Episodes 1-10
Don't Let The Old Man In: 2025 Highlights
This isn’t your typical podcast episode. Instead of one conversation, Pod O’Sullivan brings you 13 pivotal moments from the most powerful interviews of 2025. These are the insights that stopped him in his tracks, the conversations that made him think, “everyone needs to hear this.”
Understanding Shame and Midlife Transformation: Ben Larke
For midlife men, shame often lurks beneath the surface of our carefully constructed lives. We’ve built the career, bought the house, raised the kids. From the outside, everything looks sorted. But inside? There’s often a different story playing out—one we’ve been keeping secret, sometimes even from ourselves.
Ben Larke is a clinical psychologist who specialises in working with men navigating midlife transitions. He understands shame not just as a clinician, but as someone who’s done his own deep work.
Why successful men at midlife still feel like frauds: Erin Buttermore
You’ve climbed the ladder. Built the career. Earned the respect. So why does that voice in your head keep whispering you don’t deserve it? That any moment now, someone’s going to figure out you’ve been faking it all along?
In this conversation, we sit down with Erin Buttermore, a strategy consultant, executive coach and PhD candidate researching the imposter phenomenon at the University of Sydney.
Crossing the bridge: rethinking retirement with Dr Jon Glass
What if retirement isn’t really about golf and chilling out? What if it’s actually one of the most significant identity transitions you’ll ever face?
Dr Jon Glass knows this territory intimately. Starting his working life with a PhD in pure mathematics from Cambridge University, he’s made several major career transitions himself. Now, as a retirement coach, he’s on a mission to change the paradigm of what retirement actually means.
When life makes you confront mortality at 23: Dr Merran Cooper on advanced care planning and living with purpose
What happens when death arrives at your doorstep decades before you’re ready? For Dr Merran Cooper, it came when she was just 21 years old, watching her 22-year-old husband battle terminal leukaemia. But rather than breaking her, that experience set her on an extraordinary path that would eventually lead to becoming a doctor at 51 and an entrepreneur in her 60s.
Professor Virginia Cha: thriving beyond retirement in Singapore's engineered blue zone
What if the best educated, most experienced generation in history simply stopped contributing at 65? What if all that knowledge, those networks, that hard-won wisdom just… retired?
Training for Your Last Decade – with Dr. Gordon Spence
Just One Reason: Stuart O’Neill on Survival, Hope and the Power of Connection
When life falls apart, most of us search for a way through. For Stuart O’Neill, that search began in the darkest moment of his life — a moment that nearly ended it. What emerged instead was Just One Reason, a small, unassuming book that has since saved lives across the world.
Weight Loss Drugs: Miracle or Mistake?
Midlife often brings unwelcome surprises: slower metabolism, creeping weight gain, and the frustration that “what worked before” suddenly doesn’t. Dr. Kwong helps us understand why—and shows how to think beyond quick fixes toward sustainable, holistic health.
How to master the Life Reinvention Playbook with Michael Bungay Stanier
Subscribe on your favourite platform
Subscribe
Sign up to receive alerts for:
- New podcast episodes from Don't Let The Old Man In
- A weekly newsletter
- To be invited to live events
- To hear about new podcasts that are launching in early 2026
- To hear about other new products planned for launch in 2026