Happiest Retirees Ryan Doolittle

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 shell out a lot of money for that brownish-gray coloring. And it’s that positive twist that Hugh uses to change the conversation about aging. 
Hugh lives in the beautiful city of Apex, North Carolina, which is fitting because as he ages, he seems to be summiting the peak of his own happiness.
00:00-Purpose & Identity
01:13-Pivoting to a New Chapter
03:20-The Osher Institute
06:19-A Generative Direction
09:30-An Unexpected Passion
11:18-Music & Family
15:00-Audrey’s Incredible Journey
17:42-Answering “Who Am I Now?”
27:00-The Default Mode Network
30:22-Intergenerational Connectivity
32:44-Lowercase f failure & Retirement as a Transition
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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 adaptability. They've transitioned from surviving to thriving! Residing in a 3,000-square-foot penthouse apartment, they can still afford a housekeeper, dine out frequently, and cover health care costs. They even walk to their favorite yoga studio.
Ex-pat life has become more common for retirees in the U.S. According to the Social Security Administration, the number of retirees drawing Social Security outside the U.S. saw a staggering increase between 2007 and 2017.
Those looking to do so in the future might want to ask Edd and Cynthia for tips. They’ve authored three Amazon #1 best-selling books, are regularly featured in major media, and run their own online program: Retirement Reimagined!
The affordability of living in another country has given Edd and Cynthia the freedom to explore the retirement happiness they’d always dreamed of having. If you’ve ever considered the idea, today’s episode is a must-stop on your itinerary. 
00:00-Start
01:51-An Unexpected Path Forward
08:15-Timezone Matters
11:54-Walking Around Paradise
17:44-Retirement Reimagined
24:07-Committed to Community and Health
33:04-Navigating Healthcare
38:42-Life on our Schedule
44:07-Purpose and Play
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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 operation into a sprawling 236-acre farm with three satellite locations and a herd of over 255 retired former racehorses and breeding stallions. 
Retirement, if you can call it that, really suits Michael. He believes age is a free pass to say yes to the fun and no to the dreaded obligations. He’s formed friendships with celebrities like Albert Brooks and Angie Dickson. Every morning, he wakes up with a heart full of gratitude, ready to feed former Kentucky Derby winners. The thrill of it still gives him the chills.
This whole thing started because Michael, as a fan of horse racing, wanted to improve his gambling skills. But whoops! He fell in love with horses and has dedicated his life to improving their lives. Listen to Michael. It might improve your life. 
00:00-Start
03:06-It Started with Six
07:45-Old Friends
14:54-Mo Rocca & the “Rocca Generians”
18:11-Recovering Movie Critic
23:18-You Can’t Go Back Up the Stretch
27:10-Retirement’s an Odd Word
29:05-About the Horses
34:47-A Page Out of Their Book
40:11-There’s a Horse in Your Living Room
43:37-Adversity is an Asset
46:11-Let’s Take a Shot at This
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*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 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 from a tiny local station to national syndication, Phil realized the business had changed. It was no longer viable to do comedy on the radio. So, he got creative and transitioned to a daily podcast instead. Because his talent was versatile, he also picked up acting roles and voice work in movies, television shows, animation, and video games. He even retained ownership of his old radio material to repurpose for fans who wanted to listen. Don’t look now, but that adds up to multiple streams of income, and you know we love that on this show!
The bottom line is that even though Phil Hendrie is not retired, his story can still inspire people who want to be. Between that and his comedy genius, this episode is a must-listen!
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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 National Volunteer Fire Council.” This eye-opening revelation highlights how much responsibility we thrust upon volunteers to keep us all safe.
The funny thing is that Craig could’ve easily been voted least likely ever to battle flames. He’s a public radio guy—you know, the coffee-sipping, tote-bag-toting, academic type. Or, at least, he was, having spent more than 40 years as a broadcaster and journalist. He launched and edited the award-winning Climate Watch multimedia initiative for KQED radio in San Francisco. He’s also an accomplished writer/producer of television documentaries and even co-created a show called “House Detective” for HGTV. 
In 2019, he moved from California’s Bay Area to the Catskill Mountains of New York. The local firefighters pursued his services and eventually succeeded in attaining them. But the pleasure has been all Craig’s. Volunteering as a firefighter has become one of the most gratifying features of his entire life. 
I spoke with him again after our interview, and he wanted to amend one of his answers. Rather than labeling himself principally as a firefighter, he wanted to go on the record as an “evangelist for volunteerism and community service.” I understand and appreciate the distinction, but when that 911 call rings out in the middle of the night, I’m not sure Craig the evangelist is getting out of bed, but Craig the firefighter sure is. One might even say Craig the firefighter is a damn hero. 
00:00-Start
04:57-Good Morning Frankfurt
09:03-Theater of the Mind
10:01-Climate Documentaries & HGTV
15:57-Climate Refugees
19:46-The Birth of Standup
21:02-We’re Not Urban Animals
23:42-65% Volunteers
34:22-Knowing When to Say When
37:48-A Fresh Identity
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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 eventually created “The Vault by Volpe Beringer”—the world’s first and only fully accessible designer luxury platform, offering adaptable options and complimentary consultations for the disabled community.
Nancy won the 2022 Fashion Group International (FGI) Rising Star award. She was named “Best in Philly Fashion Designer for Artsy Dresses” by Philadelphia Magazine for her viral red-carpet design for Grammy nominee and rapper Tierra Whack.
This incredible journey almost didn’t happen. At age 50, Nancy already had a successful career and financial security, but she was miserable. Sure, she’d grown up sewing, but she never dared to dream of becoming a fashion designer. Then, one day, BAM! It all became so clear. Despite the fear of starting over so late in the game, she went for it! No regrets, Nancy.
If fashion is your thing, you’ll love this episode. But hell, if you like the movie Rocky, you’ll enjoy it, too. Like the Italian Stallion, Nancy is a gritty underdog from the mean streets of Philadelphia. She’s never climbed into a boxing ring with Mr. T, as far as I know, but she is definitely a fighter. So, put up your dukes, turn up your volume, and get ready to be inspired.
00:00-Fresh Starts & Accolades
03:09-Inclusive Representation
08:27-Displaced, but not discouraged 
12:33-Another Word for Retirement
16:07-I Just Want to Make a Difference
20:27-Tierra Whack at the Grammys
24:17-Make Fear Your Friend
33:18-Working with Legends
35:21-Core Pursuits
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