November 22, 2025

123. From Empty Nest To Encore Career: Finding Direction in Your 2nd Act

39 minutes

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When your children launch or your career ends, a strange silence can set in—and with it, the big question: What’s Next?

In this inspiring episode, Jack Calhoun, founder of Encore Career Lab, shares a hopeful, practical path from drifting to purposeful direction. He discusses how many of us face an identity crunch when titles no longer define us—and how to use agency, values, and curiosity to craft a second act that truly fits.

Jack unpacks the paradox of choice—why having too many options can stall momentum—and offers a straightforward antidote: start with your why and non-negotiables, identify your caring audience, and run small, low-risk experiments. He emphasizes that purpose often follows action, not the other way around, and shows how both career-related and unrelated paths can thrive if your heart is in it.

This conversation challenges outdated retirement scripts, reframing work as a fulfilling, energizing part of life’s ongoing journey. Expect honest talk about fear, ego, and indecision, along with tactical advice on surfacing your “wisdom fingerprint,” setting boundaries, and testing new ideas without risking everything.

Key takeaways:

The rise of entrepreneurship among ages 55-64
Identity enmeshment with career and parenting
Finding purpose through purposeful action
Defining your core values and non-negotiables first

Jack Calhoun Bio
Jack J. Calhoun is the founder of Encore Career Lab and a seasoned entrepreneur with over two decades of experience managing a wealth management firm. After selling his business, Jack faced his own post-retirement questions about purpose and fulfillment, inspiring him to help others navigate similar transitions. He specializes in guiding high achievers—particularly those aged 50 and above—toward designing meaningful second careers that blend passion, impact, and income. Through his insights and frameworks, Jack empowers professionals to turn uncertainty into opportunity and create purpose-driven encore careers that enrich their lives well beyond traditional retirement.

Find Jack Online: LinkedIn, Website

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