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

Send Jay comments via textWhen 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and shows how both career-related and unrelated paths can thrive if your heart is in it.This conversation challenges outdated retirement scripts, reframing work as a fulfilling, energizing part of life’s ongoing journey.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 55-64Identity enmeshment with career and parentingFinding purpose through purposeful actionDefining your core values and non-negotiables firstJack Calhoun BioJack 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, WebsiteSupport the showSUPPORT THE MISSION: If this episode provided you any value or insights, please Follow and Save the show on Apple Podcasts or Spotify. Your "Save" is a vital signal that helps us reach the Top 50 Education charts and reach more families navigating change.WORK WITH JAY (1:1 PRIVATE ADVISORY): You’ve spent decades building the framework of your life. If you find that you’ve finally outgrown the very life you’ve engineered, general advice isn’t enough. You need strategic perspective. Jay works with parents ready to create their second act. Explore his Private Advisory👉 Click here.THE WISDOM COUNCIL (VIP COMMUNITY): Gain exclusive access to proprietary frameworks and early-release content for just $5/month. 👉 Join the Council.GUEST INQUIRIES: Ready to share expert insights with our audience? Connect with Jay Ramsden on PodMatch. 👉 Inquire here. OFFICAL GEAR: This Empty Nest Life MerchandiseENJOY THE SHOW? Leave a review us on ...