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Six Lessons Learned On The Happiest Retirees Podcast

Happiest Retirees Podcast with Ryan Doolittle

It’s been six months since we launched the Happiest Retirees podcast. As the title might suggest, the mission was to find the world’s happiest retirees and ask them how they got so happy. The hope was that if we extracted the answers from the people who had them, we might be able to help others follow suit.

The time felt right to put some cards on the table and share six valuable lessons I’ve learned so far.

Lesson #1: Thank You For Your Service With Tom Georgi

Tom Georgi at the USS Midway Aircraft Carrier Museum

What I Learned: Volunteering for service creates opportunities for happiness.

Tom Georgi served on active duty in the Marines for twelve years, so when it comes to patriotic duty, he’s checked that box and then some. However, when I visited him at his beloved retirement post, volunteering as a safety officer aboard the USS Midway Aircraft Carrier Museum in San Diego, he was more interested in talking about someone else’s service: his son.

Lieutenant Colonel Chris “Yeti” Georgi is a decorated pilot. More specifically, he’s an experienced Marine EA-6B Prowler Electronic CounterMeasures Officer (ECMO) and Mission Commander with two Japan-based deployments to the Western Pacific and three supporting Operation Iraqi Freedom, with over 800 combat flight hours.

When the Marines donated a Prowler jet to the USS Midway Museum, Tom discovered that by some miraculous coincidence, Chris had flown that exact one in multiple missions. So he added Chris’s name to the exterior for all museum-goers to see. He teared up when telling me, and seeing such love and reverence from one patriot to another was beyond moving.

Tom wasn’t sure what to do in retirement. A friend suggested volunteering at the Midway, so he gave it a shot. Now, he says it’s the best job he’s ever had, even though it doesn’t pay him a penny.

Lesson #2: Follow Through With Nancy Kruh

Nancy Kruh: Happiest Retirees Podcast

What I Learned: We can find inspiration from dilettantes.

Nancy Kruh 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, life drawing, singing in a choir, photography . . . you get the point.

Part of Nancy’s charm is her openness to new adventures. She knows most of them won’t become longtime passions, but so what? She wants to live! She promised she would “rage against age” on a recent trip to Costa Rica, and she made good on that. In her words, she had to block out that she was putting her “entire life in the hands of a very modest harness,” but despite that, she zip-lined through the pouring rain. What a rush!

Nancy never really liked the label “retired,” and she certainly doesn’t fit neatly within it. She still does impressive work, 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, and she’s not afraid to quit pursuits that don’t give her a sense of purpose.

Nancy is 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 reasonably ambitious retirement plan for a dilettante.

Lesson #3: Never Insult A Condor At The Zoo

Santa Barbara Zoo Train Conductors

What I Learned: Sometimes retirement is a promotion.

Last 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 conductors act as tour guides, animal advocates, and stand-up comedians. As it turned out, a couple of them are also happy retirees.

In his primary working years, Pete Georgi was the co-owner of the Santa Barbara Insurance Agency and President of the Board of the Carriage and Western Art Museum of Santa Barbara. Andy Liepman spent thirty years at the Central Intelligence Agency (CIA) and ended up as the Deputy Director of the US National Counterterrorism Center.

One day, Pete made the mistake of commenting on the vulture-like appearance of the California Condors. When his train returned to the station, he was promptly reprimanded. To an animal’s caretaker, beauty looks a little different. Pete learned his lesson, and Andy got a chance to laugh at his buddy’s expense.

During their careers, Pete and Andy were both at the top of their respective fields. Now, Andy says the most significant decision he has to make is which otter gets which fish. They’ve gone from being the boss to wearing overalls and driving a miniature train. And they wouldn’t have it any other way.

Lesson #4: Just Get Started With Jill Smith Entrekin

Jill Smith Entrekin: Happiest Retirees Podcast

What I Learned: The time to get started is now.  

A native of Thomaston, Georgia, Jill Smith Entrekin taught high school English in the Atlanta area for more than 30 years. Retirement finally allowed her to write some herself. With the encouragement of her family, she decided to get started doing what she’d always wanted to do. She’s now published three books, “Star of Flint,” “Buck’s Junction,” and the latest, “Bonnie Mac’s Cafe.”

On the Happiest Retirees podcast, we emphasize the importance of core pursuits—activities that evoke passion and purpose. Jill has so many that she had to skip yoga just to make it to our interview. Life has thrown her some tragic hurdles, and it has undoubtedly informed her writing. In fact, she believes Southerners are more inclined to wear their feelings on their sleeves, which can make for colorful characters and heart-wrenching tales.

Jill is perhaps just as colorful as the characters she creates—a southern girl who’s eaten Georgia peaches and climbed magnolia trees all of her life. We’re all lucky that she decided to put down the classroom chalk and publish stories about people who, as she puts it, “bubble with uniquely Southern messages.”

If you’re looking for guidance on overcoming grief, finding purpose, and being happy, Jill can inspire you to get started.

Lesson #5: Diversify Your Life With Phil Hendrie

Phil Hendrie: Happiest Retirees Podcast

What I Learned: Sometimes, the man behind a thousand voices needs to listen to his own.

Phil Hendrie is considered a genius in the comedy world. In a recent documentary about his career, an array of famous comedians (Bill Hader, Judd Apatow, Kevin Pollak) all rave about his unique talent. Suffice it to say, he is not retired. 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 eventually realized the business had changed. It was no longer viable to do comedy on the radio. This led to a creative transition from terrestrial radio to a daily podcast, as well as 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.

Phil had to ask himself the question that so many retirees ask: What do I do now? By listening to the answer, he found the path to happiness.

Lesson #6: How To Get To Carnegie Hall With Gail And Dickson Grimes

Carnegie Hall With Gail And Dickson Grimes

What I Learned: It takes more than directions to get to Carnegie Hall.

How do you get to Carnegie Hall? Google Maps can get you to the front door, but it takes practice to make it onto the stage.

Gail and Dickson Grimes have been playing the clarinet since elementary school. They both have music degrees and an intense love for music, but the realities of raising a family didn’t leave much time to pursue their dreams. Dick earned a living as a CPA, and Gail as an IT Disaster Recovery Consultant. But, neither those long work days nor the monumental task of raising their beloved children could extinguish their musical fire. They still found time, whenever possible, to play. As Gail said, “It is so much who we are.”

They joined Tara Winds, a renowned community band in Atlanta. Surprised by a woodwind section that was crawling with clarinetists, Dickson eventually became the music director of a newly formed Tara Winds Clarinet Choir (TWCC), and after his 2018 retirement, there was nothing to stop him from going full-bore. With Gail and their son also in the group, they took a zeal for the clarinet all the way to a Carnegie Hall performance.

Gail and Dickson could’ve given up their dream. Instead, when retirement gave them the chance, they made it happen. At Carnegie Hall, they got a standing ovation. If we learn from them, one day, we might get one, too.

Bottom Line

I’m so grateful and, to be frank, lucky that I get to host the Happiest Retirees podcast. Who wouldn’t want to spend their time laughing and learning from cheerful, funny, successful members of society? It’s my job to capture the essence of their anecdotes and bottle their accumulated acumen. I take the job seriously but always leave room for humor. The happiest retirees want to enjoy their lives, and they’ve taken the steps to make sure they can.

Let’s keep listening to them so we can too.

This information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations. This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions. The views and opinions expressed are for educational purposes only as of the date of production/writing and may change without notice at any time based on numerous factors, such as market or other conditions.

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