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Chris Taylor & Dan Haylett Interviews: 3rd Annual Meet the (Un)Retirement Experts

Diana Landau | August 04, 2026

Chris Taylor & Dan Haylett Interviews​​​​​​​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."
 
*************
 
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:
 
  • “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.”
  • “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.”
  • “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.”
  • “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!
Check out more super fun unretirement ideas - Click here for this week's newsletter!​​​​​​​
 
• Chris Taylor Interview: 4:16 Timestamp
• Dan Haylett Interview: 36:30 Timestamp
• More about Chris Taylor
• More about Dan Haylett​​​​​​​
• Sponsored by How to Retire and Not Die
• Sponsored by Capital Advantage
• I Used to be Somebody World Tour: September 2027 Bordeaux, France
• Subscribe to the I Used to be Somebody Newsletter
 

 

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" 

 

Tags:    Dan Haylett   Chris Taylor   Unretirement   Carl Landau   Experts   Interview   Blog  

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