#42 – The Final Chapter: Retiree Reinvention & The Launch Of Tryin Ryan
Don’t just retire, ignite your life! 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), Jerry Williams (FBI agent turned author/podcaster), John Hiles (pickleball enthusiast), and Andy Leitman (former CIA […]
#41 – Retirement’s New Era: How to Thrive in a Life Chapter That Never Existed Before
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 […]
#40 – Final Approach: A Pilot’s Viral Send-Off and the Flight Plan for a Thriving Retirement
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 […]
#39 – From Burnout to Revival: How Dr. Jordan Grumet Resuscitated His Purpose and Retirement
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 […]
#38 – From Ad Exec To Cartoonist: Retirement Laughs & Lessons In Barcelona With Darryl Kluskowski
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 […]
#37 – Staying Social, Staying Sharp: Gail Zugerman On Growing Older With Gusto
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 […]
#36 – An Open Mind On The Open Road: Traveling With Mike Taylor
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 […]
#35 – From Someday to Today: Retirement in Portugal With Cynthia Wilson & Craig Bjork
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 […]
#34 – Boomer Grandma With A Little Edge
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 […]
#33 – MARTA: Public Transportation For Retirees
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, […]
