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Scholarship in migration demography emphasizes that trajectories unfold over the life course, yet few quantitative studies link pre-arrival pathways to post-migration labor outcomes within a bounded institutional setting. Using survey data on Filipino and Indonesian domestic workers in Hong Kong, we apply sequence analysis to reconstruct multi-country migration paths from adolescence to early adulthood and classify them into common trajectory types. We identify three predominant patterns—direct migration to Hong Kong, prolonged stepwise migration, and complex serial/multinational transitions. Multivariable regressions relate trajectory type to two subjective outcomes: job satisfaction and perceived job–match quality. Results show meaningful within-group heterogeneity: workers who arrived in Hong Kong as their first and only destination, especially at younger ages, report higher job satisfaction than those with more complex routes; differences in job–match are smaller and not universal across clusters. These findings underscore the value of integrating life-course migration sequences into research on migrant labor experiences and highlight how pre-migration mobility can shape workplace well-being even among migrants who share the same origin and destination contexts.