This chapter analyzes the drivers’ circular migration between Bangkok and their villages. It focuses on the predicaments of this mobility. On the one hand, their experiences, stories, and trajectories contribute to reproducing narratives in which Bangkok and the villages sit at opposite ends of the spectrum of development and modernity. On the other, the drivers modulate between the two spaces, constantly attempting to pull them together, connect and mediate them, struggling to find a place for themselves in between the two. This chapter explores how the drivers navigate this complex position, torn between their participation in reproducing narratives of distance between the city and the village, which drove them to migrate in the first place and keeps them suspended between the two spaces, and attempts to reconcile it though their life trajectories. Whichever strategy they adopt to cope with these tensions, in their migration, the drivers take the same gamble that they accept while riding the city: a gamble that makes them both aware of and concerned with the fragility of their lives and the material effects of these unresolved tensions on their families and villages.