Chapter X with Michael Kay

Michael F Kay
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  • SELF-IMPROVEMENT
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Chapter X with Michael Kay

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.

  1. MAY 7

    Living the Ikigai Way with David Marlow

    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 talk about identity, daily rituals, the power of reflection, and how a few small steps can open the door to something meaningful.   We also explore:   What ikigai means (and what it doesn’t) How to quiet the noise enough to hear what’s true for you Why a beginner’s mindset is key to moving forward What it looks like to create your own “ikiverse” How old memories and stories can point you back to what matters most   Resources: Follow David on LinkedIn  Subscribe to the Ikiquest Newsletter David’s website   Where to find The Ikigai Way:  Amazon   Barnes and Noble  Wiley Books

    46 min

  2. APR 23

    Richard Eisenberg Talks Unretirement

    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 our conversation, Richard shares his latest stories on medical debt, telehealth access, and the renewed value of travel advisors. He also opens up about caring for his mom during her dementia journey and what it taught him about starting financial conversations early.   Listen in to hear what Richard’s been up to since the last time we spoke.   We discussed:   What “unretirement” really looks like in practice The importance of having early financial conversations with aging parents Why telehealth access matters—and what could happen if it’s rolled back A fresh look at travel advisors and how they’re evolving Richard’s book recommendations and resources for deeper learning The challenge of caregiving for aging parents with dementia Resources The View From Unretirement Next Avenue Fortune | Richard Eisenberg Fodor’s Travel    Friends Talk Money   The Friday Afternoon Club by Griffin Dunne The Purpose Code by Jordan Grumet Retirement Intelligence by Robert Laura

    34 min

  3. APR 10

    Letting Go of Old Identities with Jordan Grumet, MD

    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 podcast, brings a perspective shaped by both his work in hospice care and his own experience of stepping away from a path that no longer felt right.   It’s a conversation about what happens when we let go of old identities and start figuring out what comes next. In this episode, you’ll hear: Why purpose feels like such a monumental challenge in retirement Jordan’s story of legacy, loss, and what medicine couldn’t give him The slow burn of professional misalignment and how he woke up to it How powerful external voices influence our life choices The Purpose Code path forward into a more meaningful second act   Resources jordangrumet.com The Purpose Code

    36 min

  4. MAR 26

    Planning a Home for Aging in Place with Greg Cantori

    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 company dedicated to making homes safer and more accessible for aging individuals.   Your home should support you as you age. Find out how Greg is helping make that a reality for so many. We discussed:   How universal design makes homes safer and more accessible as we age Greg’s career journey—and how it led him to create Little Deeds The challenges people face with aging in place  Simple ways to make your home safer and more accessible Why it’s important to plan ahead with home modifications   Resources   Little Deeds

    51 min

  5. MAR 12

    How to Keep Moving & Feeling Great After 60 with Mark Firehammer

    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 keeps you moving without intense workouts.   If you care about moving well, feeling good, and staying strong as you get older, you’ll want to hear this one.   In this episode, we discuss: Simple daily moves to check how well your body is working Why your nervous system is the key to better movement How paying attention to your body can improve your health The problem with mainstream fitness advice and what actually works What it really means to be "Out of Function" (and how to fix it) A small mindset shift that could help you avoid serious health problems   Resources: myFeelness Living Well Without Fitness on YouTube Mark Firehammer on Instagram Mark Firehammer on LinkedIn

    48 min

  6. FEB 19

    Aging Well Starts with a Plan: Dr. Corinne Auman

    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.   Today, Dr. Auman shares why planning ahead is so important, how to talk to loved ones about it, and what steps you can take now to have more options later. I think you’ll find this episode both eye-opening and helpful.   We discussed:   Start planning your future home in your 50s What we often get wrong about retirement communities How to bring your loved ones into the conversation The 3 main phases of retirement Who we can turn to for guidance on our next steps   Resources: Keenagers by Dr. Corinne Auman www.CorinneAuman.com

    42 min

  7. FEB 5

    How Women Navigate Life’s Transitions with T. Kari Mitchell

    Today, we’re taking a different approach. Instead of focusing on men’s transitions, we’re diving into the journey women face in their next chapter.   My guest, T. Kari Mitchell (TK), is a transformational speaker, author, and integrative wellness coach who has dedicated her second half to helping women reclaim their health, confidence, purpose, and power after retirement so they can truly flourish in their golden years.   After 32 years as a teacher, she boldly transitioned into holistic coaching and motivational speaking at 62. Now, through her programs, TK helps boomers overcome challenges and rediscover their potential. We explore the transitions women face, including shifting identities, hormonal changes, and societal expectations.   Guys, this is the episode to share with the women in your life because growth is better when we do it together. TK’s energy is contagious, and I think you’ll walk away with a new perspective on how we can all grow into the next stage of life.   We covered:   The mindset shifts that help women step into their next chapter with confidence How past experiences can open the door to new passions and opportunities The societal challenges that women face as they age (and how to push back) Practical ways men can better support the women in their lives How women can start reclaiming their purpose today Resources https://www.lifestyle120.com

    40 min

  8. JAN 22

    Boredom is Optional with Paul Wilson

    With freedom comes the risk of losing direction. When we’re younger, the world feels full of possibilities. But as we get older, our focus narrows—one job, one partner, one path. Over time, our routines can make it harder to see new opportunities.   In this episode, Paul Wilson explains how mental blocks can keep us stuck and shares how to break free and explore what’s still out there. After a bicycle accident and a broken arm in 2017, Paul found a new career path.   Now, Paul is a life coach, business coach, and hypnotherapist who helps people overcome feeling stuck through his practice, A Happy Head. He developed the Shift Process, a method that uses small mindset shifts to create big transformations.   Paul shares how to remove the mental “blinkers” that limit personal growth, especially as we navigate life transitions like retirement.   How a broken arm led to a new career When Paul realized he had found a superpower 3 ways to discover new hobbies or interests What hypnosis can do for you (and what it can’t) The difference one phone call can make for retirees Connect with Paul: A Happy Head Business Coaching with Paul

    46 min
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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.

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