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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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
Final Approach: A Pilot’s Viral Send-Off and the Flight Plan for a Thriving Retirement with Mark Hardcastle
Happiest Retirees
34 minutes
7 months ago
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.
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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
