Advertise on podcast: Chapter X with Michael Kay

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: www.insighstudiotherapy.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: brentbeanphd.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

We tend to avoid anything we won't be instantly good at. Richard Sparks has spent forty years proving that instinct is wrong.   Richard is a writer who has spent 40 years bouncing between comedy sketches, TV scripts, opera translations, and now fantasy novels. He wrote for a young Rowan Atkinson before anyone knew his name, then somehow ended up translating operas with no background in the form.   In this episode, Richard shares why he never expects a first draft to work and how that same patience helped him build a fantasy series after decades of writing scripts.   We cover: The strange side job that taught Richard he could actually get paid to write What happened the first time he watched an actor perform a sketch he wrote The one thing Richard tells every young writer about a bad first draft Why he walked away from decades of scriptwriting for something he'd never done before A story structure mistake he says ruined the ending of a hit TV series The line from Mel Brooks that reframed how Richard thinks about comedy vs. tragedy -- Resources Get free chapters at: https://richardsparks.com

We spend decades working toward the exit. But what happens once we actually get there?   Today I'm speaking with Jack Calhoun, who sold his wealth management firm in his fifties expecting to finally relax and write. Instead he found himself restless, then stuck running a company he didn't even like after a bootstrapped venture went sideways.   In this episode, Jack shares what that wrong turn taught him and how it led him to create Encore Career Lab, a program built to help high achievers figure out what comes next.   We cover: The moment selling his firm turned from a lottery win into "what have I done?" Why the freedom of retirement gave way to isolation What his coach's "autopsy" exercise taught him about walking away Why ego is the real enemy of reinvention Jack's case for treating your next chapter like a series of sprints (instead of one big bet)   — Resources Website: encorecareerlab.com  Email: [email protected]  LinkedIn: https://www.linkedin.com/in/jack-calhoun-encore

What can we learn from someone who spent weeks living in retirement communities and interviewing dozens of retirees?   That's exactly what today's guest set out to discover. Dr. Andi Simon is a corporate anthropologist whose curiosity about retirement led her to study how people navigate life after work.   Although every story was different, she found that many retirees shared the same struggles and the same opportunities as they entered this next chapter. We discuss: 4 questions almost everyone wrestles with after leaving their career behind What surprised Andi after interviewing dozens of retirees Why "Saturday every day" isn't always as fulfilling as it sounds How friendships often change more than we expect after retirement What an anthropologist sees that the rest of us often miss about retirement   — Resources: Website: andisimon.com     Book: Rethink Retirement

Jake Fishbein joined his first men's group for research.   He was helping write a novel about men's groups and thought he should probably see one from the inside.   What he didn't expect was that the experience would change the course of his own life.   In this episode, we discuss why retirement can trigger an unexpected identity crisis, the challenge of separating who we are from what we do, and what it means to stay engaged with life long after a career ends.   We cover:   Why retirement can trigger an unexpected identity crisis The challenge of separating who you are from what you do What it means to transition from achievement to eldership Why staying "in the arena" matters at every stage of life The fear of becoming irrelevant as we grow older Lessons from a woman who began her most meaningful work in her seventies -- Keep Exploring If you enjoyed this conversation, check out Jake's novel, The Men's Group: A Novel of Messy Friendships. Amazon Print Amazon Kindle Barnes & Noble Print Barnes & Noble Nook