Don't Let The Old Man In

In this special deep dive episode of Don't Let The Old Man In, Dr Jon Glass joins Pod O’Sullivan to unpack all things retirement.

If you’re a man navigating midlife and wanting real talk, practical wisdom, and a community that gets it, you’ll find this one hits home.

Watch, learn, take something with you, and keep moving forward.

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In this special deep dive episode of Don't Let The Old Man In, Erin Buttermore joins Pod O’Sullivan to unpack the imposter phenomenon.

If you’re a man navigating midlife and wanting real talk, practical wisdom, and a community that gets it, you’ll find this one hits home.

Watch, learn, take something with you, and keep moving forward.

Hosted on Acast. See acast.com/privacy for more information.

In this special deep dive episode of Don't Let The Old Man In, author Michael Bungay Stanier joins Pod O’Sullivan to discuss midlife reinvention.

If you’re a man navigating midlife and wanting real talk, practical wisdom, and a community that gets it, you’ll find this one hits home.

Watch, learn, take something with you, and keep moving forward.

Hosted on Acast. See acast.com/privacy for more information.

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."

What we discuss in this episode

Dr Gordon Spence on health span vs lifespan

• The cruel gap between how long we're living and how well we're living
• Why physical decline doesn't fall off a cliff until 70 (if you've been doing the work)
• How negative age stereotypes undermine our actual physical capacity
• Training for your last decade starts now, not at 65

Dr Merran Cooper on having conversations about death

• How a 21-year-old woman faced her husband's terminal diagnosis
• The chaplain who gave permission to prepare for death while maintaining hope
• Why every single older person is thinking about death and waiting for someone to talk about it
• The power of advanced care planning for your loved ones

Ben Larke on shame and vulnerability

• Understanding the difference between shame and guilt
• How shame keeps us stuck and prevents growth
• Why vulnerability is the pathway through shame
• Practical tools for recognising and addressing shame in our lives

Erin Buttermore on imposter phenomenon

• Why high achievers often feel like frauds
• The difference between imposter syndrome and imposter phenomenon
• How imposter feelings can actually signal growth opportunities
• Reframing self-doubt as evidence you're stretching yourself

Virginia Cha on Singapore's Distinguished Fellow Program

• How Singapore leverages experience from their aging workforce
• Redefining contribution in the second half of life
• The value of wisdom and experience in a youth-obsessed culture
• Alternative models for aging and work
• The distinction between existing and truly living
• Building resilience through intentional choices
• Creating a life of vitality beyond your working years
• Small daily practices that compound into transformation

Stuart O'Neill on personal reinvention

• Why men struggle to talk about mental health
• The importance of connection and community
• Breaking through isolation in midlife
• Practical steps for building meaningful relationships
• Navigating major life transitions in your 40s and 50s
• The courage to start again
• Redefining success on your own terms
• Finding freedom in uncertainty

Dr Angela Kwong on preventative health for men over 40

• Why your metabolism changes and what to do about it
• The essential health checks every man should get (but most don't)
• Waist circumference matters more than your weight
• Testing fasting insulin levels before diabetes develops

Michael Bungay Stanier on relationships

• The secret to a good marriage: both thinking they got the better deal
• Maintaining connection through life's transitions
• Why relationships require intentional effort
• Creating mutual value and appreciation

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What if the voice in your head that says "you're not good enough" isn't actually true? What if the secret behaviours you've carried for decades aren't defining you, but rather haunting you? Clinical psychologist Ben Larke helps men untangle the difference between guilt about what we've done and shame about who we are.

In this raw and remarkably accessible conversation, we explore:

• The critical distinction between shame and guilt—and why one is far more dangerous
• How childhood experiences code our default responses decades later
• Why men at midlife suddenly find themselves caught up by unresolved pain
• The relationship between shame, addiction and compulsive behaviour
• Ben's own midlife reinvention from UN humanitarian work to clinical psychology
• Why sharing secrets with another human being is often the first step toward freedom
• The powerful metaphor of "parts" in the driver's seat—and how to recognise which part is steering your life
• What your 75-year-old self might want to tell you right now

This isn't therapy—it's permission to be human.

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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. Erin brings a refreshingly practical approach to what's often called "imposter syndrome", but she's quick to correct that term. It's not a syndrome at all, she explains.

Key insights include:

• Why "imposter phenomenon" is a better term than "imposter syndrome" and what that shift in language reveals about the real problem
• How men at midlife experience self-doubt differently from women, often withdrawing rather than doubling down on perfectionism
• The toxic role of meritocratic culture in reinforcing feelings of fraudulence
• Why successful people attribute wins to luck and losses to personal failure
• The surprising link between stereotype threat and imposter feelings
• Practical techniques for managing automatic negative thoughts in real time
• How organisations, not just individuals, need to address impostorism

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Dr Jon Glass knows about identity transitions 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.

In this wide-ranging discussion, Jon and Pod dig into the practical and emotional realities of

retirement:

• The bridge metaphor: How to think about what you'll miss as you cross from work to retirement, and what you want to carry with you.
• Identity reconstruction: Moving beyond "I am a..." to discovering who you want to become.
• The six Fs of retirement: Including the "wet leaf syndrome" and other dynamics that catch people by surprise.
• Friendship in later life: Why men struggle to maintain friendships after work, and practical strategies like the TCS approach (text weekly, call monthly, see quarterly).
• Meaning versus busyness: How to create a portfolio of activities that brings genuine purpose, not just a full calendar.
• The honeymoon period: Why it will end, and how to prepare for what comes after.
• Energy management: A hidden consideration that's often overlooked in retirement planning.

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Merran Cooper isn't your typical doctor-turned-entrepreneur. She started medical school at 50 and then founded Touchstone Life Care to solve a problem she witnessed daily: people dying badly because no one knew what they wanted.

In this conversation, we explore:

• The power of ambivalence – How preparing for dying and hoping for the best aren't opposites, but can coexist 100% at the same time
• What happened when a chaplain used the "D word"; – The conversation that changed everything for Merran and her dying husband
• Why "be a soul, not a role" matters – Especially at someone's bedside
• The sandwich generation challenge – Practical ways to start conversations with aging parents who don't want to talk about death
• How to have "the conversation"; – Using falls, not death, as your starting point
• Why advanced care planning is a love letter – Not a legal document
• The RSL Club test – How one man defined his minimum quality of life in terms his family could actually understand
• Reinventing yourself after 50 – What it's like to become a medical student when your daughter is also in first year uni

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In this episode, we explore

• Singapore's blue zone engineering: How deliberate policy and social cohesion created one of the world's healthiest, longest-living populations
• The thriver philosophy: Why Virginia rejects the word "seniors" and what it means to truly thrive in your third act
• Building the Distinguished Fellow Program: The entrepreneurial journey of creating Asia's first fellowship for accomplished professionals in their 60s and beyond
• The magic of bringing people together: How 21 fellows aged 47 to 82 found deep friendship and renewed purpose through learning
• Buddhist principles in design: The hidden philosophy behind the program's "random" curriculum
• The male energy shift: Virginia's surprising observation about how men transform when given new purpose

Virginia shares candidly about everything from stalking professors to get them to teach, to the unexpected joy of being 65 ("Nobody thinks that's going on anymore"). Her LinkedIn bio starts with "I am old";—not as resignation, but as a badge of honour earned through experience.

This isn't a conversation about winding down. It's about what becomes possible when we stop measuring success by conventional business metrics and start asking: how can I be helpful?

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Healthy ageing doesn’t begin at 70; it starts right now. In this inspiring episode of Don’t Let The Old Man In, Dr Gordon Spence shares how midlife can become the launchpad for a stronger, healthier, more connected future.

At 48, Gordon realised he’d drifted into the common midlife slump: carrying extra weight, catching colds, sleeping poorly, and exercising rarely. One cruise-ship treadmill session sparked a complete re-engagement with movement. That decision led to marathons, postgraduate study, and eventually a mission: to help others live active, meaningful lives across their lifespan, not just extend it.

What we explore in this episode:

• The critical difference between lifespan and healthspan – and how to narrow the gap
• Why training for your last decade is the smartest investment you can make now
• How negative age stereotypes quietly limit physical and mental potential
• Gordon’s four-stage Health Activation Model: Reflect · Project · Inspect · Connect
• The importance of community, connection and accountability in staying active
• Real stories of reinvention – from marathon runners to dragon-boaters and a 60-year-old who fell in love with fencing

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