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

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.

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