness, renunciation and contentment as ‘light’ and material world full of miseries and sufferings as ‘darkness’ is the crux of John Steinbeck’s novel. The emphasis of winter associated with misery, discontent and ambition is laid out for all as it envelops human soul signifying lack of holistic vision to life. To thrive in spiritually barren world, Ethan’s has to renounce his selfless quest to self-love and happiness akin to darkness and the forces of discontent affects him to the point of suicide. The moral awakening, the distinction between good and bad redeems his soul to seek light, as the panoramic view of humans see themselves as a paradox between light and darkness.