society
Hosted by Ryan Doolittle · society · EN
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 <a href
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Contact path
Verified email
Booking probability
22%
Guest openness
Selective
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Signup to Generate a PitchAs 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?
Happiest Retirees is hosted by Ryan Doolittle. The show has published 41 episodes to date.
Recent episodes include "The Final Chapter: Retiree Reinvention & The Launch Of Tryin' Ryan" (16 April 2025, 15 minutes), "Retirement’s New Era: How to Thrive in a Life Chapter That Never Existed Before with Eric Thurman" (2 April 2025, 34 minutes), and "Final Approach: A Pilot’s Viral Send-Off and the Flight Plan for a Thriving Retirement with Mark Hardcastle" (20 March 2025, 34 minutes).
Happiest Retirees publishes roughly every two weeks, with episodes averaging 40 minutes across 41 episodes.
Booking probability for Happiest Retirees is 22%, and the host is rated Selective on guests. Happiest Retirees requires a Pod Score of 80 or higher. Happiest Retirees's contact route on record: verified email.
Ryan Doolittle hosts Happiest Retirees, a society podcast with 41 episodes published.
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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)...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest 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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Happiest Retirees
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...
Recent guests on Happiest Retirees. Study who booked and why before you pitch.
Retired FBI Agent & Host of FBI Retired Case File Review, FBI
hospice physician, personal finance expert, author of The Purpose Code, Earn & Invest Podcast
podcaster
former Hackfort director and local event organizer, National Basketball Association
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