What Makes Retirement Different for Executives
Chapter X with Michael Kay
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...
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You're More Creative Than You Think
Chapter X with Michael Kay
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...
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The Joy of Becoming a Beginner Again
Chapter X with Michael Kay
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: ...
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What Happens After You Sell the Business
Chapter X with Michael Kay
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...
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The Four Questions That Shape Retirement
Chapter X with Michael Kay
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...
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Retirement Is Not Leaving the Arena
Chapter X with Michael Kay
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...
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What Success Can't Give You
Chapter X with Michael Kay
Loneliness isn't something we usually associate with successful people. When the career ends, where do purpose, connection, and belonging come from next? My guest today is Carl Nassar. He's an engineer, teacher, businessman, and eventually, psychotherapist. After achieving everything his parents had hoped for, Carl realized the one thing he was still searching for was a sense of belonging. So he walked away from a tenured professorship, started over, and spent the next twenty-five years helping people find their way back to each other. In this episode, we covered: ...
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Becoming the Father You Needed
Chapter X with Michael Kay
Larry Hagner was nine months old when his father left. For years, he searched for answers about the man he barely knew and the impact that absence had on his life. Today, Larry is the founder of The Dad Edge podcast, where he has spent more than a decade helping men become better husbands, fathers, and leaders. In this episode, Larry shares his story, from growing up without a father to raising four sons of his own. We discuss fatherhood, generational patterns, personal responsibility, and what it takes to be the father you didn't have. In this episode, we covered: ...
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What Matters More Than Living Longer?
Chapter X with Michael Kay
What if the goal isn't just to live longer, but to remain capable of doing the things you love for as long as possible? After decades as a physician, surgeon, and medical innovator, Dr. Arnon Krongrad believes we've been asking the wrong question. Rather than chasing longevity, he's focused on something he calls "functional supremacy." Today, Arnon challenges conventional thinking about health and aging. You’ll hear why he believes physical, cognitive, and emotional function may matter far more than simply adding years to our lives. We discuss: How to prepare for a life you still want to be...
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Why the Things We Loved as Kids Stay With Us
Chapter X with Michael Kay
What if the things you loved most as a kid still hold clues about the life you actually want now? I still remember Yankees games crackling through a transistor radio tucked under my pillow long past bedtime. For Ben Orlando, it was realizing those moments were never really about baseball at all. I’m talking with psychotherapist, writer, and Midnight Library of Baseball host Ben Orlando about masculinity, nostalgia, and what happens when men lose the thread back to themselves. We explore why the hobbies we dismiss as “not serious” often point to something much deeper,...
info_outlineDoug Fleener woke up on an airplane with no idea how he got there. That was the moment his life began to change.
Today, Doug shares the story of hitting bottom and rebuilding his life one decision at a time. He reflects on addiction, recovery, and the importance of learning how to pause before reacting.
Today, Doug is an author and speaker whose work centers on a simple but powerful question: What if? We talk about how that question creates space for perspective and action, especially during major life transitions.
We discuss:
- The moment Doug realized his life needed to change
- Why hitting bottom didn’t immediately lead to transformation
- How asking one simple question interrupts old patterns
- The role of identity and routine during life after career
- Why action matters more than insight alone
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Resources:
Get a free book excerpt at StartWithWhatIf.com
Visit DougFleener.com