Happiest Retirees

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 p...

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. Reti...

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 embr...

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 b...

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...

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...

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.” I...

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...

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 p...

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 Metropolit...

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 th...

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 servin...

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....

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 Ap...

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 ha...

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 ac...

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...

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 i...

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...

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 tho...

After a successful 35-year career as a psychotherapist, Hugh Willard decided to embark on a new journey as a writer. Currently pursuing his Master’s Degree in Creative Nonfiction, he authored a book and hosts a podcast about finding beauty in the gray. I have more gray hair than I used to, and sometimes, I feel insecure about it. But it’s funny; my barber recently told me some of her clients would...

Edd and Cynthia Staton were on track for a happy retirement, but life had other plans. The Great Recession killed their careers, home value, and savings. Instead of throwing in the towel, they devised an outside-the-box solution: moving to Cuenca, Ecuador.  Initially, they were banking on the lower cost of living to make ends meet. Today, their story is a testament to the power of resilience and a...

Michael Blowen loves “being old.” Those are his words, not mine!  After years as a film critic for the Boston Globe, he snapped. In the middle of an awful movie, he stood up and yelled at the other critics: “How can you endure this?”  Today, he’s so much happier. As the founder of Old Friends, a Thoroughbred aftercare facility in Georgetown, Kentucky, he’s helped turn a modest mom-and-pop operatio...

*In the new documentary "Hendrie," some real heavy hitters, like Bill Hader, Judd Apatow, and Kevin Pollak, all discuss their admiration for Phil's unique and hilarious creativity. So, we decided this was the perfect time to reintroduce you to the interview he did for our show.* Phil Hendrie is not retired, not even a little bit. He’s creating as much content as he ever has. But his story still re...

At nearly 70 years old, my guest, Craig Miller, is one of the oldest firefighters in the world. He doesn’t get paid for it, and he wasn’t even sure he wanted to do it, but the question that gnawed at him was, “If not me, who?”  In 2023, he shared a startling statistic: “Volunteers comprise some or all of the staffs of more than 85% of fire companies across the U.S., according to an estimate by the...