Happiest Retirees

About Happiest Retirees

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

Publisher

Ryan Doolittle

Category

education · society & culture

Language

en

Explicit

No

First episode

19 Sept 2023

Latest episode

16 Apr 2025

Latest episodes

42 episodes in the feed.

1. 

   16 Apr 2025

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

   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 Entrekin (author), Jerri Williams (FBI agent turned author/podcaster/Hollywood consultant), Johnny Hiles (pickleball enthusiast), and Andy Liepman (former CIA turned train conductor). Transition from podcast listener to YouTube viewer! Follow the Retire Sooner Team channel on YouTube and watch Tryin' Ryan starting April 30th to fuel your post-career passion. Uncover your purpose, embrace new core pursuits, and start living your best retirement life today! Learn more about your ad choices. Visit megaphone.fm/adchoices

2. 

   2 Apr 2025

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

   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 money—it’s about curiosity, connection, and purpose. Dive into why friendships keep you thriving, how gratitude rewires your brain for happiness, and the little things that make a big difference. Retirement trailblazer and author of Thrive in Retirement, Eric Thurman, shares practical tips, a few laughs, and plenty of wisdom to help you live with more joy and meaning. Learn more about your ad choices. Visit megaphone.fm/adchoices

3. 

   20 Mar 2025

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

   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 years of high-stakes decisions and strict schedules, stepping away from the cockpit felt like losing purpose for Mark Hardcastle. Navigating the sudden freedom proved unexpectedly disorienting, but embracing a self-imposed sabbatical opened the door to healing, reflection, and new possibilities. Discover how Mark stabilized his glide path, reclaimed fulfillment, and transformed retirement into the kind of life that takes off after work ends. So deploy the landing gear, clear the runway, and get ready for a happy retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

4,123,763

Score snapshot 15 Sept 2025

Apple Podcasts (US)

4.9 / 5

23 ratings

Spotify

4.9 / 5

10 ratings

Podcast Authority Score: 64 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

57

Social presence

0

YouTube

93

Engagement

85