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: 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

--

Resources

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

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