The Retirement You Didn’t See Coming – Dan Haylett

Are you graduating from the grind in 2026? You could go it alone and wing it. But here’s what one participant said about our small group coaching program: “It was fantastic! I got to work with other people and share ideas with others on what retirement could be. It gave me clarity and confidence.” New groups are starting on January 22 & 23. Let’s go. Learn more Join us “Challenged me to get out of the starting blocks and far down the path of really thinking about this next phase of my life in very different ways. I now feel like I have a solid road map.” “I wish I’d taken this program earlier.” _____________________________ What if everything you’ve planned for financially in retirement still leaves you feeling completely lost? Today’s guest knows this paradox intimately. Dan Haylett built his career as a financial planner, helping people achieve financial independence. But what he discovered shocked him: when money stops being the problem in retirement, and that’s when the real problems show up. Dan is a retirement transition specialist helping people navigate the psychological side of retirement that no financial plan can solve. He’s learned that people plan meticulously for financial independence but rarely prepare for psychological independence. The result? Three devastating losses hit early: loss of structure, loss of relevance, and loss of identity. In this conversation, Dan shares his framework for retirement well-being built on five human pillars that have nothing to do with your bank account. He challenges what you think you know about retirement as a “reward” and shows you why the most successful retirements aren’t built on bucket lists and endless travel, but on something far simpler and more profound. If you’ve ever wondered who you are when no one needs your output anymore, this episode will change how you see the next chapter of your life. Dan Haylett joins us from the UK. ______________________ Bio Dan Haylett, who’s the author of The Retirement You Didn’t See Coming: a guide to the human side of retirement nobody warns you about. Dan is a financial planner and head of growth for TFP Financial Planning based in the UK. Dan focuses on financial planning, retirement planning, and life planning for people 50+. He also hosts a podcast called Humans vs. Retirement on the behavioral aspects of retirement. Prior to joining TFP, Dan held a number of positions in asset management. ______________________ For More on Dan Haylett The Retirement You Didn’t See Coming TFP Financial Planning Humans vs Retirement ______________________ Podcast Conversations You May Like How to Prepare Mentally for Life After Work – Joseph Maugeri Retiring: Creating a Life That Works for You – Teresa Amabile What Are The Keys To A Successful Retirement? Fritz Gilbert ______________________ About The Retirement Wisdom Podcast There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time. About Retirement Wisdom I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident. Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University. In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy. ___________________________ Wise Quotes On Structure in Retirement “So the biggest surprise for me is this. Money stops being the problem. And that’s when the real problems show up, right? So I think that’s kind of the biggest surprise for me. People expect relief. Instead, they probably feel quite disorientated. They’ve planned for financial independence...