This chapter looks at the emergent Dalit autobiographical writings in Malayalam, and the negotiations with the dominant imagination about Dalits at the capitalistic conjuncture of print culture. It attempts to read through two different autobiographies of Kallen Pokkudan: Kandalka dukalkkidayil Ente Jeevitam and Ente Jeevitam. Pokkudan is a Dalit activist from north Keralam who is popularly known for his eco-political interventions in planting mangroves in his village. The newly formed political subjectivity of the Dalit embodies the tension between a community-in-the-making and the individuated modern Dalit self. At the intersection of the grand narratives of communism and environmentalism, the image of Pokkudan as naively redefining his modern life as agricultural labourer gets registered, nullifying the eco-political dimensions of his Dalit activism. The caste-based discriminatory practices of party cadres and the ideological apathy shown by communist intellectuals towards the caste question made him realize the limitations of the communist ideology in addressing the Dalit life-world.