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

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
  

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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

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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

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:

• Why Carl walked away from a tenured professorship to start over
  
  
• The childhood lesson that fueled his drive to achieve
  
  
• What thousands of therapy sessions taught him about loneliness
  
  
• Why consumer culture promises belonging but rarely delivers it
  
  
• How becoming a "lingerer" can lead to deeper relationships
  
  
• Practical ways to build community in the next chapter of life

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Resources

Website: https://carlnassar.com

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:

• How Larry's experiences growing up influenced the father he became
  
  
• Why repairing mistakes quickly is a critical parenting skill
  
  
• The messages our parents pass down (and how to decide which ones to keep)
  
  
• How to start breaking unhealthy generational patterns
  
  
• What Larry has learned from raising four sons
  
  
• Why good intentions are not enough and what to do instead

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Resources

Podcast: The Dad Edge Podcast

Website: The Dad Edge