100 episodes

Navigating your next chapter after traditional work requires a new kind of bravery—especially for men. Michael and his guests speak straight to how to overcome the conditioning of our hard-charging career years and explore what will bring us fulfillment.

Chapter X with Michael Kay Michael F Kay

    • Education
    • 5.0 • 51 Ratings

Navigating your next chapter after traditional work requires a new kind of bravery—especially for men. Michael and his guests speak straight to how to overcome the conditioning of our hard-charging career years and explore what will bring us fulfillment.

    Episode 182: Navigating Life’s Big Questions with Austin Dowling

    Episode 182: Navigating Life’s Big Questions with Austin Dowling

    When 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 Austin Dowling Psychotherapy 
    Austin on LinkedIn
    Austin on Facebook
     

    • 51 min
    From Inside Out with Amrit Singh Reinsch

    From Inside Out with Amrit Singh Reinsch

    In a world full of noise, it's easy to forget that real happiness can start with reconnecting with who we truly are inside. Today, that’s exactly what we’re exploring with Amrit Singh, a life coach who helps men discover what they truly want and what makes them happy.
     
    In this episode, we tackle the tough challenges men face with vulnerability and how embracing your true self can transform your relationships. Amrit shares some truly powerful tips on how vulnerability can lead to more joy and fulfillment in both personal and romantic lives.
     
    So stick around as we uncover Amrit's personal journey, his tried-and-true techniques, and how he's helping successful men reignite their passion and strengthen their marriages. It's a conversation that shows just how incredible self-reflection and building intentional relationships can be.
     
    We discussed:
     
    What triggered Amrit's realization in his twenties that he needed to change course


    How we can reconnect with our true selves beneath all the layers we've built up


    The most common challenges in making relationships meaningful after retirement


    What advice Amrit would offer to men who are questioning their relationships


    Why is exploring our relationships both daunting and rewarding?


    The source of true fulfillment (beyond external achievements)
     
    Connect with Amrit Coaching with Amrit
    Marriage Reconnection Roadmap
    Follow Amrit on Instagram
    Follow Amrit on Facebook
    Follow Amrit on TikTok
     

    • 43 min
    The Awakened Man with Alain Dumonceaux

    The Awakened Man with Alain Dumonceaux

    When we find something that drives us forward, life takes on new meaning and fulfillment. But true fulfillment isn’t just about traditional success—it’s about discovering joy and purpose in our everyday experiences, especially as we navigate the second half of life.
     
    Today, we explore this enriching path with a guest whose resilience and purpose have guided his own journey. Alain Dumonceaux joins us, a man whose own life trials have shaped his passion for helping men align their lives with their deepest values.
     
    As the Purposeful Action (Men)tor for the Awakened Man movement, Alain has dedicated himself to showing others how to live authentically. From triumphs at the Culinary Olympics to facing near ruin twice, his journey has driven him to empower others.
     
    Now, Alain’s mission is clear: to guide men in rediscovering their life’s purpose through his purposeful action plan, "The Return of The King.” This plan serves as a transformative blueprint for embarking on their Hero’s Quest.
     
    In this episode, we discussed:
     
    Why we thrive on having something to anticipate in life
    What we often get wrong about defining our purpose
    The three mentors who can transform a man’s life
    Why men need safe spaces for open dialogue
    What we must remember when confronting our pain
    One tip to keep in mind whenever imposter syndrome strikes
    Alain shares his tips for perfecting cooking techniques
     
    Connect with Alain (Free Course) Crafting Your Mission
    The Awakened Man
    Band of Brothers
    Hero’s Quest
    The Revolutionary Man Podcast
    Follow Alain on Instagram 
    Follow Alain on Facebook

    • 48 min
    Redefining Your Worth with David Chernikoff

    Redefining Your Worth with David Chernikoff

    Ever had a friend recommend a book that completely captivated you? That's exactly what happened to me. My friend Bob suggested this book written by a college acquaintance of his, and I decided to grab a copy. Little did I know, it would be one of those extraordinary reads.
     
    As I flipped through the pages, I found myself really connecting with the importance of the author's words. I knew I had to track down David Chernikoff’s email and invite him to join me for a conversation.
     
    David is a meditation teacher, spiritual counselor, and writer who taught psychology and meditation at Naropa University for many years. He currently teaches retreats throughout the United States and is one of the guiding teachers of the Insight Meditation Community of Colorado. 

    And his latest book, Life, Part Two: Seven Keys to Awakening with Purpose and Joy as You Age, is truly eye-opening. It's a roadmap to finding fulfillment and happiness, regardless of where you find yourself on life's journey.
     
    How a life-changing event at age 13 molded David's adult years
    The pressure to succeed and how it affects our self worth
    Redefining your self-worth beyond achievements in middle age
    The concept of living on two levels: the relative and the absolute
    7 keys to awakening with purpose and joy as you age
    Why David decided to write a book as he approached 70
     
    Connect with David Life, Part Two: Seven Keys to Awakening with Purpose and Joy as You Age 
    www.davidchernikoff.com 
    David's Upcoming Event Schedule

    • 54 min
    Living Retirement to the Fullest with Brian Feutz

    Living Retirement to the Fullest with Brian Feutz

    In 2015, Brian Feutz began feeling the tug towards retirement. He went headfirst into a journey of discovery, diving into the ins and outs of retirement planning, wondering what the future held, and whether he was financially ready for it all.
     
    He's not just navigated through the transition to retirement, but he's crafted a life filled with meaning and purpose, and I have no doubt you'll find his story truly inspirational.
     
    Brian is a top writer, speaker, columnist, and published author with a unique style that brings a lively perspective to the art of retirement. Whether you’re retired or considering retirement, you don’t want to miss his thought-provoking ideas that challenge the imagination. 
     
    When he's not sharing his wisdom, you can often find Brian enjoying the natural beauty of the San Juan Islands alongside his wife, whether it's on a boat, trail, bicycle, or kayak.
     
    In this episode, we’ll explore:
     
    How Brian crafted a encore career through his extensive research on retirement


    The one simple sentence Brian uses to define retirement


    What led Brian and his wife to choose the San Juan Islands as their retirement spot


    Why Brian decided to “practice” retirement on his own—and the steps he took
     
    The reason why roughly 40% of people who retire go back to work temporarily
     
    One ongoing project that is making Brian’s retirement purposeful
     
    The way Brian applied perseverance to this hobby to discover a sense of purpose
      Resources Read Brian’s Work
    https://lifeafterwork.zone
    https://brianfeutz.com/
    https://brianfeutz.medium.com/
     
    Connect with Brian
    https://twitter.com/BrianFeutz1
    https://www.facebook.com/brian.feutz.16/
    Email at Brian@BrianFeutz.com 
     

    • 53 min
    The 9 Pillars of Resilience with Dr. Stephen Sideroff

    The 9 Pillars of Resilience with Dr. Stephen Sideroff

    What if stress isn't the enemy we thought it was? Our guest today suggests that certain aspects of stress can actually be powerful motivators. But here's the catch: there's a sweet spot, and most of us tend to overshoot it.
     
    Today I'm speaking with Dr. Stephen Sideroff. This is a conversation you will want to listen to multiple times, or at least have a notepad with you so you can jot down some notes. In fact, you're going to want to listen to this multiple times because it's packed with incredible information and things that I think are essentials in our lives.
     
    Dr. Sideroff is an internationally recognized expert in psychology and resilience. Not only has he published groundbreaking research, but he has served as an associate professor at UCLA's Geffen School of Medicine. Now, he's sharing his expertise in his new book, "The 9 Pillars of Resilience," offering insights into mastering stress, aging gracefully, and enhancing vitality.
     
    In this episode, we discussed:
     
    Why stress is the master hallmark of aging 
    The power of confronting unfinished emotional business in Chapter X
    How we can get past the discomfort of exploring our buried feelings
    Discovering the starting point for challenging our inner critic 
    Dr. Stephen Sideroff breaks down the nine pillars of resilience 
    How our presence can impact each other unconsciously 
     
    Connect with Dr. Stephen Sideroff  
    The 9 Pillars of Resilience Book
     
    Purpose: The Ultimate in “Use It or Lose It” on Psychology Today
     

    • 48 min

Customer Reviews

5.0 out of 5
51 Ratings

51 Ratings

The nerdster ,

A human take on a complex part of life’s journey

Michael brings a mix of curiosity, compassion and optimism to this wide ranging podcast on the social, emotional and practical aspects of working through a transition into retirement. It has helped me to change what retirement means in my mind, and to see it as a chance to have more fun and a great impact than ever. Thanks!!

Rand-Thriving! ,

Managing A Career Transition and Thriving

Michael was a superb host. He asked penetrating questions, and my answers might be valuable to listeners. This includes the need for bravery, self-awareness, writing your legacy and living it now, and what’s involved with aging well.

Little Buckster ,

Insightful

As the population ages, Michael explores key topics to help us understand what post-career life will be like.

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