This paper aims at finding the obvious reason behind suffering of the two classical protagonists Robinson Crusoe and Hester Prynne in their life either in the sea or on a deserted island as in the case of Robinson or in a hometown as in the case of Hester. It emphasizes the assertion of individuality and its aim to find out the possible alternatives of the present life. An investigation of the particular background will shed light on our understanding of the two stories. Hester moves from the Old World of Europe to the New World of America, and settles down near Boston. After committing the adultery with Dimmesdale, Hester, all by herself, becomes a lonely woman in a totally alien land