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! Follow the Retire Sooner Team channel on YouTube and watch Tryin' Ryan starting April 30th to fuel your post-career passion. Uncover your purpose, embrace new core pursuits, and start living your best retirement life today!

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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 Thrive in Retirement, Eric Thurman, shares practical tips, a few laughs, and plenty of wisdom to help you live with more joy and meaning.

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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 opened the door to healing, reflection, and new possibilities. Discover how Mark stabilized his glide path, reclaimed fulfillment, and transformed retirement into the kind of life that takes off after work ends. So deploy the landing gear, clear the runway, and get ready for a happy retirement.

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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 shares why loving the process matters more than chasing achievements and how anyone can create a meaningful, fulfilling retirement. Plus, we explore his new book, The Purpose Code, and break down how to stop overthinking purpose and start living it. If you’re looking for inspiration, clarity, and a fresh perspective on what retirement (and life) can really be, this episode is for you.

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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 and stay for the life lessons as he walks me through a typical day of happy retirement in Spain.

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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 cancer research and the importance of keeping your health—and your passions—a top priority. 

**Want to support pancreatic cancer research? Visit the Lustgarten Foundation to learn more.

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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’s much easier to hate what we don’t know, and our beliefs and customs go unchallenged. 

Today’s guest, Mike Taylor, not only loves that Mark Twain quote, he lives by it. He’s been on so many life-changing journeys that I couldn’t even fit them all into the podcast. 

Now retired, Mike spent 41 years in the local news business for WLEX-TV in Lexington, Kentucky. Travel is his primary core pursuit. If he’s not spending time with his four adult children or nine grandchildren, he’s probably on the road, on a cruise ship, or in the air above some faraway land. 

He shares his journeys on social media. Today, we are lucky to have him share them with us. If you yearn to find retirement happiness beyond your corner of the world, let Mike’s stories be your inspiration.

00:00-40 Years in Journalism

07:01-Falling in Love with Travel

10:31-Retirement is Awesome

13:05-Big Bend TikTok Story

18:15-38 Countries, One Pass

21:54-Nine Grandchildren

25:31-Better than the Alternative

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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 unconventional, this episode might ignite your passion to pursue it with the same vigor (or even more) as you did your career. Your someday could start sooner than you think.

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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 has 144,00 followers on Instagram and 52,000 on TikTok. A grandmother of three on TikTok! Not exactly what she thought she’d be doing in retirement.

Shannon’s satirical and good-natured approach sheds light on the evolving language around mental health and the importance of setting boundaries—even when they sometimes go overboard. She has a great relationship with her family partly because she’s learned to keep some thoughts to herself. If she “zips it” about touchy topics like “weight loss,” she can get away with making fun of toddler bento box lunches.

So, even though there’s a chance she’ll trigger your childhood trauma, that is not her goal. She wants every generation to know that we’re all in this together, so we might as well have some laughs and enjoy the ride.

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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 has 48 miles of rail track, 38 subway stops, and an abundance of bus routes. From Hartsfield-Jackson Atlanta International Airport to Sandy Springs, Buckhead to Brookhaven, And Decatur to Doraville, MARTA is taking people where they want to go today and tomorrow. And it can’t do that without today’s guest.

Donna E. DeJesús joined the team in 1993 and has over 30 years of advanced experience in transit call center and customer service management. She’s now the Director of Customer Service, but I just call her the Queen of MARTA.

Nowadays, I do own a car. I had to have somewhere to put my toddler’s car seat. I don’t get many nights out, but when I do, I ride the light rail or the bus whenever possible. If you find yourself craving the rails, or maybe you’ve retired and just want to drive a little bit less, this conversation can empower you with the tips and tricks you need to get where you want to go via the mode of transportation with which you want to get there.

So pay that fare, sit back, relax, and let Donna DeJesús dazzle you with some MARTA magic.

00:00-Hot MARTA Bochinche

03:58-All Aboard!

05:45-Reduced Fare Program for Seniors

09:36-MARTA Accessibility Committee

13:09-Exciting Updates

15:51-Access to All the Atlanta Fun & Senior Centers

19:21-Mobility Service

21:41-Getting to the Battery

23:12-Art Bound: Performances on the Platform

27:46-MARTA’s Best Kept Secret

30:44-Donna’s Team & Sustainability in Motion

35:31-Music in the Park

36:33-Overhauls and Tech by 2026

41:07-Staying Safe on MARTA

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