This paper examines how Peruvian migrants fare economically in two historically and culturally distinct host countries, Japan and the US, drawing upon a survey and interviews conducted in both countries. Peruvian migrants surveyed share similar socio-economic backgrounds and migrated to both countries for similar reasons roughly around the same time. Yet, over time, they achieved more occupational upward mobility in the US than in Japan. Japan has not done quite as well as the US in providing immigrants with occupational opportunities due to its less diversified immigrant labor market, limited entrepreneurship opportunities, and restricted modes of immigrant incorporation. Does it mean, however, that Peruvian migrants are less successful in Japan than the US? Although occupational mobility is a commonly used measure of social mobility, the definitions and meanings of “success” are context-dependent. Peruvians in the US do experience more occupational mobility, but diverge more greatly in economic achievement amongst themselves. In Japan, on the other hand, while they experience little occupational mobility, they have had more economic equality with relatively stable and high wages. The paper examines Peruvian migrants’ distinct economic trajectories over time, focusing on their occupational mobility. We conclude that occupational mobility matters, not necessarily because it accompanies higher income, but because it shapes migrants’ aspirations. In the context where immigrants’ destinations have become more diverse in the world, the paper provides insights into how immigrants “make it” and what it means to “make it” in recent destinations, such as Japan, in comparison to more traditional immigrant countries, such as the US.