Jul 15, 2026

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