Giving an overview of the extant research on social mobility, we claim that it is mired in the same “Individualism-Collectivism” dichotomy that plagues Social Sciences tackling the “Structure-Agency” conundrum. Critical Realism (CR) offers an archetype that allows us to go beyond this fault line and analyze social mobility as a transformational endeavor. We discuss this in the context of studying social mobility in the new Information Technology (IT) sector of India, where CR provides us with a solid bulwark for our ethnographies in two organizations in this sector. We show that mobility is enhanced in an arena of multiple and diverse structures when agents are able to go beyond the apparent (empirical) circumstances thrown up by structures in a flux and discern the actual forces at work. The intransient real encompassing these multiple structural possibilities offers them the flexibility to carve such a path.