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The Retirement Wisdom Podcast

The Retirement Wisdom Podcast

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  • The Retirement You Didn’t See Coming – Dan Haylett

    The Retirement You Didn’t See Coming – Dan Haylett
    Jan 5 2026
    Are you graduating from the grind in 2026? You could go it alone and wing it. But here’s what one participant said about our small group coaching program: “It was fantastic! I got to work with other people and share ideas with others on what retirement could be. It gave me clarity and confidence.” New groups are starting on January 22 & 23. Let’s go. Learn more Join us “Challenged me to get out of the starting blocks and far down the path of really thinking about this next phase of my life in very different ways. I now feel like I have a solid road map.” “I wish I’d taken this program earlier.” _____________________________ What if everything you’ve planned for financially in retirement still leaves you feeling completely lost? Today’s guest knows this paradox intimately. Dan Haylett built his career as a financial planner, helping people achieve financial independence. But what he discovered shocked him: when money stops being the problem in retirement, and that’s when the real problems show up. Dan is a retirement transition specialist helping people navigate the psychological side of retirement that no financial plan can solve. He’s learned that people plan meticulously for financial independence but rarely prepare for psychological independence. The result? Three devastating losses hit early: loss of structure, loss of relevance, and loss of identity. In this conversation, Dan shares his framework for retirement well-being built on five human pillars that have nothing to do with your bank account. He challenges what you think you know about retirement as a “reward” and shows you why the most successful retirements aren’t built on bucket lists and endless travel, but on something far simpler and more profound. If you’ve ever wondered who you are when no one needs your output anymore, this episode will change how you see the next chapter of your life. Dan Haylett joins us from the UK. ______________________ Bio Dan Haylett, who’s the author of The Retirement You Didn’t See Coming: a guide to the human side of retirement nobody warns you about. Dan is a financial planner and head of growth for TFP Financial Planning based in the UK. Dan focuses on financial planning, retirement planning, and life planning for people 50+. He also hosts a podcast called Humans vs. Retirement on the behavioral aspects of retirement. Prior to joining TFP, Dan held a number of positions in asset management. ______________________ For More on Dan Haylett The Retirement You Didn’t See Coming TFP Financial Planning Humans vs Retirement ______________________ Podcast Conversations You May Like How to Prepare Mentally for Life After Work – Joseph Maugeri Retiring: Creating a Life That Works for You – Teresa Amabile What Are The Keys To A Successful Retirement? Fritz Gilbert ______________________ 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 Structure in Retirement “So the biggest surprise for me is this. Money stops being the problem. And that’s when the real problems show up, right? So I think that’s kind of the biggest surprise for me. People expect relief. Instead, they probably feel quite disorientated. They’ve planned for financial independence...
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    29 m
  • Best of 2025 – Part Two

    Best of 2025 – Part Two
    Dec 29 2025
    Are you ready to graduate from the grind in 2026? Then here’s your most important project: Future You. Join our small group coaching program and design your new life after work. Learn more “Eye opening and provocative.” “Challenged me to get out of the starting blocks and far down the path of really thinking about this next phase of my life in very different ways. I now feel like I have a solid road map.” “I wish I’d taken this program earlier.” __________________________ Start the new year right with new habits. FREE 3 session program – 3 Fridays in January at Noon Eastern January 2, 9 and 16 Sign up here ____________________________ Thank you for joining us and listening this year. This special year-end Best Of episode is a collection of valuable insights from our recent guests. If you missed Part One, you can find it here ____________________________ Listen in to full conversations: Harry Agress Kerry Burnight Nathalie Martin Ken Stern Joseph Magueri Christine Platt Michael Long Carl Landau Francine Toder Diane Button ________________________ You May Also Like The Very Best of 2024 – Retirement Wisdom Best of 2023 – Part Three _________________________ 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.
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    39 m
  • The Vintage Writers – Kim Gottlieb-Walker & Roselyn Teukolsky

    The Vintage Writers – Kim Gottlieb-Walker & Roselyn Teukolsky
    Dec 22 2025
    Are you ready to graduate from the grind in 2026? Then here’s your most important project: Future You. Learn more “Eye opening and provocative.” “Challenged me to get out of the starting blocks and far down the path of really thinking about this next phase of my life in very different ways. I now feel like I have a solid road map.” “I wish I’d taken this program earlier.” __________________________ Start the new year right with new habits. FREE 3 session program – 3 Fridays in January at Noon Eastern January 2, 9 and 16 Sign up here __________________________ What if the most creative chapter of your life hasn’t happened yet? Today’s conversation is about second acts that arrive not quietly—but boldly. Kim Gottlieb-Walker published her debut novel at age 78 after a 50-year career as a photographer. She also leads the Vintage Writers, a lively weekly Zoom group of women authors over 70. Joining her is Roselyn Teukolsky, a former math and computer science educator who retired and now writes fiction. This conversation explores creative courage, identity shifts, the power of starting something new – and the value of community. Kim Gottlieb-Walker and Roselyn Teukolsky join us from California. _________________________ Planning for retirement? Check out our recommended Best Books for Retirement _________________________ Bios Kim Gottlieb-Walker’s career as a photographer covered a wide range of subjects, from classic rock and roll, reggae, and politics in the ‘60s and ‘70s to major motion pictures and television shows. Now in her late 70s, she has reinvented herself as a novelist. While still at UCLA (where she received a BA in Motion Picture production) and shortly thereafter, she shot for underground LA newspapers and magazines including Crawdaddy, the Staff, and Music World. She also shot the stills for John Carpenter’s Halloween, The Fog, Christine and Escape from New York and worked at Paramount Pictures for nine years as the production photographer for Cheers, and five years for Family Ties. For three decades she was an elected representative for still photographers on the National Executive Board of IATSE Local 600, the International Cinematographers Guild. Her coffee-table photo books Bob Marley and the Golden Age of Reggae and On Set with John Carpenter were published by Titan Press (UK) distributed by Random House (USA) and both are now in multiple printing. They have editions in Japanese, Russian and French. She’s had gallery shows in London, Los Angeles and New York. Her novels are Lenswoman in Love – a novel of the 1960s & ‘70s (her debut) and the not-yet published historical novel Caterina by Moonlight, about a girl growing up in renaissance Florence in the late 15th century. Her short story “Summer of Love – 1967” appears in the multi-award-winning anthology Feisty Deeds. Former math and computer science teacher, Roselyn Teukolsky, is the author of A Reluctant Spy, an unconventional spy thriller, and The Fourth Woman, a cautionary tale about online dating. Teukolsky has long been intrigued by the dilemmas faced by smart women in male-dominated settings. Working as a computer science teacher has given her the familiarity to create an authentic female protagonist, a brilliant computer scientist, who, in the latest novel, must ward off a ransomware attack and an online-dating predator. Teukolsky has a B.Sc. in Math and Chemistry from the University of the Witwatersrand in Johannesburg, and an M.S. in Math Education from Cornell. She is the author of the Barron’s review book for AP Computer Science, which is currently in its 12th edition. Roselyn’s favorite pastime is tournament bridge. She wrote How to Play Bridge with Your Spouse … and Survive (Master Point Press) in 2002. She lives in Pasadena, CA, with her husband, Saul Teukolsky. ________________________ Have a Question You’d Like Answered on the Podcast? Click here to leave a voice message or email me at joec@retirementwisdom.com _________________________ For More on Kim Gottlieb-Walker Lenswoman in Love www.Lenswoman.com for an overview of her photographic history www.TheRenaissanceWoman.net www.KimGottliebWalker.com – her author website. — For More on Roselyn Teukolsky A Reluctant Spy The Fourth Woman _________________________ Podcast Conversations You May Like Why Retirement Was Just the Beginning – Neal Lipschutz A Creative Pursuit with an Intergenerational Assist – Neil & Michelle McLaughlin Edit Your Life – Elisabeth Sharp McKetta __________________________ 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...
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    29 m
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