This paper presents a series of observations arising from the experience of translating Jibanananda Das’s Bengali poetry into English. Though the emphasis is on the practice of translation the observations in question are foregrounded against the perspective of theories of translation studies. The first part demarcates the scope of the paper in theoretical terms. Several possible approaches to translations of Jibanananda Das (in terms of process, end product, and sociological connotation) are considered with a view to focusing on practical observations. In the course of this process of theoretical delimitation some sense of the linguistic and literary context within which Jibanananda worked, and which the translator must appreciate, is conveyed. The second part is guided by Roman Jakobson’s notion that the activity of translating is influenced more by what languages must convey rather than by what they can convey.