This episode analyzes the impact of AI on the white-collar labor market and employer-sponsored health insurance. It explains how AI is transforming job roles, creating new positions, and shifting employment structures towards more contract and gig work. This shift challenges the traditional employer-sponsored health insurance model, leading to coverage gaps for non-traditional workers and financial strain on existing systems. The text explores potential solutions, such as portable benefits, health stipends, individual coverage HRAs, and hybrid employer-government models. It also suggests that companies need to modernize their benefit strategies to remain competitive in attracting and retaining talent in an AI-driven world.