Navigating Life’s Big Questions with Austin Dowling
Release Date: 07/17/2024
The Stories We Tell Ourselves with John Geraghty
Chapter X with Michael Kay
When John Geraghty was 29, he looked at his life and realized the path he was on wasn’t leading anywhere he wanted to go. Struggling with alcohol, he decided to change everything. That choice set him on a journey of growth and helping others find what lights them up. In this conversation, John shares what he’s learned about why the traditional idea of retirement often leaves people feeling lost, and how discovering your strengths and staying curious can bring meaning to every stage of life. We talk about how small steps, honest self-reflection, and contribution to...
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Get Busy Living with Alex Potts
Chapter X with Michael Kay
Alex Potts helped thousands of people plan for retirement until it was his turn. And like so many of us, he found himself asking what now? This episode is a special one. Alex isn’t just a respected leader and former CEO. He’s also a longtime friend. We’ve known each other since the ’90s, and I’ve had the privilege of watching him grow into an authentic, grounded, and service-minded leader. Our conversation explores what it means to live with intention. We talk about resilience, identity, letting go, and how to step into your next chapter with curiosity and...
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When It’s Time to Pivot with Agi Keramidas
Chapter X with Michael Kay
Agi Keramidas made a major life shift when he left behind a stable but unfulfilling life in Greece to follow a calling he couldn’t quite explain. Today, he shares how a midlife awakening (his words) sparked a journey of personal growth. Eventually it would lead Agi to launch his podcast, Personal Development Mastery, and write his book, 88 Actionable Insights for Life. He talks about listening to that quiet voice that says something needs to change. Even when it means starting over in a new country with no safety net. We explore the role of self-awareness, the discomfort that often...
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You Are Not Your Resume with Rich Alderton
Chapter X with Michael Kay
When Rich Alderton left his high-powered corporate role on a Friday, signing off millions and fielding nonstop calls, he expected Monday to bring more of the same. Instead, the phone was silent. That stark contrast was the wake-up call: people had been in love with his title, not with him. What followed was a journey into reinvention. Rich stepped away from corporate leadership to help others become more adaptable in a rapidly changing world. Along the way, he discovered just how unprepared most of us are for life’s biggest transitions. Today, Rich joins me to talk about how to...
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Living the Ikigai Way with David Marlow
Chapter X with Michael Kay
David Marlow is known as the Ikigai Guy. I didn’t know that when I first came across his writing. What I did know was that something in his work resonated deeply with me. Today, we talk about what happens when your career comes to a close, and you're left facing the question: who am I now? David shares how he discovered the concept of ikigai, what it means to him, and how it shaped the way he moved through the end of his own career. He offers a thoughtful process for reconnecting with purpose, and for paying attention to the parts of your life that make you feel most alive. We...
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Richard Eisenberg Talks Unretirement
Chapter X with Michael Kay
Richard Eisenberg is back. And this time, we’re diving into what his unretirement looks like now. If you don’t know Richard’s story, he’s an “unretired” journalist who writes a column for MarketWatch and freelances for Next Avenue, Fortune, AARP, and Fodor’s. Richard calls this chapter “unretirement” — living it with purpose and intention. Before all that, he was an editor at Next Avenue and Money magazine, and held senior roles at Yahoo! and Good Housekeeping. He’s also the author of two personal finance books and a proud Northwestern grad. In...
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Letting Go of Old Identities with Jordan Grumet, MD
Chapter X with Michael Kay
What happens when the career you built your life around stops feeling like it fits? Today, I’m talking to Jordan Grummet about what it really looks like to wrestle with purpose—especially during big life transitions like retirement. Jordan opens up about losing his father at a young age, pursuing medicine to honor his legacy, and eventually realizing that career wasn’t fulfilling him. We covered the struggle between societal expectations and our own authentic path, and how to find meaning after a life-altering shift. Jordan, an author and host of the Earn & Invest...
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Planning a Home for Aging in Place with Greg Cantori
Chapter X with Michael Kay
Only 5% of homes in the U.S. are moderately accessible. Stairways, sunken living rooms, poorly designed bathrooms, and trip hazards are just the start. Greg Cantore’s journey has spanned bicycle mechanics to defense work and leading nonprofit programs. But his mother-in-law’s experience living in a house that wasn’t designed for her needs opened his eyes to the bigger issue. After modifying her home, and later adjusting to her needs in assisted living, Greg realized there was a larger need for accessible, supportive home solutions. Today, he runs Little Deeds, a...
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How to Keep Moving & Feeling Great After 60 with Mark Firehammer
Chapter X with Michael Kay
You don’t have to spend hours in the gym to stay strong and mobile as you age. My guest, Mark Firehammer, created myFeelness to help men remain functional without grueling workouts or fitness gimmicks. At 43, Mark’s body started pushing back. There were aches, stiffness, and limits he couldn’t ignore. He knew something had to change but wasn’t willing to spend hours in the gym. That led him to rethink movement entirely. Mark found a way to stay strong, mobile, and pain-free through small, mindful movements. Now, he’s helping other men do the same with a system that...
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Aging Well Starts with a Plan: Dr. Corinne Auman
Chapter X with Michael Kay
If you had to make an important healthcare decision today, would you know what to do? My guest, Dr. Corinne Auman, is an expert in aging. She helps people and families figure out senior healthcare, retirement planning, and life’s unexpected changes. She’s a psychologist, CEO of Choice Care Navigators, and author of Keenagers. Most of us don’t think about aging until we have to, like when a parent falls or we realize our own home might not work for us as we get older. Suddenly, we’re faced with tough choices about Medicare, long-term care, and what it means to age well....
info_outlineWhen is the right time to start asking yourself life's big questions? My guest, Austin Dowling, who shifted from a corporate attorney to a psychotherapist, is here to discuss the vital role of self-reflection in finding fulfillment in retirement.
Originally from Ireland, Austin is a practicing psychotherapist and executive coach based in New York. He helps professional adults at a crossroads in their personal or professional lives, many of whom struggle with anxiety or a lack of motivation and are striving to reach their full potential.
Austin has navigated some incredible transitions in his own life, and his insights strike at the heart of the challenges many men face in retirement. And here's a little secret: this won't be the last time you hear from us.
In today’s episode, you’ll hear about:
Austin’s path from corporate law to helping people with their mental health
Understanding the roots of our inner critic—and how to manage it effectively
The reasons why men often face an identity crisis post-retirement
Why you must shed certain habits after transitioning out of your career
How to build a better community through these small steps
When it’s the right time start asking yourself the big questions
Connect with Austin