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"
Jim Beezley Interview: Former Police Captain's Second Act with Major League Baseball
Diana Landau | July 14, 2026
Host Carl prides himself on finding people that have interesting and different kinds of careers. It took Episode #110 but he finally found his first ex-cop. It's a fun one to listen to and an extra bonus is you can enjoy the banter live from Carl's Tiki Bar. After decades in law enforcement, including high-stress work in narcotics investigation and hostage negotiations, Jim Beezley the former Police Captain is now realizing a childhood dream by working with Major League Baseball.
Jim grew up in Sacramento and sports were the main activity in his neighborhood. He says he was a stubborn and independent child. “I was self-sufficient fairly young.” He attended CSU, Sacramento and earned a master's degree in criminal justice. Jim also graduated from the FBI National Academy.
He joined the Sacramento police force and eventually worked his way up to Captain. He talks about the challenging transition from being “one of the guys” to management. There’s hiring, firing, big budgets and more. “90% of police work is communication,” Jim adds. “It’s also a great, rewarding job that you can be proud of after 35 years.”
Jim retired from the police force and went on to serve as Senior Director of Protective Services at Sutter Health, where he specialized in healthcare investigations, workplace violence prevention and systemwide security strategy. He retired from his second act in 2025.
For Jim’s third act, he has combined his investigative background with his lifelong passion for sports—and more specifically the Oakland A’s. “When I was a kid in the early 1980’s, the A’s were MY team. It took another 45 years for this opportunity to present itself. What a great job!" It turns out the A’s left Oakland and are playing in Sacramento for three years. When Jim heard the team was coming to town, he started making calls to the right people and landed the position as an authenticator for Major League Baseball.
Jim loves being an authenticator. “It’s multi-tasking and negotiating with lots of people," he says. He gets to interact with his sports heroes all season and he's even traveled to Japan for the World Baseball Classic. Working with the A's is a dream come true for him. When not in the dugout, Jim is totally obsessed with pickleball. He plays almost everyday!
Jim's (Un) retirement advice:
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Financial planning: "I'm fairly frugal and (decades ago) I put together a big spreadsheet and tried to be as financially literate as possible. I look at all the trends, making sure it all pencils out and makes sense. I do it myself. I taught a class on financial planning for new recruits to set them up for success. I'm very proud of that."
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Health and Routine: "For me, I want to live as long and healthy as possible. See a doctor. Find something you like to do that's healthy. I guarantee there are days you don't want to get up and do it. But I say, 'Just 5 minutes.' And then you do another 5, and another 5, and soon you've got a workout." 
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.
Pat Belding Interview: The Dream! Operating a Sports Bar in Retirement
Diana Landau | May 19, 2026
It’s baseball season again so you can be sure Carl is interviewing someone connected to the sport. In this interview, Pat Belding, a former marketing agency owner is now running a Sports Bar at age 66. Sure, some people have always thought it would be fun to have their own restaurant or bar “some day” but Pat is actually doing it. After he passed on his agency to his employees in 2021, he came face-to-face with his first retirement. Pat shares with us experiments tried, lessons learned and he’s still knocking it out of the park.
Pat is a native San Franciscan, growing up in the West Portal, the oldest in a family of 5. He says that as a kid, he was always curious, always trying something new and different. He also pushed the boundaries with his parents. “I had a great group of friends to keep me on track,” he says.
After college, he trained and worked in the graphic arts and creative industry, founding his own marketing agency, Belding Associates in 1984. He worked with Fortune 100 companies like 3M, Cisco, Google and more. Pat adds, “1992 was an exciting time. The whole industry was changing so dramatically.”
By 2021, the marketing industry had been utterly transformed by technology and social media. Pat shares that something shifted for him and he realized it was time to step away. “The transition was surreal. "I quickly learned I wasn't quite as relevant as I thought was!” But he began to realize that in (un)retirement he had the chance to do all things he had never had time for while he’d been working.
After completing all the house projects, Pat says his wife gently hinted that maybe he could find other places to put his energy. “I wasn't necessarily frustrated or bored. I just left myself be open to things.” Like many of our podcast guests, this was a period of experimentation for him. He volunteered to help restore hiking paths, worked for the US Census where he hired people and learned what it’s like to work with the federal government. He also worked for the SF Giants for a while. He says he never really had an “Aha” moment. “I still don't know if I’m doing it (unretirement) right, but it drives me to succeed.”
Pat is still pushing way beyond his comfort zone, this time with his current venture. Three years ago he started helping out at Frankie’s, a cool sports bar on the South Beach marina and just a short walk from Oracle Park, where the SF Giants play. Frankie's, originally named the Java Hut, has a special history--it's the oldest operating eatery on the San Francisco waterfront. It's been around for over a century.
One year into it, and with no prior experience in the food service industry, Pat started managing Frankie's and he's a part-owner as well. He says that daily he deals with customers, employees, food and beverage vendors, and everything in between. He’s building a solid team and hopes to be able to step back sometime in the future. “Right now I’m in the trenches! Be careful what you say ‘yes’ to.” In the off-season, Pat travels with his wife and spends time with family and friends, but Franke’s still keeps him pretty busy. And of course, he’s always cheering for the SF Giants to win.
Pat’s tips on (un)retirement:
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“Don’t be afraid to take chances. Stay curious!”
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“I think it’s really easy to stay in your comfort zone, especially as we get older. Now is the time to adopt a ‘Why Not? "mentality!”
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“Get engaged as much as possible, (with all ages) because there’s so much more you can add value to in your community and our world.”
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.
Andrew Motiwalla Interview: Mr. Travel - The Good Life Abroad
Diana Landau | April 14, 2026
Have you ever dreamt of living the good life abroad in your retirement? Carl's guest this month, Andrew Motiwalla, has created the perfect travel experience for those who want to spend a month or two in an European country while enjoying a built-in community for shared adventures. As a successful entrepreneur and CEO with 30 years of experience designing transformational programs, Andrew’s latest venture is The Good Life Abroad. This network of residential communities is designed specifically for active older adults who want to truly immerse themselves in European living.
Born in Chicago to Peruvian and Indian parents, Andrew’s passion for travel was ignited during a study abroad program in South America and later through his service in the Peace Corps. He founded an organization providing Peace Corps-like experiences for high school students, and he has since served as Chief Revenue Officer for several global groups. "They (the former students) have gone on to do amazing things. I'm very proud of the work I did there."
Now in his 50s, Andrew began reimagining his own "(un)retirement." He wanted to travel extensively without the burden of property ownership. "I wanted to go live somewhere and I wanted people to do stuff with," he explains. The Good Life Abroad offers exactly that: an immersive experience for active adults aged 55+ that provides both a local concierge service and a community of like-minded travelers.
"That process of immersion and then adaptation leads to growth that's super important as we get older," Andrew says.
Andrew Motiwalla's (Un) Retirement Tips:
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"Avoid "Tourist Mode": Don't try to pack everything in. Slow down to avoid burnout and leave space in your itinerary for serendipity".
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"Prioritize Friendships: As you age, focus on connections that give you energy rather than maintaining friendships that no longer serve you".
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"Push Your Comfort Zone: Continue to engage with new and different experiences. Pushing past your comfort zone is essential for continued growth".
• I Used to be Somebody World Tour: Croatia
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.
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.
