The author, podcast host, and financial advisor discusses how to avoid a letdown after retirement, how retired couples can find harmony, and other secrets to maximizing well-being later in life.
Our guest on the podcast today is Dan Haylett, who’s the author of a new book called The Retirement You Didn’t See Coming. 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 over age 50. He also hosts a podcast called Humans vs. Retirement that is centered on the behavioral aspects of retirement. Prior to joining TFP, Dan occupied several positions in the asset management industry. Dan, welcome back to The Long View.
Humans vs. Retirement podcast
“Dan Haylett: Retirement Planning = Life Planning,” The Long View podcast, Morningstar.com, Dec. 5, 2023.
“Can You Afford to Retire?—3 Questions to Ask Yourself!” Humans vs. Retirement video, youtube.com, June 2025.
“The Fragile Decade: Retirement’s Danger Zone,” by Dan Haylett, humansvsretirement.com, June 30, 2025.
“Your Brain Has Two Sides. Retirement Needs Both,” by Dan Haylett, linkedin.com, October 2025.
“A Plan for Your First 12 Months in Retirement,” Humans vs. Retirement video, youtube.com, 2024.
“Few and Deep: The Retirement Lens That Changes Everything,” by Dan Haylett, humansvsretirement.com, Sept. 9, 2025.
“Why Retirement Can Feel More Like a Void Than a Victory,” by Dan Haylett, humansvsretirement.com, March 28, 2025.
“The Best Things in Retirement Aren’t Things at All,” by Dan Haylett, humansvsretirement.com, Feb. 6, 2025.
“Don’t Let the Fear of the Future Steal Your Retirement Joy,” by Dan Haylett, humansvsretirement.com, Jan. 14, 2025.
“Longevity and Brevity: The Two BIGGEST Risks in Retirement,” by Dan Haylett, humansvsretirement.com, Sept. 3, 2024.
(Please stay tuned for important disclosure information at the conclusion of this episode.)
Christine Benz: Hi, and welcome to The Long View. I’m Christine Benz, director of personal finance and retirement planning for Morningstar.
Amy Arnott: And I’m Amy Arnott portfolio strategist for Morningstar.
Benz: Our guest on the podcast today is Dan Haylett, who’s the author of a new book called The Retirement You Didn’t See Coming. 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 over age 50. He also hosts a podcast called Humans vs. Retirement that is centered on the behavioral aspects of retirement. Prior to joining TFP, Dan occupied several positions in the asset management industry. Dan, welcome back to The Long View.
Dan Haylett: Christine, thank you so much for having me back on your wonderful podcast.
Benz: We’re really excited to have you here. We wanted to talk about your new book, which is called The Retirement You Didn’t See Coming. And I wanted to talk about this human side of retirement. You’ve worked with clients on their retirement plans for years. What were your first clues in working with people about to retire or in retirement that the human side of retirement planning is actually more important than the numbers?
Haylett: I say that I was both lucky and slightly unfortunate in some of my very first dealings many years ago with some wonderful clients. It really hit me hard. I’d done what I thought was a wonderful job. I think it was the second-ever client I worked with when I became a financial planner and was let loose on delivering this stuff out in the world. At that point, it was very much numbers-focused to me. All of my training was pretty much numbers-focused, although I was definitely interested in the human side of it and done what I thought was a pretty decent job talking about life and what they want to do with their retirement, but very, very focused on the numbers thereafter. I remember building what I thought was the most wonderful spreadsheet, the most wonderful cash flow plan. Everything was fine. They had a load of money. They were never going to run out and sent them on their way. I remember meeting them six months later to check in and see how things were. When they walked through the office door, the vibe was very, very different to what it had been after initially working with them. I could see the look in their eyes. I could feel the energy was low.
It really took me back. I didn’t know where to go and I said, “How are you? What’s going on?” They were so kind of overwhelmed with emotion. They just couldn’t help but spill stuff out. “It’s not what I thought it was, Dan. Our relationship has suffered a little bit. We’re not as happy as we thought we would. I’m not really sure what I’m doing with my time,” and all of this. It really hit home to me that they’d worked so hard to get to the position they’re in. We had done a little bit of work about what they were going to do but focused a lot on the numbers and built what I thought was a really, really robust, visually pleasing retirement plan—income and everything. Yet, something was crucially missing.
I vowed at that point that I would make sure that all of my learning and research was going to be around the human element of retirement. What it means to transition from a career, what it means to have a different relationship, what it means to question what you’re going to do in the mornings and who you are, and so on. That led me down this wonderful, messy, slightly slippery path I found myself on over the last seven, eight years to really focus on the human side of retirement because that is the thing that makes or breaks it. That is the thing that’s going to give you the most fulfilling second half of life, not having enough money on a spreadsheet.
Arnott: And in thinking about the human side of retirement, I think it might be surprising for a lot of people that they do experience this sense of letdown when they retire. And you compare it in the book to someone who has spent years and years to climb Mount Everest and they sweat and sacrifice. They push themselves and finally they get to the top, but there’s no view. Why do you think it’s so common for people to have that sense of letdown when they finally reach the summit of being able to retire, but it’s maybe not as positive as they thought it might be?
Haylett: Yeah, kind of no view, altitude sickness, bit disorientated. It’s kind of like, what the hell’s going on here? I think it’s like anything, isn’t it? That old adage around the thrill of the chase is better than when you reach the goal. It’s why lots of people like dating all of the time and don’t like being in a relationship. The thrill of dating and the chase and once you’ve got what the thing you’re chasing, it’s like, well, actually, what’s next? I think that’s part of the problem with goals. People have retirement as the finish line. Retirement is the end goal. And they sacrifice so much to get there that they spend little time actually wondering what they’re going to do when they get there. And so, yeah, I think it’s a real problem because it’s focused on the money primarily, or too much in my opinion. It’s a save hard, sacrifice the time. Hit the enough number that I thought, put all my energy into that. And I’ll figure it out once I get there. And the trouble is, it just is fog and thin air and there’s a big decline and you’ve got to figure out how you get down the mountain, which is, by the way, is harder than getting up the mountain.
And people just freeze at that point. And because they haven’t put the work in to understand what they’re retiring with and to, it becomes hugely challenging. And as you said, at that point in your life, there’s huge amounts of kind of loss. You’ve got to a point where you’ve lost a lot. You’ve hit the summit, but you look back and you think, gee, now I’ve lost my purpose, and I’ve lost my identity and my relationships have changed. And I’ve lost structure of what I’ve been doing every day. And it feels really disorientating if you haven’t thought about it before you hit the summit about how you’re going to get down.
Benz: Does everyone experience that sort of existential crisis in retirement? It seems like when you look at surveys of retirees, self-stated happiness, they’re a pretty happy lot by and large. I’m wondering if you can generalize about the characteristics of retirees who are most likely to have this sort of like, what am I doing here moment and the ones who are most likely to avoid it?
Haylett: I think there might be a slight kind of definition problem with happiness, maybe. I think people are happy, but it doesn’t mean that they don’t feel frustrated. Does that make sense? You can feel frustrated where you’re at. You can feel a bit lost and disorientated. It doesn’t mean you’re kind of unhappy. And so I do think most people that enter into this phase of life—and I’ll caveat what I mean by most in a second to answer your second point—do go through some period of loss, some period of disorientation, some period of frustration and doubt. They may not go through it in a linear way, but they will at some point question certain things that they’re experiencing. And I think some people question it more than others. What’s interesting for me, and this is where a modern-day retirement is much more challenging. If you were very much manually focused in your work, hard manual labor, I would imagine not doing hard manual labor when your body aches is a really happy thing. You’ve retired from something that you just physically can’t do anymore, that you’re mentally checked out on and you’re now looking forward to this phase of life. Knowledge work and the modern worker, really outside of the trades that still exist, it’s a very different retirement.
It’s one where identity and purpose and creativity and wisdom and everything might be at its peak when actually we’re deciding to step back. And it’s a real challenge for people that are modern-day knowledge workers to feel like that everything that’s kind of made them happy, they’re looking to reshape and sacrifice. If you’re a tradesperson with hard work, you’re not looking to reshape that. You’re looking to do something very, very different. So I do think that the blueprint for a modern retiree, a knowledge worker retiree that’s got accumulated wisdom in their 50s and 60s is a very, very different emotional beast than it was maybe 30, 40, 50 years ago.
Arnott: So it seems like that ties into the downside of focusing too much on the rest and leisure aspects of retirement if you are someone who was more in that knowledge worker type of job. What are people likely to miss out on if they’re mainly trying to focus on leisure in retirement? Is that that sense of purpose and mental engagement?
Haylett: I think that the problem with it is, we all love our holidays or vacations, leisure time, and everything, right? But we enjoy them because they’re not forever. We look forward to going on holiday. We look forward to playing paddle tennis or pickleball or golf or something at the weekend with our pals and friends. And if that’s 24/7, it isn’t something to look forward to or maybe enjoy as much anymore. So I think there’s a big problem when it comes to that and it’s not necessarily this deep-rooted purposeful, get-out-of-bed-every-day type activities that you’d have. Look, I’m a big golfer and I know people that have retired and played golf for three or four days a week for about six months and then stopped playing for six months because they just got fed up with it.
And I think that is part of the problem. It’s the elation phase that this retirement honeymoon phase that everybody should embrace because it’s a wonderful time of your retirement to go away and to let off some steam and do a couple of big bucket list items and play some more golf and go away on holiday and spend more time with family. We have to understand that that bit has to and should come to an end in its entirety in terms of doing it all the time to get to a much better rhythm and pace of everyday life. And I talk about, there’s 365 days in a year, you can’t be on holiday for all of them. We need to understand what we’re going to do on a Tuesday morning at 9:47 when the dogs look at us a bit funny going, what are you doing in my house all the time? We need to figure out what that looks like, not three weeks in the Maldives or Florida. So, yeah, I think that that’s a big problem. I think people have this kind of brochure, retirement brochure-type outlook. It’s dressed in white linen on a beach with cocktails and a golden retriever running by your side. And that’s OK, but that’s not that rainy Tuesday morning that we all need to figure out. That needs to give us a bit of purpose and joy as well.
Benz: At the other extreme, Dan, I found myself relating to, as I was reading the book, the retiree who packs every day with various tasks and obligations. It seems like there’s the potential for some of us to go too much to the other extreme. Why can that be a mistake? And how can people find that middle ground where they’re getting stuff done, still maybe have a sense of purpose, but they’re also giving themselves a little bit of a break?
Haylett: A couple of things. One of the favorite phrases I use is to find anchors and rhythm. So this kind of packed schedule of saying yes to everything and busyness, I think is a kind of a hang up of, again, this modern-day working environment where productivity equals success. And so for these, knowledge workers, corporate workers, again, this knowledge, wisdom-based work, we’ve had KPIs, we’ve had productivity measures, busyness for some strange reason has equaled success. As long as we’re busy, we’re OK. And a lot of people take that into their retirement, and they end up saying yes to a load of things that actually suck their energy and bring them down a bit. Don’t give them the joy because they feel like busyness and a packed calendar will make sure everything’s OK.
So I talk about finding a rhythm, having anchors, being comfortable in silence, being comfortable with time to think, not feeling like you have to be doing something. You can be very content by reading a book or listening to a podcast or just sitting down and being silent and enjoying a cup of coffee. You don’t have to be doing something all of the time and that, I think, is a hard transition for people to get into. And so, yeah, the big thing for me there is find anchors during the week. On a Monday morning, I’m going to spend time with friends. It doesn’t say what you’re going to do and who you’re going to spend time with. It just says that that’s one of the anchors I’ve laid down for the week. And the other thing, which is really hard for everybody, I’m absolutely rubbish at this. And since I’ve launched the book and written the book, I’m equally more rubbish by saying no to things. I say yes to a lot, and I love saying yes. But for people in retirement, if you say yes to everything, it’s going to cause you issues. So you’ve got to learn to understand what does bring you joy and what doesn’t and celebrate those markers when you say no to stuff.
I had a wonderful conversation with Hal Hershfield about this last year and this no-yay effect that they call it. It’s if you say no to something, put it on your calendar. And when it comes around to the event that you said no to, you can go, yes, I’m glad I’m not going to that. And it kind of gives you some of those feelings that you know why you’re saying no to stuff because it frees you up to say more yeses to the things that you truly want to do.
Arnott: So related to advice, to practice saying no to things is a common piece of advice about retirement that we often hear is not to commit to anything in the first year of retirement. It’s just kind of live, try some new things, see how it goes. Do you agree with that advice?
Haylett: The honest answer is yes and no, which is a really bad answer, I know. I do agree with the premise that you definitely need to feel like you have a bit of downtime. I think if you prepare very well for it, the downtime can be a little bit less, but you definitely need to find time with very little pressure to be able to get comfortable with a new rhythm of life. But what I think you should do in that first year of retirement is have a beginner’s mindset and a growth mindset and not be afraid to fail and therefore try loads of stuff. And so, it’s not necessarily about relaxing, but I would say that this is about, it’s a great opportunity to figure out what you want to do a bit more longer term. If you don’t know, if you know that you want to keep fit, but you don’t know what hobby to take up, go and try five of them. You don’t have to commit to anything but be a beginner again. Find the stuff that really starts to give you that feeling of, I quite like this, and I’d like to learn more. Because we know for cognitive stuff, and it doesn’t have to be a sport, it can be starting a new hobby. You might think I’d love to learn a musical instrument, but I haven’t decided which one yet.
Well go and try five of them. I think that is a really important part for the first year of retirement. It’s that beginner’s mindset, that growth mindset. And I think a lot of people struggle with this because maybe they’ve been pretty successful, and they probably felt like they haven’t failed in a long time, whatever that means. But I’ve done very well. I’ve been successful. I’ve earned money. I’m the boss. I’m the man. I’m the woman. I’ve done this stuff. I’m the CEO and all of this. And to actually kind of be humble enough to go back to a point where you’re going, well, I’m actually going to start again with everybody that doesn’t know what they’re doing. But the best and most joyful retirements I see are from people that have that attitude. So that’s how I would define that first year. And if it means you’re really busy, then great. If it means that you’ve got some downtime to think about these things that you’re trying, then you should have that, too.
Benz: Dan, I’ve come to be a big fan of phasing into retirement very gradually versus the kind of hard-stop idea. And I’m wondering if you can share your take on that and also maybe give us some thoughts on how that phased-in retirement has worked for your clients. Has that worked well for them?
Haylett: I’m a fan of it too, for all of the reasons we touched on a bit earlier when I talked about the loss of stuff. I think if I look at what I call the five pillars of a thriving retirement, and we could easily rename these as the five pillars of a thriving life. And they are purpose, identity, relationships, structure, and well-being. Work, in a sense, gives us huge amounts of those five pillars. And we know that if you do hard-stop retirement, you quite rapidly go through a period of loss in those five environments. And that can be really, really challenging. And in fact, it’s akin to grief. There’s lots of research that talks about the emotional impact of hard-stop retirements and losing this stuff is very, very grief-laden and the same kind of reaction emotionally. So what I love is for people that actually figure out the bits of work that they really like, dropping the things that they don’t like, but it doesn’t mean that they stop completely—maybe going down to reduced hours, maybe agreeing to taking on lesser responsibilities, but those responsibilities you do have, truly lay into your purpose and your identity. And I think to me that is, again, this isn’t a financial decision. And I think that’s key.
The best decisions at this point are where people probably feel like the money thing has kind of taken care of itself. So this is now more about human being stuff. This is more about making sure that I can retain that sense of purpose to pull back the duvet. I feel like I can give back maybe by mentoring younger people within the organization that I work for. Maybe I could start some consultancy work on the side and do some things. So, yeah, keeping this in is really, really, really important. And I think going back to that knowledge work scenario, this will happen more and more, given lots and lots of people are exiting full-time work, or want to exit full-time work, at what I would say is again, peak wisdom. So we should encourage people to want to give back and mentor and stay in organizations for a bit longer on their terms because it will really help in the overall transition and overall happiness state that they’re in in their second half of life.
Arnott: I wanted to expand on that issue of loss of identity. And it sounds like you’ve had a lot of experience with people in high-status professions, people like executives, doctors, attorneys who do experience a pretty big loss of identity in retirement. What kind of steps can they take ahead of time to address that potential loss of identity? Is the best answer to continue to leverage their skills and peak wisdom in some way, through volunteering or part-time work, for example?
Haylett: Yes, is a short answer. But also, it’s really important for me, even if people are going to continue to stay in work, either full time or—I’ve got people I’ve worked with that have started the whole retirement planning process and have realized through the work that we’ve done that they’re actually OK and want to stay on for the right reasons. Not because they need to save more money, but because they’ve got some things that they want to do and finish, and they feel like that’s fine. And my tip would be to be able to take away the job title. So if you can figure out who you are, what your identity is, without saying your job title, that will put you in a really, really good space to be able to think about what you’re going to do going forward. And your identity title can be a paragraph; it can be a couple of bullet points where we don’t have to be rigid to one line or three letters.
And that will allow these people to really figure out what’s important to them and who they want to be when they start to slow down or take reduced hours or take reduced responsibilities. So, things like, if someone is an attorney or a doctor, I’ve had it before where they start calling themselves a mentor and therefore, a mentor in the law profession. And so therefore part of their identity going forward as they start slowing down is to feel like they can search out people, younger people in the profession, that they can take under their wing and give back some time to them. There’s lots of businesses coming up with mentor programs for people in their 50s and 60s where they want to keep them on, pay them a wage, and get them mentoring younger people coming in.
So I think that’s really important to me is to figure out some way to have a business card that says your name and something underneath it that isn’t an actual job title. That takes a bit of work, a bit of creativity. I get people to design their own business cards. That’s been quite a cool and fun exercise and getting them to be quite creative with that. But if done well and if thought about and if done over a period of weeks and months as people start to really think about what this looks like, it can be really transformational for people to figure out that identity piece beyond the job title.
Arnott: I really like that idea of the business card. It seems like that’s a really tangible way of having an identity that you can physically give to people.
Haylett: Yeah, for sure. Again, that’s that. It’s a typical thing, isn’t it? If someone says, what do you do? We answer with our job title when we might give them a business card, and I’m going, actually, I’d love you to have something to give to someone if you’re at a barbecue or a family event or something, to go, actually, this is what I do now and be proud of that sentence that sits on it.
Benz: Dan, for people who are phasing into retirement, have you heard of two-way mentoring where you’re working with a younger person who’s imparting some knowledge to you and vice versa? It seems like those things are getting some traction. I’m involved in a relationship like that at work, and it’s been absolutely amazing. Certainly for me as the more senior worker, and I hope for the younger person who I work with. I’m wondering if you have any experience with that setup?
Haylett: Yeah, not directly, but absolutely heard of it, and I can see the benefits, the huge benefits in this. On a very similar vein, I say to my clients that please don’t have friends all your own age. Because two things—I don’t want you to go through a sense of grief and loss when everyone starts dying at the same time. Sounds really harsh. I don’t actually say those words to them. But you know what I mean? And actually to feel like you get a better perspective on the world, this kind of keeping you feeling young, all of that stuff, and engaging in different demographics, different viewpoints, it really, really does add a lot of value to people to have those different types of conversations, and again, it’s stereotypical. But when you get a bit older, all you talk about is the weather and your health.
And, and I do listen to these conversations and conversations can get a little bit sterile as we get a little bit older. If we’re not hanging out with people that are doing other things, maybe slightly more interesting things that we’d never think about, then I do think we’re missing out. So I love the fact that that kind of thing is happening in a way that allows younger people to impart some of their views, as well as people thinking about their second half of life, learning from them and imparting some of their views. There’s a TV program that’s just coming on over here in the UK. I can’t remember the name of it, but they’ve basically paired up a teenager and someone over the age of 60 to tour around India and to journal it and have a time, and they hang out together and they do things—like four couples. They’re unrelated. And I think I can’t wait to watch it. How the dynamics of a 17-, 18-year-old and a 65-year-old and how they want to hang out and the things they want to do and the things they want to see. So yeah, I think it’s absolutely amazing, and everybody listening should really think about something like that.
Benz: One thing I’ve enjoyed about it is that some of the things you hear about younger-age cohorts are so untrue. Some of the generalizations that you hear. And that’s been really eye-opening to truly get to know someone who puts the lie to a lot of the things you hear about certain generations. So it’s been a fantastic learning experience for me.
Haylett: And vice versa as well. I think young people might have a slightly weird view of people in their 50s and 60s. And I think if we can make that much more rounded and worldly for everybody, the society is going to be a much better place for it.
Arnott: Dan, we also wanted to talk to you about the whole topic of relationships, which is one of your five pillars of a thriving retirement. And you’ve worked extensively with couples on their retirement plans. And I’m curious, what kinds of questions should you be asking your partner or spouse as you’re both starting to think about retirement?
Haylett: My experience suggests that people should just—any question is really good because a lot of them don’t actually ask any questions with one another. And don’t get me wrong, I’ve worked with some couples that have been very open about what they want to do and how they want to do it with one another before coming in and seeing me. But in general, I sit down with a couple and I’m like, have you two just met before you walked in here? Like, it doesn’t feel like you’ve ever had this discussion or know deeply what one another’s thinking about this stage of life. So, any question is great.
However, I think what they should be really curious about is what this stage of life looks like for each other. What are the things that they would like to achieve? Not assume that you want to achieve the same things. So, one of the exercises I try and do is create the kind of “my plan, your plan, our plan” type scenario. And I do this through various different sketches. But the easiest one is to do that Venn diagram, and you get them to go, well, actually, what are the kind of things that you want to feel and do? What are the kind of things that the other spouse wants to feel and do? And what are the things that you want to feel and do together? And just to open up that conversation, I think, is so vital because you often get people that either sacrifice their own thoughts for the other person, or they have very different thoughts and both of those come out in that meeting. “I’ll just do what he or she wants to do,” which doesn’t feel great. And the other one is when one of them goes, “Well, I want to travel around Europe.” And the other one goes, “I want to look after my grandchild and tend to my garden.” And they both look at each other like, gee, we’ve got a problem here. And who’s going to give in? Which one do we want to do?
So, I think understanding before any buttons are pushed to feel like you are going to give yourself more time and maybe phase into retirement or even the hard stop. And feeling comfortable that it’s OK to have three journeys in retirement. It’s OK for you to have your separate things that you’d like to do. And it’s OK then, obviously, and vital to have the things that you want to do together. Because for the first time in your marriage, you’re going to be spending day times together. Really, unless you’ve been ill or you’ve been working from home a couple over the last few years, this is a real litmus test for that changing dynamic of a relationship and being truthful about that and having those conversations and asking curious questions about one another’s wants and desires and dreams and fears is really going to make each other understand about what this phase of life looks like.
Benz: Speaking of a litmus test, the retirement researcher, Michael Finke, made the point to me that the early covid days were a good litmus test for couples. And his point was like, did you enjoy that time with your spouse or did you drive each other crazy? Do you think that’s a good mental reference point for people as they’re thinking—and of course that was extreme—but as they’re thinking through what this phase might be like with more togetherness?
Haylett: Yeah, I do. And I think it’s a really good reference point. It’s one that can be a little bit strange because it was such a strange time. It wasn’t as clear-cut as you’re home now and everything is fine. We were forced to be within—you couldn’t be at home and then nip out for a coffee for two hours and see your friends to give yourself a break from whatever you need to give yourself a break from. So yeah, I do think it was a litmus test about how we can interact and spend time with one another, how we can respect each other’s space. And without being too stereotypical here, it’s definitely women have been very, very good, much better at men than creating, I think, better, longer lasting relationships, deeper relationships.
Men’s relationships on the whole are much more superficial and potentially more work orientated. And what that’s given—and I know that’s nuanced and it has changed quite a bit—but what that has given is you feel like you kind of invade on each other’s life. And so what’s really interesting for me is—let’s just go for the whole stereotypical thing to make it easy—but, the man is home and [says], “Do you want to go out for lunch on Tuesday?” And the wife will tell him, “Well, no, that Tuesday is when I go out with my friends. I’ve been doing that for 10 years. You just haven’t known about it because you’ve been at work.” That kind of thing. And so it’s to kind of understand and respect each other’s structure, each other’s anchors, and to understand and respect that everyone has their own things that they want to do. And this is why I think it’s really interesting to be comfortable in each other’s company and comfortable in silence. If you try and force the issue with this, then I think it really does start to highlight some issues. This is about making sure that you can respect each other’s time and space.
Arnott: Yeah, and I think it could be helpful to realize that you don’t have to spend 24 hours a day, seven days a week together, and it’s OK to have time by yourself or time with friends in addition to time with your spouse and have a more balanced way of spending your time.
Haylett: In fact, I would say, please don’t spend 24 hours, seven days a week with each other. It’s not that you shouldn’t. It’s that you absolutely shouldn’t. And that won’t lead to, on numerous occasions, won’t lead to the positive outcomes that you want. And again, let’s go back to the leisure thing. If you want to enjoy time away with your spouse, then time away with your spouse will be exactly the same. It might just be in a different country. It might be a bit hot or a bit colder. That’s the problem. So if you’re spending all of this time together every day, when you decide to go away, the impact of leisure time and holiday time actually doesn’t have anywhere near the impact that you thought it might have. In fact, it has the opposite. I’ve seen people come home and be really, really deflated because it was just like being at home, but just in another country. And so I think that’s why it’s really important to make sure there is still this magic time together that you have. And there are still things that you can talk about and bring to the conversation because you’ve been doing different things with different people. And that just keeps that relationship energized and fresh.
Arnott: Yeah, I’ve heard the expression for better for worse, but not for lunch.
Haylett: There you go. I love that. Absolutely.
Arnott: What’s your advice about retirement dates for couples? And we’ve heard that sometimes two people retiring at the same time could be too much change all at once. Do you agree with that? And what kind of advice do you have regarding the timing of retirement for a couple?
Haylett: You think of the modern-day retirement, again, step out of the stereotypical thing here, more and more couples will retire with very, very similar emotional baggage or problems. It is absolutely more common now than not that this knowledge and wisdom work with identity and purpose, and so on, is both sides of the relationship. So if that happens all at once, that’s a tricky environment to probably navigate. And I also think it’s really important for every individual to have their own timeline and to not sacrifice that timeline for one another. So it is a real challenge. But I think if you decide to retire at the same time, one person out of that relationship is going to be on the back foot from the word go, because they probably have stepped away from work at a time that they didn’t actually want to feel ready for. And they might have unfinished business, or they might love what they do.
So, yeah, I think it’s not only just too much change, I think there could be an element of resentment or regret from one of them that feels like they might have been forced into retirement, because again, the brochure tells you really it’s well, retire together and have long, happy lives sitting on a beach, sipping cocktails. You need to do this together. It comes back to that point, and you don’t. This is about your individual purposes, individual identities, individual timeline, and the bit, like I said about the Venn diagram thing—on one half of it, it might be continuing to work for a little bit, but I’ve got more time off. So in the middle bit, we can do some more stuff that we want to enjoy together. I think it’s dangerous for people to retire at the same time, unless it’s absolutely the right thing for them. But in general, I don’t see that.
Benz: So sticking with relationships, I wanted to ask about people who have family obligations and they’re working, and they maybe have a good balance going. When they retire, it seems like there could be a risk—and this little bit of a personal question from me—but it seems like there could be a risk that like if you suddenly have this void of time, your family obligations like taking care of elderly parents will just like step in and utterly fill that void. So how can people who are retiring ward against that problem?
Haylett: Yeah, I do see it a lot. And elderly parents is definitely one of them. The other one is your children. If you have them, if you have children that have their own children, such as you have grandchildren, that could be. But I do see it a lot where there is an assumption that mum and/or dad are now retired, and they can look after little Johnny three days a week and I can go back to work. And there’s an assumption from people, and it comes back to the yes/no scenario. And the hardest people to say no to are going to be your kids and your parents. It’s going to be the hardest people that you say no to. The problem I see is that one or two days a week turns into three days a week, which then means that your ability to actually go on holiday is scuppered. Because over here in the UK, for instance, going away on holiday when the kids are off school is you can almost pay double the amount in price.
The holiday companies just push the prices up during school holidays. And I’ve seen people retire, start looking after the grandchildren and then get on the same timeline as the school holidays because they can’t go on holiday until the kids are off school because the parents then have to kind of take some time off work to look after their own children. And the price of their holidays is through the roof because they’re having to go off at the same time as all the families. So I think it’s a real challenge for people. But what I try and say to people is you need to start prepping this before you retire. And there are potentially some hard conversations to have. If your children have children already, if you’ve got grandchildren, you’re still working, you should sit down with them and set some boundaries. “This is what we’re going to do with our time. I don’t mind helping out when you need me. I don’t mind committing to doing this if that’s what you want to do. But just to let you know that this is what we’re doing and why we’re doing it. And I’m not going to overcommit to this stuff that puts our time at jeopardy.” And I think a lot of people think that’s quite selfish of them.
But I think we need to make sure that we get over that barrier when it comes to that. And caring for elderly parents is a real challenge. Because I think a lot of people actually don’t have the kind of caring for elderly parents when they retire. It can sneak up on them pretty quickly or hit them pretty early on if their parents become ill or they need that care. So it can become a real, real challenge. And I do see that impacting the people I’m speaking to now. They’re going through that with their parents and they’re going, actually, I never want this to happen to my children. So they’re putting provisions in place to help with care or something like that. So they don’t have to take that burden into their worry about what they have to do.
So it’s a real tricky one. But I do think, and I know what you said—it’s a lot of people don’t want to communicate this with their families because they’re scared of saying no and scared of [saying], “Well, actually, I thought you were just going to be wonderful grandparents for me. So I could go back to work, mum, please.” But these family conversations are so important for everybody to know where some of the boundaries might lie. Because again, one shot. One second half of life, one life, one chance when health, time, and money are aligned over a five to 10 year window for you to probably have the best, one of the best opportunities to be the most happy and content and joyful that you can be. So it’s really important to sit down and have those conversations early on with your family members.
Arnott: We’ve talked a lot about the nonfinancial aspects of retirement and that’s really the focus of the book. But we also wanted to spend a bit of time talking about the financial piece. What are some of the key mistakes you’ve seen preretirees and retirees make on the financial side?
Haylett: I’ve been thinking about this a lot actually. And I hope this answer fits into what you’re thinking. And I think we’re going to probably get on to spending money in a second. And I think that is a mistake, particularly in retirement, that people don’t spend enough. However, if you think about that preretiree bit leading into this—so let’s talk to people that are age 50 to 60. Is there a an oversaving, overworking problem? Notwithstanding everything we’ve talked about in that work can be an important part of people’s glide path into this phase of life. So one of the mistakes I think is people just don’t have an idea of what life they want to lead and how much that life will cost them. And the people that I’ve started working with the vast, vast majority of people are shocked about how little that costs compared with what they thought it would cost.
And I’ve had many people go, “Gee, I could have done this two or three years ago, couldn’t I Dan?” Like, well, you probably could have done it five years ago, to be honest with you. And so I think, one of the mistakes I see people make with their money is to feel like there’s this arbitrary number that everyone tells them, “Your mate down the pub says you need $1 million or GBP 1 million or 2 million. And I saw another stat today that said 35-year-olds need GBP 2.8 million pounds in their pension.” And I’m like, man, I think we’re setting up the wrong behaviors here because then you’re getting to a point where you don’t actually know what you want to do with your money and your time. And I think that’s the biggest mistake that people do. They don’t spend the time on it, and they end up oversaving, which then ironically leads to an underspending problem because they can’t actually spend the money they’ve got because they probably saved too much. Does that make sense?
Arnott: It does. Thank you.
Benz: Dan, I wanted to ask about this concept of permission slips, which you discuss in the book, which relates to this idea of spending. Can you talk us through how that would work? And also, how can retirees ensure that they’re not giving themselves too much permission to spend because overspending is potentially a problem for some as well?
Haylett: Yeah, no, it is. And, I think that’s, I say that people don’t have a kind of like an income problem or a product problem, they have a permission problem. And that permission is that it takes skill and courage to give yourself permission to spend assets, spend money that you’ve worked so hard to save. And during that saving period, it’s giving you a lot of security and status and identity, and it’s given you this kind of future freedom vibe that you want. And all of a sudden, you’re told to go and intentionally spend it. I say it’s a bit like spending 30 years, 40 years building the most beautiful sandcastle in the world. You’re going to get quite attached to it. And if someone says, by the way, now go and knock it all down and have fun and excitement and joy doing it, you’re going to feel a little sad. And so, you need to give yourself permission to spend your money. And I think permission slips are a great way.
Start writing down: “I give myself permission to spend money on …” And then figure out some of these things. These don’t need to be $30, 40,000 dollars’/pounds’ worth of stuff. It doesn’t have to be big. But I see people struggle just with everyday type spending with what they want to do. So, giving yourself permission, having someone to hold you accountable to some of those spending decisions is really important. And in terms of ensuring that they’re not giving themselves too much permission, this is about finding out what you really, really enjoy spending your money on. What is more intrinsic than extrinsic? And by that, I mean, what gives you that inner joy, not the joy that you want to take a photo and put it on Instagram and share it with the world. This is the stuff that you don’t care if the world sees it. This is the stuff that you know will give you memories and experiences and deep-held joy.
Now, that might be a boat and you might take a photo of the boat, but you’re going to be on the boat six months of the year because you love sailing. You haven’t bought it just because it feels like it should be a good purchase. You’ve bought it because you love that. And so I think once you start realizing what that is, people’s understanding about how much they’re going to spend and what they’re going to spend it on, actually becomes a little bit less than what they thought. And then they find it easier to kind of write those permission slips to enable them to actually spend that money and what gives them that intrinsic joy.
Arnott: What do you think about the strategy of maybe continuing to work a bit longer while also giving yourself permission to spend? So doing something like taking your family on a really nice trip while you’re still working instead of waiting until retirement. Do you ever recommend that to your clients?
Haylett: Yeah. Listen, if you can have the time, then absolutely. Carve out the time, and timing is all important in all this. I’m starting to realize it myself. I’ve got a 17-year-old daughter who, we went on a family holiday this year and the dynamics of—and I’ve got a 14-year-old daughter as well—the dynamics of that holiday were very different to every other holiday that we’ve been on. And I said to my wife, I’m not sure how many of these we’ve got left. We might not have any. She might not want to come away with us. I mean, I’m sure if it’s a free holiday, she might say yes. But, the dynamic of this changes, so timing is important. If you’ve got grandchildren, there’s probably a limited number of magical years that Disney would appeal. I think Disney appeals to everybody. But that true magic that you might want to see from your grandchildren. So don’t sacrifice those moments when the timing feels right. I absolutely encourage it.
And again, staying at work might mean that from a money and finance point of view, you can go that little extra mile and really create that wonderful experience and memory that you want to do. And I’m all for that. But, have a look at the time because everyone’s timeline is very different—yours, your children’s, your grandchildren’s, your dog, everyone’s timeline is very, very different. And you need to take advantage of it when they align at certain points.
Benz: We’ve all heard stories about someone who’s planning retirement and then they’re immediately hit with something really terrible right after they’re retired, often kind of a health crisis. Is the key takeaway to not wait until retirement? Don’t come into retirement with this pent-up list of joyful things that you want to do. You should be trying to do them earlier in your life, right?
Haylett: Yeah. Again, I think we spoke a little bit before we hit record about the word retirement, didn’t we? The word retirement is, I think has a lot of negative connotations. We spoke really early about the goal of retirement and the sacrifice that people do to get there. And I absolutely agree. We shouldn’t be waiting till this point in life to be able to live it to its fullest. I do think a lot of people could do this a lot earlier on. When we have money, time, and health in alignment, and there’d be different stages in life. When we’re early on in our career, we haven’t got a lot of money, but we’ve got lots of time and health and we save up. And, those three dynamics will change in what we have in terms of its abundance to a point where we might get into our mid-40s to early 50s, where we have an equilibrium between time, health, and money, or one of them might, we might have, a really good amount of money and our time feels like it’s slipping away. And therefore, that’s at the point when we need to go, “You know what, we need to not wait until we do this. Let’s design the life that we want to live.”
There’s an old phrase, Christine, “design the life you never want to retire from.” And I think that’s really, really true. Particularly now, going back to the type of workers the vast majority of people are, most people can work wherever they are in the world. A lot of people can. And if that’s the case, then I think we should take advantage of some of those privileges that might afford us to be able to feel like we can really set our life up that has more meaning early on, that has much more, I don’t know, much more aligned to our values early on. And then that allows us to actually probably to develop the skill of spending early on. Don’t wait until we’re fully retired with a pot of pension money that’s all the weights on our shoulders. We’ve got to draw this down to figure out, my God, I need to learn how to spend this. If you learn how to spend it a bit earlier on, I think the whole transition, the whole second half of life, whether you’re working or you’re not, will become much easier, much better, and much more fulfilled.
Arnott: Well, I think we’re running up on time here, but I wanted to just squeeze in one last question. How have you changed your mind about your own retirement during the years that you’ve been working on retirement planning?
Haylett: Yeah, it actually kind of plays into the last point. I see people living wonderful lives, and it kind of makes you think that you can design this thing now. So, I’m trying to create something that I never want to retire from. I’m trying to create something that has purpose and passion beyond the paycheck. And I feel like what I’m doing now, I could continue to do forever. And I think that’s really, really important. And it’s about narrowing down the things that you love becoming truly passionate about something that you feel like you could talk about or do or of play around with for years. So, yeah, my views have definitely changed around it. It isn’t a full stop. It isn’t an end date. It’s not a monetary amount. It’s more of just a transition into a different way of life with different relationships, different responsibilities, but ultimately making sure that you design—let’s ban the word retirement—design your second half of life in a way that you know what you’re bringing into it and what you want to do when you get there.
Benz: Well, Dan, you’ve given us so much good food for thought today. Thank you so much for being our guest.
Haylett: Thank you for having me. It’s been such a pleasure. Thank you.
Arnott: Thanks, Dan. This has been great.
Benz: Thank you for joining us on The Long View. If you could, please take a moment to subscribe to and rate the podcast on Apple, Spotify, or wherever you get your podcasts.
You can follow me on social media at @Christine_Bez on X or at Christine Benz on LinkedIn.
Arnott: And at Amy Arnott on LinkedIn.
Benz: George Castady is our engineer for the podcast and Kari Greczek produces the show notes each week.
Finally, we’d love to get your feedback. If you have a comment or a guest idea, please email us at TheLongView@Morningstar.com. Until next time, thanks for joining us.
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