This chapter explores the international career trajectories of immigrants from emerging contexts, emphasising how intrinsic motivations, systemic barriers, and sociocultural dynamics intersect to shape their professional paths. Drawing on career embeddedness theory, institutional theory, and critiques of boundaryless career models, it addresses two key research questions: (1) how intrinsic drives and systemic constraints jointly shape immigrant careers and (2) how historical, institutional, and cultural factors influence career embeddedness over time. The discussion critiques overly optimistic applications of the boundaryless career model, highlighting persistent challenges such as the liability of foreignness and outsidership, which create barriers in adapting to cultural norms, navigating institutional discrepancies, building networks, and overcoming bias. Special attention is given to self-initiated expatriates, particularly female entrepreneurs, whose international experiences demand cognitive flexibility, strategic networking, resilience, and socio-political advocacy. By analysing emerging patterns such as adaptive crafters, resilient navigators, and network crafters, the chapter demonstrates how immigrants reshape traditional career management frameworks. Finally, it underscores the importance of targeted policies—credential recognition programmes, mentorship initiatives, entrepreneurial support systems, and cultural intelligence training—to mitigate systemic barriers. The chapter ultimately argues that understanding immigrant career navigation is vital not only for advancing academic discussions on career sustainability and global labour market dynamics but also for informing policies and organisational practices aimed at fostering greater social inclusion, innovation, and economic resilience in an interconnected yet unequal world.