This paper offers a multidimensional reading of Rabindranath Tagore’s short story Atithi (“The Guest”) through postcolonial and psychological frameworks, foregrounding the themes of rootlessness, freedom, and resistance to institutional authority. The narrative of Tarapada, a wandering boy who resists domesticity and social containment, becomes a powerful metaphor for the modern subject caught between freedom and belonging. Situating the text within the socio-historical context of colonial Bengal, the paper argues that Tarapada’s refusal to submit to family structures, education, and eventual marriage reflects a deeper resistance to colonial discipline and the imposition of normative identity. Drawing upon postcolonial theorists such as Homi K. Bhabha and Gayatri Chakravorty Spivak, the study interprets Tarapada as a liminal subject who destabilizes fixed categories of identity, belonging, and authority. Simultaneously, psychological frameworks—particularly Freudian and existential perspectives—help illuminate his compulsive mobility as both a symptom of internal conflict and an assertion of autonomy. The paper further explores the colonial education system as represented in the text, revealing how institutional pedagogy functions as a tool of control, which Tarapada instinctively rejects. A comparative reading with Tagore’s The Postmaster extends the discussion, highlighting recurring motifs of displacement, emotional detachment, and the impossibility of stable belonging in Tagore’s fiction. Through close textual analysis and critical engagement, the paper ultimately argues that Atithi is not merely a story of a restless boy but a profound meditation on the human condition, where freedom emerges as both a liberating and isolating force.