This paper draws from the authors’ experiences of teaching sociology and social anthropology in academic institutions in India and the possibilities and predicaments they entail. Cultivating the sociological imagination has been at the heart of pedagogical practices in social anthropology; however, in the new, neoliberalized and privatized higher education spaces, invoking this link between individual and society is increasingly becoming challenging thus making the authors contemplate whether the preconditions for teaching critical sociology and sociological imagination are diminishing. With sociology's relevance for employability often called into question, sociologists in such spaces find themselves conflicted between caring for the students, their need for more skill-based sociology, and caring for the discipline's fundamental critical approach that forces individuals to encounter uncomfortable truths of inequality, marginality, oppression, privilege, and domination. The paper argues that alterity and diversity are fundamental and necessary preconditions to both cultivating a sociological imagination and a pedagogy of care that elicits values of solidarity, empathy and the collective.