Best Midlife Pilot Podcasts (2025)

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

4h 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

3h 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

24h 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
The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half 2:05:30

5d 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

7d 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

7d 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 1:58:19

8d 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
EP124 - Parking: The Episode That Goes Nowhere 57:29

14d 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

14d 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 1:33:29

15d 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
Power, Property, & Prestige: Kurt Sutter & Katey Sagal Share The Unfiltered Truth About Marriage, Recovery, Success Addiction & The Path Back To Purpose 2:07:31

19d 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

21d 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

21d 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 1:54:47

22d 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
EP122 - "I Plan My Stops Around Food" and IFR Training: CFII Erica Gilbert 1:04:36

28d 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

28d 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 1:53:57

29d 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…

1
ROLL ON 2025 So Far: Navigating Uncertainty, Getting Unstuck, Elmo, Psychedelics, ‘Adolescence’ & More 2:02:07

1M ago2:02:07

2:02:07

Roll On is back baby! Today Rich and Adam Skolnick catch up on the decade that is 2025. On tap is SXSW, Elmo, psychedelics, the LA fires, and practical strategies for navigating the turbulence of our current moment. They also go deep on the Netflix hit “Adolescence” and its many important themes, including the impact of social media on teenagers an…

1
EP121 - Information Whiskey: Between Patience and Numbness 1:03:48

1M ago1:03:48

1:03:48

Join Ben, Brian, and Ted for hangar talk about the joys (and pains) of annual inspections in this episode of the Midlife Pilot Podcast. The guys commiserate over their planes being simultaneously grounded, with Ben's Beast down to five cylinders and showing remarkable "patience" (or is it numbness?). Brian dishes on his new book of aviation essays …

1
A Middle-Aged Couple Made Porn to Spice Things Up. Then One of Them Got Fired. 52:33

1M ago52:33

52:33

When Joe Gow was fired from his position as chancellor and professor at the University of Wisconsin at La Crosse, his superiors said it was due to “abhorrent” behavior. Joe had made porn videos with his wife Carmen and uploaded them onto the internet under the name “Sexy Happy Couple.” This week, Joe and Carmen tell their side of the story and expl…

1
The Explorer's Gene: Alex Hutchinson On Humanity’s Drive To Seek The Unknown, The Science Of Uncertainty, & Why Effort Creates Meaning 2:24:47

1M ago2:24:47

2:24:47

Alex Hutchinson is a National Magazine Award-winning journalist, Cambridge-trained physicist, and bestselling author of “Endure” and “The Explorer’s Gene.” This conversation explores Alex’s transcendent perspective on our primordial drive to seek the unknown. We unpack his fascinating evolution from elite runner and NSA researcher to becoming the v…

1
Introducing Ask Lisa: The Psychology of Parenting: "Should I Talk with My Teens About My Own Mental Health Challenges?" 1:01:54

1M ago1:01:54

1:01:54

Today I’m sharing an episode of Ask Lisa: The Psychology of Parenting hosted by Dr. Lisa Damour and Reena. In this episode, Dr. Lisa Damour and Reena explore the topic of "Should I Talk with My Teens About My Own Mental Health Challenges?" Subscribe to Ask Lisa: The Psychology of Parenting on Spotify and Apple Podcasts. Find out more about Voicing …

1
EP120 - Descending from Mount Stupid: with Paul Craig 1:04:17

1M ago1:04:17

1:04:17

For this very special episode we welcome Paul Craig, author of "The Killing Zone," "Be a Better Pilot," and numerous other aviation books including his memoir "Flight Times: Stories from the Second Best Instructor." In this episode, we explore how aviation has evolved since Paul's last book edition, from the rise of electronic flight bags to the We…

1
Life After Blowing It All Up: A Sugar Baby Story Revisited 49:31

1M ago49:31

49:31

In 2020, we made an episode about a listener who cheated on his wife with sex workers and was going through a divorce. He told us the idea to go on the website Seeking Arrangement came from an episode we made about sugar babies. A few weeks ago we called “Ethan” back to see what’s changed in his life since our first conversation, and how he navigat…

1
Good Stress: Jeff Krasno On The Health Benefits of Deliberate Discomfort, How To Have Hard Conversations & Applying Eastern Wisdom To Western Medicine 2:23:12

1M ago2:23:12

2:23:12

Jeff Krasno is a wellness entrepreneur, author of “Good Stress,” and co-founder of the iconic global yoga festival Wanderlust. This conversation explores Jeff’s journey from “wealth and hellness” to authentic well-being. His thesis on hormetic stress offers an antidote to our convenience-obsessed world. We discuss the political horseshoeing of well…

1
The Man Who (Literally) Owns Nothing: Radical Minimalist Robin Greenfield On Barefoot Walking 1,600 Miles, Living In Harmony With Earth, & Finding Freedom Through Simplicity 2:35:53

2M ago2:35:53

2:35:53

Robin Greenfield is a transcendental environmental activist who has taken the concept of simplicity to its existential extreme. This conversation explores how Robin's radical approach to consumption challenges our assumptions about possession, examining his 1,600-mile journey down the Pacific coast, his current experiment living in Griffith Park wi…

1
EP119 - The Cockpit Lies, Data Doesn't: Flysto Debrief 54:42

2M ago54:42

54:42

Join Ben, Ted, and special guest Mark (aka 1DullGeek) as they talk Flysto, the flight-tracking app that brutally reveals they're better and worse pilots than they thought. Geek out over landing scores, wind data, and traffic playback that "takes the emotional component out of the debrief" – perfect for analyzing that crosswind landing you swore was…

1
Call It ‘A Midlife Awakening’ 58:21

2M ago58:21

58:21

Anna talks to writer Ada Calhoun, author most recently of the novel Crush, about a married woman succumbing to extramarital temptation (she wrote it while she herself was separating from her husband) and then to comedian Rosebud Baker about her new Netflix comedy special, The Mother Lode, which is all about late-stage pregnancy and early motherhood…

1
Annaka Harris On Why Consciousness Just Might Be Fundamental To Reality 1:42:39

2M ago1:42:39

1:42:39

Annaka Harris is a New York Times bestselling author and creator of the groundbreaking audio documentary series “Lights On.” This conversation explores the profound question of whether consciousness is fundamental to the universe rather than merely an emergent property of complex matter. We discuss the ineffable nature of felt experience, the illus…

1
EP118 - All Aboard the Pain Train: The Trials of Aircraft Ownership 49:21

2M ago49:21

49:21

"Freedom to go broke." The guys dive deep into the bittersweet reality of aircraft ownership—from the freedom it provides to the unique challenges it presents. Brian compares airplane ownership to marriage, Ted discusses his aversion to suction cups, and Ben reveals he's "fully funded on my pro rata share" of an eventual engine overhaul. They discu…

1
From Uncertainty to Total Chaos, Your Stories About the New Trump Term 55:14

2M ago55:14

55:14

Since the inauguration in January, we’ve been getting emails and voice recordings from people whose lives have been thrust into uncertainty due to changes made by the Trump administration. Many federal workers and people who rely on federal money have lost their jobs. Others feel vulnerable and uncertain. This week, we’ll hear from a range of peopl…

1
Emotional Fitness: Dr. Ethan Kross On Dealing With Difficult Feelings, Controlling Your Inner Voice & The Science of Emotional Regulation 2:22:58

2M ago2:22:58

2:22:58

Dr. Ethan Kross is a renowned psychologist, bestselling author, and expert on controlling the conscious mind. This conversation explores his innovative approach to mental fitness and how our emotions function as an operating system. We examine why difficult emotions serve a purpose, how our inner dialogue shapes our reality, and why we have more co…

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