The pressure is high on career educators to develop information literacies as a life skill for themselves as well as for youth, particularly those from disadvantaged communities, and to document and process career information in a rapidly changing world of work that is relevant to their sociocultural and environmental contexts. We employ a critical or transformative approach to information literacies to explore young people’s socially situated practices of collecting, validating, and processing career information as well as how they might “democratically transform structures of authority over information exchanges, and then maintain scrutiny over this authority” (Whitworth A, Radical information literacy: reclaiming the political heart of the IL movement. Elsevier, 2014, p. 2). We draw from qualitative interviews with ten boys studying in 10th grade at a government school in Delhi, India, and videos produced by them to map their career information landscapes. Using an education for sustainable development lens, “bumps” were made visible in their information landscapes, that is, the tensions that emerge between multiple informational actors for reimagining sustainable futures. We suggest that these tensions can serve as cultural resources that students can democratically engage with in developing crucial career and life skills for their futures.