The self is both a sociological and a psychological construct. It is investigated in this paper from the perspectives of sociology of work, critical management studies and employment relations. Accordingly, drawing upon ethnographic research, this article seeks to unravel how an employee defines herself or himself in two realms—the organizational and the personal—respectively against the background of changing Indian IT industry marked by uncertainty and rising job insecurity. It examines how these two realms converge to bring about an individual’s sense of ‘dasein’ or being. The self is entwined in the value chain of the Indian IT labour process and, within it, soft HRM discursive practices seek to constitute and mould the ‘disciplined confessional self’ who is supposed to be not only autonomous but a proactive and proactive team player. This article identifies the sources from which the self finds definitions and validation in the liquid modern context of the ‘gig economy’. It seeks to reflect upon the ramifications arising out of the interplay between Western and Indian managerial repertoires and, finally, the interplay of caste and class against changing Indian societal norms and expectations. In doing so, it looks at the micro and macro means through which the self seeks to obviate its incoherence and find resonance and fullness. Given the volatile political economy of the Indian IT industry labour process, much of the work is repetitive and fragmented, and individuals feel alienated and burnt out after the initial excitement of experiencing the Sapient or Cisco way of life. They adopt various coping mechanisms reminiscent of Burawoy’s (1985) respondents to fight job insecurity and to secure their peer group’s acceptance. Thus, the onus of negotiating inherent dualities for finding meaning in the organizational realm, and yet leaving room for a transcendental individual coherent self whose larger ‘internal conversation’ transcends the existential concern of the structured antagonism of the wage–employment relationship, lies upon the individual rather than the organization.