Best Midlife Pilot Podcasts (2025)

1
EP129 - Debriefing the Debriefs: Part 1 - Private Pilot Checkrides 1:04:40

4h ago1:04:40

1:04:40

In this first installment of their two-part check ride series, the Midlife Pilot Podcast crew mines gold from their community's private pilot exam experiences through intimate Patreon debriefs. Ben, Brian, and Ted tackle everything from the anxiety-inducing oral exam (which Ben likens to "walking into the delivery room") to those heart-stopping lan…

1
From The Vault: Neuroscientist Matthew Walker On Why Sleep Is Your Superpower 3:11:40

2h ago3:11:40

3:11:40

Rich is joined by Dr. Matthew Walker, renowned sleep scientist, to discuss the impact of sleep deprivation on immunity, brain health, and longevity.By Rich Roll

1
From The Vault: Neuroscientist Matthew Walker On Why Sleep Is Your Superpower 3:06:59

3d ago3:06:59

3:06:59

Dr. Matthew Walker is a world-renowned neuroscientist, sleep expert, and the bestselling author of “Why We Sleep.” In this conversation, we explore sleep not as a passive state, but as the biological foundation of life itself—the platform from which wakefulness emerges. We dive into the architecture of sleep, its vital role in immune function, dise…

1
Guy Makes Your Home Better (Pilot One) 13:33

9h ago13:33

13:33

Bonus Guy needs a new podcasting gig.By Paul Watkinson

1
Why Chef José Andrés Googled ‘How to Be a Father’ 41:05

5d ago41:05

41:05

José Andrés is at the helm of more than a dozen restaurants and is famous for the humanitarian work that his organization World Central Kitchen does everywhere from Haiti to Gaza. But when it comes to parenting, José says he’s often felt less than confident. In this episode, he discusses his somewhat rocky upbringing in Spain, his successes and str…

1
Olympic Coach Stuart McMillan On The Science Of Speed, Unlocking Your Body’s True Potential & Why Sprinting Is The Ultimate Human Activity 1:55:58

7h ago1:55:58

1:55:58

Rich is joined by Stuart McMillan, an elite track & field coach to Olympic champions, to discuss the alchemy of speed and human movement.By Rich Roll

1
Olympic Coach Stuart McMillan On The Science Of Speed, Unlocking Your Body's True Potential & Why Sprinting Is The Ultimate Human Activity 2:04:13

6d ago2:04:13

2:04:13

Stuart McMillan is an elite track and field coach who has guided 70+ Olympians to over 30 medals across nine Olympic Games. As CEO of ALTIS, a global leader in sports education, he's revolutionized how we understand human movement. This conversation is an exploration of speed—not just as a metric, but as a kind of alchemy. At the heart of Stuart's …

1
The Simulation Hypothesis 11:06

12h ago11:06

11:06

Guy tries to work out if it’s all just a game.By Paul Watkinson

1
EP128 - Two Bounces and a Skip: Planning vs. Reality 1:08:00

9d ago1:08:00

1:08:00

Join the Midlife Pilot Podcast crew as they return from their epic Texas fly-in adventure with tales of triumph, near-misses, and one unfortunate set of wheel pants. Ted recounts his 28.3-hour post-fly-in journey that somehow went east instead of west ("Look, you can only chase tailwinds for so long"), while Brian shares his VFR limits revelation (…

1
Your IRL Dating Stories 54:35

6d ago54:35

54:35

A man delivers an unforgettable pickup line. A woman asks her Uber driver out on a date. A rancher swears off men and then, years later, suddenly develops feelings for the guy down the road. This week, listeners share offline dating stories for the ages, including charming meet-cutes, frustrating missed connections, and happily ever afters. We also…

1
High Functioning: The Hidden Depression That May Be Stealing Your Joy & The Tools To Get It Back With Dr. Judith Joseph 1:50:21

7d ago1:50:21

1:50:21

Rich is joined by Dr. Judith Joseph, NYU psychiatrist, to explore high-functioning depression and why achievers struggle to feel joy despite success.By Rich Roll

1
High Functioning: The Hidden Depression That May Be Stealing Your Joy & The Tools To Get It Back With Dr. Judith Joseph 1:58:31

14d ago1:58:31

1:58:31

Dr. Judith Joseph is a Harvard-trained psychiatrist, clinical professor at NYU Medical School, and a renowned voice on high-functioning depression. In this conversation, we explore the paradox of achievement and anhedonia—the curious, often painful reality that success doesn't always equate to joy. Judith shares her clinical insights into why so ma…

1
Final Warning 10:13

8d ago10:13

10:13

Guy faces a perilous situation, but finds further evidence that he might be related to God.By Paul Watkinson

1
Earth’s Hidden Wisdom: Paul Hawken On Reframing Carbon, Consciousness & Why Hope Lies Within Nature’s Intelligence 1:45:03

11d ago1:45:03

1:45:03

Rich is joined by Paul Hawken, environmentalist and bestselling author, to discuss carbon as life's foundation and symbiotic climate solutions.By Rich Roll

1
Earth's Hidden Wisdom: Paul Hawken On Reframing Carbon, Consciousness & Why Hope Lies Within Nature's Intelligence 1:42:09

18d ago1:42:09

1:42:09

Paul Hawken is one of the great elder statesmen of environmentalism, a bestselling author, and the mind behind Drawdown and Regeneration. This conversation explores the biosphere's intrinsic intelligence through the expansive lens of Paul's latest book, Carbon: The Book of Life. We discuss carbon's improbable origins, examine the mycelial networks …

1
EP127 - Big Texas Send Live from T82: Between Two Wheelpants 1:13:21

12d ago1:13:21

1:13:21

The Midlife Pilot Podcast hosts the Big Texas Send fly in at T82 in Fredericksburg, TX and lands with a thud (but "didn't dent the runway") at the gorgeous TAC Aero hangar. Ben, Brian, and Ted swap harrowing journey tales involving everything from Brian's "measured scud running" to Ted mysteriously ascending to 15,000 feet in a light sport ("Try a …

501
Isabel Allende on Grief, Ayahuasca, and Dating After 70 53:01

20d ago53:01

53:01

Isabel Allende didn’t publish her first book until she was 39, after losing nearly everything in the wake of the Chilean military coup. More than four decades later, she’s become one of the most beloved Spanish-language authors, with over 80 million copies of her books sold worldwide. After political exile, writing books became Allende’s way of mak…

1
Kate Courtney Is Sending It: The Champion Mountain Biker On Redefining Elite Performance, Finding Joy In The Struggle & Seeing Sport As An Authentic Expression 2:17:31

14d ago2:17:31

2:17:31

Rich is joined by Kate Courtney, a world champion cyclist, to discuss She Sends Racing, Olympic journey, and the mission to empower women.By Rich Roll

1
Kate Courtney Is Sending It: The Champion Mountain Biker On Redefining Elite Performance, Finding Joy In The Struggle & Seeing Sport As An Authentic Expression 2:14:16

20d ago2:14:16

2:14:16

Kate Courtney is a world champion mountain biker, Olympian, and the palmarès-rich face of American cycling. This conversation examines Kate's Olympic torch moment with Tom Cruise, her athletic philosophy, and her groundbreaking She Sends Racing initiative. We delve into mountain biking's Marin County roots, the tension between data and intuition, b…

1
Corporate Sustainability 10:10

21d ago10:10

10:10

Guy explains how companies can save the world, using squirrels, floods, hair, solar power, intern safety and wildfires.By Paul Watkinson

1
EP126 - Information Whiskey: "Like Oregon Trail Without Dysentery" 56:08

20d ago56:08

56:08

The Midlife Pilot crew prepares for their "Big Texas Send" fly-in at T82 while navigating spring weather challenges. Brian celebrates returning to flying after a 42-day maintenance hiatus, sharing stories of tower tours and smoke-signaling air tractors. Ted plans his epic 1800-mile cross-country journey in his LSA, which Brian dubs "Oregon Trail wi…

1
The Patient and Cunning Work of Defending LGBTQ Rights with a Republican Supermajority 56:14

27d ago56:14

56:14

In West Virginia, Republicans hold one of the largest supermajorities in the country, and it’s growing. Just 11 Democrats — down from 14 last year — are in the 134-member Legislature. It's a political reality that isn't necessarily conducive to advancing LGBTQ rights. But that's Andrew Schneider's job. As head of Fairness West Virginia, Andrew has …

1
Inside ‘The Telepathy Tapes’: Creator Ky Dickens Reveals The Extraordinary Story Behind The Podcast Sensation 2:00:15

27d ago2:00:15

2:00:15

Ky Dickens is the award-winning filmmaker behind "The Telepathy Tapes," the viral podcast phenomenon. This conversation explores the intersection of neurodiversity and consciousness as Ky shares her journey documenting non-speaking autistic individuals with apparent telepathic abilities. We discuss her transformation from pragmatic skeptic to someo…

1
Inside ‘The Telepathy Tapes’: Creator Ky Dickens Reveals The Extraordinary Stories Behind The Podcast Sensation 1:52:01

22d ago1:52:01

1:52:01

Rich is joined by Ky Dickens, filmmaker of "The Telepathy Tapes," to explore telepathic abilities in non-speaking autistic individuals.By Rich Roll

1
Intellectual Property 10:00

28d ago10:00

10:00

Guy probably needs a new landlord, and helps interns to navigate intellectual property.By Paul Watkinson

1
The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life’s Second Half 2:07:47

25d ago2:07:47

2:07:47

Rich is joined by Chip Conley, founder of Modern Elder Academy, to discuss transforming midlife from crisis to chrysalis and navigating life's longest phase.By Rich Roll

1
The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half 2:05:30

1M ago2:05:30

2:05:30

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical gr…

1
EP125 - "What Am I Doing?": Extinguishing Helmet Fires Before They Consume You 1:04:59

27d ago1:04:59

1:04:59

When your CFI asks for your name and you respond with "standby" – you're experiencing what pilots call a helmet fire. In this episode, Ben, Brian, and Ted dive into the phenomenon of task saturation that affects pilots at every level, from Ben's instrument approach adventures where he made what sounded like "Charlie Brown's teacher" over the radio,…

1
Are Airline Pilots Allowed to Be Depressed? 54:32

1M ago54:32

54:32

To fly a plane, pilots must prove to the Federal Aviation Administration that they’re physically and mentally fit. But when it comes to mental health, the rules are complicated and, some say, outdated. Pilots who need antidepressants are limited to a short list of approved medications and must take a mandatory six-month leave. Even common diagnoses…

1
Beyond 10% Happier: Dan Harris On Meditation As A Superpower, Transforming Anxiety, & Finding Peace In Uncertain Times 1:58:01

1M ago1:58:01

1:58:01

Rich is joined by Dan Harris to explore meditation's transformative power beyond stress relief, revealing the path to equanimity in uncertain times.By Rich Roll

1
Beyond 10% Happier: Dan Harris On Meditation As A Superpower, Transforming Anxiety, & Finding Peace In Uncertain Times 1:58:19

1M ago1:58:19

1:58:19

Dan Harris is the former ABC News anchor whose on-air panic attack catalyzed his transformation from skeptical journalist to meditation ambassador. This conversation explores Dan’s journey with meditation—from stress management tool to profound inquiry into consciousness and uncertainty. We discuss his practice evolving far beyond his bestselling b…

1
Internship Podcasting Awards 10:01

1M ago10:01

10:01

Guy really really really really wants to win an award.By Paul Watkinson

1
EP124 - Parking: The Episode That Goes Nowhere 57:29

1M ago57:29

57:29

Join the Midlife Pilot Podcast crew as they tackle the surprisingly complex world of airport parking that flight schools never teach you. Between Brian's maintenance woes with Lucy, Ted's triumphant return of "the egg" from annual, and preparations for their upcoming Texas fly-in, the hosts share hilarious stories about confusing marshaling signals…

1
How the ‘Subway Takes’ Guy Became His Own Nepo Baby 56:19

1M ago56:19

56:19

Kareem Rahma, host of the viral web series Subway Takes, says he’s been working since he was 14 and hasn’t really taken a break. In high school, he worked service jobs. In college, he bought and re-sold motorcycles, jeans, and whatever else he thought he could flip. This week on the show, Kareem explains why he’s had so many jobs, including posts a…

1
Phil Stutz & Elise Loehnen Share Tools For Inner Well-being, How To Embrace Pain, Uncertainty & Constant Work As Divine Invitations, & Why Everything You’re Avoiding Will Transform Your Life 1:36:27

1M ago1:36:27

1:36:27

By Rich Roll

1
Phil Stutz & Elise Loehnen Share Tools For Inner Well-being, How To Embrace Pain, Uncertainty & Constant Work As Divine Invitations, & Why Everything You’re Avoiding Will Transform Your Life 1:33:29

1M ago1:33:29

1:33:29

Phil Stutz is the legendary psychiatrist, author, and protagonist in the Netflix documentary “Stutz.” Alongside co-author and writer Elise Loehnen, they explore their new book “True & False Magic.” This conversation delves into “Part X”—the destructive force within us all—along with Universe 1 vs. Universe 2 thinking, and how pain, uncertainty, and…

1
Nature 10:40

1M ago10:40

10:40

Guy gets arguably too close to nature.By Paul Watkinson

1
Power, Property, & Prestige: Kurt Sutter & Katey Sagal Share The Unfiltered Truth About Marriage, Recovery, Success Addiction & The Path Back To Purpose 2:10:06

1M ago2:10:06

2:10:06

Rich is joined by Kurt Sutter and Katey Sagal to explore how success threatens relationships and the journey back to what truly matters.By Rich Roll

1
Power, Property, & Prestige: Kurt Sutter & Katey Sagal Share The Unfiltered Truth About Marriage, Recovery, Success Addiction & The Path Back To Purpose 2:07:31

2M ago2:07:31

2:07:31

Kurt Sutter and Katey Sagal are the Hollywood power couple behind “Sons of Anarchy,” numerous iconic performances, and hosts of the podcast “PIE.” This conversation strips bare the intoxicating trap of fame, the parallel paths that led them both to sobriety at 31, and the brutal honesty required to save their relationship when “money, property, and…

1
EP123 - The Answer to All Solutions: Level Seven Hangar Living 1:03:41

1M ago1:03:41

1:03:41

In this episode, Ben, Brian, and Ted dive into the challenges of finding and maintaining hangar space, or not having one. From ratchet straps (BAD) and tornado warnings (ALSO BAD) to the joys of electricity and the sorrows of cold starts, the guys discuss how far they'd travel for a good hangar and why sometimes your plane becomes 'an outdoor pet.'…

1
Scorpion Venom and Coffee Enemas Didn't Cure My Mother's Cancer 44:18

2M ago44:18

44:18

At a time when skepticism about conventional medicine has become even more mainstream, we’re revisiting a story about the causes and effects of that mistrust. Archie Matlow’s mother refused to get a surgery that could have saved her life, which led to her and Archie trying to love each other while bitterly at odds. You can listen to the full audio …

1
Let Them Theory: Mel Robbins On Reclaiming Your Power, Finding Freedom In Letting Go & The Simple Tool That’s Transforming Millions of Lives 1:56:09

2M ago1:56:09

1:56:09

Rich is joined by Mel Robbins, bestselling author, to discuss her “Let Them Theory” and how surrendering control paradoxically gives us true power.By Rich Roll

1
Let Them Theory: Mel Robbins On Reclaiming Your Power, Finding Freedom In Letting Go & The Simple Tool That's Transforming Millions of Lives 1:54:47

2M ago1:54:47

1:54:47

Mel Robbins is a celebrated podcast host, #1 New York Times bestselling author, and one of the most sought-after experts in mindset and behavior change. This conversation explores the paradox at the heart of human suffering—that we exhaust ourselves trying to control the uncontrollable. Mel’s counterintuitive “Let Them Theory” offers a deceptively …

1
The 24-Hour Podcast Marathon 10:03

2M ago10:03

10:03

Guy tries to host a 24-hour episode, but seems slightly unwell.By Paul Watkinson

1
Plurals 11:22

2M ago11:22

11:22

Bonus Guy struggles with singularities.By Paul Watkinson

1
EP122 - "I Plan My Stops Around Food" and IFR Training: CFII Erica Gilbert 1:04:36

2M ago1:04:36

1:04:36

Join us for special guest Erica Gilbert, a CFII and TBM pilot who brings her expertise on cross-country planning and adult learning to the show. While Ben mourns his grounded "Beast" waiting on engine work, and Mark celebrates his impressive 693-nautical-mile nonstop flight in his upgraded Cherokee 235, Erica shares her refreshing approach to fligh…

1
Laughing About Hard Things 1:11:29

2M ago1:11:29

1:11:29

Alongside life's darkest moments there often are moments of absurdity that make us laugh. In this episode, from a live San Francisco comedy festival in January, Anna and guests talk about the special kind of comedy born of something sad. Comedians Guy Branum and Carl Tart share stories of writing a sitcom about Zoom-era social relationships. Chanel…

1
You Are Already Enough: Maria Shriver On Finding Your Voice, Healing After Heartbreak, Brain Health Advocacy, & The Power Of Self-Acceptance 1:53:32

2M ago1:53:32

1:53:32

Rich is joined by Maria Shriver to explore poetry as healing, finding authentic self beyond family legacy, and her work in women's brain health.By Rich Roll

1
You Are Already Enough: Maria Shriver On Finding Your Voice, Healing After Heartbreak, Brain Health Advocacy, & The Power Of Self-Acceptance 1:53:57

2M ago1:53:57

1:53:57

Maria Shriver is a renowned journalist, Kennedy family scion, and award-winning advocate for women's brain health. This conversation explores the parasocial relationship between public figure and audience as Maria shares her authentic journey of self-discovery through poetry. We discuss her upbringing in America's political "royalty,&q…