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
From Someday to Today: Retirement in Portugal With Cynthia Wilson & Craig Bjork
Happiest Retirees
45 minutes
10 months ago
From Someday to Today: Retirement in Portugal With Cynthia Wilson & Craig Bjork
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 contrasting personalities—Cynthia, a creative dynamo, and Craig, the embodiment of laid-back calm—they’ve created a life of joy, affordability, and deep community in Portugal.
If you’ve ever dreamed of a bold retirement, no matter how unconventional, this episode might ignite your passion to pursue it with the same vigor (or even more) as you did your career. Your someday could start sooner than you think.
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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
