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"
Meet the (Un)Retirement Experts: Paul Long, Gary Sirak and Dr. Ron Kaiser
Diana Landau | August 27, 2024
We're celebrating the end of summer with a special bonus episode, Meet the (Un)Retirement Experts. It's a little different from the typical I Used to be Somebody episode. Instead of just one guest who's had a really interesting second act, we're talking to 3 great minds in the (un)retirement world. A little twist is that they are from 3 different age perspectives too. Paul is in his 60's, Gary is in his 70's and Ron is in his 80's!
Paul Long
As founder-creator of New Way Forward, Paul helps retired people pursue a new life of relevance, impact and income that is aligned with what they truly want. Paul grew up in Dallas, Texas and says he literally grew up in the radio business, going with his dad to work. He had careers as a TV reporter and TV weathercaster.
After 20 years, Paul pivoted to the production side of the business and founded Paul Long Productions, developing Emmy-award-winning content, executing video, live, events, campaigns and more. In his 50's, Paul noticed more and more people were looking to pivot their lives from the default one to a life that was right for them. Now, as an experienced storyteller and journalist, New Way Forward has given Paul his own fulfillment as he helps people transition and realize their best life.
Paul's Tips on Unretirement:
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"Take some time, self-evaluate, look for relevance and purpose."
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"When you change the way you look at things, the things you look at change."
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"Ask yourself: What do I want holistically in my life, not just professionally or about earning income?"
Gary Sirak
Gary is an author, speaker and financial advisor from Canton, Ohio. Growing up his parents struggled financially for years until his dad turned his American dream into a reality, becoming very successful in the insurance business. "I got to see both sides, having a little and a lot," Gary tells us. After graduating from Miami University in Ohio, Gary worked so hard that he realized he was at the peak of his career and he wasn't happy. A friend told him to look back to where he came from. Gary says he had been pushing so hard he never took the time to celebrate his successes. "That really opened up a light I hadn't seen."
He lost some friends almost right after retirement and Gary felt there must be a better way. He wrote the successful book, How to Retire and Not Die, to help others have a better life in retirement. When not consulting, writing or speaking, Gary also enjoys mentoring and writing songs--he's written 35 so far. Gary says, "If I can impact people in a positive way, how important is that!"
Gary's Tips on Unretirement:
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"Look for someone you know who is successfully retired, and take them to lunch, or coffee. I call them 'retirement mentors.' You can learn from them."
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"Have a purpose, a passion, a plan" Stay active, be involved in community service and have financial peace of mind."
Dr. Ron Kaiser, Ph.D.
"Dr. Ron" is 87 and lives in Philadelphia, PA where he is now the Chief Immersion Officer at Better Age. He is a psychologist, coach, author, podcaster, keynote and TEDx speaker. He is author and host of the podcast of REJUVENAGING: The Art and Science of Growing Older with Enthusiasm.
Ron grew up in Minneapolis in a middle-class, close-knit community. He had a successful, decades-long career in psychology, (he's still doing it in addition to everything else), but in his 60's he noticed that some of his peers seemed to thrive after retirement while others thought retirement meant decline. "We've now got the science that people are retiring and living 30 years or more. I felt an obligation to spread the word." He tells us that after he wrote his book, he assumed everything would fall into place, which it did not. "I needed to learn social media, use my voice for good, be more assertive and teach," he says.
Dr. Ron's Unretirement Tips:
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"You have to discipline yourself. When you're retired, you don't have to go somewhere at a certain time, eat at a certain time, etc. But if you want to be productive, the stuff that got you there is the same thing that's going to get you further in life."
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"Age is a number, not an excuse!"
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"If you're looking for purpose, you have to find it within yourself. It's important to set goals through every stage of life."
There's a common thread with these wise guys. They all have a driving force to help people live their best life. How cool is that? 
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.
