Through the lived experiences of Himmat (pseudonym), a school peon in Mumbai, we attempt to understand the yearning for justice and dignity that underlies enactments of resistance. The peon, while performing his duties, acquires master’s degrees in arts and education, and aspires to be appointed as a teacher in the school. He comes up against barriers of feudal subordination, caste discrimination, authoritarianism, corruption and a control of educational trusts by politicians who view it as an entrepreneurial endeavour. We read his lived experiences of resistance as an attempt at de-prisoning, as a method of dismantling the legitimacy of imprisoning and exploitative discourses.