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)

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Resources

Website: encorecareerlab.com

Email: jack@encorecareerlab.com

LinkedIn: https://www.linkedin.com/in/jack-calhoun-encore

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

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Resources

Get free chapters at: https://richardsparks.com

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

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Resources

A Joyful Rebellion

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

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Resources

Email: KellyOttman@LeadershipPortals.com

Website: LeadershipPortals.com

LinkedIn: linkedin.com/in/kellyottman

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

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Resources

Tame the Noise

Roaming Coaches

Connect with Mark on LinkedIn

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

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Resources

Lifetime Arts

Ed Friedman's website

I Will Not Be Ignored

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

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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