David Brooks: Discerning Purpose in Life's Second Half

What does it mean to find purpose in life's second half? In this conversation hosted by the University of Chicago Graham School, New York Times columnist and bestselling author David Brooks explores why the most important question you can ask isn't "What do I want from life?" but "What is life asking of me?" Drawing on his book The Second Mountain and his experience teaching in the University of Chicago Leadership and Society Initiative, Brooks examines what it takes to move from a first mountain of career and achievement to a second mountain of genuine purpose, commitment, and contribution. Brooks illustrates the journey through his own experience, tracing a transition from emotional withdrawal to genuine openness. The catalyst was not a career decision but a period of personal difficulty that led him to a remarkable community in Washington, D.C., one that demanded vulnerability and offered belonging in return. He and host Seth Green, Dean of the Graham School, dig into why suffering can break people open rather than simply break them, why excavating intrinsic desire after decades of extrinsic reward is harder than it looks, and why the transition to a second chapter is not a change of job but a change of consciousness. The conversation draws on Viktor Frankl's Man's Search for Meaning, Frederick Buechner's concept of vocation, and the theology of Paul Tillich to ground the discussion in a serious humanistic tradition. The conversation ultimately turns outward. With Americans now living far beyond the age the Social Security system was designed around – Brooks notes that someone who is 60 today has roughly a 50% chance of living to 90, compared to a system built when people retired at 65 and died at 67– two new and under-institutionalized stages of life have emerged, and society has done little to structure them. Brooks argues that the crisis of social alienation and declining trust is one of the defining problems of this era, and that the same older adults who are best positioned to address it – warmer, more conscientious, and less threat-oriented than younger generations – have no adequate scaffolding to help them find and activate a purposeful next chapter. LSI, as both Brooks and Green reflect, is one attempt to build that scaffolding. Chapters 00:00 Welcome and Introduction 01:43 The Second Mountain: Origins and Core Idea 03:00 Portrait of a First Mountain Life 05:52 Being Broken Open: The Community That Changed Everything 08:59 Recognizing Your Own Inflection Point 13:19 Excavating Intrinsic Desire in a World of Extrinsic Rewards 17:43 Why Relationships and Cohorts Drive Reinvention 20:31 Viktor Frankl, Humanistic Texts, and the Nine Big Questions 25:08 The Curse of Relevance: Learning to De-center Yourself 29:43 Activating the Next Chapter: A Bias Toward Action 36:06 The Societal Gap: Longevity and the Crisis of Social Trust 42:43 What the Fellows Teach: Reflections on the Leadership and Society Initiative About the Speaker: David Brooks is a columnist for the New York Times and the author of, among other books, The Social Animal: The Hidden Sources of Love, Character, and Achievement (2011), The Road to Character (2015), and The Second Mountain: The Quest for a Moral Life (2019). In addition to his work at the Times, Brooks has been a reporter and op-ed editor for the Wall Street Journal, a senior editor at the Weekly Standard, a contributing editor at Newsweek and The Atlantic, and a commentator on NPR and the PBS NewsHour. Brooks was a Senior Fellow at Yale’s Jackson Institute and currently serves as chair of Weave: The Social Fabric Project at the Aspen Institute in Washington, D.C. About the Leadership and Society Initiative: The University of Chicago Leadership and Society Initiative (LSI) supports accomplished leaders in envisioning and activating purposeful next chapters beyond their longstanding careers. Through a yearlong fellowship in UChicago's environment of open inquiry and free expression, LSI Fellows engage with eminent faculty, build lasting peer connections, and develop a concrete plan to apply their skills and experience toward meaningful contribution to society. LSI is grounded in three pillars: knowing oneself, understanding the world, and envisioning the future. Learn more at https://leadforsociety.uchicago.edu