Freakonomics Radio: A Question-Asker Becomes a Question-Answerer

Podcast: Freakonomics Radio (in conversation with Design Matters host Debbie Millman)
Date: October 17, 2025
Host: Stephen J. Dubner
Guest Host: Debbie Millman (for this episode)
Duration: ~1 hour 20 minutes

Episode Overview

In this special “feed drop” episode, Freakonomics Radio host and Freakonomics co-author Stephen J. Dubner finds himself on the other side of the microphone. Interviewed by Debbie Millman for her podcast, Design Matters, Dubner reflects on 20 years of Freakonomics, his own formative experiences, the profound influence of family and identity on his curiosity, the quirks of creative and professional growth, and why the human dimension in economics and journalism remains critical. They dive deeply into adaptation, change, the courage to be oneself, and the enduring value of real conversation—a timely prelude to Dubner’s forthcoming TV project, "Better In Person."

Key Discussion Points & Insights

Stephen Dubner’s Origin Story: Writing, Mentors, and Teachers

• Early Writing and Encouragement (04:10–06:32)

  • Dubner recounts his first taste of publication—his fourth-grade poem, “The Possum,” printed in Highlights magazine, thanks to his teacher Mrs. Peterson’s support, which had a long-lasting effect on his self-confidence as a writer.
  • Quote:
    "I'm not saying I wouldn't have become a writer had Mrs. Peterson not done that, but, oh, my goodness, what a vote of confidence that was." (05:20)

• The Power of Teaching and Self-Recognition (06:40–08:24)

  • Dubner discusses his experience as a young college teacher and realizing his own limitations in selflessness, leading him to embrace writing over teaching as a career.

Family, Religion, and Identity

• Childhood and Upbringing (08:24–11:07)

  • Growing up as the youngest in a large family on a farm in upstate New York; shares eccentric family customs and discusses how being fundamentally a “city boy” shaped him.

• Dual Religious Heritage and the Search for Belonging (11:07–16:25)

  • Both of Dubner’s parents were born Jewish, converted to Catholicism separately, then married—a story that inspired his first book, Turbulent Souls, and marked by the pain and reconciliation around interfaith identity.
  • Reconciliation Through Dialogue: Dubner details how Cardinal O’Connor’s concept of the “informed conscience” helped heal a rift between him and his mother regarding his return to Judaism.
  • Quote:
    “As a mother, ...she saw this as a sort of family tragedy. As I began to understand the import of that I wanted to try to fix it, I guess.” (16:25)

Curiosity, Creativity, and Conversation as Core Values

• The Lifelong Fascination with Questions (20:25–26:13)
  • Dubner traces his career to an intrinsic curiosity, the value of being a “question-asker,” and the delight in pursuing how things—and people—work.
  • Critiques the media for defaulting to gossip over genuine curiosity-driven investigation.
  • Teases his upcoming TV talk show, Better In Person, as a new venue for more character-driven, personal conversations.
  • Quote:
    “The curiouser you are, I think, the smarter you are. So for me, it’s really important...to look at any occupation, institution, place, person, and just kind of want to figure it out.” (21:15)

Parasocial Relationships, Hero Worship, and Authentic Encounters

• Franco Harris and Meaningful Disillusionment (29:41–36:26)
  • Fascination with football star Franco Harris as a child, pursuit of meeting him as an adult, and the realization of the limits of hero-worship—finding a man, not a messiah.
  • Memorable Quote:
    “I came looking for a savior, but what I found was a man. And maybe that’s the truer gift.” (36:40)
  • Reflects on the nature and complexity of parasocial relationships prompted by fame and media.

Reinvention: From Rock Musician to Public Voice

• Making and Leaving The Right Profile (37:09–41:02)
  • College years in a rock band, the evolution from terrible gigs to a real contract (with Arista), and walking away just before their big break, valuing personal anonymity and stability over stardom.
  • On preferring radio and writing:
    “If they don’t know your face, that counts for a lot in my book.” (41:02)

Writer’s Craft, Influence, and Authenticity

• On Writing from Good and Bad Examples (45:25–49:45)

  • Dubner discusses how imitating great writing early on was both necessary and limiting; the journey to developing confidence and an authentic voice is about trusting your own “science experiment” of self.
  • Parallels in learning golf and writing: you must “swing your swing” rather than copy others.
  • Quote:
    “...There are elements of a swing...that are certainly transferable, but there’s also a great deal of individuality...Write your writing, sing your song.” (47:58)

• Handling Negativity, Vulnerability, and Self-Management (61:42–66:25)

  • How Dubner learned, partly through working with psychologist Angela Duckworth, to treat the mind as a “muscle” and intentionally redirect focus after setbacks or embarrassment.

The Freakonomics Phenomenon—Genesis, Regrets, and Legacy

• The Oddball Roots and the Power of Data-Based Storytelling (53:05–56:43)

  • How the term “Freakonomics” was coined, resistance from publishers, and the book’s unexpected explosive success.
  • Quote:
    “It was all these stories that illustrated no concept at all...[Freakonomics] was so just outrageous and outlandish. It’s so bad that it’s great.” (54:46)

• Mistakes and Corrections (66:49–70:43)

  • The pain of discovering and correcting an erroneous story featured in the book about Stetson Kennedy; reflects on the challenges and importance of deep research and accountability.

• Lasting Influence (71:32–77:09)

  • On journalism: champions “storytelling with data” and warns about the echo chamber effect and anecdote-based reporting.
  • On economics: urges economists to remember the human (not just mathematical) element.
  • On legacy: hopes Freakonomics inspires ongoing curiosity, courage, and a sense of possibility, rather than cynicism.

Notable Quotes & Memorable Moments

• On the Power of a Great Teacher:
  “Very few people who have accomplished a lot in life have not benefited from a teacher who is really just extraordinary.” (06:40)

• On Professional Disillusionment:
  “I wish I don’t want to say, I wish more people did the kind of stuff that you do and that I do, but I do wish it. Because I think so much of what people consume that they think is media or information or news is really just gossip.” (23:50)

• On the Role of Courage:
  “There are many things that are abundant, which are often good. Some things are abundant that are bad. But then there’s one thing that I think is rare...that’s courage.” (59:24)

Key Timestamps

• [04:10] First published poem thanks to Mrs. Peterson
• [06:40] Choosing career: teaching vs. writing
• [11:07] Family's religious conversions and identity
• [16:25] Cardinal O’Connor and reconciling faith/family
• [20:45] Curiosity’s role in career and worldview
• [26:18] Announcing upcoming TV talk show
• [29:41] Franco Harris: lessons in hero worship
• [37:09] Rock musician years and leaving the band
• [41:02] Reflections on fame, anonymity, and starting TV
• [46:37] Developing authentic creative voice
• [53:18] Freakonomics book title origins
• [66:49] Regret and correction of Stetson Kennedy story
• [71:32] Freakonomics' legacy in journalism and economics

Tone and Style

Dubner is affable, open, and thoughtful, frequently self-deprecating and quick to credit influential figures in his life. Millman’s interviewing style is warm, deeply researched, and conversational, encouraging Dubner to explore personal territory, philosophy, and broader insights about culture, creativity, and economics. The discussion is peppered with humor, candor, and humility, making even heady topics accessible and engaging.

Final Reflections

This episode offers a rare, intimate glimpse into Stephen Dubner’s life and psyche, charting the intersections of family legacy, curiosity, creative struggle, and public impact. It underlines Freakonomics’ origin as an act of radical curiosity—a hunger to see the world’s hidden side without cynicism—and doubles as an inspiring treatise on why genuine questions (and the courage to answer them honestly) matter more than ever.

Recommended for:
Fans of Freakonomics, creatives, journalists, teachers, economists, or anyone curious about the intersection of human behavior, data, and personal growth.

Next steps:

• Freakonomics 20th Anniversary Edition out Nov 11, 2025
• Watch for Dubner’s new TV project, Better In Person, launching early 2026
• Check out the No Stupid Questions podcast archive