As non-linear, multi-role career patterns become more common, understanding how multiple jobholding (MJH) influences career sustainability is essential. Although there has been extensive research on the motivations for and outcomes of MJH, its role in career sustainability has not been thoroughly explored. This study aims to address the overlooked challenges and opportunities that MJH presents in shaping career sustainability, providing insights into how workers balance multiple roles and navigate their complex career paths. Using the sustainable career model as a framework, this study assesses career sustainability through three key indicators: health, happiness, and productivity. Previous studies have predominantly focused on the depleting role of MJH, emphasising conflicts and challenges. However, guided by resource expansion theory, this study shifts the focus to enrichment potential of MJH. Drawing on qualitative interviews with sixty multiple jobholders, the findings reveal MJH as primarily offering opportunities for enrichment and compensation, where diverse roles expand resources and skills enabling individuals to sustain their careers. MJH can enhance career sustainability when individuals strategically balance multiple roles and trade off the indicators of career sustainability. These insights expand the sustainable career model by showcasing the dynamic, adaptive, and individualised strategies that multiple jobholders employ to maintain fulfilling and evolving careers amidst competing demands.