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“Now I know what I’m retiring to.”

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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.

Are you in Survival Mode? Take Jon’s quiz

Jon Rosemberg joins us from Toronto.

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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.

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For More on Jon Rosemberg

A Guide to Thriving: The Science Behind Breaking Old Patterns, Reclaiming Your Agency, and Finding Meaning

Website

LinkedIn

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Retirement brings so many tough questions.

Share your question to be answered in an upcoming retirement podcast episode.

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or send me an email at [email protected]

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Podcast Episodes You May Like

The New Happy – Stephanie Harrison

Living Like You Mean It – Jodi Wellman

Everyday Vitality – Dr. Samantha Boardman

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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.

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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 really good way to define survival mode.  Now let’s try and define what thriving is not. And I think what thriving is not is success. And we’ve often confused thriving with success. I would say success is often measured by money, status, and power. These are three things that we’re all very familiar with, especially because we live in a system that it’s meant to help us be successful. I’m sure many of your listeners experience most of their lives trying to accomplish these extrinsic motivators that are the success motivators, money, power, and status. Thriving on the other hand is a little bit different. Thriving is about agency, meaning, and connection. And when I mean connection, I mean human connection, connecting with other people. Those are kind of like the three big intrinsic motivators of thriving.”

On Agency

“Agency is a skill. It’s not an innate thing that we’re born with. It’s something that we develop. It’s like going to the gym, like doing strength training to get more muscles. Agency is also a developed skill. And as I went deep into the research, I found three things that kept coming up and I synthesized them in an acronym, which is AIR, A-I-R, which stands for Awareness, Inquiry, and Reframing.”

On Negativity – and Hope

“We find ourselves today, because we’re surrounded by so much negative information and constantly bombarded by negative information, we tend to our negativity bias, which is this kind of survival mechanism. And by the way, every second we’re exposed to about 10 million, between 10 million and a hundred million stimuli. Every second we’re exposed, and only about 10 to 50 of those make it into our conscious awareness. And of those 10 to 50, not 10 or 10 to 50,000, just 10 to 50 of those bits of information actually make it into our conscious awareness. And of those, the ratio is about, by some estimates, nine to one of negative to positive. So what I’m suggesting with this idea of positive prospection is hope, really. It’s this idea that if we can be hopeful about the future, then we can create that future. If we give up and there’s no hope, then it’s very difficult. If we’re in that hopeless state, which is very much correlated to survival mode, then it’s much harder to do that.”