Education promised opportunity—but for many millennials, it delivered disconnection. Shane Hewitt and Ryan O’Donnell explore the mismatch between what school prepared for and what work delivers, with Gallup data showing widespread disengagement.

They examine generational shifts in job expectations: millennials craving purpose but often finding workplaces without stability or mentorship. Ryan shares firsthand examples of peers trading financial security for fulfillment, while Shane questions whether jobs should provide meaning at all—or if true satisfaction comes from contributing beyond the workplace.

The episode also tackles the financial pressures shaping a generation, including housing affordability, and tees up future conversations on youth unemployment.

Originally aired on 2025-09-15