Happiest Retirees

Helping 1,000,000 People Retire Happier

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.

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All Episodes

#29 – In Between Songs: Gregg Russell Is Happy In Harbour Town

If you grew up in the South, you’ve probably heard Gregg Russell sing. If you were lucky

#28 – One-Year Anniversary Show

On this very special episode, Ryan breaks out his tuxedo and invites Producer Mallory into

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

Kathy Sperl-Bell has an abstract painting called “Dinner Time.” In it, a Pelican stare

#26 – The Biggest Risk Of All With George Jerjian

Albert Einstein once said, “Look deep into nature, and then you will understand everyt

#25 – Ending Ageism With Friendly Vibes: Jan Golden

Think about the last time you bought a birthday card. You were probably in a hurry, maybe

#24 – Uncork Your Bottle of Happiness With Steve Hoffman

My conversation with Steve Hoffman was deep and engaging, largely due to his eloquence a

#23 – It’s Your Life: Live It! Beyond Retirement with Jacquie Doucette

As Americans, we tend to believe our jobs define us. Think about that last time you met so

#22 -Embracing the Beauty of Aging With Hugh Willard

After a successful 35-year career as a psychotherapist, Hugh Willard decided to embark o

#21 – Recession Blues to Ecuadorian Views: Edd and Cynthia’s Retirement Adventure

Edd and Cynthia Staton were on track for a happy retirement, but life had other plans. Th

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