The most dangerous day of retirement is a psychological challenge more than a financial one.
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By Rory Henry CFP®, BFA™
For CPA Trendlines
When most people think about retirement planning, they picture spreadsheets and savings targets. But as Dan Haylett, author of The Retirement You Didn’t See Coming and host of the Humans vs. Retirement podcast, explains, the real challenge of retirement is not mathematical—it’s psychological.
“People focus on the numbers because they think that will solve all their challenges,” Haylett says. “But retirement is a complex human problem. Spreadsheets will not tell us who we are without a business card or what gets us out of bed in the morning.”
Haylett distinguishes between “complicated” and “complex” problems. For instance, he says a tax return is complicated but solvable, while retirement is complex—filled with uncertainty, emotion, and shifting identity. That’s a huge distinction, and Haylett argues that advisors who only solve the math side miss the messy human side of the client relationship.
Haylett urges advisors to help clients plan beyond their finances – for instance, how they will structure their days in retirement, as well as their relationships and purpose. “Retirement is an emotional human transition,” Haylett says. “It requires people to think about who they are, what they are doing, and how their relationships might change.”
Planning for Two (or Three) Retirements
Retirement is also a relationship event. Haylett often reminds couples that they are not just planning one retirement, but three: yours, mine, and ours. He uses a simple Venn diagram exercise in which each partner lists their own goals before finding the overlap.
“Respect each other’s space and aspirations,” he said. “The most successful couples I see in retirement have three plans that all work together.”
Many clients want clarity before making changes, but Haylett argues that clarity comes afterward. “People expect to be clear about what they will do before they do it,” he says. “It simply isn’t true. You get clarity by thinking, taking action, and learning from what works.”
Haylett has found that many retirees or near-retirees are afraid of taking up new hobbies, passions, and activities because they don’t feel like being a beginner again. The fear of failing, he says, can get in the way of personal growth. Instead, he encourages retirees to adopt a “learner’s mindset” and to experiment with new activities rather than waiting for clarity first
After years of full calendars and constant activity, Haylett believes many retirees equate being busy with being valuable. “We have been rewarded for productivity our entire careers,” he says. “Then retirement comes, and we no longer have an inbox pinging or meetings filling the day. People struggle when they no longer feel productive,” or needed, he says. As a result, Haylett advises his clients to decouple their self-worth from “busy-ness” in retirement and to find meaning in their new routines, relationships, and interests.
Haylett sees identity loss as one of the hardest challenges in retirement – even tougher than the productivity traps. After decades tied to a job title, Haylett says it can be difficult to let go of that professional identity. He encourages retired clients to design a new “business card” that describes who they are now—not who they used to be.
“You can’t build a fulfilling future if you are living in the past,” he says. “Figure out who you are beyond the job title.”
Some clients take symbolic steps, like donating old suits or selling items tied to their work life. “It can be a powerful way to mark the transition,” he says.
The Most Dangerous Day of Retirement
In his aforementioned book, Haylett calls day No. 182—the six-month mark—the most dangerous day in retirement. “That’s when the [retirement] honeymoon period ends,” he says. “People have done the holidays, the house projects, and the lunches. Then silence sets in, and they start asking, ‘Is this it?’” Haylett warns that this six-month juncture of retirement is a psychological challenge more than a financial one. So, advisors who help clients anticipate this “messy middle” can play a key role in easing the emotional transition.
Haylett maps the emotional journey of retirement into three phases: Release, Rebuild, and Reignite.
- Release involves letting go of old routines and personal identity.
- Rebuild is the messy middle where retirees experiment and recalibrate.
- Reignite is when they rediscover rhythm and purpose in their new stage of life.
“It’s not a cliff edge,” Haylett says. “It’s a map of emotions. At some point, you stop talking about being retired and start saying, ‘This is my new life.’”
The Five Pillars of a Thriving Retirement
Haylett identifies five core elements of retirement that sustain a meaningful life after work.
1. Purpose.
2. Identity.
3. Relationships.
4. Structure.
5. Well-being.
“These are the foundations of a thriving life, not just a thriving retirement,” he says. “Work gives us many of these things. If we don’t plan how to replace them, it can be challenging.”
He adds that purpose doesn’t have to be grand. “It doesn’t have to be saving the sea turtles,” he says with a laugh. “It’s about having a reason to pull back the duvet every morning.”
Haylett encourages clients to start working on the non-financial aspects of retirement several years in advance. He says “trial runs”—sabbaticals, longer vacations, or part-time work—can help couples test routines and expectations. Communication, he notes, is critical, especially when it comes to adult children and family members who may have assumptions about how retirees will spend their time.
“Well-being is the foundation that keeps everything else running,” Haylett says. “If the engine isn’t working, you will not enjoy the freedom you’ve earned.” He cites research showing that people are living longer but not necessarily living healthier. He urges clients to care for both body and mind, highlighting the links between loneliness, depression, and physical health.
Time, Money, and the Art of Spending
Haylett believes time is our most precious resource—but few people know how to use it wisely. “Having time and knowing how to use it are two very different things,” he says. He also calls spending a learned skill. After a lifetime of saving and working, many clients struggle to spend without guilt, especially when they no longer have a paycheck to replace the money they’ve spent. He says it can be very difficult for retirees when they enter into their new phase of life, when they are suddenly being told to “intentionally deplete the money” they’ve worked so hard to accumulate.
“One of the most important jobs of a financial planner,” he says, “is to help clients spend their money in line with their values, without the fear of running out.”
5 Advis-ROR® TAKEAWAYS
- Retirement is human. The biggest challenges are emotional, not mathematical.
- Relationships matter—plan for yours, mine, and ours.
- Encourage clients to experiment and learn by doing.
- Prepare for day 182. The retirement honeymoon ends; purpose must begin.
- Redefine success. Move from productivity to fulfillment.
BONUS Takeaway: Spending is a skill. Learn to master it.
More About Dan Haylett
Dan Haylett is a financial planner and head of growth for TFP Financial Planning based in the United Kingdom. Haylett specializes in financial planning, retirement planning, and life planning for individuals over the age of 50. He also hosts a podcast called “The Humans vs. Retirement,” which is centered on the behavioral aspects of retirement.
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Transcript
(Transcripts are made available as soon as possible. They are not fully edited for grammar or spelling.)
Rory Henry: All right. Hello, everyone. I have another great guest joining me today. He’s the author of the book, The Retirement You Didn’t See Coming. He’s also the host of the podcast, Humans Versus Retirement, where he dives into the emotional, psychological, and deeply human side of life. After work, we’re right here to discuss how we can guide clients through one of life’s biggest transitions. So without further ado, let me introduce my friend, Dan Haylett. Dan, welcome to the show.
[00:01:11] Dan Haylett: Rory, thank you so much for having me. Can’t wait for this conversation. Good to see you again.
[00:01:15] Rory Henry: Yes, you are one of the main thought leaders when it comes to retirement. And for many folks out there, when they think about retirement, they always think about accumulating enough money for retirement. But as you talk about, retirement is more of a human problem than a math problem. Can you kind of walk us through what you mean by that?
[00:01:33] Rory Henry: Yeah.
[00:01:34] Dan Haylett: So I think I would say that it’s to do with the focus of people, number one. So as you said, it’s, you know, if I get the numbers right, everything will be fine, right? That kind of thing. So they focus on the math problem. They focus on the spreadsheets and the numbers because they think that will solve all of their challenges. And really, my thought around that is that there are two types of problems in this world, Rory. There are complicated problems and complex problems. And math’s problems are in the complicated realm. Complicated problems are solvable, right? You can kind of go, it’s an input process, output thing, like building IKEA furniture. Tax return. Tax return. Exactly right. These things, they have a logical kind of sequence that delivers the output. And that’s fine, right? You know, part of retirement is a complicated math problem that is solvable. But in my mind, retirement is much more of a complex human problem. Yeah. Messy, unpredictable. I talk about, I’ve got two teenage daughters, right? A 17-year-old and a 14-year-old. They are a complex problem. I love them to bits, but they’re human. There’s no real handbook for that, right? We’re all… Yeah. And I think that’s what I mean by this. Retirement is more of an emotional human transition that requires people to really think about who they are, what they’re doing, how they’re doing it, how they’re going to transition from having purpose to not, from having identity to not, how their relationships might shift. So spreadsheets can tell us a lot of things, but they’re not going to tell us what gets us out of bed in the morning. They’re not going to tell us, you know, who we are without a business card, et cetera. So, you know, it’s very, very human in its essence.
[00:03:32] Rory Henry: Yeah. Well, you touched on relationships. And as you know, I trained with Vice Roar, which is having a greater return on relationships. And all the research shows, as you know, that the number one predictor of satisfaction in retirement is those relationships. And I love the part of the book where you talked about the importance of couples. Because really, when retiring, you have your retirement, you have their retirement, and you have our retirement. Can you kind of break down that philosophy?
[00:04:00] Rory Henry: Yeah.
[00:04:01] Dan Haylett: I mean, how many times have we sat across from clients and they’re having a conversation and they look really puzzled to one another, right? One will look over the other and go, well, what are you, you know, why are you saying that for? Why have you never told me that? And I’m thinking, have you two just met on the street? How have you been married for 30 years? And I think, you know, retirement is such a big relationship event. The dynamic of your relationships, particularly with your spouse, husband, wife, partner, et cetera, will change because probably ever since you’ve known them, been married to them or been with them, you’re not going to, you haven’t spent or will not spend this amount of time together. Yeah. So I heard the saying the other day, I married you for better or worse, but not for breakfast every day. Right? That kind of thing. So, you know, they change massively. And I think one of the real challenges I’ve seen with people is that there is some sort of expectation that the other person is thinking the same as them. And they’re just going to waltz into this thing together and enjoy their time together. And then one of them says, well, I want to buy a camper van and tour around Europe. And the other one says, I want to stay at home and look after my grandchildren. And all of a sudden, because they haven’t talked about it, the conflict. So I say that really what you want in retirement is almost three plans. You want to respect each other’s space, respect each other’s desires and aspirations and wants, and respect each other’s, you know, things that they want to do with their time and create a yours, theirs and ours plan. So the way I do it with clients is to draw a Venn diagram. And, you know, you go, right, write for me what you want to do. And then your partner will come up and write what they want to do, you know, that’s uniquely both for you. And then the bit overlapping bit in the middle, find out the stuff you want to do together. And then respect all three of those plans. And think about how you’re going to achieve them. And I think if there’s one exercise I do that really helps couples throughout this transition to understand that dynamic, that is exactly it.
[00:06:06] Rory Henry: Yeah, I loved the illusion that you had of clarity comes first, because most people think clarity, thought, then action. But as you lay out, especially in retirement, it’s really thought, action, clarity. Can you expand on that concept?
[00:06:25] Dan Haylett: Yeah, listen, I think this is a bit of a life lesson as well, isn’t it? I think, and particularly for people in retirement, but, you know, this thing that we expect to be clear about what we’re going to do before we do it. And it simply isn’t true no matter what stage of life we’re in. But I think particularly in retirement, there is this real fear of failure, this real kind of understanding that I’m at a stage in my life when I really should know exactly what I’m doing. I shouldn’t, you know, have to go and try and experiment and do all this stuff. I should have it all figured out. And there’s a sense of probably, I don’t know what the word is here. There’s a sense of guilt or frustration or ego that might stick in here and go, I don’t want to be a beginner again. But you will never get clarity unless you think about it and take action. And I say to people, if you want to really figure out what you want to do in your retirement, you need to fail. You need to do a lot of things. Yeah, exactly. So think, take action and become clear whether you like it or not. Become clear whether you enjoy it. Get the clarity afterwards. And I think that’s such a big thing I see with people that struggle in their retirement. They’ve got it the wrong way round. Instead of being a beginner again, you know, this beginner mindset, growth mindset, learning mindset, think, take action, then get your clarity afterwards.
[00:07:52] Rory Henry: And I know you touched on the fact that we live in a culture of productivity and we’ve measured productivity, you know, in our career. But really, we need to take a step back and really do some introspection and find out that there’s other things besides just being productive. We can kind of map out our day with other things. Can you kind of talk about this fallacy or whatever about productivity in retirement?
[00:08:19] Dan Haylett: Yeah, it’s kind of this productivity guilt, I call it, right. And it’s that, you know, particularly for knowledge workers as well here, where, you know, the sense of always being busy, having a full inbox, having a calendar full up, you know, this where productivity is equal success, this kind of hustle culture in at seven, leave at seven, you know, and irrespective of whether you’re doing anything or not, that’s valuable or worthwhile. So, you know, the busier I am, the better my results. And actually, the trouble is, many people may have been rewarded like that through their career. And then you enter into this period of life where you’re told to have space and silence and your inbox isn’t pinging off anymore, your diary’s not full and you’ve got this productivity guilt and productivity trap where you’re not productive anymore. And you think, well, actually, that means that I’m not successful or that I’m failing or, you know, that my days don’t mean anything because we’ve not allowed ourselves to actually figure out what we want to do properly with our time without this, I don’t know, this real kind of trap of productivity. So for me, this is actually saying to people, if you if you’re three to five years away from thinking you’re going to pull back from work, whether you retire fully or not, but you’re going to start to pull back, understand that productivity isn’t your measure anymore. It’s not your measure. If you’re not measured by productivity and actually if you’re not measured at all by anything, you’ve got to get used to that, that feeling.
[00:10:01] Narration: Yeah.
[00:10:02] Rory Henry: You had a pre-arrival plan that you outlined in the book and you posed questions that you could ask yourself. What am I hoping for in retirement? Right. What would a fulfilling week look like for me now? What am I waiting for that I could start shaping today? Because, you know, much of our identity is tied to our occupation and our work. And we want to, you know, we’re used to being productive. And and that’s part of the issue around that transition retirement, because, you know, our identity is tied to who we are as an occupation. But to have you touch on that, because I know it’s a big part of the book, identity and really shedding the skin of who we are so we can become someone new in retirement.
[00:10:48] Dan Haylett: Yeah, I think this is one of the toughest things, right? I mean, you know, again, if we’ve if we’ve had a long and successful career, maybe one or two companies, you know, our identity is so interwound into our job title. And actually to kind of feel like we’re going to give that up can be a really psychologically wrenching thing that we do. And so and actually coming back to the productivity thing, if part of our identity is having a full diary, if part of our identity is working seven to seven, if part of our identity is being the person that fix everything, you know, or the leader or the manager or the CEO or the whatever that looks like, then this can be a real big step for people to take. And we run one of the things I’ve really that fills me with actually quite a big bit of sadness here is when I start working with people and they may have already retired. Yeah. And they and I talked to them about their identity a little bit and that and they and and they would answer the question with kind of who are you or that with I used to be a they talk in past tense, right? So and you can never move on to build a fulfilling future if you’re living. To let go. Yeah. In the past. And, you know, I see it all the time. I mean, people people don’t say happily that they’re retired. They say I used to be the CEO of a company or I used to be a managing director or I used to be a doctor and and they just haven’t let go of of what they of their past. So one of the things I try and get people to do is is actually get quite creative. To get maybe a little bit. I don’t know, you know, to not take this bit too seriously, but start to design their own business card. So if you if you if you had to give a business card away that had your name on it and then a couple of other sentences, but you couldn’t you couldn’t put your job title of what it was or what it is now, what would it say? Right.
[00:12:55] Rory Henry: So funny. Now you’re saying that I think of my mother and she’s Dodger super fan. She’s going to the World Series as a Dodger super fan. She’s a pickleball player. She’s a book club member. So she’s all those other things. She’s no longer a principal or an educator. She’s all these things in retirement. So it made me think of my mom when you just said that down all the titles she has in her retirement years.
[00:13:18] Dan Haylett: How cool would that be if if if someone said to your mom, OK, you know, what do you do? She would say, I’m a I’m a Dodger super fan. I’m a pickleball player. And what was the other thing? Book club member. Book club. Right. You know, and these are things that people should, you know, introduce themselves with like that, you know, that’s because that’s who they are right now and who they and who they love being. So I think it’s it’s so it’s such a hard I think it’s one of the hardest things that people go through, particularly for people that have, as I said, you know, had long, successful careers in jobs that have given them a status that have given them that identity. And I do think it’s a really, really challenging thing for people to let go of. But such important work to figure out who you are beyond the job title.
[00:14:06] Rory Henry: Yeah. And there’s symbolic ways we could do this, too, because I remember the book. You said that you had a client actually sell off their watches, cleared out their suits, you know, which give I mean, it sold the car, which symbolize them moving away from the former identity into this new life.
[00:14:22] Dan Haylett: Yeah. Again, that’s all that’s all built in psychology, right? If you know you the symbol, symbolizing the letting go of something is what’s happened throughout centuries of different things. Right. So, you know, if things if you do truly want to move on and there are things that remind you of of that, then then you can get rid of them. You can start again. And there is a lot of research around that kind of decluttering bit that people go through as they enter into retirement. You know, they within the first six months, there’s actually professionals that do this for a living. They go into people’s homes that have just retired. There’s some in the UK and they work with them to declutter their house and go, you know, let’s simplify things down. Let’s get things out. What’s in the garage that will remind you? And I think it’s a great thing to symbolize that that transition.
[00:15:14] Rory Henry: I love it’s like a Marie Kondo, but it’s niche in for retirement folks.
[00:15:17] Dan Haylett: Yeah, yeah, yeah, yeah.
[00:15:19] Rory Henry: I love it. Well, I know you talk about the most dangerous day in retirement. You open the book describing that day 182 is the moment that novelty wears off. Why do you call day 182 the most dangerous day of retirement here?
[00:15:34] Dan Haylett: Yeah. So, yeah, I said this before. This isn’t necessarily something that I I would say that I’ve absolutely 100 percent found out. This is a little bit tongue in cheek, but also actually baked in real life conversation. So for those that have got their calculator out, it’s six months. So apart from a leap year, I think there’s 182 days in six months. And I call day 182 the most dangerous day because, you know, it’s a moment. It might be six months in. It might be a year in. It might be 18 months in. But day 182 to me is the moment that kind of the honeymoon period is over. You know, people have done the holidays. They’ve decluttered the garage like we just talked about. They’ve done the DIY. They’ve done the long lunches. And then suddenly this kind of silence kicks in. It’s, you know, it’s kind of and this the I suppose the phrase that comes to mind is like, you know, people go, is this it? Is this what this is about? Right. I’ve done the thing. And it’s the moment when, you know, that messy middle bit, Rory, where novelty has kind of worn off a bit. Identity hasn’t yet reformed. And you kind of realize that you’ve retired from something, but not necessarily to something. Yeah. And so that’s we talk about the human number side. This danger isn’t financial. This is psychological, right? Day 182 is a psychological problem. And so that’s the moment I think people go, oh, man, what’s this? And I say in the book, I mean, this is probably it’s 947 a.m. in the morning. Yeah. It’s probably a Tuesday. You’re probably in your dressing gown. You’ve probably had three cups of coffee. Yeah. You know, you’re looking at the dog and the dog’s looking at you going, what are you doing in my house? You know, it’s that kind of moment where, you know, you realize that there’s 340 days, you know, in a year outside of some of the holidays that you want to take. You know, you need some sort of rhythm and structure to be able to, you know, be able to live in those days. So, yeah, I think to me, it isn’t the day you leave work. You know, it isn’t that day. It’s six months, eight months, nine months in when that reality starts to really kind of hit home.
[00:17:51] Rory Henry: Yeah.
[00:17:51] Rory Henry: Speaking of reality, you talk about the retirement reinvention curve, which you have three phases of the release, the rebuild, the reignite, because people fall into, you know, one of those time periods. Can you talk about those three phases and what each means and how to identify when you’re in one of those phases?
[00:18:12] Narration: Yeah.
[00:18:13] Dan Haylett: So the book goes into a bit more detail. I mean, there’s three phases and eight stages, and I put it on a curve. It’s not linear in that, you know, people don’t go through each one of these stages and phases in order. You know, people six months in might find themselves in rebuild and then three months later move down a couple of phases into release. Right. And I explain what they are. But so the reason why I put this together is I wanted to create an emotional journey that people could resonate with, you know, stages that people could resonate with and therefore have a bit of a language and an outlook to go, you know, this is I feel this, but it’s OK because it’s perfectly natural. And, you know, and I’m in that stage and I’ll get out of it. So if I think about stage one, which is release. This is kind of where you let go of old routines and identity. And to me, this is kind of the cocktail of excitement and disorientation, right? You kind of have this initial downward trend of retirement shock, and then you might go into elation or the honeymoon phase. And that kind of picks up, you know, you think really cool. And then that day 182 thing, right? Then you go into this uneasy type. Oh, God, what’s going on here? And then the messy middle hits. And this is when you get into rebuild. But the thing about rebuilding is in order to rebuild, you probably need to go a little bit lower, if you know what I mean, in your emotion. So this is that experimenting, recalibrating type phase where you might feel frustrated. You might get into a period of doubt whether you’ve done the you know, the right thing here. But you do come out the other side where you start to recalibrate and think, well, actually, you know, I’ve I’ve I’ve got a new plan. I know what I want to do with my time. And as you move out of that, you go into reignite reignite.
[00:20:10] Rory Henry: Good.
[00:20:11] Dan Haylett: No, no, no. And that’s where things click, right? I think to me, that’s where you stop talking about retirement. And you start saying this is my new life, right? You get a new rhythm and a new purpose. You start flourishing. You’re not retired anymore. You’re just living. And I think, you know, most people think that retirement is a cliff edge, like one day at work, the next day you’re done. But in truth, it’s just this this map of, you know, and weave of emotions that you go through.
[00:20:38] Rory Henry: Yeah, let’s talk about the different emotions here. Or actually, let’s talk about the thriving pillars of retirement, because I know you talk about the five pillars of a purpose, identity, relationships, structure and then well-being. So let’s kind of hit on those points here and give folks an idea about why those pillars are leading to a successful retirement.
[00:21:03] Dan Haylett: Yeah, and to be fair, I think I probably could you could get the word retirement off this and just say the five pillars of a thriving life, right? You know, I mean, just this these I think are are the foundations of a thriving life. And actually, that’s the point, right? So if you think about purpose and identity and relationships, which you rightly talked about earlier on structure and well-being, those are the things that that actually work gives us a lot of. So if we step away from work and we haven’t thought about in this new phase of life, what is our purpose? Who are we? You know, what’s going to give us the reasons to pull back the duvet, these changing dynamics of our relationships, not with our spouse, but with our work colleagues, our friends, our children, our grandchildren. If we don’t have structure to our days and we don’t look after the engine, you know, that kind of takes us through this, our mental and physical health, then then we’re going to lose a lot. And it’s going to be quite challenging. So I think that’s why I think they are the five pillars to a thriving retirement, because you have to understand that there’s going to be huge amounts of change across those five pillars and change that will happen to you no matter whether you plan for it or not. And if you don’t plan for it and you don’t understand it and you don’t try and work with it and work through it, then it could crumble. And it only takes one or two pillars to kind of start challenging people’s people’s, you know, happiness and joy at this phase of life. So, yeah, I talk about, you know, what you need to do is make sure that you’ve got a reason to pull back the duvet. And this doesn’t this doesn’t have to be what Jordan Grumman in his book, The Purpose Code talks about. It doesn’t have to be big P purpose. You don’t have to go and set up a foundation to save the sea turtles. Right. Although if you want it, that’s wonderful. I mean, it’s great. But this is about, you know, small P purpose. This is about what gives you the reason to pull back the duvet in the morning. And it can be simple, structural, foundational things that give you the purpose every day. This who are you without a job title scenario that we talked about before. So what is that identity? We talked about relationships and how crucial relationships are to a long, happy life. And so, you know, making sure that we deal with those and I talk a lot. These five pillars, we need to work on these before we retire. Right. Again, this this kind of clarity comes before that. That’s part of that. This thought, action, clarity. We need to, you know, when we start planning our retirement, we need to plan for things we’re taking with us into retirement and things that we’re taking to retirement. Don’t always plan what we’re going from. And I think that’s why it’s really important to think about those five pillars that we have. Because, I mean, retirement will shine a light on these. It will shine.
[00:24:11] Rory Henry: Magnifies, right. The life that we’re living. If we didn’t do the planning beforehand, it just magnifies, you know, the issues we’re having or magnifies the flourishing life that we did have.
[00:24:21] Dan Haylett: Yeah. Yeah, yeah. And I think that’s, yeah, and I think that’s the challenges I see with people when they don’t fully realize the how, the gravity of the loss that you might have across those five pillars or the gravity of the change that those five pillars might have. It doesn’t mean you need to figure it all out day one at all. You just need to understand that these are things you’re going to have to work on. Yeah.
[00:24:50] Rory Henry: Now, is there a way to ease into this? Because obviously the change in identity for many who’ve, you know, identified with their occupation, there’s going from working all these hours, now living with a partner, you know, full time. Is there a way to ease into this here? Do some pre-planning, like we said before, that makes it easier for folks during this transition so that it’s not such a cliff to fall off of?
[00:25:14] Dan Haylett: Yeah, I think there weren’t many blessings that come out of COVID, right, if any. But I think one of them I’ve seen with people I’m working with now is that they had a bit of a trial run with this. So, you know, they did spend some time together. They, you know, they had to figure some stuff out. And it wasn’t obviously, you know, nowhere near what a normal retirement would look like. But it showed people that they didn’t have to have the level of work that they once had, etc. So just with that in mind, I think it’s really important as you lead up, as again, three to five years is my time frame that you’d want to build into this. You know, if work allows you, take some sabbaticals, take a little bit longer off. If you’re thinking about maybe in your retirement moving to a different part of the country or the world or something, go and explore that. Don’t go on holiday there. Go and hire an Airbnb and live there for two weeks or three weeks or a month, right? Figure out and talk to your family. It’s really important to understand that you start to communicate what you’re doing and the boundaries that you might have as people that are now retired and have free time and what you want to do with that free time. And so I think the giving yourself time to ease into this, to allow yourself to kind of take some sabbaticals, to take some vacation holiday time that has that in mind, right? Don’t, if you are thinking of this, don’t go and take a two week holiday and do it as a sun lounger holiday around the pool. Think about how you would enjoy your time together and do some trial runs and etc. Yeah, and again, I think communication is so important. I’ve worked with people before where they haven’t communicated to their children. And as soon as their children realise that mum and dad are at home a lot or have a lot more time on their hands, they’ve had this assumption that they’re going to look after little Johnny three days a week. You want to be a grandparent. That’s great. You can look after them while I go back to work. And they say yes, thinking it’s going to be a three month thing. And then six months in, they’re committed and they’re frustrated, right? So that, you know, and so I think it’s really important to speak about this early to understand what it looks like. Yeah, absolutely.
[00:27:40] Rory Henry: Yeah, I love it. Now, I mean, well being is one of the fifth pillar there, obviously, you know, encapsulates the others, you know, having your health, your wealth, you being wise is all part of of having a well being here. Can you talk about, you know, maybe the well being aspect of why that’s the foundational piece that makes all the other pillars here flourish?
[00:28:08] Dan Haylett: Yeah, I mean, again, if you can have a wonderful, you know, I’m, I’m not necessarily a massive car fan, or I like but I like cars, I mean, you can have a wonderful body, I an outward looking thing. But if the engine isn’t carrying you forward, right, I mean, that’s, you know, and I think about this is, you know, you people have, a lot of people have, have definitely had a had a goal in mind, you know, they’ve saved an amount of money, not necessarily to retire, but I think to give them a point in time, more freedom, more choice, more independence. And whether that’s retiring, or whatever, they want a point in time that that that happens. And if the engine is not going to allow you to carry out that, both mentally and physically, I think it’s going to be a real challenge, particularly, as we know that health, your health does decline as you get older, people are living longer, but they’re not healthy longer. And I wrote about this the other day, our health span has not kept up with our lifespan, in fact, it’s gone a bit backwards. So, you know, so we are, you know, we’re kept alive longer, but we’re not, you know, the gap between health span and lifespan has gone up by about two and a half, three years over the last 20 years. So, so, so, to me, this is kind of saying, look, when you don’t need to be a fitness guru, you don’t need to go and have like, kale blended stuff in the morning.
[00:29:44] Rory Henry: Doing crazy crafts, but yeah.
[00:29:46] Dan Haylett: Exactly. Yeah, right. If you want to, perfect. But this is about making sure you’re taking care of the engine because you have a window and that window probably starts to close in your early to mid 70s. And in your early to mid 80s, the window might even be shut. It doesn’t mean that you can’t peek outside, but you’re definitely not going to have the opportunity to take advantage of that open window that you had maybe 10, 15 years ago. And so I think it’s vitally important to make sure you take care of your body. But actually, Rory, I think one of the most important things is your mind, because we’ve talked about this psychological transition and there’s some really horrific stats coming out, I think now around, you know, how much more likely people in retirement are to be clinically diagnosed with depression than if they were working. How loneliness is, you know, there’s a loneliness pandemic epidemic, right? And I think, you know, what they’re saying, actually, loneliness has the same reaction in our body and our mind. Smoking is it like 15, 20 cigarettes a day, right? I mean, it’s, you know, so that’s why I think mentally it’s so important to make sure that you surround yourself with good people. That’s the relationship. Yeah. Keep yourself mentally sharp, you know, and all of that stuff, because if you haven’t done that, then you are simply not going to enjoy those, you know, those go go exploring years that allow you to kind of go and do everything you want to do with the money and time that you’ve now got available.
[00:31:24] Rory Henry: Yeah. Speaking of time, I know you say that time is more important than money, but you said in the book, something like, you know, having time and knowing how to use it are two totally different things. And we’re just not good at really understanding time and how to use it. Can you expand on that for me, Dan?
[00:31:42] Dan Haylett: Yeah, I mean, just I suppose my own views here, I think human beings in general are really rubbish at using time wisely. I think we don’t I think we undervalue it. I don’t think we appreciate it as much as what we should. I I definitely don’t. And I try and work on it every day. But I slip back into into old habits. And I think when it comes to these retirement years and the second half of life, time is now ours. Right. That that’s kind of ours and more so than ever. And so, you know, having time and using time are two very different things. And in fact, you know, time on a watch and time as in a kind of a period of where you were, where you are two very different things. Yeah. So this is about understanding time in a way that is actually baked in reality, because as we get older, time becomes more important. Time is asymmetric from that point of view. Right. It’s kind of a year in our 30s is very, very different to a year in our 50s and a year in our 60s is very, very different to a year in our 50s.
[00:32:54] Rory Henry: And Dan Gilbert talked about this. And yeah, the end of history illusion.
[00:32:58] Dan Haylett: Yeah, absolutely. And so, you know, I mean, I talk about that one a lot. End of history illusion is brilliant. But and the research suggests that every year past 60, the compounding effect of time gets even more worse. Right. If that makes sense. So it’s really important.
[00:33:17] Rory Henry: Real quickly, dive on that for our audience.
[00:33:19] Dan Haylett: Yeah. So this is kind of saying, you know, that if you, you know, 61, 62, the decline of your ability to use your time wisely compounds quicker than it’s ever done post 60. Because if you think about, you know, I think about when I was 20, if I think about when I was 30, right. And then I think about when I was 20, there isn’t that much difference between Dan, the 30 year old and Dan, the 20 year old. Right. But for people listening, if you think about if you think about you as a 50 year old and you as a 60 year old, there’s there’s much bigger difference if you think you as a 70 year old and you as a 60 year old and even wider difference. So health and and and not even just like your desires and your aspirations and things like they just decline a bit quicker as we get older. And so that’s why that that first piece of retirement, those go go exploring years are so important because that is where we need to have the reality that time now is much more finite and we need to use it wisely. Yeah.
[00:34:36] Rory Henry: Speaking of wisely, I know you talk about spending money is a skill. And, you know, for people in retirement, it’s difficult to truly spend what they can want and need in retirement. Can you dive in here and talk about this is a skill that no one really teaches, but it’s something we can learn.
[00:34:56] Dan Haylett: Yeah, I mean, like if I think about how people that, you know, people in retirement have got to where they’ve got to, they’ve got to where they’ve got to because they’ve had skill and discipline in saving. Right. So, you know, investing and they’ve had education around, you know, compounding interest and tax breaks and why you should save in pensions and and all of that stuff. So, you know, they’ve been nudged both through kind of governments and society, as well as family and friends and HR departments and all this stuff. Right. We’ve been kind of shown the discipline and the rewards of saving. What we haven’t actually ever been taught properly is the skill and courage and the rewards of spending. And it’s, again, thinking about this China spotlight in retirement, the spotlight is shining even more because, I mean, I’ve worked with people that would say that they are good spenders. They love spending their money and they know what they like spending their money on. But they’re very happy spending it, knowing that next month there’s a paycheck going to come back in to replace the money that they’ve spent. So the sense of fear and trepidation and, you know, to spend is gone because the spending just gets, you know, the money gets replaced. When you enter into this phase of life, when you are now being told to intentionally deplete the money that you have worked so hard for, that’s given you status.
[00:36:29] Rory Henry: You’ve been told for 50 years that you cannot deplete this money.
[00:36:33] Dan Haylett: You need this money. Exactly, right? So everyone goes, this is for a rainy day. But for some reason, people don’t think the rainy day is the day when they should start spending it, right? And you think about all the psychological hurdles that that gives you. I mean, I call spending money and spending time the psychological battleground in retirement. And it’s the psychological battleground because, again, if you think about the good old Venn diagram of those two things, in the middle, you’ve got doubt and fear and courage and permission and, you know, and all of these psychological challenges that you’ll go through about how you spend your money and your time. And so, you know, trying to learn how to spend it in a way that gives us happiness and joy without fear of it being, you know, going down every month and without the fear of it running out completely before we pass away is a massive skill that needs to be taught. We need to educate people around this stuff. And I think one of the most foundational jobs of a financial planner is to give those skills and education to our clients to allow them to spend their money in line with their values, allow them to create those memories and experiences that they want without that fear of running out of money, because it’s entirely possible for everybody to be able to do that. Yeah, I agree.
[00:38:03] Rory Henry: All right. Well, let’s end it there, Dan. If anybody wants to get in touch with you or buy the book, what’s the best way to do so?
[00:38:10] Dan Haylett: Yeah, so LinkedIn is the best place to see me. I’m on there a lot. The book is on Amazon, although because I self-published it, it’s a little bit sketchy certain areas. So I’ll send you the link. It’s on my website and on an online store called The Great British Bookshop. And that’s where you can go and buy the book.
[00:38:29] Rory Henry: Awesome. I’ll put all that information in the show notes. Thank you so much for coming on, Dan. I really appreciate it. Look forward to having you on again.