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.”

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“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.”

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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.

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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.

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For More on Dan Haylett

The Retirement You Didn’t See Coming

TFP Financial Planning

Humans vs Retirement

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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

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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.

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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, but not necessarily psychological independence. And so I think the three big shocks or surprises, I think, tend to hit quite early. You get this loss of structure. So there’s kind of no diary or no default rhythm. People get this loss of relevance. Nobody needs you at 9 a.m. anymore. And this loss of identity that job title that once explained you to the world has quietly disappeared. So I think that to me is probably the three big,money stops being the problem. And then the real problems of loss, particularly structure, relevance and identity, really start to take hold. I think one of the things that I really want to reframe when it comes to structure, structure doesn’t disappear in retirement. I think it just stops being imposed on us. For decades, work has  spoon-fed you your structure to a degree, right? Work gave us a reason to get up, a place to be, people to see, and problems to solve. And I think if you remove that overnight, your brain will just panic. And I think the mistake that people try to make, or sorry, the mistake people make is trying to recreate work this kind of same hours, same busyness, just without the meaning. And instead, what I encourage people to do is to build what I would describe as kind of light scaffolding, I suppose, something like that, not rigid schedules, just kind of what I would describe as anchors.”

On Identity

“The question is, who are you when no one needs your output? Let that breathe for a second. Who are you when no one needs your output? And then you start widening identity whilst you’re still working, right? Develop interests that don’t pay you. Spend time with people who don’t care what you do. And I think really importantly, notice what gives you energy outside of kind of performance and status. Because I do think if your entire sense of self is wrapped up in your role in your job, retirement will feel less like freedom and kind of more like redundancy, right? It’s that kind of instant, you’ve lost this thing and you didn’t want to lose it. So I do think it’s a massive challenge because it’s been, you know, our identity that we’ve had has given us so much, has given us status, has given us structure, it’s given us a sense of self-worth. It’s given us many things that provide us with joy and happiness. And, you know, for the first time, we’re free probably to explore with a really decent chunk of wisdom who we actually are as a person. I think the first question you ask is, what’s your name? Hopefully, if you want to kind of start building a bit of a rapport and bond with someone. And maybe the second question is, what do you do? And as we’ve just explored, you would typically answer that question with, I am a ___________. Or on a lot of occasions, someone still gives you a business card or now modern day, it’s like a QR code, right? That kind of gives you a little thing. But, if you give a business card and on that business card, it will have your name. And underneath your name, it will have your job title. It’s kind of, here you are. This is what I do. This is who I am. And my challenge I do to people, I say, well, if you didn’t have a business card, what would you give out or what would you say? And actually, let’s create a business card. Let’s think about what your business card would say. And you can be creative, you can be funny, you can be jovial, you can be serious, you can be whatever you want. But what if your business card said free to explore or, you know, just make up something creative? I’ve got a client who on his business card wrote, trying to play the top 100 golf courses in England before I die, right? That kind of thing. It’s kind of like, that was one of his missions. And you can have multiple business cards, multiple things that you want. So it’s just trying to kind of frame this thing where I think people will, because what I do see, Joe, which I think is actually quite sad, is when people hang on to past identities.”