Going Beyond the Portfolio: Transitioning Into Retirement with Confidence with Kyle Britton – Ep 090

For most of your life, retirement planning has likely centered around saving and building wealth. But what happens when the paychecks stop and it’s time to start replacing your income withdrawing from your retirement savings and investments?

In this episode, SHP Financial Co-Founder Derek Gregoire is joined by Kyle Britton, Lead Advisor at SHP Financial. Together, they explore what it truly means to go beyond the Xs and Os of investing and step into retirement with purpose, clarity, and confidence.

You’ll hear Derek and Kyle talk about how the biggest retirement challenges are often psychological, not financial. They discuss why so many retirees struggle to give themselves permission to spend what they’ve earned, and how purpose and identity—two things often tied to careers—must be redefined as we enter this next phase of life.

Drawing from real client stories and recent research, Kyle highlights what truly drives happiness in retirement and how to create a plan that supports both your finances and your fulfillment.

In this podcast interview, you’ll learn:

• Why retirement planning goes far beyond investments and tax strategies.
• The biggest psychological hurdle retirees face: giving themselves permission to spend.
• How to shift your mindset from “Do I have enough?” to “What’s possible?” in retirement.
• The four key ingredients of a fulfilling retirement, according to a recent MassMutual study.
• How to redefine your purpose and legacy in the next chapter of your life.

Inspiring Quotes

• “Real retirement planning goes far beyond managing investments and taxes, which is important by the way. It’s not only building the life that you love but having a life with purpose.” – Derek Gregoire

• “Take it a step further and make sure you don’t have just an investment plan, but an income plan, a tax plan, a healthcare plan, and a legacy plan.” – Derek Gregoire

• “One of the hardest transitions we see is not about inflation. It’s not about market volatility. It’s really about giving yourself permission to spend the money you’ve worked really your entire life to build.” – Kyle Britton

• “If they’re not happy in living a life of purpose, that’s so disappointing to us.” – Kyle Britton

Interview Resources

• 2024 MassMutual Retirement Happiness Study

[INTERVIEW]

Derek Gregoire: Welcome, everyone, to another edition of the SHP Retirement Roadmap Podcast. I’m your host for today, Derek Gregoire, one of the partners here at SHP Financial, and today we’re looking beyond the portfolio. Everyone always thinks retirement planning, financial planning is all about portfolios, but we’re going to help clients and everyone listening shift from working to actually living in retirement, and we’re calling it Going Beyond the Xs and Os of Retirement Planning. So, today we’re going to dive into a topic that every current and future retiree needs to hear: how to go beyond the portfolio and step confidently into the next phase of life, retirement, with purpose, clarity, and confidence.

For decades, your identity has been tied to your career, right? You go to work every day. Come home. You always have that work to look forward to. You’ve been in the accumulation mode, saving, building, protecting, but now it’s time to shift gears. And that shift, it’s not just financial, it’s emotional, psychological, and extremely personal. So, today we’re going to explore how we help clients make that transition from paycheck to purpose, from working to living. Because real retirement planning goes far beyond managing investments and taxes, which is important by the way. It’s not only building the life that you love but having a life with purpose. So, today, we’re joined by Kyle Britton, one of the lead advisors here at SHP Financial. How you doing, Kyle?

Kyle Britton: Excellent. How you doing today?

Derek Gregoire: I’m good. And I think as we get into this, Kyle, I think the main thing people always say, “Why do you work with SHP?” or, “What’s different about SHP?” And we say, “Well, we do so much more besides just a portfolio.” We have a full team with CFAs and CFPs and every acronym you can imagine, but the portfolio is one piece of it. We always say, “Take it a step further and make sure you have not just an investment plan, but an income plan, a tax plan, a healthcare plan, and a legacy plan.” But even then, that’s still not the end of it, right? Because then it’s like, “What’s your purpose? What’s your identity in retirement?” Like, some people have their identity and work, and then when they lose that, it’s like, where do we go from here?

Kyle Britton: Yeah, that’s huge. I loved what you said about going beyond the Xs and Os of the portfolio, and two words that just jumped off the page to me is purpose and identity. That really is what roots you and grounds you in life, right? It’s like you get up every day, you go to work for 30, 40 years, and now you’re making this transition to retirement. It’s like, how do you continue to live a life that has purpose and gives you that identity too? It’s such a different transition, and a lot of people just think, “Okay. Am I going to have enough money? Am I going to be able to retire and do the things that I want to do?” Yeah, that’s great. It’s like we can put the Xs and Os together to make that happen, but how do we really walk alongside you to give you purpose in retirement?

Derek Gregoire: Yeah. And also, I love the question. Some clients, when they first come on board, they’re like, “Oh, I’m so happy we can cover our grocery bills and taxes, and car payments, and we can have enough.” And it’s like, “Well, do you want to know what’s possible? Is getting by and just barely having enough and watching Jerry Springer, and just going through your day, is that going to be satisfactory?” Or what are things that you want to do? We’re going to share some stories later in the show about some cool stories with clients that we’ve seen living with purpose, living with clarity in retirement, going beyond the Xs and Os. But the Xs and Os obviously is a huge part of it.

One of the things we always hear in the financial planning world is when you’re working, and I talked about it in the opening, going from accumulation, everyone’s growing money, growing money, growing money. You don’t even think about what it means. And then transitioning from the accumulation stage, which is your working years to the distribution stage, which is very scary, but the distribution stage is now taking the investment, taking the money out of what you’ve saved to cover your expenses in retirement.

Kyle Britton: Yeah, that’s a great question. One of the hardest transitions we see is not about inflation. It’s not about market volatility. It’s really about giving yourself permission to spend the money you’ve worked really your entire life to build, and it’s such a huge psychological shift for most workers that have been in the work mode, even in the save mode. So many families that we work with, they come in and they’ve really done a great job saving their entire life, right? They’ve built this great nest egg. They’ve worked hard, they’ve saved in their 401(k) plans, IRAs. But now, how do you make that psychological shift to not go to work every day to get up and actually live a life of purpose?

How do you give yourself permission to spend, right? It’s one of those things. Do you want to leave behind millions of dollars when you’re no longer here? Is it one of those things that you actually want to like enjoy the money that you’ve worked so hard to save for? In our job as planners, it’s a lot more about than just designing withdrawal strategies. It’s about giving you the confidence to really enjoy your money and enjoy your retirement.

Derek Gregoire: But also, you still need to have a plan for that because once you have that money and you’ve saved that money, you still just can’t be like, “Okay,” because the biggest fear for retirees is still running out of money. So, you want to make sure once you get that covered then we get to the next part. Even when it comes to running out of money being a big concern, I always think like any money’s a lot of money. 10,000 is a lot of money, 20,000. But to retire, you used to be like, “Oh, I need a couple of hundred thousand.” And then now some people think, “I need a million.” Some people think you need 5 million or 10. The number moves for everyone, really, based on how much you’re spending.

But I will say you can’t go beyond the Xs and Os until the Xs and Os are covered for, right? Like, you need to make sure you have that plan where, hey, you stop working, your income’s coming in. And the last thing you want to do, like you said, you want to make sure there’s purpose and there’s confidence in retirement because you don’t want that money to wake up one day and be like, “Oh, that money’s not there anymore, because we didn’t plan properly.” So, when clients approach retirement, obviously, the spreadsheets, performance reports, all these things, but there’s a lot of questions that we ask that really don’t show up in traditional planning conversations.

So, like you mentioned, for many clients, right, what’s your structure in retirement and identity and connection? What fills that gap now that work’s gone? Is it travel? Is it volunteering? Consulting? Time with grandkids? So, there are so many things that go on. So, yes, give us an example of some stories or folks that you’ve worked with over the past that really have built some clarity in their retirement plan.

Kyle Britton: Yeah, absolutely. One of the things that I found really interesting when we were talking about this earlier is MassMutual, massive insurance company. They did a study last year. They studied 2,000 people in retirement, and the findings was the amount of people that were actually happy in retirement. Were they more happy in retirement or not? 67% of people said that they’re more happy being retired than they were when they were working. I mean, 67%, that’s a great number. But what that tells us as retirement planners, that there’s a third, one out of every three retirees is not happy in retirement.

And that really presents a problem for us. And that’s kind of the one thing that we see as retirement planners. It’s just going beyond the Xs and Os. It’s like, great, we can build a plan to show you how you can accomplish X, Y, and Z, but how do you actually create that step to give yourself purpose, to make yourself happy in retirement? One story that I love, it’s probably one of my favorite stories out of any that I’ve heard within the last year, a family that we work with, they retired this past year. One of their goal was to go on a big trip. They basically have like a bucket list trip each and every year that they want to take. We built the plan. We allocated X amount of dollars towards this.

And they’re coming in for a meeting, and we’re going to review their retirement plan and see if they’re on track and everything. And before the meeting even starts, the wife looks at me, she goes, “Kyle, I just want to let you know, like we ended up doing what you told us to do.” And I’m thinking in my mind, I’m like, “Shoot, hopefully, I told them something good because I don’t know what she’s talking about here.” And. I’m like, “Hey, jog my memory. Like, what are we talking about?” And she goes, “We ended up booking that trip, and we booked it first class.” And I thought that was so cool because some people think traveling first class, right? And for some people, it’s a lot. They’ll just never do that. They just don’t have the mindset to do that.

And I think they were that same way. Either they never thought that they wanted to do it, or really never thought it was possible financially. We built it in their plan to show them, but what that gave them the ability to do, because this was a big trip, like they were going on a safari trip to Africa, right? I mean, we’re talking 25 hours in a plane. So, to be able to sit on a plane, be able to lie down and rest like you’re getting off that plane, you’re fully rested, ready to go for that trip. That’s such a shift in retirement, being able to do that and kind of live that lifestyle. And you could just see the smile on their face light up. I mean, that’s one of the more favorite stories that I’ve heard recently.

Derek Gregoire: The other thing, too, they had confidence that they could do that. Obviously, you and, obviously, the team at SHP built a plan for them where not only did they book their dream trip, but they, obviously, were confident that they could book first class as well. And think about it, like if you look at the way people think, it’s like, alright, remember you talked about just getting by and covering your base bills. That’s obviously good. You don’t want to retire until you know you can do that. That’s the first start. That’s just the beginning point. That’s the foundation of any retirement plan is making sure you have enough, right? But then beyond that, it’s like, “Well, what if we could show you what’s possible?” Because we have someone coming in, in a couple of weeks, that Natalia and I met with, and they were like, “Yeah, I want to retire so bad, but I think I have to go like 5, 10 more years.”

And they started sending us financials and their information. I’m like, “They can retire right now.” You know what I mean? So, it’s like now it’s like, “All right, I can retire now, but can I retire and am I just getting by?” And some people, that’s worth it because they don’t want to work, but a lot of times they want a lot more than that. And so, the next phase we look at is what’s possible. And that’s the conversations we have with them. What are your dreams, aspirations? What would be an awesome retirement? And there might be a point where we said, “All right. You can’t have the safari trip, first class, new Porsche.” Eventually, there’s going to be an end line, but a lot of times we can show them what’s possible. And for example, I have a client, they always wanted a house in Florida, and we ended up building a plan. They bought it.

Now, they have a place up here and a place in Florida. Now, we said we’re going to keep tracking that for the next several years. They’re in their late sixties, and I said the plan shows it should be fine the rest of their life. But I said, “In the worst-case scenario, you might have to sell at 82. Let’s just say things don’t go well. Inflation kicks in. You have to sell at 82. As soon as you sell, you get the asset of whatever money that’s worth in Florida for the house, and all the expenses drop significantly because you’re not traveling, you’re not paying for cleanup, and pools and taxes down there, right? So, at that point, you’re back to square one, you’re in a great position, and you get to enjoy it for 15, 20 years.”

So, there are all different ways to plan, and sometimes it can’t be done, but a lot of times, if I’m in the shoes of a retiree or someone thinking about retirement, I don’t want to know, “Am I going to be okay?” That’s the first thing I want to know, but then I want to know what’s possible. And that’s kind of the second step.

Kyle Britton: Yeah. And I love that piece really, thinking outside of the box is what is possible, and that really, I think that’s where our jobs come in, so importantly, where it comes alongside our clients to really push them, right? Because what I hate seeing more than anything is if we sit down with a family that we work with, and their portfolio’s in great shape, that’s awesome because the plan’s been built out correctly. But if they’re not happy in living a life of purpose, that’s so disappointing on us. And it’s really like that psychological shift where it’s like, “All right, what are we doing?”

And to go back to that MassMutual study, they actually looked at four specific areas of living in retirement that identified people’s happiness. The first one was spending time with loved ones, which we can all relate to. The second one was exercising regularly. The third was pursuing hobbies. I think a lot of that comes down to purpose. And then the fourth was traveling and traveling often. And it’s funny, I think for some people, taking a trip to Africa to go on a safari might actually seem like a nightmare. So, maybe that’s not for everybody.

Derek Gregoire: I’m looking at these, and I’m like, all right, spend time with family, awesome. Exercise, I think I do that kind of regularly.

Kyle Britton: Try to at least.

Derek Gregoire: Oh yeah, I try. Hobbies, I like to golf, so I got that. Travel, I like travel. I would do it. I just wouldn’t be doing it all the time.

Kyle Britton: Oh yeah. I mean, it’s so funny because…

Derek Gregoire: When you think of these questions, I’m 45, and hopefully, but you just think down the road, what does that look like?

Kyle Britton: Yeah. Well, we sit down with people all the time and we ask them, “Hey, what are your goals? Like, do you want to retire? What does retirement look like?” And they say, “Oh, I want to travel. I want to golf.” And I ask them, “Okay. You want to travel? When’s the last time you did a long weekend with your significant other?” Right? And they look at each other, and they can’t figure out when. It’s like you want to golf, but the problem is you had a hip replacement last year. You haven’t been to the gym in 15 years. It’s like, what does that realistically look like, getting out on the golf course without ending up at your local physical therapist, right?

Derek Gregoire: Yeah. So, when we think about all the questions and Xs and Os beyond retirement, question number one was, what will give your retirement and what will give your life in retirement purpose? What would that look like? What will give you purpose throughout your retirement years? It could be 60 to 100. It could be a long time. Second question is, what does your ideal day look like in retirement? Like, what’s your day look like? And the funny thing is I’m asking you that question, but before you answer, I mean, everyone, my parents, everyone I talk to, say, “I don’t know how I had time to work because I’m so busy in retirement with this, that, and the other. It’s like, I don’t know how I had time to work.”

Kyle Britton: That’s what we want to hear.

Derek Gregoire: Yeah. Was that a question you’ve asked clients in the past?

Kyle Britton: Yeah, absolutely, because I mean, you think about it. You’ve been working for 40 years, and what do you do? The alarm goes off 6:00, 6:30, 7:00 AM every day. You get out of bed. You have purpose. You’re going into the office. You’re sitting down with your colleagues, your coworkers. You’re in your routine. You’re kind of doing your thing at that point. But when you go for that shift of working to retirement, what does a Tuesday in March look like? What is that going to look like?

Derek Gregoire: Depends on the weather, I guess.

Kyle Britton: Yeah. Well, what’s a Tuesday in June look like? I think that’s when it really starts to make it real for people. And you’d be surprised, again, like how many people just give us that generic answer of, “Oh, I want to golf. I want to travel more,” but let’s actually map this out. How are you going to have that purpose and really that motivation to continue to get up each and every day and live your life?

Derek Gregoire: And if you want to do the things, if some of that involves physical activity, question number three is what’s the plan for your health? We have plans for health insurance and long-term care insurance, but you know, in terms of like wellbeing, exercise, what’s your plan for that? Obviously, that’s a big part of retirement. You want to be as healthy as possible, and we know there are ailments. Everyone is dealing with something for the most part, but what does that look like? What does that routine look like? I think in retirement, if you have more time than when you’re working, a lot of our clients will take, “Hey, every day I start my first hour with a walk or yoga,” or whatever they do. I think there’s more time, so they can actually fit it in a little bit easier into their schedule.

Kyle Britton: Yeah, exactly. And I mean, this isn’t a health and fitness podcast by any means at all, but you can go into the research in the numbers on people that stay active and exercise. Do strength training and eat properly. I mean, it has such a profound impact on all areas of life. And a lot of times, it’s like you mentioned, it’s like a health problem comes up or a concern. How does that longevity in retirement actually impact you? It’s like if you’re not taking care of your health, as soon as you have a health concern pop up, like I hate to say it. It doesn’t matter how many millions do you have in the bank or in your portfolio. It’s like that becomes kind of the main thing in life that you’re going to focus on at that point.

And it’s like you want to be a grandparent, right? You want to be able to toss your grandkids up in the air and go on vacation with your family, right? And really, without that health foundation, what is that going to look like?

Derek Gregoire: Yeah. And there are people out there too, they can do everything in their power to take care of it, and they still have unlucky health things that come up no matter how healthy they are. So, it’s about like exactly doing what you can to control what you can control. But maybe I would say having that part of your routine in retirement would be a good strategy with more time that you’d have to dedicate to it. Question number four is what legacy do you want to leave? Not just financially, but what’s your life legacy? That’s a big one.

Kyle Britton: Yeah. And a great line that we often use, or we will ask families this is, would you rather give with a warm hand or a cold one? You probably use that from time to time.

Derek Gregoire: Well, I know I’ve heard it, but, yeah. It’s more of like, also too, it’s like so many things about when you’re dealing with a client, the other question too is like because sometimes our clients are lucky enough to be in a position with they’re not going to spend all their money. And they’re going to have plenty of money left over. So, it’s like, one question is, do you want to just leave it behind, or do you want to help them when they can use it? If you are 70 and your kids are 40 or 50, they can probably use it more than when you’re 90 and they’re 70. You know what I mean?

Kyle Britton: Yeah.

Derek Gregoire: So, a lot of our clients, if they can, again, once a plan’s built out, once everything’s covered on their side, a lot of times we use gifting strategies to lower estate taxes. But also, it’s a great way they can see their kids and grandkids, whether it’s through 529 plans or whether it’s through just helping the family through whatever it is. It’s a great way to kind of help leave a legacy while you’re alive and watch that legacy in real time.

Kyle Britton: Yeah. And that might seem harsh to some people talking about ultimately death. It’s like warm hand or cold hand, but oftentimes like that unlocks something in people’s minds. Many people would rather see their family or community benefit from their generosity while they’re alive, right? Whether it’s helping a grandkid with college, supporting a charity, gifting to your kids at Christmas, legacy is a big part of that life plan. And one thing just that I’d want to add to that, because not everybody has kids or grandkids, like we work with a lot of families that don’t have kids, they don’t have grandkids, right? And I think a lot of times that can be a challenge and a struggle for people to realize, “I’ve done this great job. I’ve saved so much. I’ve worked so hard. And now there’s the unknown of when I’m going to pass. Like, what’s going to happen to all my money left behind?”

I think it’s really important to come up with a plan and start to give those people, those families purpose. It’s like, what are you going to now do? How are you going to leave your legacy behind knowing that you maybe don’t have kids or grandkids? I think that’s something important to note, too, because we just assume like, hey, everybody has kids and grandkids, but it’s not always the case with all the families we work with.

Derek Gregoire: So, now that we’ve had like we’ve talked about the goals and purpose and building clarity in retirement, we do have to kind of go back to the Xs and Os, right? Because I always say, how do you support a good retirement? One of the first things, to be able to do the things you want to do, is a strong income plan, making sure you have plenty of income with inflation ongoing. Part two, though, is once you have that income in place, what are things that could affect that income? What are things that could affect your assets? Well, taxes is one. So, now we go, actually, back to the Xs and Os. Tax is a huge part of retirement planning that if we can do some planning for maybe a legacy and leaving tax-free money behind is a big goal. Well, that’s something that we can work into a plan. So, we still have to get to the Xs and Os to design that plan, but we kind of go back and forth between vision and planning, vision planning.

Kyle Britton: Yeah. And I love that. And it’s really all about building the vision. When we sit down with families for the first time, or if we’re working on a plan that we’ve been working with this family for 10 years, right? Like, we always want to come back to the vision. It’s like, “Hey, how’s your life going? Income, taxes, investments, healthcare, legacy.” We go through the five areas of planning. We go, “Well, what’s the vision?” It’s like, “What do you want to do? Like, do you still feel like you have that purpose and that happiness?” And once they have that vision and they’ve really kind of helped create that picture for us, that’s when we’ll fine-tune it through the Xs and the Os. And it’s so important because that’s when it really starts to bring the plan to life.

A Roth conversion isn’t just about reducing taxes. It’s about creating future flexibility so you can check things off your bucket list or leave assets tax-free behind to your family or to charities. An income plan becomes your go-live-your-best-life paycheck, not just income, but actual freedom in retirement. And then that travel fund in your retirement plan becomes lifelong memories with your spouse, your kids, or even your grandkids. Depending on your grandkids, that might be stressful. It might not be stressful if you want to bring them on vacation or not. That’s a conversation for another day.

Derek Gregoire: Well, I think if you look at retirement, some people have this like morbid thought, like, “Oh, that’s the golden years. I’m just going to sail off into the sunset.” But we think of that as like a starting line, not a finish line, right? That’s where, in our opinion, like if you think about what we do, that’s for how the magic happens. That’s like the start of our journey. So, I shouldn’t say the start because a lot of our clients are with 10, 15 years before they retire, but every single week, year, month, I probably should have said that in a different order, week, month, year, we have tons of clients retiring. And that’s the coolest thing. We make a big deal of it. They get little champagne and like send them off.

I love that part because so many clients have been working with us for years, and I remember when they first came in, we had a conversation a couple of weeks ago, like, “It seemed like such a pipe dream. It seemed like so far away, and now we’re here, and now we’re retiring.” And I was just golfing with one of my clients last week. I’m like, “Hey, do you guys miss working?” He goes, “Heck no.” He’s like, “This is the best of all, like we’re having a blast. My wife’s doing this. I’m doing this.” And they were just like happy as can be. So, it’s awesome. But when they first started, I remember they were like grinding at work and long nights, and just like, when is this going to end? But when it got there, that’s the start of a new journey.

And so, I think from our point of view, since we opened the doors in 2003 here at SHP is like and it evolves as we build our team, but like first, it’s like making sure you have a really strong plan beyond a portfolio around income, investment, taxes, healthcare, and estate planning, right? If we can build a plan around all those areas, that actually give you confidence that, hey, every I is being dotted, T’s being crossed, we’re looking at all areas of planning. But what the result of that should be is having the retirement that you’ve worked so hard that you’ve dreamed of. How do we support that? How do we make sure you transition to retirement without the fears of running out of money or whatever it is? How do you build confidence so you can take those trips once a year, depending on your financial situation?

It sounds almost like this is something I’ve gone back and forth on for years, because we try to help everyone, but we did raise our minimum to a million dollars recently. Because it’s almost like to do the type of planning, this level of planning, there are family offices that have like $50 million to $100 million minimums. Obviously, we’re nowhere near that, but we try to provide as close to that level of planning as we can for more than just a few families, for several families. So, for what we do, it just takes some money to be able to build these plans and to be able to do these things in retirement, but so many listening have that. They’ve worked hard. They got to that point. They might be nervous if they’re not a client. And this is the perfect opportunity to start thinking about what this is going to look like for you.

Maybe you’re not retired, maybe you’re thinking about retirement, but it’s a good time to start thinking like we love the weekends. What happens when the weekends just keep going? Are we going to miss the job? Are we going to have an identity? And so, I would urge you. If you’re a client, you already know this. If you’re not a client, there’s a ton of cool resources on our website. One is we have a new guide, I believe, around planning for high-net-worth investors. That’d be a good one to start, and there’s a lot of other cool guides and materials on there as well, as well as podcasts and just good educational material to get you ready for retirement.

So, Kyle, as always, great stuff. I love the content in terms of just getting beyond the Xs and Os and really providing a good vision for your retirement. Thanks always for joining us as always. And any other final words? Are you good?

Kyle Britton: Yeah. I mean, just to add kind of one thing to what you were saying is I really would just challenge people out there listening to this to kind of take a step back and really just figure out, use the great analogy. It’s like retirement is a starting line, right? Do you feel like you’re at that point where you’re really fulfilling your life? You have as much purpose and identity as possible, right? Because going beyond the Xs and Os of the portfolio, again, it’s hugely important, right? But how do you really give your life purpose in this final chapter, I think, is the biggest thing. If you’re looking for something else there, there are teams out there, and I believe our team does a really good job just at wrapping our arms around a lot of the families that we work with and really just challenging them to push them farther and harder in retirement and make sure that they’re living their life to the maximum that they can.

Derek Gregoire: Awesome. Well, it’s shpfinancial.com, SHP Financial, if you need more research, you need more information on this topic. And again, as always, thank you so much for joining us. And I’m sure you’ll be hearing from us soon on another topic on the Retirement Roadmap Podcast. Thank you.

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