The dynamic and evolving landscape of the gig economy presents unique challenges and opportunities for gig workers. An interesting issue is to understand how these gig workers navigate through their long-term career trajectory in the context of their well-being and the precarity associated with the gig work. The focal point was the career anchors proposed by Schein. In this study, we adopted qualitative methodology to understand this dynamic. We interviewed 52 gig workers and after the analysis of the data our key findings were that the gig work on one hand presents some resources in terms of flexibility and independence. On the other hand, there are certain demands like financial and economic insecurity that are being present by the non-traditional gig work. In this study, we see that how the gig work both aligns with and expands upon Schein's career anchors. The non-traditional nature of gig work introduces new considerations into the career decision-making process, emphasizing the need for adaptability, proactive management, and personal responsibility. These additions to the career anchors model reflect the evolving nature of work and the growing significance of gig employment in the modern labour market necessitating a multifaceted approach from organizations to support them effectively. This study also enriches the understanding of the psychological contract in gig work by highlighting the expectations and perceived obligations of gig workers, which have been largely under-examined in the extant literature.