Episodes 41
Avg. Duration 42m
Activity Dormant
Since Sep 2023
Latest Episode Apr 2025

Publishing Details

Schedule
Every 2 Weeks
Format
Episodic
Hosting
feeds.megaphone.fm

Contact & Outreach

About This Podcast

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. 00:00-You Can Do Just About Anything 03:29-Transitions & Empowering Older Adults in Tech 09:21-Mindset Matters 10:33-A Birthday Card Contest Turned Etsy Business 15:48-Tradeshows & Strategy 22:06-Immerse Yourself in Something Joyful 28:21-Retirement Rewirement 33:30-Practicality Problems 36:42-Ikigai! 40:50-Core Pursuits & Staying Active

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Recent Episodes

The Final Chapter: Retiree Reinvention & The Launch Of Tryin' Ryan

Apr 16, 2025 14m

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…

Retirement’s New Era: How to Thrive in a Life Chapter That Never Existed Before with Eric Thurman

Apr 02, 2025 33m

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…

Final Approach: A Pilot’s Viral Send-Off and the Flight Plan for a Thriving Retirement with Mark Hardcastle

Mar 20, 2025 34m

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…

From Burnout to Revival: How Dr. Jordan Grumet Resuscitated His Purpose and Retirement

Mar 05, 2025 33m

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…

From Ad Exec To Cartoonist: Retirement Laughs & Lessons In Barcelona With Darryl Kluskowski

Feb 19, 2025 32m

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…

Staying Social, Staying Sharp: Gail Zugerman On Growing Older With Gusto

Feb 05, 2025 24m

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…

An Open Mind On The Open Road: Traveling With Mike Taylor

Jan 22, 2025 30m

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…

From Someday to Today: Retirement in Portugal With Cynthia Wilson & Craig Bjork

Jan 08, 2025 45m

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…

Boomer Grandma With A Little Edge With Shannon Nelson

Dec 11, 2024 51m

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…

MARTA: Public Transportation For Retirees

Nov 27, 2024 50m

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…

I Used To Be Somebody With Carl & Diana Landau

Nov 13, 2024 44m

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…

The Federal Bureau of Happy Retirements with Jerri Williams

Oct 30, 2024 50m

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…

Carving Out A Spooky Retirement: Halloween With Ken Klinker

Oct 16, 2024 41m

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…

In Between Songs: Gregg Russell Is Happy In Harbour Town

Oct 02, 2024 53m

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…

One-Year Anniversary Show

Sep 18, 2024 41m

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…

Pelican Persistence and Glass-Ceiling Breakthroughs: Kathy Sperl-Bell’s Guide to Winning at Work and Retirement

Sep 04, 2024 43m

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…

The Biggest Risk Of All With George Jerjian

Aug 21, 2024 49m

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…

Ending Ageism With Friendly Vibes: Jan Golden

Aug 07, 2024 50m

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…

Uncork Your Bottle of Happiness With Steve Hoffman

Jul 24, 2024 51m

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…

It's Your Life: Live It! Beyond Retirement with Jacquie Doucette

Jul 10, 2024 31m

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…

Frequently Asked Questions

How many episodes does Happiest Retirees have?

Happiest Retirees has published 41 episodes since September 2023, covering topics in Documentary, Education.

Is Happiest Retirees still active?

Happiest Retirees is currently dormant with new episodes every 2 weeks. Average episode length is 42m.

How do I contact Happiest Retirees for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Happiest Retirees, including email and social media links.

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