Jack Calhoun is someone who deeply understands the emotional and practical challenges that come with stepping away from a successful career. That understanding led him to create a powerful framework to help others navigate this transition with clarity, confidence, and meaning.

Today we discuss:

• The career invested
• When you can do anything, how do you define what anything is
• The paradox of choice, analysis paralysis
• The effect of longer life expectancy
• The cultural mindset about retirement
• “crystalized” and “fluid” intelligence
• “portfolio of small bets”

Jack’s insights allow high achievers – the “career invested” – to forgive themselves for not acing the transition to career divested, and his words ring true for anyone making the transition.

Listen below and then share this episode!

Jack Calhoun is someone who deeply understands the emotional and practical challenges that come with stepping away from a successful career. He is the founder of Encore Career Lab, a program born from his own experience of selling a thriving wealth management firm and then facing the unexpected question: What now?

Like many high achievers, Jack found that freedom without purpose can feel more like drifting than liberation. That realization led him to create a powerful framework to help others navigate this transition with clarity, confidence, and meaning.

Encore Career Lab is designed specifically for successful professionals who are approaching or have recently entered retirement and are asking themselves, “What’s next?” It’s for those who don’t want to lose their sense of purpose and accomplishment, and who are ready to design a fulfilling encore career—one that offers freedom, impact, and income on their own terms.

If you’re coachable, decisive, and resourceful, Jack’s approach could be exactly what you need to turn uncertainty into your most exciting chapter yet.