Advertise on podcast: Chapter X with Michael Kay

There's a whole industry devoted to helping us find ourselves. Samuel Strauch discovered that the search itself can become a trap.   We spend so much of our lives striving for success, solving problems, and looking for ways to improve. But sometimes, the constant need to do more gets in the way of finding fulfillment.   My guest today is Samuel Strauch, a real estate entrepreneur and author of Dear Humans. After an unexpected medical crisis, Samuel began a journey of self-exploration that changed how he viewed himself and the world.   We explore how the same drive that makes us successful can also hold us back, and what happens when we finally learn to let go of needing control. We covered: Why we don't need a crisis to recognize when it's time for change How confronting our fears can open new possibilities Why Samuel's pursuit of wellness and spirituality became another trap What he discovered when he finally stopped searching for answers Why looking beyond our professional identities matters in life after work -- Resources Book: https://dearhumansbook.com Website: https://samuelstrauch.com

The most meaningful advice can take years to fully understand. Just two weeks before his death, Gary Coulton's father asked him a question about who would attend his funeral. It took Gary ten years to understand the wisdom behind it. My guest today is Dr. Gary Coulton, a former biomedical scientist and executive coach turned writer and poet. Gary describes himself as a "successful misfit" and a work in progress. In this episode, we explore Gary's journey of self-discovery, how to make wiser decisions, and the "positive echoes" we can leave in other people's lives. We covered: What Gary discovered about himself at 65 that changed how he viewed his past Why he walked away from a successful 30-year career in science The surprising lesson learned from spending two hours looking at flowers A simple exercise to discover the values that matter most to you How your heart, head, and gut can work together to make better decisions -- Resources: Substack: https://garycoulton.substack.com  LinkedIn: www.linkedin.com/in/garycoultonaic  Website: https://garycoulton.co.uk    Books: Wisdomize – See Clearly. Decide Wisely. Live Fully: https://mybook.to/wisdomize Demons to Champions – How I fell in love with my neurodivergent maverick mind: https://amzn.eu/d/00oSXlxo

Sometimes finding purpose in retirement is as simple as picking up the phone and calling an old friend.   After decades of chasing success, it can be hard to imagine that something so small could make a difference. We're used to measuring our accomplishments by the size of the impact we make.   My guest today is Jonathan Logan, a coach who's reinvented himself several times throughout his life. Along the way, he's learned a thing or two about change, identity, and what makes life fulfilling.   We talk about letting go of old identities, building new habits, and finding purpose in unexpected places. Jonathan has some wonderful insights and practical advice to share as we think about our own next chapter.   In this episode: 3 fears that make us resistant to change How to prepare for retirement beyond financial planning Why finding purpose doesn't have to involve grand accomplishments The simple act that can help men rebuild friendships and social connections Jonathan's practical advice for breaking old habits    -- Resources YouTube - https://www.youtube.com/@LifeSuccessTools LinkedIn  - https://www.linkedin.com/in/jonathanlogan/ Smoking Cessation - https://stopsmokingforever.life/

Retirement is filled with decisions, and the choices we make today can have a lasting impact on our lives. With so much conflicting advice out there, how do we know we're making the right ones? My guest today is Dan Goldie, a former professional tennis player, financial advisor, and author of The Retirement Answer: The Six Key Decisions Every Retiree Needs to Make. In this episode, Dan shares the experiences that shaped his life, the importance of being open to help, and why understanding what matters most to us is essential as we plan for retirement. I think you'll appreciate Dan's common-sense approach to some of retirement's toughest decisions. We covered: How a difficult childhood led Dan to a career in professional tennis The four mentors who helped shape Dan's life and career Why being open to help is essential for personal growth How one retirement decision can impact your financial future Why your personal values should guide your retirement plan Dan's plans to help younger generations build financial literacy    -- Resources The Retirement Answer by Dan Goldie: https://lnk.to/theretirementanswer

The first six months of retirement may be the easy part.   At first, there may be travel, projects, and long-awaited plans to fill the time. But once the dust settles, retirement can begin to feel very different.   Psychotherapist Austin Dowling joins me again on Chapter X to talk about what can surface after the initial transition. We explore loneliness, identity, self-reliance, and the challenge of adjusting habits that may have served us well throughout our careers.   We covered: Why loneliness often appears after the first few months of retirement How senior roles can make relationships feel increasingly transactional Why successful people may struggle to ask for help How over-scheduling can become another way to avoid discomfort How to adapt your career strengths instead of leaving them behind -- Resources Website: https://www.insightstudiotherapy.com Email: [email protected]  Phone: 347-454-2799

We spend a lot of time thinking about the past or worrying about the future. What gets lost in between?   For Dr. Evan Fishman, that question became more personal after he was laid off from Facebook in 2023. The experience forced him to rethink how much of his identity was tied to work, achievement, and what came next.   Today, Evan helps others navigate similar questions around identity, uncertainty, and being present.    In this episode, we cover: How Evan's Facebook layoff changed the way he saw his life What we use to avoid uncomfortable feelings Why fear can create stories that feel true (even when they aren't) How to become more comfortable with uncertainty Why the present moment matters during times of change   -- Resources www.evanfishman.com https://www.linkedin.com/in/evanfishman https://www.instagram.com/dr.evanfishman https://x.com/evan_fishman https://belovedinstitute.substack.com

For people who've spent decades succeeding at work, life comes with a scoreboard. There are goals to hit, problems to solve, and clear ways to know when you're succeeding.   Then comes a stage of life when those measurements don't work quite as well. My guest today is psychologist Brent Beam, who works with executives and men navigating major life transitions.   We talk about what happens when the focus shifts from achievement to experience, and why that can require a new way of measuring a good life.   You'll hear about: Why Brent encourages men to shift from external KPIs to internal ones How being willing to be bad at something can make life more expansive Why making friends may need to become your new "job" How retirement can put unexpected pressure on a marriage What to consider before assuming a board seat and more golf will be enough   -- Resources: Website: brentbeamphd.com The How of Happiness by Sonja Lyubomirsky

How long can you keep doing what you're supposed to do before you realize it isn't working anymore?   Ted Kopecko built a successful architecture practice, worked 16-hour days, and kept pushing forward until the life he created became one he no longer wanted to live.   Today, Ted is the author of Finding Joy: The Journey of You. In this episode, we talk about breaking old patterns, questioning the stories we've been taught, and creating a new direction for life after work.   We cover: The warning signs Ted ignored before walking away from his practice Why success without joy eventually became impossible to sustain Why leaving your career can force you to ask who you are  The four pillars Ted believes can help us create a different future Why Ted believes failure can become a setup for what comes next   --  Resources Email: [email protected]  Get the Free "Finding JOY" Workbook: https://FindingJOY.us  LinkedIn: https://www.linkedin.com/in/ted-kopecko-event-speaker-ceo-7x-life-36592441

One partner's retirement dream may look very different from the other's.   Maybe one of you imagines traveling and spending every day together. The other likes the life, friendships, and routines they already have. If you haven't talked about what retirement will actually look like, you may be planning two very different futures.   My guest today is therapist, coach, and author Dorian Mintzer. Dori contributed an important chapter to my book, How to Craft Your Chapter X, and she is the co-author of The Couple's Retirement Puzzle.   In this episode, we explore the conversations couples should have before and during retirement. We also share what inspired us to create an in-person workshop where couples can speak openly, learn from one another, and begin shaping a vision for this next stage of life.   We covered: Why your partner may not share your retirement dream The danger of assuming you know what your spouse wants What happens when work no longer provides purpose or friendships How to make room for separate interests and a shared life Why retirement can feel surprisingly similar to an empty nest The best time to begin these conversations On October 24, Dori and I are hosting a workshop for eight couples in Brookline, Massachusetts. Couples will have honest conversations about what they each want from retirement and begin creating a plan for their next chapter together. See the workshop details → -- Resources: Learn more about the October 24 couples workshop The Couple's Retirement Puzzle How to Craft Your Chapter X

What happens when you love your work too much to retire from it?   David Fiala has spent more than 35 years helping people better understand themselves. When someone once asked him about retirement, his response was: "How can I retire from what I am?"   David is a clinical social worker and author of *The Courageous Seeker*. His own path has taken him from working in casinos to exploring monastic life, with plenty of unexpected turns along the way.   In this episode, David shares what he's learned about looking inward, letting go of old pain, and continuing to grow throughout every stage of life.   We covered: The life-changing experience that sent him in a completely new direction Why experiences from decades ago can still influence us today How to take care of yourself without feeling selfish A simple practice for becoming more present in everyday life Why asking for help can be an important part of personal growth Why David doesn't see his work ending with retirement   -- Resources: Website: https://www.mindyourego.com  Resource Page: https://www.mindyourego.com/resources  Sign up to read the opening pages of The Courage Seeker: https://www.mindyourego.com/the-courageous-seeker

You're never too old to learn something new.   Ed Friedman didn't grow up around the arts. In fact, he didn't see his first stage play until his late 20s. But as an adult, creativity became a big part of his life.   Ed went on to act, write plays, and co-found Lifetime Arts, a nonprofit that helps older adults learn and create through the arts. Today, he's retired from the organization but still writing, acting, and trying new things.   In this episode, Ed and I talk about creativity, community, and why getting older shouldn't stop us from being beginners.   We covered: What finally gave Ed the courage to step onto a stage for the first time Why being a beginner can get harder as we get older The most damaging kind of ageism Ed believes we put on ourselves What happens when we stop worrying about being good at something new Why Ed believes it's never too late to follow a new interest -- Resources Lifetime Arts Ed Friedman's website I Will Not Be Ignored

Life has a way of telling us when something needs to change, even when we aren't ready to listen.   My guest today, Mark Feinberg, spent years building companies, serving on boards, and chasing success. From the outside, everything looked right. But internally, Mark knew something was missing.   After the sudden loss of his business partner and close friend forced him to stop, Mark began letting go of the identity he had built around achievement and exploring who he was beyond his career.   In this episode, we explore what can happen when we silence the noise long enough to listen to ourselves.   We discuss:   Why Mark believes "reconnecting with yourself" might be the wrong advice The wake-up call Mark gives clients who've spent most of their energy on one area of life Why aiming for a 10 in every part of your life might actually work against you What we may need to unlearn before we can move forward The unexpected place Mark found one of the most important lessons of his next chapter   -- Resources Tame the Noise  Roaming Coaches  Connect with Mark on LinkedIn

What did you love before work and responsibility took over?   As kids, we followed our curiosity without worrying whether an interest was productive or impressive. Somewhere along the way, many of us leave those parts of ourselves behind.   My guest today, therapist and author Alexander Osterman, believes they're worth going back for. He even has Lego castles on his office wall simply because he always wanted one as a kid.   In this episode, we talk about rediscovering old interests, separating who you are from what you did for a living, and giving yourself permission to explore again in Chapter X.   We discuss:   The surprising place Alexander looks for clues about what comes next How to tell when you might be drifting through your days One small practice Alexander uses to help people get unstuck What happens when we spend too much time trying to think our way forward 3 questions that can change how you look at your day   -- Resources Website: alexanderosterman.com Instagram: instagram.com/alexanderosterman

Retirement isn't just the end of a career. For many executives, it's the first time they've had to redefine who they are without the title they've spent decades earning.   So why do so many accomplished leaders struggle with this transition? And what can they do now to prepare for what's next?   My guest today is Dr. Kelly Ottman, executive coach, researcher, and founder of Leadership Portals. After interviewing executives before and after retirement, she uncovered surprising patterns about identity, relationships, and the skills people need to thrive in the next chapter.   In this episode, we covered:   Why the word "retirement" makes executives flinch The surprising skills many leaders find out they're missing after leaving work Why "I'll just join a few boards" isn't as simple as it sounds Losing your prestige vs. losing your credibility (and why they're not the same thing) What Kelly encourages people to create instead of a bucket list What organizations overlook when preparing leaders for retirement -- Resources Email: [email protected]   Website: LeadershipPortals.com  LinkedIn: linkedin.com/in/kellyottman

Creativity isn't reserved for artists. It's something we use every day to solve problems, adapt to change, and discover new possibilities.   That becomes especially important in Chapter X. Retirement reimagines how we spend our time, where we find fulfillment, and what comes next.   Today I'm speaking with James Walters, photographer, podcaster, and author. He shares why curiosity is at the heart of creativity, why success and fulfillment aren't always the same thing, and how a shift in perspective can open the door to new possibilities.   We cover:   Why James sees creativity as problem-solving in disguise   Why imposter syndrome doesn't retire when you do What it means to rebel against inherited definitions of success Two brothers who waited until their 70s to hike the Appalachian Trail together 3 phases of retirement James has seen in the people he interviews   -- Resources A Joyful Rebellion