A Guide to Thriving – Jon Rosemberg

Two New Designing Your Life groups kicking off in January 2026 is coming soon. Is It Time to Design What's Next?. Learn more and sign up today Early registration discount ends 12/15 "Now I know what I'm retiring to." _________________________ What if everything you've been chasing in your full-time working years—the promotion, the bigger paycheck—hasn't been leading you toward the life you really want? Today's guest, Jon Rosemberg, knows this tension firsthand. After 25 years of climbing the corporate ladder and finally "making it", he found himself in a heated Zoom call, heart racing, feeling trapped—until a moment with his kids playing Legos changed everything. Within two weeks, he left his job, went back to school, and wrote A Guide to Thriving: The Science Behind Breaking Old Patterns, Reclaiming Your Agency, and Finding Meaning, a roadmap for moving from survival mode to genuine fulfillment. In this conversation, Jon reveals the crucial difference between success and thriving, why thriving is both a choice and a skill set, why discomfort is essential for growth, and how the beliefs we carry shape every choice we make—especially as we approach retirement. If you feel stuck on the hamster wheel or are wondering what comes next, this episode offers a fresh lens on what it means to truly thrive. Jon Rosemberg joins us from Toronto. ___________________________ Bio Jon Rosemberg empowers leaders and organizations to shift from survival mode into thriving. With 20+ years of expertise in leadership development, coaching, organizational transformation, and workplace culture, Jon combines real-world business insight with cutting-edge research to help people reclaim their agency and find meaning. Jon has successfully led high-impact initiatives at Walmart, Procter & Gamble, Indigo, and GoBolt. He holds an MBA from Cornell University, a Master of Applied Positive Psychology from the University of Pennsylvania, and advanced certifications in leadership, coaching, and complex negotiations. As CEO of Strongpoint Group and co-founder of Anther, Jon guides individuals through powerful personal transformation with clarity and confidence. Originally from Caracas, Venezuela, Jon’s journey to thriving has taken him from New York and Montreal to Toronto, where he lives with his wife, Adriana, and their two sons. _____________________________ For More on Jon Rosemberg A Guide to Thriving: The Science Behind Breaking Old Patterns, Reclaiming Your Agency, and Finding Meaning Website LinkedIn ______________________________ I’m Just Asking for a Friend Retirement brings so many tough questions. Share your question to be answered in an upcoming retirement podcast episode. Click here to leave a voice message or send me an email at [e-mail] ______________________________ Podcast Episodes You May Like The New Happy – Stephanie Harrison Living Like You Mean It – Jodi Wellman Everyday Vitality – Dr. Samantha Boardman ________________________________ About The Retirement Wisdom Podcast There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time. About Retirement Wisdom I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident. Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University. In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy. ______________________________ Wise Quotes On Surviving versus Thriving "You feel like you're putting out fires, like you're just moving from one thing to the next. And it's very hard to see a lot of options. So that's a ...