Design Matters with Debbie Millman

Guest: Chris Duffy
Episode Date: February 9, 2026
Podcast Theme: Exploring how creative people design their lives

Episode Overview

This episode features comedian, writer, and podcast host Chris Duffy in conversation with Debbie Millman. Chris discusses his new book, Humor Me: How Laughing More Can Make You Present, Connected and Happy, reflecting on the power of humor and how it shapes connection, resilience, and creativity. The conversation traces Chris's journey from childhood, through education and teaching, to a career spanning comedy, podcasting, and writing. Chris and Debbie delve into the mechanics of humor, the challenges of vulnerability, and how laughter helps navigate hardship and fosters authentic connection.

Key Discussion Points and Insights

1. Early Influences & Family Background

• Chris's Childhood Use of Humor

  • Shared story of bringing a joke book to cheer up his great-uncle after a heart attack, motivated both by attention and a sense of connection.

    "I knew that laughing made people feel good… It felt like this incredible magic trick that I wanted to do." (Chris, 03:46)

  • Credits his mom with fostering a love of reading by always providing books.

• Growing Up in New York

  • Raised in Manhattan; father from Michigan, worked at Port Authority in the World Trade Center during significant events (1993 bombing, 9/11).

    "You have that sense... when push comes to shove, people are here for you." (Chris, 06:20)

2. Education, Improv, and Early Comedy

• Brown University & Journalism Aspirations

  • Clarifies he majored in English (not philosophy or economics).
  • Thought he'd become a journalist, but the job market was poor, leading him to teaching.

    "At the time... I was applying to jobs at papers... the paper would go out of business." (Chris, 09:26)

• Improv Beginnings

  • Tried out for and joined Brown’s improv group "Starlinsons" after initial rejection.

    "We created this thing called Starlinsons... that shaped so much of my creative life." (Chris, 10:51)

  • Realized he was truly funny through packed performances and collaborative creative energy.

    "You have these 300 people packed in a room... when there’s that explosion of laughter, I felt like nothing’s better than that." (Chris, 12:22)

3. Teaching and the Peak of Creativity

• Teaching Fifth Grade & Creativity

  • Became a teacher in Boston, selected the age group for its openness to play and imagination.

    "Fifth grade was nice... the most mature where they would still go along with you in playing imagination games..." (Chris, 14:26)

  • Discusses research on how fifth grade is a peak for uninhibited creativity.

    "Fifth grade for many people is kind of the peak of totally uninhibited creativity... they have no thought of what are other people gonna think of this idea." (Chris, 15:37)

• Improv for Adults: Unlocking Creativity

  • Taught adults improv focusing on breaking down self-criticism and embracing spontaneity.

    "Most of the exercises... were to get them to let go of the self-critical part of their brain..." (Debbie (reading Chris), 16:25)

  • Leads Debbie through the “categories” exercise to show how pushing past planned responses yields authenticity and surprise.

    "At a certain point... you just start saying the real things." (Chris, 18:14)

4. Burnout, Rediscovering Humor, and Purpose

• Burnout from Teaching

  • Faced burnout dealing with difficult classroom situations and personal hardship stories from students.
  • Lost his sense of humor, felt laughter and seriousness were incompatible.

    "It really was not working... comedy became this release for me when I actually found it again." (Chris, 24:31)

• Reintegrating Humor

  • Realized the need to deliberately inject laughter back into his life and career for authenticity and sustainability.

    "This is not who I am. And not being who I am is impossible to sustain." (Chris, 25:18)

  • Seeks to combine education with entertainment: "I want to entertain with a purpose."

5. Comedy Career Development

• Leaving Teaching for Comedy
  • Took a year off with safety net of returning to teaching if needed; cobbled together an income from various creative and non-comedy jobs.

    "The response that my dad had... I can't believe you paid your bills. And that kind of is still how I think of it all." (Chris, 27:49)

• On Writing Stand-Up
  • Emphasizes the process: notice oddities, write them down, attach emotions to observations.

    "You walk through the world and you pay attention to things... it's seeds, not the full-grown harvested plant." (Chris, 28:50)

• Handling Failure
  • Failure is part of stand-up; people only remember the greats, not the bombs.

    "When you bomb... people don’t really remember that." (Chris, 30:28)

6. Transition to Podcasting and TV

• From Live Shows to TV Writing

  • Created "You're the Expert," a comedy panel show guessing and explaining scientists’ work, to combine humor with meaningful content.

    "It was a thing that played exactly to my strengths, which is I was so curious about the scientists..." (Chris, 35:19)

  • Led to TV writing roles (National Geographic, Wyatt Cenac's Problem Areas).

• "Wrong Answers Only"

  • Continues the blend of comedy and science, now as a live, multimedia game show.

    "You get these really funny comedians, and they've never made jokes about sea urchins... it's so fun." (Chris, 36:00)

7. Personal Work: Love, Connection, and Vulnerability

• One-Person Show: "How to Stay in Love"
  • Combines research and deeply personal experience (helping his wife through depression) to explore relationships.

    "Sometimes you need to have metabolized it more to make it into good art." (Chris, 41:30)

  • Chris's lesson: Commitment is about building something brick by brick, weathering hard years, and honesty.

    "Some days you just get another brick on... but there’s still a lot there." (Chris, 42:51)

8. Podcast Hosting: "How to Be a Better Human"

• Entering Podcasting

  • Stems from a recommendation after a TED staffer saw his comedy show.
  • Emphasizes accessible, humor-laced dialogue rather than performative self-seriousness.

    "It was the first thing that I did where it was in no way edited for laughs." (Chris, 48:28)

• Negotiating Comedy vs. Earnestness

  • Had to learn new ways to engage authentically when laughs were not the only goal.

    "[I had to] trust the editors and producers that they weren’t going to make me look like little Tony Robbins..." (Chris, 49:19)

9. Humor in Daily Life & New Book: "Humor Me"

• On Writing "Humor Me"

  • Argues laughter is about presence, connection, and generosity—not just performance.

    "Humor done right is so much more generous and it’s so much more about laughing with people." (Chris, 58:03)

• Book’s Core Message

  • It's about increasing laughter in daily life, not teaching stand-up.

    "This book is about laughing more. How do you have more laughter in your life?" (Chris, 59:15)

• Pillars of a Good Sense of Humor

  1. Paying Attention: Notice absurdity in everyday life.
     • "If you're on your phone... you will certainly not notice the dog wearing a costume..." (Chris, 61:36)
  2. Laughing at Yourself: Admit and embrace your messiness.
     • "People like us so much more if we acknowledge our flaws and laugh at them..." (Chris, 63:54)
  3. Taking Social Risks: Offer and accept conversational "doorknobs"—ways to move into unexpected, playful areas.
     • "Any good conversation, you will both be accepting and turning the doorknobs and offering the doorknobs." (Chris, 65:44)

• Difference Between Being Funny & Having a Sense of Humor

  • The funniest people aren’t always comedians—they’re present, engaged, and able to laugh easily with others.

    "It's not really because they're saying prepped lines... it’s because they're so in the moment with you." (Chris, 60:49)

10. Humor, Social Change, and Ethics

• The Power and Responsibility of Humor

  • Acknowledges humor can be weaponized; those skilled in comedy have a real responsibility.

    "Bullies are actually funny... that's something that they're able to do... you have to be thoughtful of how we use [humor]." (Chris, 69:39)

  • Concepts of “punching up” and “punching down”—good comedy challenges power, not the vulnerable.

• Humor as a Tool for Coping/Connecting

  • Humor helps people metabolize discomfort and grief; it creates solidarity and a sense of being seen.

    "When you have that clear moment of, oh, they get it, we are on the same page, and we know because we're laughing about it in a way that only people who get it can laugh…" (Chris, 76:28)

11. Memorable Personal Anecdotes

• Dad’s Social Media Advocacy

  • Chris’s dad earnestly DM’d Drew Barrymore to book him on her show after Chris won a Webby.

    "[He] messaged Drew Barrymore... 'You gotta have [Chris] on the show, you two would, like, love each other.'" (Chris, 51:24)

• “Becoming” CEO of LinkedIn

  • For a joke, Chris made himself CEO of LinkedIn—caused viral confusion until LinkedIn suspended his account.

    "I made a profile and I said, My job is CEO of LinkedIn... Not only did it allow me to, it sent an email to everyone in my contacts..." (Chris, 54:22)

  • Further mischief: he now runs "Linked Inn," a fictional networking bed & breakfast.

Notable Quotes & Timestamps

• On the Magic of Connection (06:20):

  "When push comes to shove, people are here for you." — Chris Duffy

• On Performing Improv (12:22):

  "When there's that huge explosion of laughter, I felt like nothing's better than that. But... I made that happen." — Chris Duffy

• On Teaching vs. Stand-Up (24:31):

  "Comedy became this release for me when I actually found it again. But there was this period where it felt like: 'You're dealing with real stuff, you shouldn't have any space for this.'" — Chris Duffy

• On Humor as Generosity (58:03):

  "Humor done right is so much more generous and it’s so much more about laughing with people." — Chris Duffy

• On Laughter and Coping (60:37):

  "You can have a really hard day. And if you find a way to laugh really hard during that, so much of the stress and anxiety and residue is washed away." — Chris Duffy

Timestamps for Important Segments

• 03:46: Chris shares early memory of using humor for connection
• 06:20: Impact of 1993 WTC and 9/11 on his worldview
• 10:51: Discovering improv and finding creative voice
• 14:26: Why teaching fifth grade—peak creativity
• 18:14: Improv exercise for authenticity
• 24:31: Losing and reclaiming humor while teaching
• 27:49: Taking the leap to comedy career
• 30:28: Lessons from failing at open mics
• 35:19: Creating "You’re the Expert"—blending comedy and knowledge
• 36:00: Launching "Wrong Answers Only"
• 41:30: Using humor to process difficult times in personal life
• 48:28: Hosting "How to Be a Better Human" and moving beyond comedy
• 58:03: Core theme of new book: generosity and laughter
• 61:36: Three pillars of building a sense of humor
• 69:39: The ethical responsibility of those skilled at humor
• 76:28: How laughter helps metabolize grief

Conclusion

Chris Duffy’s journey demonstrates that humor is more than just performance—it’s a deeply human, connective, and resilient force. His work shows that anyone can cultivate more laughter and presence in their lives, and that humor, approached thoughtfully, can foster communal bonds, personal healing, and even social change. Humor Me offers accessible, practical tools to unlock more joy and authenticity for everyone, and this episode brims with stories and wisdom perfectly in step with Design Matters’ exploration of creative lives.

Recommended:

• Humor Me: How Laughing More Can Make You Present, Connected and Happy by Chris Duffy
• Chris’s podcast: How to Be a Better Human

For more on Chris Duffy:
Website: chrisduffycomedy.com
Newsletter: Bright Spots
Podcast: How to Be a Better Human

“The things that we pay attention to and document are what we will remember and what will shape us.” —Chris Duffy (84:36)