The rise of the gig economy has redefined work by offering flexible, on-demand opportunities across various sectors. While this model provides autonomy and income generation avenues, it also poses challenges to the long-term career sustainability of gig workers. This study explores the critical factors that affect gig workers’ ability to sustain their careers over time. Relying on secondary data and industry-based case studies—including the notable efforts of Salauddin Shaikh, who pioneered unionization for gig workers—the research examines the impact of technological tools, income fluctuations, skill levels, and industry differences. The study further assesses how these elements influence job stability, career growth, and economic resilience. Based on the findings, the research offers constructive recommendations at three levels: industry, government, and individual. Key suggestions include implementing fair wage policies, expanding access to social protection, promoting digital upskilling, ensuring legal safeguards, and encouraging self-driven financial planning. The study underscores the importance of a collaborative and well-regulated approach to ensure that the gig economy evolves into a more equitable, secure, and sustainable employment ecosystem.