People in Transition 134. Jack Calhoun - Founder, Encore Career Lab
This week on "People in Transition", our guest is Jack Calhoun—an inspiring guide for anyone exploring what comes after a successful first career. As the founder of Encore Career Lab, Jack helps high-achieving professionals design meaningful “second acts” that blend purpose, flexibility, and fulfillment. His passion comes from experience: after leading Capital Directions, LLC from $50 million to over $1.5 billion in assets under management, Jack sold the firm in his early 50s—and quickly discovered how little guidance there was for life after career success. That realization became his mission: to help others bridge the gap between retirement planning and life planning.
During our conversation, Jack shared powerful insights and practical guidance for listeners thinking about their next chapter, including:
- Redefining identity: How to deal with the loss of identity that often comes when stepping away from a long career.
- Rethinking retirement: Why the traditional idea of “retirement at 65” no longer fits our longer, healthier lives—and what sustainable reinvention really looks like.
- Evolving goals: How success, satisfaction, and fulfillment shift as we enter the third phase of our lives—and how to measure meaning, not just achievement.
- Giving back wisely: The role of volunteering in encore careers, and why it won't fill the void where "work" used to be.
- Real-life transformations: Inspiring stories of people who discovered unexpected “callings” far different from their earlier careers.
- Sharing hard-earned wisdom: How to recognize and use the insights you wish you’d known 30 years ago to help others—and yourself—today.
If you’ve ever wondered, “What’s next for me?”—this episode is a must-listen. Jack’s perspective will leave you inspired to see the years ahead not as a winding down, but as a powerful new beginning. Tune in to hear how you can transform experience into impact and uncertainty into opportunity. To connect directly with Jack or learn more about Encore Career Lab, visit encorecareerlab.com or email Jack at jack(at)encorecareerlab.com.