Jack Calhoun

Jack Calhoun Profile Photo

Founder | CEO

Jack Calhoun has spent more than three decades building programs and companies that meet people exactly where they are and where the world is heading.

A graduate of the University of Georgia's Henry W. Grady College of Journalism and Mass Communications, Jack joined with his father in the mid-1990s to scale his small investment firm, Capital Directions. Jack ultimately became the majority owner and managing partner of the firm before selling the company in 2015.

What came next was unexpected. With no framework, no roadmap, and no program to turn to for guidance, Jack found his post-career phase more disorienting than intoxicating.

That experience inspired Jack to found Encore Career Lab in 2023 to help people create amazing Third Acts for themselves beyond the “life of endless leisure” that has always defined the conventional approach to retirement.

11
June 4, 2026

Reinventing After A Successful Exit with Jack Calhoun

You can “win” your career, sell the business, and still wake up wondering who you are without the role. Host Eric Dickmann talks with Jack Calhoun, founder of Encore Career Lab, to get honest about the emotional and practical mechanics of a second act after a big professional exit. Jack had something many people don’t: financial runway. What he didn’t have was instant clarity, and that gap is where the real reinvention work begins.
Guest: Jack Calhoun
Send Me a Message!