The human psyche becomes confused when faced with a difficult situation. An instinctive temperament instigates a man to contemplate before acting on a decision. Sigmund Freud develops the ‘theory of personality’ to discuss how one’s behavioral characteristics are expressed under the direction of the ‘driving forces’ (i.e., id, ego, superego). These ‘forces’ perform a crucial role in maintaining equilibrium between two diametrically opposed possibilities, and they aid in navigating the ‘anxiety.’ To substantiate the argument, the paper delineates a comparative study between William Shakespeare’s How Heavy Do I Journey on the Way and Robert Frost’s Stopping by Woods on a Snowy Evening, where they depict two different kinds of ‘love’ (desire) and ‘duty’ (responsibility) through the journey(s) of the poets. These poems bring the nuances of the characters and their psychological complexity to light in the midst of two options and how they surpass their ‘dilemma’ by making one decision.