This paper attempts to avoid both overly optimistic and pessimistic accounts of the ‘on-demand’ global economy and of ‘platform labor’ in the Global South. It instead considers both how the socio-cultural and economic complexities of the worker environment might drive the attractiveness of this form of labor and how histories of colonialism might make local employment and upward mobility less of a viable option for workers from the Global South. Drawing from in-depth interviews and analysis of multiple texts circulating in online freelance forums, Facebook groups, and ‘freelancer’ events, we look at how freelance workers and platform managers enacted and articulated classed and colonial digital labor imaginaries. We identify three such interconnected imaginaries and label them as follows: that of ‘distinction,’ ‘transcendence,’ and ‘flexibility’. In fleshing out these digital labor imaginaries, we discuss the role of virtual spaces, online communities, and the influencers who help push these imaginaries within the digital platform. And in exploring digital labor in the context of its socio-political and cultural embeddedness, we aim to show how workers constituted a sense of self and agency while being embedded in aspirations that were fraught at best and false at worst.