My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now.
If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves?
I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow.
So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism!
Let’s grow together.
PodSkip has analyzed 1 episode of A Bit of Optimism, averaging 1.0 ads per episode (1% of runtime).
Revisited: Why Relationships Are the Secret to a Long, Happy Life with Psychotherapist Esther Perel
Oct 13, 2026
Hello from Team Simon! We’re taking a few weeks off and will be back with brand-new episodes of A Bit of Optimism on Tuesday, October 27.
Until then, we’re revisiting some of our favorite…
Revisited: Your Instincts Know What You Want with Happiness Expert Arthur Brooks
Oct 06, 2026
Team Simon here! A Bit of Optimism is on a short break, and brand-new episodes return October 27. Until then, we're revisiting a few conversations we keep coming back to.
This week it's Arthur…
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Revisited: The Power of Saying "Screw It" with Rob Lowe
Sep 29, 2026
Hello from Team Simon! We're taking a few weeks off and will be back with brand-new episodes of A Bit of Optimism on Tuesday, October 27. Until then, we're revisiting some of our favorite…
What Mentally Strong People Do on Their Worst Days with Psychotherapist Amy Morin
Sep 22, 2026
Be honest: you've taken a mental health day that made you feel worse. You stayed in bed, you avoided the thing, and by evening it was still waiting for you—with less of the day left to face it.
Amy…
The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan
Sep 15, 2026
Why Trying to “Sound Smart” is Losing You the Room with Strategic Story Producer Rob Willis
Sep 08, 2026
Your Limits Are Learned (And They Can Be Unlearned) with Brain Coach Jim Kwik
Sep 01, 2026
How to Trust Yourself When Everyone Has an Opinion with Love Thy Nader's Mary Holland Nader
Aug 25, 2026
What Happens When You Bet on Yourself with Ted Lasso’s Brendan Hunt
Aug 18, 2026
How to Say the Hard Thing and Keep the Relationship | A Bit of Optimism: Feelings at Work | PART 5
Aug 11, 2026
Why Being Right Is Costing You Trust | A Bit of Optimism: Feelings at Work | PART 4
Aug 04, 2026
What Is Your Team Afraid to Tell You? | A Bit of Optimism: Feelings at Work | PART 3
Jul 28, 2026
The Secret to Better Conversations Isn't Talking | A Bit of Optimism: Feelings at Work | PART 2
Jul 21, 2026
The Hidden Cost of Always Saying Yes | A Bit of Optimism: Feelings at Work | PART 1
Jul 14, 2026
Why We Fall for the Wrong Person with Couples Therapist Dr. Harville Hendrix
Jul 07, 2026
How to Tell If Fear Is Protecting You or Holding You Back with Extreme Athlete Nelly Attar
Jun 30, 2026
Remembering Bob Chapman: The Mentor Who Changed My Life
Jun 23, 2026
The AI Skills Nobody is Teaching (And Everyone Needs) with AI Expert Ethan Mollick
Jun 16, 2026
How to Stop Letting Your Own Thoughts Make You Sick, Stressed, and Stuck with Dr. Ellen Langer
Jun 09, 2026
What Happens When You Stop Optimizing and Start Committing with Former LA Lakers President Tim Harris
Jun 02, 2026
Revisited: Choose Your Seven Humans Wisely with Author Fredrik Backman
May 26, 2026
How to Stop Being Socially Awkward (According to Science) with Behavioral Scientist Vanessa Van Edwards
May 19, 2026
Stop Telling Us Everything Happens for a Reason with Anti-Victim Tom Nash
May 12, 2026
The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner
May 05, 2026
The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby
Apr 28, 2026
The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger
Apr 21, 2026
Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole
Apr 14, 2026
Ken Burns and the Art of Telling the Whole Story
Apr 07, 2026
What Happens When You’re Naive Enough to Try with KIND Founder Daniel Lubetzky
Mar 31, 2026
AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara
Mar 24, 2026
