Happiest Retirees Ryan Doolittle
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- Society & Culture
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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 Retire Sooner podcast. He’s a writer and comedian living in Los Angeles. He’s been both unhappy and happy, and he prefers the latter.
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Projecting Runway Vibes with Nancy Volpe Beringer
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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The Aloha Spirit with Dave Kenney
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 leave. Since then, he’s owned and operated just about everything: a convenience store, a t-shirt business, a fishing boat, and nine or ten different Honolulu bars, restaurants, and nightclubs.
During the Covid-19 outbreak, Dave and his wife, Margie, bought a place in Henderson, Nevada, just outside Las Vegas. Now, they hop back and forth between the two. That journey is a common one: Las Vegas has been called “The Ninth Island” because of its sizeable Hawaiian population.
Dave retired at 55, but Margie’s real estate business is booming, and he lends his hoteling expertise whenever she needs it. Otherwise, he does Zumba four days a week, walks several miles daily, and enjoys his afternoon cocktail.
Dave finds a perfect day no matter where he is, and as much as he travels, that could be just about anywhere. For a guy who claims he’s never worked a day in his life, he sure has had a lot of jobs. Maybe that’s the beauty of the Aloha spirit.
When life handed Dave lemons, sometimes he made lemonade. Other times, he traded the lemons for limes and made a gin and tonic to enjoy by the pool. That sounds like a happy retirement to me.
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Chapter titles:
00:00-Start
02:24-From First Jobs to Hawaii
09:58-Taste of Honolulu
12:14-Transatlantics
17:19-Staying Fit
21:50-Booze Cruisin’
24:19-Earn a Little, Keep a Lot
30:50-I’m Happy Where I’m At
38:16-Core Pursuits & Identity
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Retirement is The Best Job I've Ever Had with Tom Georgi
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 dander into the house, so when a friend suggested volunteering at the USS Midway Aircraft Carrier Museum in downtown San Diego’s Embarcadero, he gave it a shot.
More than a decade later, he’s never looked back.
Named after a WWII naval battle that helped turn the tide of the war with Japan, the Midway was the United States’ longest-serving carrier of the 20th century and is now an immensely popular tourist destination. As a safety officer, Tom greets guests at the entrance and exit, roams the floor, monitors the flight deck, and loves every minute of it.
Tom spent twelve years on active duty in the Marines, then taught Air Force Officers how to fire the Cruise missile weapon system for General Dynamics and eventually moved to a computer science corporation. That sounds like an exciting career. But without hesitation, Tom says that working at the Midway is the best job he’s ever had, even though it doesn’t pay him a penny.
00:00-Start
04:31-Bend with the Breeze
06:10-A Professional Volunteer
09:14-Hotfooting it For the Grandson
10:49-For the Love of Cruises
14:29-Fully Retired, Semi Planned
17:17-EA-6B Prowler and Yeti
19:50-Facing Challenges
24:54-Midway Naval Museum History
30:01-That’s My Definition of Retirement
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Rookie of the Year with Johnny Hiles
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 full career, Johnny has no regrets about retiring, and he’s hoping his story will help others decide the right time in their own lives.
As a professional, he went by John. Now, more and more people call him Johnny. In a way, retirement has recreated his identity. John had to get up every day and go to work. Johnny gets to explore the world, enjoy his family, and even tackle that honey-do list.
John had to act like a grown-up. Johnny’s far too happy for that.
After a year in the retirement game, it’s safe to say Johnny is well on his way to a promising career of happiness.
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00:00-Johnny’s Identity Shift
02:50-The Big Questions
05:43-Johnny’s Career Journey
08:11-A Very Good Mentor
10:48-Staying Active
12:22-Atlanta Living
14:05-Two Out of Three
16:33-Getting Involved at Church
18:38-The BC Boys Ski Trip
21:00-Doing the Same Stuff, just More of It
22:20-Upsizing Again
26:10-“Retirement Recreated Me.”
27:47-Financial Planning and Confidence
29:19-Retirement is Limitless
31:34-Comparison is the Enemy of Contentment
32:49-A Rookie Season, But…
33:48-Plan, but Go For It
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Volunteering For Service with Penny Martinez
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 shelter, writes holiday cards to care facility residents, picks up trash, supports a pregnancy center, fights human trafficking, organizes blood and clothing drives, coordinates a local veterans group and community neighborhood watch, puts wreaths on veteran graves, and even dabbles in politics.
As a two-time breast cancer survivor, one could argue she’s earned the right to spend more time pampering herself. But that’s not Penny. Oh, she definitely has fun, but she insists that the true joy of life can be found in serving others.
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00:00-Start
01:38-A Service Heart
04:17-First Investments
09:44-You Want It? Go Get It.
13:11-Surviving Cancer. Twice.
15:15-Being Pulled Like Gumby
20:35-Things Didn’t 'Pan' Out
25:18-Everyone Should Give One Hour
35:06-Faith, Family, Foundations
42:27-A Perfect Day
44:25-Thread Kindness Through 365 Days
49:51-Redefining Retirement
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The Purpose Driven Dilettante with Nancy Kruh
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 Magazine and People.com. But unlike during her 25-year career at the Dallas Morning News, she’s not tied to the grind. She works for fun and creative fulfillment. She only writes about the topics that interest her.
Nancy says people call her a dabbler, but she prefers “dilettante.” She’s not afraid to try all sorts of new tricks: oil painting, knitting, video editing, home renovation, playwriting, screenwriting, fiction writing, life drawing, singing in a choir, photography . . . you get the point.
But she’s also not afraid to quit the pursuits that don’t bring her a sense of purpose.
It’s slowly dawning on Nancy that she’s in a new phase of life that allows for more freedom. She’s driven to feel relevant, purposeful, and creative. She doesn’t expect to change the world, but she does want to matter.
I’d say that’s a fairly ambitious retirement plan for a dilettante.
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BONUS: Check out Nancy’s curated Spotify playlist featuring some fantastic female country music artists! https://open.spotify.com/playlist/2LXSCnDgZHhPp2rDnorZzy?si=76a30b268ad545b0
00:00-Start
02:26-The Glitzy World of People Magazine
11:42-Volunteering Victories
15:35-Be Choosy
21:37-Semi-Retired, Fully Alive
23:19-Retire the word ‘Retired’
25:27-Scriptured Up
29:34-Selfless or Selfish? Nah, Self-ful.
32:32-Wellness Wisdom
40:43-Happiness Blueprint
46:09-Family Bonds & Vibrant Energy
51:47-Dilettante
53:52-A Feast of the Senses
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Customer Reviews
Love this!
It’s awesome to hear how people reinvent themselves as the age. This is such an inspiring podcast!