Chris Taylor & Dan Haylett Interviews: 3rd Annual Meet the (Un)Retirement Experts
Diana Landau | August 04, 2026
You’re in for a real treat! It's the “Ask the Experts” bonus episode. We feature two unretirement experts who know alot about what’s really important. What you are actually going to do in retirement that will be new, super fun, intellectually stimulating and meaningful?
This year, we give you the best of both worlds by tapping into retirement wisdom on both sides, the financial strategy and planning but also the equally important emotional side. In both interviews, the experts give us some solid practical advice. Far from boring, this episode will also give you some new perspectives to ponder for your second half of life.
First, we have Chris Taylor, an experienced journalist who has written financial articles for Reuters, NBCNews, Kiplinger, Fortune, Money , AARP, Wall Street Journal and more. As an award-winning personal finance writer, he focuses on the kitchen table financial topics faced by every American family: Budgeting, borrowing, spending, saving, investing and RETIRING.
Chris’s financial takeaways at different ages and stages:
• Teens: “Talk to young teens about it and be transparent. It’s really like the last taboo for people. They don’t like talking about it (money). They’re not good at it and they don’t know what to say to their kids. I think transparency is important to get the kids thinking about these issues at a young age and it will prepare them for later in life. I would say, get over your hang-ups about it.”
• 20’s to 40’s: “There’s this saying, ‘It’s not about the timing in the market but the time in the market.’ Investing at an early age and all along is key.”
• 50’s: “Gen X is behind where they need to be. Take full advantage of the ‘catch-up’ contributors every year, whether it’s your 401K or IRA, that you can take at 50+. Also, don’t be a hero and sacrifice your own retirement to pay for your kid’s college….you have to have a balance between helping them out and helping yourself out.”
• 60’s and 70’s: “You’re pulling the trigger on when you start taking Social Security, Medicare, etc. Consider part-time work in the transition and even try out mini-retirements in different locations—it will ease you into retirement.”
“This is a phase of life we’re not good at—SPENDING. We’ve been always thinking about savings. Think of your portfolio in a different way. Good savers are often not good spenders. Also, start thinking about estate planning, legacy giving and your long term medical needs for later down the road."
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Our second expert, Dan Haylett, delves into the human side of “What’s next after retirement?”
He is the host of the widely recognized “Humans vs Retirement” podcast, author of book, “The Retirement You Didn’t See Coming” and he also advocates inverting traditional retirement advising by focusing on an individual’s personal purpose and desired lifestyle before mapping out the math.
Dan’s takeaways on the emotional side of retirement:
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“The #1 financial mistake I see people make is their “enough” number. I think people aim too high. Typically the retirement they need is less than they thought. You see people work longer, save more and kind of have that mindset. Some have never really dug into their personal finances.”
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“Look internally at who you are without a job title. It’s important to get the numbers correct, but some people just keep optimizing. You have to shift from a saving mindset. When you start financial planning in the second half of life, you have to learn how to spend your money in a way that makes you feel confident and comfortable.”
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“You’re at your peak in your 60’s and then you stop work, you're not the boss anymore. But you can still use all of those skills, all of that knowledge, all of that wisdom to continue being a thought leader, giving back and mentoring. I see too many people who cold-turkey it and they need to keep going.”
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“Be curious! Of all the people I’ve observed, the successful ones have a growth mindset and are curious. They explore, they’re not afraid to try, they’re not afraid to fail and I applaud that mindset. People who have that massively flourish in retirement.”
A big thanks to Chris Taylor and Dan Haylett for sharing their time with us. Be sure to listen to this episode in full to get more thoughtful insights on how to live your best (un)retirement life!
• Chris Taylor Interview: 4:16 Timestamp
• Dan Haylett Interview: 36:30 Timestamp
Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody"
Alex Jeffery Interview: Director of The Power of Pickleball
Diana Landau | March 24, 2026
Bonus episode! Carl combined his two passions in this interview with Alex Jeffery -- Pickleball and Documentaries. Alex is an accomplished documentary filmmaker who recently released an in-depth documentary called the The Power of Pickleball. Alex co-owns the production company Bespoke Works with his friend and long-time collaborator, Paul Petersen. His first feature film, “A Chance Encounter,” won the audience choice award at the Heartland Film Festival in 2020 and then was released by Samuel Goldwyn Films.
His film “The Power of Pickleball” captures the essence and spirit of one of the country’s fastest-growing (and evolving) sports and it just was just released on Prime Video and Apple TV. Alex points out that although many people think pickleball just happened overnight, it has a history going back to the 1960’s.
A few years ago he was spending time with his Mom and Aunt, who are pickleball fanatics, and they said, “What if we made a documentary about Pickleball?” Not knowing much about it, Alex says they started reaching out to people to learn more. What struck him was how welcoming everyone was. “People opened their arms to us and started telling us their stories and wanted to share more about the sport.”
The documentary, which took several years to make, starts at the beginning of the sport in Bainbridge Island, WA, weaves very personal stories of how the sport has changed players’ lives, covers the controversies and also the growth of the professional circuit. “The response has been overwhelmingly positive,” Alex adds. “It’s really cool to see people from all walks of life discover pickleball and it gives them purpose again.”
Alex originally wanted to be an actor and moved to LA after college. Realizing LA was not right for him, he created his second act as a low-budget, independent film director. Based in Shreveport, LA, Alex loves mentoring film and acting students of all ages and experience. He also strives to a life-long student of the world and an avid traveler.
Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog.
Jillian Johnsrud Interview: Learn How To Take Mini Retirements
Diana Landau | January 13, 2026
How can you retire soon, and often? Carl talks with author/speaker/coach Jillian Johnsrud about the how’s of taking mini-retirements and why they're so good for you. Jillian is the author and host the popular podcast “Retire Often” that helps individuals, companies and financial advisors make sabbaticals a reality—through coaching, consulting and training. Jillian is also an in-demand speaker on the subject of taking multiple mini-retirements.
Jillian grew up in a small town in Montana and after many years away has been back in Montana for over a decade. She grew up in a blue-collar family and she didn't really have big dreams back then. She was an anxious, shy kid with dyslexia. But she says one firm, earnest high school teacher inspired her. She told Jillian, “The spelling doesn’t matter, it’s a low skill set. A better skill set is to be able to tell a good story.” This concept had a huge impact on Jillian.
She worked her way through college, juggling various retail positions. After marrying, living very frugally and saving, she felt she had the financial independence at age 32 to take the leap to become a professional writer. And yes, she also has 5 kids. “I just truly enjoyed the process of writing,” she says, not worrying so much about financial gains from it at that time.
Jillian has personally taken a dozen mini-retirements. She tells us why it's important to do it, and how to create a sabbatical for yourself, including how to talk to your employers, even what to say to your questioning family and friends about it. For example, she says to develop a positive story around your time off, not just the "I'm so stressed out" approach. Think through how it might also work for your employer and how they can manage while you're out and benefit when you get back. She says it may even take a year to plan it. But it can be done!
Jillian says the first mini-retirement she took gave her time to refresh, regroup and find her creativity again. One of her mini-retirements included a 10-week road trip to 10 National Parks with her family. “So often we recognize there’s this window of time to do something, and if we don’t do it now, we will have missed the opportunity.” Now with teens at home, Jillian still finds time to take mini-retirements for extended travel, improving her mental and physical health, and more.
Jillian Johnsrud’s Tips for the Mini-Retirement Life:
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“Give yourself permission to pause from the life you've created. Taking off one, two or three months can change everything—including your perspective and goals for your future.”
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“View your retirement as a non-judgmental science experiment. Try new things, try other things, observe and discover what works best for you.”
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“Schedule some, but less in mini-retirement. Just winging it doesn't work. Experiment with different plans, routines and boundaries to help you realize the outcome you’re looking for.”
Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog.
Kevin Blake Interview: Mystifying Second Act as an Illusionist
Diana Landau | December 09, 2025
Carl is amazed when he interviews the one and only Kevin Blake. Kevin is different from most of our podcast guests in that he is only in his 30’s. But he definitely took a big risk to dive into his very successful second act and he shares what he learned with the rest of us. Kevin is a former marketing exec who left a successful career to follow his dream of becoming a magician/illusionist/mentalist. He now has a wildly popular show in San Francisco at the Palace Theater.
Kevin grew up in suburban Sacramento, CA. A big part of his childhood was spent going to swim practice and becoming a star swimmer in high school and the collegiate level (He would later go on to swim in the Trials for the 2012 and 2016 Olympics!)
After college and a degree in Psychological and Brain Science, Kevin landed at Wells Fargo and pretty quickly felt he wanted something different. Walking around one day in SF he saw a sign for a “Creative Agency” and knew he would rather be following a much more creative path. As a marketing exec, he created brand identities through digital, print, motion and video for big brands such as Lagunitas Brewing Company, Duraflame, JanSport Backpacks, Intel, and more.
While Kevin enjoyed that career, he always had a passion for magic and performing shows. He developed a side gig of online magic shows for companies all the while honing his craft. The pandemic actually became a big new opportunity for him. “I was making more (money) in two months than I was making for my yearly salary.” (You'll have to listen to the podcast to learn more about that!) “It gave me the freedom to be able to quit,” he tells us. He decided to go for it and work in magic full-time. His family and friends were nervous for him and supportive. “Nervous? Yes. But I was confident.”
Kevin has performed and has competed on a national level -- America's Got Talent and Penn & Teller: Fool Us. Now he performs for sold-out, live magic shows at the Palace Theater as well as for corporate business events. “I’m lucky I have a marketing background so I can sell tickets and promote my business,” he adds. When not performing, Kevin is constantly working on his show, and also spending time with his family. And yes, he’s still swimming.
Kevin Blake, on beginning a Second Act:
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“Your time is open. What do you do with that time? We all have to fill our time with things that create meaning for us.”
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“If you've always had a passion sitting in the back of your mind, try it as a side gig. Go for it, try it, experiment and see what you find. The only thing that can happen is that you'll learn a lot.”
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“If it (second act) was really, really comfortable I wouldn't have that same fire to hustle!”
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“Finding or creating your own small network of people who do what you do is critical.”
Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog.
Fritz Gilbert Interview: Mr. Retirement -- Author of "The Retirement Manifesto"
Diana Landau | October 21, 2025
Ok, this is a BIG DEAL! Carl interviews a retirement legend in this 100th EPISODE!
Carl chose retirement expert/book author/speaker/do-gooder Fritz Gilbert as his 100th podcast guest. Fritz's award-winning blog, The Retirement Manifesto, is focused on helping people achieve a great retirement. Since 2015, Fritz has written 441 articles and 1 million words about how to live your best life in retirement. Fritz retired after more than three decades in corporate America, where he progressed through the various levels of a multinational corporation serving the global aluminum industry. He's still changing lives, read on!
Fritz grew up in the small town of Hillsdale, MI with his parents and two older sisters. His father was a college professor and his mother a teacher. This meant their summers were free to explore the great outdoors, one of Fritz's true passions. It's no surprise that Fritz was a curious, hi-energy kid. He says he wanted to be an NFL punter growing up, then to be a doctor. He attended Wittenberg University in Ohio. He says, "My father always told me I could be whatever I wanted to be." On a whim as a senior, he interviewed with an aluminum industry exec that evolved into a highly successful 33-year career.
Tired of the corporate world's politics, he retired in 2018. But, three years before retirement and this is important, he started thinking and strategizing about what his ideal retirement life would look like in 2015. "I got out at 55," he tells us. He started a blog, which he had never done before and kept on writing. He wrote the 10 Commandments of Retirement, which focuses on attributes to keep in mind daily in retirement, such as; have a great attitude, pursue your passions, stay flexible to change, try new things and more. "I would have never dreamed that 10 years later the blog would become so successful with over 16,000 followers. I was curious and I took that first step!"
He wrote and wrote about not just the financial parts of retirement, but the equally (if not more so) purpose parts of retirement. "I love the relationships I've had too. It's a deep subject, I'm still writing. It's turned into something I love to do." Recently Fritz decided not to do a full-time blog after 10 years so he has time to pursue other passions. He loves to mountain-bike in the Blue Ridge Mountains of Georgia, spend time with family, work in the garden, and lots more.
Fritz is also helping his wife with her passion, Freedom for Fido, a community group that builds fencing for low-income families that have dogs chained in the yards. They've built 187 fences in 6 years with the coordination of several hundred volunteers. "It's created this incredible network, we're getting exercise building fences, and I can't even begin to tell you about the impact we're making on the community." Just like that little kid in Hillsdale, Fritz is still high-energy, loving the outdoors and still curious!
Fritz Gilbert's (Un)Retirement advice:
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"Learn to listen and follow your curiosity. Look for things that might interest you and take that step."
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"The path to fulfillment and enjoyment is to just try new things. Do as many as you can. Some will hit and some will miss. But enjoy the ones you like and keep going!"
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The 90-10 Rule: People focus 90% on the financial part before retirement. It's amazing--once you're in retirement, you spend about 10% thinking about the financial part and 90% thinking about what you are going to do now. It's the purpose side of retirement that people need to think about before they retire."
Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog.
