Ryan Doolittle

Happiest Retirees

Society EN ↓ 41 episodes

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,...

Be sure to visit the podcast's website and support the creator: www.retiresoonerteam.com

Author

Ryan Doolittle

Category

Society

Podcast website

www.retiresoonerteam.com

Latest episode

Apr 16, 2025

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Episodes

Projecting Runway Vibes with Nancy Volpe Beringer 17.04.2024

Nancy Volpe Beringer made history as the oldest designer to ever appear on the hit show Project Runway. At 64, she made it to the finale at New York Fashion Week, using her talent and can-do attitude to promote more sustainability and inclusivity in the fashion industry. You’re in a wheelchair? No problem. A prosthetic leg? Nancy’s got an idea to make your outfit glamorous and runway-ready. She ev...

The Aloha Spirit with Dave Kenney 03.04.2024

Don Ho, the famous Hawaiian singer, walked into Dave Kenney’s bar and said, “I like the way you operate.” I don’t know Don Ho, I don’t know that much about Don Ho, but I do know that Don Ho seems to have excellent judgment. I, too, like the way Dave Kenney operates. Originally from England, Dave’s work in the hotel industry eventually landed him in Hawaii, and understandably, he didn’t want to lea...

Retirement is The Best Job I've Ever Had with Tom Georgi 20.03.2024

Tom Georgi’s wife, Suzanne, was horrified to discover that by age 60, he had saved enough money to retire. “You’ve got to get another job, she insisted.” Marines know how to follow a chain of command, and there was no wiggle room in this code red. So, Tom took his marching orders. Being a golf marshal meant miserably early mornings, and dog walking for the animal shelter would track too much dande...

Rookie of the Year with Johnny Hiles 06.03.2024

Johnny Hiles just completed his rookie year of retirement, and his stats are lookin’ really good. He plays pickleball 4-5 times per week and works out even more. He attends a weekly men’s Bible study and volunteers as a greeter every other week at church. He and his wife just took their first trip to Greece and Turkey, with their sights set on taking a big trip at least every other year. After a f...

Volunteering For Service with Penny Martinez 21.02.2024

Penny Martinez started saving money at six and investing at 18. Her goal was to retire early, be debt-free, and find opportunities to give back to her community. She accomplished all three and has never looked back. Penny volunteered for service throughout her life, but retirement allows her to pursue it full-time. She reads to children in elementary schools, works in the kitchen at an emergency s...

The Purpose Driven Dilettante with Nancy Kruh 07.02.2024

Nancy Kruh didn’t realize she was retired until we asked her to be a guest on the Happiest Retirees podcast. She never really liked the label “retired,” and she certainly doesn’t fit neatly within it. Nancy’s not the first person to struggle to accept and embrace retirement. And, to be fair, it’s not like she isn’t still out there, doing impressive work. She covers country music for People Magazin...

Wheels of Fortune with Dave Hogan 24.01.2024

Dave Hogan’s favorite core pursuits are writing and cycling. Whether it’s his fingers on the keyboard or his feet on the pedals, Dave Hogan is on the move. A CERTIFIED FINANCIAL PLANNER™ and former journalist, the now semi-retired author of E-BIKES – Putting the FUN Back into Cycling (and Life) at Any Age is passionate about riding e-bikes and spreading retirement joy. He runs two blogs: one about...

Serving up Pickleball Championships with Owen Mitchell 10.01.2024

Pickleball is the fastest-growing sport in the United States. LeBron James, Michael B. Jordan, Tom Brady, and Drake have all made sizable ownership investments in pickleball teams. One of them needs to get today’s guest onto the roster. Owen Mitchell won first place in the 2023 National Senior Games in Pittsburgh. He’s also won the Florida state championship for his age group in four of the past f...

All Aboard! The Happy Retirement Train at the Santa Barbara Zoo 12.12.2023

This past summer, my wife and I took our son to the Santa Barbara Zoo, about two hours north of Los Angeles. The featured attraction is a miniature train that runs the perimeter. The train conductors act as tour guides, animal advocates, and stand-up comedians. My happy retiree radar was beeping like crazy, and it turned out to be accurate. So, a few months later, I returned to the zoo with all my...

Motion is Lotion with Nancy Erwin 28.11.2023

Motion is lotion. That’s Nancy Erwin’s motto. The laundry list of health problems she’s faced is only outdone by the longer list of solutions she’s found to overcome them. Her spine has a 75 percent curvature—anything above ten is considered scoliosis. But through a dedication to active core pursuits like yoga, strengthening exercises, pickleball, and cycling, she’s carved out a really happy life...

Multiple Streams of Talent with Phil Hendrie 14.11.2023

Phil Hendrie is not retired, not even a little bit. He’s creating as much content as he ever has. But his story still resonates with happy retirees because he had to make a giant change in the middle of his career. In essence, that’s what retirement is—a change. It doesn’t mean you stop doing anything; it means you start doing more of what you’ve always wanted to do. After taking his radio show fr...

Retirement Shock with Mike Drak 31.10.2023

After working in the banking industry for thirty-eight years, Mike Drak was exhausted. With high blood pressure and low motivation, he searched for an exit. To his surprise, the bank showed him the door. Instead of quitting for free, he was now flush with freedom and a severance at fifty-nine years old. The retirement honeymoon didn’t last. After a few weeks, he was miserable. His wife and friends...

To Carnegie Hall and Beyond with Gail & Dickson Grimes 03.10.2023

The realities of life—raising a family and earning a living—don’t always leave us much time to pursue our dreams. So when retirement rolled around, Gail & Dickson Grimes jumped full force back into theirs. On today’s episode, we’ll find out how they took a love for the clarinet all the way to the hallowed stage at Carnegie Hall and how the journey has given them a more robust and happy retirement....

Unbelievably Unretired with Richard Eisenberg 19.09.2023

Richard Eisenberg is often met with a furrowed brow and a question: “Didn’t you retire?” “Yes,” he says. And then, without skipping a beat, he cranks out another freelance article or co-hosts another episode of his podcast. He knows that the happiest retirees stay busy, but he does it on his own terms. After a prolific career writing and editing for outlets like USA Today, Good Housekeeping, and C...

Ingrid Reckard Doesn’t Like Being Unhappy 19.09.2023

Ingrid Reckard says some people like being unhappy; she just isn’t one of them. On the day of her retirement, she was already on a plane to Costa Rica. That’s how much she loves traveling. It’s her number one core pursuit. Chances are, it’s near the top of your list, too. But Ingrid was so passionate about it that she became a certified travel advisor. Now, the exotic locales come with tax write-o...

Let’s Get Started with Jill Smith Entrekin 19.09.2023

Jill Smith Entrekin taught high school literature for over thirty years, but retirement allowed her to write some herself. She’s now published two books, with a third on the way. On the Happiest Retirees podcast, we emphasize the importance of core pursuits—activities that evoke passion and purpose in life. Jill has so many that she had to skip one just to make it to our interview. Life has thrown...

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