Design Matters with Debbie Millman

Guest: Stephen J. Dubner
Date: September 15, 2025
Episode Theme: The Art of Curiosity, Identity, and the Enduring Impact of Freakonomics

Overview

In this richly personal and inquisitive episode, Debbie Millman sits down with Stephen J. Dubner—journalist, best-selling author, and co-creator of the Freakonomics franchise. They trace Dubner’s journey from a creative childhood in upstate New York through his explorations of identity, curiosity, and reinvention, culminating in the 20th anniversary of Freakonomics. Throughout, Dubner shares candid reflections on family, faith, writing, and the importance of courageous, curiosity-driven living.

Main Topics & Key Discussion Points

1. Early Creativity and the Power of Teachers

[04:14 – 08:33]

• Dubner’s First Publication: At age 11, his poem "The Possum" was published in Highlights magazine, submitted by his fourth-grade teacher without his knowledge.

  • "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." (05:25, Stephen J. Dubner)

• The Impact of Teachers: Dubner reflects on the transformational power of a great teacher and shares his own stint as a teacher at Columbia, realizing he was too focused on his own writing to teach selflessly.

2. Family, Unusual Traditions, and Religious Identity

[08:33 – 26:27]

• Absurd Family Traditions: Dubner’s birthday cake tradition involving silence, molasses, and chickens—a custom more threat than reality—anchors his memories of a large, eccentric family.

• Religious Heritage and Conversion:

  • Dubner's Jewish parents each independently converted to Roman Catholicism before meeting.
  • "So what started as a novel...became a real investigation into both my parents' conversions and my own identity." (12:40, Stephen J. Dubner)

• Name Changes: Parents adopted new names—Solomon became Paul; Florence became Veronica (her ballet stage name).

  • "If nomenclature is destiny, especially within a religious context, then yes, we are a good example of that." (20:20, Stephen J. Dubner)

• Returning to Judaism: Dubner did not have to formally convert due to matrilineal tradition but faced an emotional family rift, resolved with guidance from Cardinal O’Connor and the notion of an "informed conscience."

  • "That was really the beginning of a new kind of relationship between the two of us. I remain very, very grateful to Cardinal O'Connor for having done that." (25:05, Stephen J. Dubner)

3. Curiosity and Career Evolution

[26:27 – 33:43]

• Fascination with Identity, Belonging, Belief: Dubner views curiosity as a vital, childlike quality—and laments how education and adulthood often diminish it.

  • "If you can manage to get into your adulthood with that drive intact, then I think it makes life a lot more interesting." (26:40, Stephen J. Dubner)

• Making Freakonomics Radio: Driven by "how things work" and genuine curiosity, Dubner’s shows have tackled odd markets (e.g., candles, horses) and unexpected questions.

• Upcoming TV Show: Dubner is developing a talk show built on in-depth, character-driven conversations, aiming to explore "how people work," with plans to film in New York, Los Angeles, and London.

  • "I want to have conversations...that are less interviews about a topic and more conversations with a person." (32:09, Stephen J. Dubner)

4. Role Models, Hero Worship, and Disillusionment

[33:43 – 41:16]

• Franco Harris as Childhood Hero: After his father’s death, young Dubner became infatuated with Pittsburgh Steelers star Franco Harris—a relationship explored in his book "Confessions of a Hero Worshiper."

  • "I came looking for a savior, but what I found was a man. And maybe that's the truer gift." (40:32, quoted by Millman)

• Meeting Your Heroes: His real-life interactions with Harris were polite but distant, leading Dubner to accept the complexity and humanness of heroes.

  • "He was awesome. I loved him...I wish he’d loved me back a little bit more. But if I were him, I think he played it just right." (40:46, Stephen J. Dubner)

5. From Rock Band to Writing

[44:15 – 52:52]

• The Right Profile: Dubner’s college band, named after a Clash song, evolved from "terrible" to genuinely good, eventually signed by Arista Records. He ultimately left, wanting a more stable and private life.

  • "I'm not sure I want to lead a life where my main professional activity is drawing attention to myself, you know." (45:01, Stephen J. Dubner)

• Experiences with Recognition: Dubner discusses handling fame following the Freakonomics documentary—and notes his preference for the relative anonymity of writing and radio.

  • "I just don't like it...many people who are recognizable love being recognized. I get that...but that's just not a conversation that I'm crazy about having." (48:55, Stephen J. Dubner)

6. The Art and Philosophy of Writing

[52:52 – 60:38]

• Finding Your Voice: Dubner cautions against imitation; real creativity comes from honest self-expression and confidence in one's own taste, not merely modeling on admired works.

  • "Be that, be you...There's individuality in all of those things...write your writing, sing your song." (54:04, Stephen J. Dubner)

• On Success and Reception: He advocates for creating work true to oneself, even if it is not well-received, and acknowledges the pain of rejection but the necessity of trying.

7. The Making, Impact, and Legacy of Freakonomics

[60:40 – 77:57, 82:42-88:45]

• Book Genesis: The idea grew out of an NYT Magazine profile of Steve Levitt, evolving into a unique, data-driven book about odd questions and human incentives. The eventual title, Freakonomics, was suggested by Levitt’s sister.

  • "So we were looking for titles...when Levitt and I saw [Freakonomics], we both, like, burst out laughing with joy. And like, this is so...just so outrageous and outlandish. It’s so bad that it's great." (61:20, Stephen J. Dubner)

• Bestseller Phenomenon: The unexpected, transformative success of the book and its spinoffs (Super Freakonomics, Think Like a Freak, podcast, film).

  • "For those of you who hate me because, like, I get it, like, it's just too much luck for one, for two people, it's just too much luck." (65:52, Stephen J. Dubner)

• Hidden Incentives in Publishing: Dubner observes the tendency for industries to copy whatever’s successful, which stifles novelty; he calls for more courage among creators, publishers, consumers.

  • "There are wonderful things about civilization...but there is one thing too rare. And that thing is courage. I just think people need to understand that they need to give themselves permission to be courageous about everything." (68:19, Stephen J. Dubner)

• Journalism’s Role: He hopes Freakonomics' legacy is a reminder that "storytelling with data is better," encouraging journalism to move beyond anecdotes and embrace curiosity and rigorous evidence.

  • "The plural of anecdote is not data...you really have to work to get better data to represent more of the totality of...any issue." (82:42, Stephen J. Dubner)

• Economic Thinking as Human Thinking: Advocates for economics to always remember the human variables behind the data and formulas.

8. Confidence, Courage, and Training Your Mind

[69:41 – 77:17]

• Where Confidence Comes From: Confidence grows with successful repetition, but both Dubner and Millman agree it is fleeting and often needs to be actively cultivated.

• Training the Brain: Dubner describes learning—well into adulthood—that the mind is a muscle that can be intentionally redirected toward productive thought and away from negative rumination.

  • "Your mind or brain is a muscle, and you can control it." (71:24, Stephen J. Dubner)

Notable Quotes & Memorable Moments

• On Courage and Creation:
  "I just think people need to understand that they need to give themselves permission to be courageous about everything. About who they are, about what they make, about what they think."
  — Stephen J. Dubner (00:31, 68:19)

• On Meeting Franco Harris:
  "I came looking for a savior, but what I found was a man. And maybe that's the truer gift."
  — Quoted by Millman (40:32)

• On Writing with Data:
  "Storytelling is great. Storytelling with data is better."
  — Stephen J. Dubner (82:42)

• On Creative Philosophy:
  "Write your writing, sing your song. You know, I think it's really important to get to that point, to feel confident in your ability to do what you want to do."
  — Stephen J. Dubner (54:04)

Timestamps for Key Segments

• Early publication/teacher influence: 04:14 – 08:33
• Family tradition & religious upbringing: 08:33 – 26:27
• Curiosity, career, mindset: 26:27 – 33:43
• Hero worship/Franco Harris: 33:43 – 41:16
• Band years & move to writing: 44:15 – 52:52
• Writing, finding your voice: 52:52 – 60:38
• Freakonomics genesis & publishing: 60:40 – 64:26
• Impact, legacy, and data/journalism: 82:42 – 88:45
• Conclusion: 88:53 – End

Closing Thoughts

Dubner’s story is one of restless curiosity, thoughtful reinvention, and the honest, sometimes painful search for meaning and selfhood. From family rituals to striking book titles and data-driven storytelling, he repeatedly returns to the essential value of asking questions—of oneself, of others, of the world. As he says:
"I believe curiosity is natural for everyone... and the curiouser you are, I think the smarter you are, and the smarter you are, the curiouser you inevitably are too." (26:37, Stephen J. Dubner)

For more, listen to Freakonomics Radio or visit freakonomics.com. The new 20th anniversary edition of Freakonomics is released November 11th, 2025.