Seth Green, Dean of the University of Chicago Graham School, discusses the art of navigating career transitions with a focus on lifelong learning and purpose. He emphasizes moving from the 'first mountain' of material success to a 'second mountain' shaped by personal values. Green highlights the evolution of education in response to longer lifespans and stresses the importance of joy over financial gains. He advocates for pursuing passions and maintaining healthy relationships as key to personal fulfillment in an ever-changing world.