In this chapter, we discuss the pre- and post-migration narratives of young Punjabis around employment expectations and experiences. This work is based on qualitative interviews conducted with young Punjabis in Punjab, India, and Toronto, Canada, as part of a study on COVID-19 and Punjabi migration. The literature on immigrant employment in Canada has largely emphasized either a structural analysis around obstacles faced or their integration and sense of belonging and identity, both in a post-migration context. We expand this literature by emphasizing the agentive manoeuvring of young Punjabis around structural obstacles across both contexts by drawing on the framework of “transnational navigation.” We argue that the migrants’ pathway framed by state policies, their stage of migration and social networks shape their employment expectations and navigations. Across both sites, migrants use the idea of temporariness to cope with the precarious working conditions they expect to face or are facing in the immediate aftermath of migration. These navigations are oriented at enhancing the migrants’ positioning within the existing social hierarchy and do not question the basis of their structural disadvantage.