Happiest Retirees

Happiest Retirees

As children, we’re all asked what we want to be when we grow up. We tend to see the decision as finite when it isn’t. The Happiest Retirees podcast refocuses the lens to ask, now that you’re grown up, what do you want to do? How do you want to reinvent yourself? Who do you want to be? By going straight to the source — the happy retirees themselves — we capture the essence and the stories of their post-career lifestyles. Where have they stumbled? Where have they triumphed? How did they discover the core pursuits and passions that get them out of bed in the morning? Over the past decade, host Ryan Doolittle has worked with Wes Moss to research and produce two books, countless articles, the long-running Money Matters radio show, and his successful Retire Sooner podcast. He’s a writer and comedian living in Los Angeles. He’s been both unhappy and happy, and he prefers the latter. 00:00-You Can Do Just About Anything 03:29-Transitions & Empowering Older Adults in Tech 09:21-Mindset Matters 10:33-A Birthday Card Contest Turned Etsy Business 15:48-Tradeshows & Strategy 22:06-Immerse Yourself in Something Joyful 28:21-Retirement Rewirement 33:30-Practicality Problems 36:42-Ikigai! 40:50-Core Pursuits & Staying Active

Episodes

April 16, 2025 14 mins
In the final episode of the Happiest Retirees Podcast, we celebrate the show's journey and launch into our next adventure: the Tryin' Ryan YouTube series. Hear from vibrant retirees like Jill Smith Entrekin (author), Jerri Williams (FBI agent turned author/podcaster/Hollywood consultant), Johnny Hiles (pickleball enthusiast), and Andy Liepman (former CIA turned train conductor).  Transition from podcast listener to YouTube viewer!...
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Retirement today isn’t what it used to be—it's a whole new life chapter! People are spending 20, 25, even 30 years in retirement. So, how do you make those years truly fulfilling? It’s not just about money—it’s about curiosity, connection, and purpose. Dive into why friendships keep you thriving, how gratitude rewires your brain for happiness, and the little things that make a big difference. Retirement trailblazer and author of Th...
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A legendary airline captain’s final flight, a viral send-off, and the unexpected turbulence of retirement—this episode snaps your seat back and tray table into their full upright position. After 40 years of high-stakes decisions and strict schedules, stepping away from the cockpit felt like losing purpose for Mark Hardcastle. Navigating the sudden freedom proved unexpectedly disorienting, but embracing a self-imposed sabbatical ope...
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We’ve all had jobs we didn’t want. I just never considered the idea that doctors might feel that way, too. We tend to elevate them to some higher status, but they’re human, too. In today’s episode, I uncover Jordan Grumet’s incredible journey from a burned-out physician to a fired-up, purpose-driven author and speaker. He opened up about how he escaped the identity trap of his medical career and built a life he loves.  Jordan share...
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What happens when a creative powerhouse trades the ad world for a life of storytelling, adventure, and clumsy Spanish in Barcelona? I sat down with Darryl Kluskowski—award-winning cartoonist and children's author—to talk about his journey from agency exec to expat artist. He told me how he finds inspiration in unexpected places (including the bathroom—his latest book, The Flush Files, is certainly on-brand). Tune in for the laughs ...
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Gail Zugerman is a podcaster, golfer, book club enthusiast, and advocate for aging with purpose. She gave me insights from her show Growing Older with Gusto, highlighting the power of social connections, lifelong learning, and maintaining a positive mindset. From golf greens to canasta tables, she proves that retirement isn’t about slowing down—it’s about finding what fuels you. She also opened up about her dedication to pancreatic...
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Mark Twain may be the father of American literature. He’s got a million great quotes; even the apocryphal ones are good. A particularly penetrating one leans into the importance of travel. He called it fatal to prejudice, bigotry, and narrow-mindedness.  The general idea is that only by experiencing different cultures can we hope to overcome our human tendency to fear the world’s other “tribes.” If we stay in our little bubbles, it...
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Chef Cynthia Wilson and Craig Bjork had envisioned retiring to Portugal "someday," but when COVID brought their bustling food truck business to a halt, "someday" became "today." Despite their contrasting personalities—Cynthia, a creative dynamo, and Craig, the embodiment of laid-back calm—they’ve created a life of joy, affordability, and deep community in Portugal. If you’ve ever dreamed of a bold retirement, no matter how unconven...
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Every generation tends to blame the one prior for its problems. Right now, the Baby Boomers are taking most of the heat. Today’s guest empathizes with the premise, but she has a few notes.  Inspired by her own family's intergenerational dynamics, Shannon Nelson’s musings about the clash between Boomer and Millennial parenting styles spilled over onto social media. And, well, apparently, a lot of people online can relate. She now ha...
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November 27, 2024 50 mins
On my first date with my future wife, I picked her up in an Uber. I played it off as a romantic gesture, but the truth was that I didn’t own a car. I’d given it up because I love public transportation. There’s just something about it. You can clear your head, get work done, and actually see the city rather than focus on the traffic. Atlanta’s version of the LA Metro is called MARTA. The Metropolitan Atlanta Rapid Transit Authority ...
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In the first part of our lives, we’re busy working toward a career. Then we’re busy doing it. By the time we’re done, we’ve gotten pretty good at whatever it is we do, so it can be pretty intimidating to try anything else. What if we’re terrible at it? Carl and Diana Landau want all of us to embrace the idea of being a beginner. As co-authors of the Amazon best-seller Pickleball for Dummies and the team behind the I Used to be Some...
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I’m a massive fan of books and movies about the FBI. If my wife sees me reading, she can often assume it’s some story about counterintelligence or criminal profiling. One night, I was enjoying a podcast called FBI Retired Case File Review, and it dawned on me that as someone with my own podcast, I could just ask the host to be a guest. To my delight, she agreed. Jerri Williams retired after serving 26 years as a special agent in th...
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Ken Klinker loves carving pumpkins. He started doing it for his kids 30 years ago. He’d come home from work and head straight to the shed—eager to sculpt some groovy orange gourds. His wife spent so much time alone in the house that she started calling herself “The Pumpkin Widow.”  But retirement has given Ken the freedom to turn that passion into a thriving core pursuit that even pays for itself. He switched to foam pumpkins becau...
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If you grew up in the South, you’ve probably heard Gregg Russell sing. If you were lucky enough to vacation on Hilton Head Island, South Carolina, you’ve probably heard it live. He’s been singing for kids and their families in Harbour Town under a 300-year-old oak tree since 1977. Two of those kids grew up and made a movie about him. The Gregg Russell Story became the #1 trending documentary on Apple TV earlier this summer.  After ...
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September 18, 2024 41 mins
On this very special episode, Ryan breaks out his tuxedo and invites Producer Mallory into the studio to celebrate one year of interviewing happy retirees. They explore some of the most dynamic lessons learned and what they hope the listeners will use as inspiration in their own lives. Break out the champagne glasses and help the gang toast all the smart, brave, resilient, and joyful guests who have taken the time to share their st...
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Kathy Sperl-Bell has an abstract painting called “Dinner Time.” In it, a Pelican stares down into the sea as dark shadows betray the location of fish who, unbeknownst to them, are in serious jeopardy. What strikes me about this particular Pelican is his ability to keep his eye on the prize. His hunger is evident. That patient facade is a practiced skill, not a breezy indifference. He knows that accomplishing his goal will require c...
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Albert Einstein once said, “Look deep into nature, and then you will understand everything better.” George Jerjian gave it a shot. What he noticed was that nothing in nature retires. Polar Bears don’t leave with severance packages, and Komodo Dragons don’t get a gold watch or cake in the office kitchen. Wildlife is typically either growing or dying.  In short, George says the word “retirement” is past its sell-by date and prefers “...
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Think about the last time you bought a birthday card. You were probably in a hurry, maybe even running late for the party you needed the card for. You scanned the racks, noticing that cards now cost more than the gift. But even more than that was the overwhelming bombardment of “over-the-hill” birthday themes: sagging body parts, balding heads, bad jokes about fading attractiveness. If you found it a little depressing, you’re not a...
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My conversation with Steve Hoffman was deep and engaging, largely due to his eloquence and profound self-reflection. Steve is a Minnesota tax preparer and a French-loving food & wine writer. I don't know if one person has ever been both of those things. His writing has garnered significant recognition, winning multiple awards, including the prestigious 2019 James Beard M.F.K. Fisher Distinguished Writing Award. His work has been fe...
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As Americans, we tend to believe our jobs define us. Think about that last time you met someone new. What’s the first thing you asked? “So what do you do?” How we make a living is so ingrained in our self-worth recipe that we often neglect the other ingredients.  Jacquie Doucette wants to change all that. She says our jobs don’t define us, and she’s dedicated to helping people remember some of those other ingredients. What did you ...
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