Happiest Retirees

Ryan Doolittle
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

  1. The Federal Bureau of Happy Retirements with Jerri Williams

    OCT 30

    The Federal Bureau of Happy Retirements with Jerri Williams

    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 podcast called FBI Retired Case File Review, and it dawned on me that as someone with my own podcast, I could just ask the host to be a guest. To my delight, she agreed. Jerri Williams retired after serving 26 years as a special agent in the FBI. In addition to her podcast, she does work as a technical consultant for major TV networks and production companies. She’s also the author of several books, both fiction and non-fiction. Through her story-telling and interviews with retired FBI agents, she debunks myths and misconceptions with a mission to show the public who the FBI is and what the FBI does. Her podcast has more than 300 episodes and 10 million downloads, so I think it’s safe to say: mission accomplished. Jerri said that talking to me gave her an excuse to reflect on what retirement means, and it felt like therapy. Take her words to heart; perhaps it will for you, too. 00:00-Actively Participate 01:42-Am I Doing Retirement ‘Right?’ 02:31-26 Years with the FBI 07:25-A Post FBI Position 12:10-300 Episodes 15:34-SEPTA, The Podcast, & Pay to Play 24:51-Are You Happy? 27:22-The Grandparent Do-Over 34:11-TV Consulting 41:53-Crafting an Ideal Schedule 46:02-Find Your Reason to Get Out of Bed Learn more about your ad choices. Visit megaphone.fm/adchoices

    51 min
  2. Carving Out A Spooky Retirement: Halloween With Ken Klinker

    OCT 16

    Carving Out A Spooky Retirement: Halloween With Ken Klinker

    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 much time alone in the house that she started calling herself “The Pumpkin Widow.”  But retirement has given Ken the freedom to turn that passion into a thriving core pursuit that even pays for itself. He switched to foam pumpkins because they didn’t rot and launched his own Etsy shop. Take a spin down his digital aisles to find some terrific work. I never knew I needed to see John Wayne, Beetlejuice, or Barbie in pumpkin form, but it turns out I did.  Ken and I talked about his evolving art, favorite charity, media appearances, and primary collaborator. You’ll be happy to hear how a balanced retirement has allowed him to revoke his wife’s “Pumpkin Widow” status.  So, pour a cup of hot cocoa, put on your Halloween costume, and listen for ways you might be able to carve out your own happy retirement. 00:00-Ken Klinker Love Pumpkin Carving 04:44-The Birth of the Etsy Shop 06:30-400 Pumpkins on Display 09:00-Pop Culture Patterns 12:54-Ken in the News 17:13-Custom Designs 19:25-Giving Back 21:40-Knowing When to Retire 27:16-Core Pursuits 30:40-Facing Challenges 34:26-The Perfect Day 35:27-Teacher’s Aides 37:38-Grandkids & Advice for Retirees Learn more about your ad choices. Visit megaphone.fm/adchoices

    41 min
  3. SEP 4

    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 stares down into the sea as dark shadows betray the location of fish who, unbeknownst to them, are in serious jeopardy. What strikes me about this particular Pelican is his ability to keep his eye on the prize. His hunger is evident. That patient facade is a practiced skill, not a breezy indifference. He knows that accomplishing his goal will require calm focus and repeated effort. Dinner won’t come easy, but if he refuses to quit, his belly will eventually be full.  I don’t know if Kathy had all this in mind when her acrylic brush first touched the wrapped canvas, but it certainly would be apropos of her own story. As a woman trying to succeed in business in the 1960s, it’s amazing her head isn’t scarred from banging against all those glass ceilings. But like that pelican, she never quit. Each challenge strengthened her resolve. Finally, when the moment was right, she founded Active Adults Realty in Delaware in 2009, an independent real estate brokerage focused on helping Baby Boomers plan for retirement. It was a hit.  In 2021, she and her husband, Bill, sold the business and retired to The Florida Keys, where she spends her time focused on core pursuits like blogging about travel and retirement, painting, yoga, pickleball, and listening to as much jazz as she can get her hands on.  There may be plenty of fish in the sea, but they aren’t always so easy to catch. Kathy Sperl-Bell’s inspirational story is full of heartache, hope, hard work, and happiness. Maybe yours is, too. 00:00-Journey to Real Estate 02:42-Live from the Airstream 11:12-“I Don’t Want Any Obligations.” 12:40-A Trip of a Lifetime 16:25-Bucking the Tongue 19:22-From an In-Flight Detective to Director 24:32-A Shared Love of Jazz 26:29-Active Adults Realty 29:45-What Does “Retirement” Mean? 31:29-The Accessibility of Pickleball 34:13-MyRetirementStories.com 36:26-A True Partner 40:11-Perseverance Learn more about your ad choices. Visit megaphone.fm/adchoices

    43 min
  4. The Biggest Risk Of All With George Jerjian

    AUG 21

    The Biggest Risk Of All With George Jerjian

    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 don’t leave with severance packages, and Komodo Dragons don’t get a gold watch or cake in the office kitchen. Wildlife is typically either growing or dying.  In short, George says the word “retirement” is past its sell-by date and prefers “rewirement” or “refirement.” He says happiness isn’t found by losing our former identity but rather by creating our new one. That might include continuing to work if you enjoy it. But it also might mean going on a safari, eating Ostrich steak in South Africa, or cycling through the rain in Vancouver. The point isn’t that it has to be something exotic but that it should be something that excites you. Maybe even something that scares you. George says sitting on the beach is not a retirement. It’s a vacation. You can’t vacation for the rest of your life. So figure out what you want to do, then take some risks to do it. It’s hard to venture out of your comfort zone, but as George points out, the biggest risk of all is never taking a risk. To play it safe and then get to the end of your life and realize you never lived.  You get one, wild, wonderful life? What are you going to do with it? 00:00-You Can’t Vacation The Rest of Your Life 03:59-Not a Binary 09:26-An Ego Death 12:55-George’s Epic Break 23:47-Life is a Risk 26:12-DARE Method 32:30-The Fool 35:43-Don’t be an Ostrich 42:44-A Bird with Two Wings Learn more about your ad choices. Visit megaphone.fm/adchoices

    49 min
  5. AUG 7

    Ending Ageism With Friendly Vibes: Jan Golden

    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 more than the gift. But even more than that was the overwhelming bombardment of “over-the-hill” birthday themes: sagging body parts, balding heads, bad jokes about fading attractiveness. If you found it a little depressing, you’re not alone. Jan Golden decided to do something about it.  Inspired by a greeting card contest called Changing the Narrative, she combined her graphic design, tech, and creativity skills to create a line of age-friendly greeting cards. As she wound down her primary career, she was able to jump in with both feet. Now, Age Friendly Vibes is thriving, and Jan discovered that she absolutely loves doing it.  Ageism can affect anyone, but it’s often directed at older people. As you plan or execute your happy retirement journey, you won’t always be able to control when it rears its ugly head. But you can decide how to react to it. Listen to Jan’s story and be inspired by her mission to put age-positive sentiments into the world, one greeting card at a time. Now, that’s what I call all the hallmarks of happiness. 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

    51 min
4.9
out of 5
22 Ratings

About

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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