The Tough Retirement Conversations You Need to Have Before You Retire with Aidan Arone, CFP®- Ep 112

When you think about preparing for retirement, it’s easy to focus on whether you’ve saved enough, when to claim Social Security, or how your investments will generate income. But some of the most important retirement decisions have very little to do with the numbers. What will you do with your time? How will your relationships change? And what happens if retirement arrives sooner than you expected?

In this episode, SHP Financial co-founder Derek Gregoire is joined by Aidan Arone, CFP®, to discuss the emotional and logistical side of retirement planning that families often overlook. They explore why it’s important to think about what you’re retiring to, not just what you’re retiring from, and why conversations about purpose, family, healthcare, spending, and your future lifestyle should happen well before your last day of work.

Ultimately, a successful retirement isn’t just about having enough money. Derek and Aidan share why couples and families should have the difficult conversations now, how planning for your life beyond work can make the transition easier, and why having a clear sense of purpose and community can be just as important as having a strong financial plan.

In this podcast interview, you’ll learn:

• Why retirement planning needs to go beyond the numbers.
• How losing your career can affect your identity and sense of purpose.
• Why maintaining social connections is so important after leaving work.
• Which retirement conversations couples should have before their last day of work.
• Why families should discuss healthcare, caregiving, and legacy plans in advance.
• How an unexpected event can force you into retirement before you’re ready.

Resources

• “Unretiring”: Why recent retirees want to go back to work – T. Rowe Price
• Claude
• ChatGPT
• Copilot
• Hingham Road Race

Inspiring Quotes

• “You’re retiring from a career, but what are the things that you’re retiring to?” – Aidan Arone

• “Really, from 60 to beyond is the first time in life that you’re free to create your schedule.” – Aidan Arone

• “If you retire and just step away from purpose and doing things that you like and building that community, that’s when you ‘rust.’” – Aidan Arone

[INTERVIEW]

Derek Gregoire: Welcome, everyone, to another edition of the Retirement Roadmap podcast. I’m Derek Gregoire, joined by Aidan Arone. Did I get it right?

Aidan Arone: Yep. Spot on.

Derek Gregoire: We’re going to talk about the emotional side of retirement, conversations to prepare for. But, Aidan, I know you’ve been with us for a thousand years.

Aidan Arone: Feels like it.

Derek Gregoire: Although this is your first podcast.

Aidan Arone: Yeah. First time on the show.

Derek Gregoire: Which I must be getting old, because I feel like I’ve talked to you on the podcast before.

Aidan Arone: Never.

Derek Gregoire: Never happened?

Aidan Arone: First time.

Derek Gregoire: Really?

Aidan Arone: Yep, first time down here. It’s a nice studio.

Derek Gregoire: So, all those high-end philosophical conversations we have, I figured one of them was on the podcast.

Aidan Arone: All behind the scenes.

Derek Gregoire: All behind the scenes. Well, yeah, if you can maybe first just share a little bit about yourself and what you do at SHP, give everyone an idea, that’d be awesome.

Aidan Arone: Yeah, totally. So, I started at SHP about two years ago, July two years ago now. I work closely with Keith, Kyle, Mike, and the team. Started as basically an advisor before I came here to SHP, and my whole goal, really lifelong goal, was to become someone that knew answers to financial questions and was able to help and guide others through the process. Really inspired by my parents and their lack thereof of the financial education. So, that was really what drove me. I guess prior to being at SHP, I was at a firm that was less about planning and caring for those questions and finding the long-term solutions. It was more about the sales process.

And through that time, I’ve really started to lose the love of planning, and then I ultimately was introduced to Keith and you and the team at SHP, and that’s where I really realized that this is a team and an industry that cares about planning and cares about long-term planning, more about the financial and emotional side rather than sales. And that just really totally changed my love for planning, and it introduced me to open, holistic planning.

Derek Gregoire: Yeah, it’s kind of cool. Like, even looking back 2003 when we started the firm, it’s so much different now, but we really wanted to be specialized in so many different areas around, obviously, the portfolio was a huge starting point, but that’s just a starting point. So, how do we have a team that can look at all areas? I was just in a client meeting now, and we’re talking healthcare future and tax planning and income generation and what their estate plan looks like and different investment opportunities. So, it’s usually the whole picture where I think in our industry, and where you came from, and so many people that work at SHP of our 55, 60 employees, they all say the same thing. Where we came from, it’s a portfolio. You make money, you lose money, and that’s the beginning and the end of the conversation.

And even the client, or it’s a new client I just met with, they said the same thing. “Our current advisor just goes over our investments, and that’s it. We don’t ever talk about taxes or anything.” And then so planning is huge, but then even beyond the planning, it’s kind of like a lot of different, if you look at the numbers, which is around income, taxes, investments, so forth, right? But then retirement should be… There’s so much more to it than even just that. And I think today we want to get into some of those details of maybe questions people should be considering before they retire, things they should be thinking about. Everyone thinks, “I’m going to retire, I’m going to pull off my portfolio,” but what does it even look like?

Like, have you had those conversations with your spouse, with your family, or are you just kind of going to wing it?

Aidan Arone: Yeah. I think, as you said, the income taxes and investments is really just like one layer of retirement. There’s really that other layer, which is the emotional and logistical conversations that a lot of families don’t really ever have. And this conversation, Derek, as I said to you on the way down, was kind of sparked on really like a personal situation that happened. My father earlier this year was forced into retirement, and him and my mom weren’t able to have these conversations, and now they’re scrambling, trying to put everything together. So, we can touch base on that a little bit later. But that’s really what sparked this conversation, is really planning for those next 20, 30 years of life.

Derek Gregoire: So, let’s kind of dive in. Like, if you look at conversations like, so if I’m listening to this, and let’s say I’m retiring in the next few years, maybe I’m retired, right, what are some things people should be having conversations about, thinking about well ahead of time?

Aidan Arone: Yeah. I think the biggest thing that jumps off the page for me that we see a lot is families are often, they come in. They say, “Derek, hey, I’m here, I’m retiring from my career as a plumber, from my career as a doctor,” right? This is what they’re retiring from, but they never think about what they’re retiring to. And I think that’s the most important thing that families need to look at, because it’s less about, yeah, like my career’s gone, but what are you going to be, or what are you going to do for the next 20, 30 years? How are you going to find purpose in that? You’re retiring from a career, but what are the things that you’re retiring to?

Derek Gregoire: Well, I think a lot of people out there can identify with this. It’s like their identity is almost in their job, right? Because that’s what you’ve done for 30, 40, 50 years, and I think you almost have to figure out what’s your identity going to be when the paycheck stops, when you’re not going to work, when the emails aren’t coming in, when someone doesn’t need you for whatever you’re doing right now at work. You know what I mean? And a lot of people do think that through, but I noticed a lot of people don’t. And they get there, and it’s like, “Oh, shoot, everything just halted. My whole schedule’s changed. My whole day-to-day, just what I do, has changed.” And their new norm is completely different, and it’s tough to adjust to.

Aidan Arone: Yeah. I would say, right, if you think about life and how we start on this earth, from really day one to age 18, the plan is school, right? Education. From 18 to 22, some people go to college, right? Some people start out in the workforce, and then from after college to 60, 65, it’s, hey, you work, right? You wake up, you work, you do 40 hours, you have the weekends off. Really, from 60 to beyond is the first time in life that you’re free to create your schedule. And that, I guess, it hits some people harder emotionally because they don’t ever plan for that. So, what does your life look like when you have that freedom, and you have that flexibility?

Derek Gregoire: Think about if you’re on the golf course or you’re at a wedding and you’re meeting someone, what’s the first question you usually ask them?

Aidan Arone: What do you do for work?

Derek Gregoire: What do you do for work, right? And so, that’s such an identity. That’s what everyone thinks about, and that’s kind of your identity. It was funny because even when we started SHP years ago, I’ve always said, like, “I don’t want my identity to just be a guy that owns SHP. There’s more to it than that: my faith, my family, things that are so much more important.” Obviously, this is a huge part of my life, but I didn’t want it to be the only thing. And I think people that are working, it’s easy to get tied up in that, and especially if you’re working at some firm where you come home and you’re doing emails until 11:00 at night, you wake up at 6:00, 5:00 AM, go right to the office. You know, that is your life, right?

Aidan Arone: Right. Yeah. It becomes your whole life, and I think that’s probably, as we said, is the most important topic of conversation to have with your significant other, with your children, right? “Hey, Mom, Dad, I’m thinking of retiring,” or, “Don, Saughter – Son, daughter, I’m thinking of retiring.”

Derek Gregoire: Yeah. Don, Saughter, I like that one.

Aidan Arone: “Son, daughter, I’m thinking of retiring. Like, this is how I want to live my next 20 to 30 years.” Because a lot of times, how do we start our first meetings? It’s, “Hey, nice to meet you. Thanks for coming in. Like, what brought you here?” And a lot of times it’s, “Oh, we’re retiring. We’re in that stage.” “What does that look like to you?” A lot of people say travel, right? Or spend time with the grandkids. But outside of travel and spending time with the grandkids, what is it that you’re going to do? Because that’s not going to fill 40, 50-hour weeks.

Derek Gregoire: Exactly. And so, one of the things I’ll read here, there’s a pretty cool stat that you sent over on, “A T. Rowe Price study showed that 20% of retirees return to work. And nearly 45% of those who return do it for social or emotional reasons.” They tracked participants for over 80 years and found that top challenge in retirement was not financial stress or health issues. Instead, it was loss of social connection that had been integrated into their work lives. So, this creates a need for a community outside of your spouse, right? Like volunteering, the gym, golf, book club, church so many different things you can do. But that’s actually a huge point in figuring that out

Aidan Arone: Yeah. I mean, to track that over 80 years and really find that it’s not the financial stress or burden that’s forcing people back into work, it’s the fact that they’re lacking connection is concerning, right? But it’s something that can obviously be planned around, and I think now more than ever is prominent, right? Look at the use of AI, Claude, ChatGPT, Copilot, all of these things are furtherning away our social connection. We sat down with a gentleman a few weeks ago who’s retired. He’s retired young. He’s about 60 years old, and he’s like, “I need to find something to do,” right? Because his connection was all at work. His friendships were at work, which is great. That’s an awesome thing to do, but when you step away from work, and you’re no longer there for 40, 50 hours a week, where is your connection? And how are you finding that?

Derek Gregoire: So, basically, what’s another thing folks should be thinking about or conversations they should be having with their spouse? Because again, it’s amazing how I’ve seen in our industry just spouses don’t communicate regularly on important issues. And sometimes they’re deciding and arguing or figuring it out right in front of us in a meeting. You’ve seen that.

Aidan Arone: Yeah. I could think of as soon as last week I sat down with a family who, great family, right? They’re ready to retire, but they’re now trying to decide on where they want to live. One spouse loves Maine. He wants to stay up in Maine. The other spouse is like, “Hey, it’s a little cold for me,” right? So, now they’re trying to figure out if one of us wants to do Maine in the winters and the other wants to do the South Coast like, “How are we going to make that work?” Because the goal ultimately is to spend time with the family and the grandkids, but if you’re going to be on different sides of the country, how’s that going to work?

Derek Gregoire: Yeah, that’s tough. How about looping the kids in? Because that’s a touchy subject. Some people want to loop the kids in, some people want to share details, and some people, that’s like the third rail like, “No way would I tell them anything and…”

Aidan Arone: Yeah, that’s a great question, and I think that’s something that we see a lot is a lot of the families we’re working with are currently planning for their kids or their grandkids, but their kids and grandkids don’t actually know that this is coming down the pike someday. So, I think looping in the kids, whether it’s bringing them to a meeting or giving them access to the SHP portal, so they know and understand really what this is. I mean, I would say, how often do you sit down with families that say, “Hey, I want to leave behind X dollars to son and daughter,” right? But they don’t know how they’re going to handle that money. Or they don’t know what the goal is behind that money. Like, you probably see that pretty frequently.

Derek Gregoire: Oh, yeah. We have clients all the time. We just had an interesting conversation with a client before this podcast, just talking about, like, their projections looking many years down the road, was they’re going to leave $10 million behind, whatever. It was a high number. And it’s like, do you want to leave that behind? Because when you’re 90, they’re probably 65, 70. Maybe they’ve probably already saved up and done all the hard stuff at that point. Do you want to leave it to them then? Or do you want to do some gifting to reduce your estate and help them out now? And some people like to see their money being used when their children are helping their kids with college and growing up when they could use the money.

And then other families say, “Yeah, I’m not going to necessarily do that.” But every year we have some clients that take their whole family on a big vacation once a year. And so, it’s almost like you’re not necessarily helping the kids out in a way of like paying all their bills, but you’re making a memory with your family every year, but the parents are covering it. So, there are so many different ways to think about that. But those are conversations like, do you just want to live and accumulate this money and pass away, and whatever happens, happens? Or is it something you want to have more conversations about together while you’re alive, making these decisions ahead of time?

Because again, if you have a good company, like I always say with our clients, I know they’re in good hands with our planning team, our portfolio team, our advisors, our whole operational team. We’ve been doing it for so long. I feel really confident about that. But we always challenge our clients to look even beyond that. How can we push them even more to like decide, what does this mean? What does this money mean? What are the goals? What are the things you want to do? So, it’s important to have those conversations way beyond just the dollars and cents and numbers.

Aidan Arone: Yeah, that’s a good point. I was going to say, right, some of the value that we bring here at SHP, in a few of the meetings that I’ve had this year, that I would almost recommend like, “Hey, if families are comfortable doing this,” is we were in a few meetings this year where we actually brought the kids in, right? And we had the children come in and explain, “Hey, mom and dad worked so hard. They’ve saved here, here, and here, and this is the goal of that money.” And it just really creates a much stronger relationship, because now the kids know SHP, right? They know who mom and dad work with. They know Keith, Kyle, Aiden, Mike. They know the team. And they’re then able to say, “Okay, we’re comfortable this is where we’re going to be after,” right?

“If something happens to mom and dad, we know Derek’s the quarterback of the plan, and we know that this is how the plan’s going to work.” So, I would almost recommend to families that we sit down with, if they’re comfortable doing that, and the goal is to pass money on to do that. Because the few times we’ve done that this year, it has been exponential growth in the relationship.

Derek Gregoire: Yeah. That’s a great point. What about things like outside, not even… It definitely is an emotional issue, but like healthcare, plans for like healthcare?

Aidan Arone: Yeah. I think that’s a question that we ask often, and as you see, healthcare costs continue to rise. The biggest thing that we really ask is like, “Hey, what’s going to happen if one of you can no longer take care of the other,” right? Or, “If unfortunately, somewhere down the line one of the spouses is left by themselves, who’s going to take care of you?” And a lot of the times the fallback answer is, “Oh, my son will,” or, “My daughter will.” But I guess the reality is, is that really going to happen, right? With rising costs of living in the state of Massachusetts, you’re seeing a lot of young families move out of Massachusetts. So, if the kids aren’t local or can’t afford to be local, who is going to be that caretaker?

Derek Gregoire: Or even if they are local, the kids are probably in their working years.

Aidan Arone: Exactly.

Derek Gregoire: Are they going to be able to leave their job and do full-time care? That’s a big burden to ask of or assume that your kids are going to do. And some people can do it for sure, but these are the conversations that should be had. Another one I see a lot in, again, I feel like all these are so relevant in the last week or so because a lot of meetings have these type of conversations, but sometimes you have like, and you see this a ton. One of the spouses is super frugal and doesn’t like to spend, and the other one spends like crazy. What does that look like when the paychecks stops from work, and you have your Social Security and maybe a pension, your investments. Like, there are some compromises that are going to have to be made in these situations.

Aidan Arone: Yeah. I mean, these are all great points and just things that we would really push the viewers and the listeners to go out and make sure that they’re having these conversations. And, Derek, that really ties back to my story or what kind of spark this is.

Derek Gregoire: Yeah, that’d be awesome to hear.

Aidan Arone: Yeah, my parents. So, my mom, dad, maybe they’re listening, maybe they’re not. We’ll see.

Derek Gregoire: Well, your mom might be the only listener.

Aidan Arone: Probably.

Derek Gregoire: I’m joking.

Aidan Arone: Possibly down the line. My dad doesn’t know how to use technology, so he’s probably not listening. But yeah, my parents, love them both. My mom’s a nurse. My dad was a plumber. My dad’s planning to work for a few more years, and he unfortunately had an incident at work where his arm went septic, right? They’re talking about almost amputating his arm at one point, and now he was going to work for another three years just because he loves what he does, and now he’s retired. He’s at home, and he’s no longer working. He did just get a puppy to keep him busy, so he’ll have that on his hand. But what I’ve seen over the last two, three months is they’re kind of scrambling to figure out like, “Hey, what do we want to do in retirement?” because they had never planned about where they’re going to live, who’s going to take care of one another. Obviously, the fallback answer was my mom being a nurse.

Derek Gregoire: Yeah, yeah.

Aidan Arone: But that’s probably not really going to be true. So, I see all these things that retirement wasn’t really chosen for my dad or for my mom. It was kind of forced, and seeing this has really sparked that conversation and how we should be pushing this on the families that we sit down with to really have these hard conversations.

Derek Gregoire: No, it’s super important, and we’ve seen, you know, sometimes clients will just pick a number to retire because they want to retire, but their plan might not even support their lifestyle. And it’s like, “Oh, shoot, we’re two years in and now we realize we didn’t even sit down with an advisor. We didn’t even plan this out. We just thought, we’re 62, we want to retire.” But now you’re trying to go back to work at 65. Or the opposite happens. A lot of times we have clients that go to work every day, and I show them, I say, “Here’s your…” We have a portal. I show them their portal. I say, “Just so you know, every single day you wake up and go to work, you’re actually working for your three kids or your two kids.”

And they say, “What do you mean?” I say, “Because you don’t need any more money for your retirement. You’re all set.” And some people are like, “Well, that’s okay. I want to really make sure we’ll leave money behind.” And they get that. And some people will tell me, “Oh, we want to bounce our last check,” but then they’re going to work when they don’t need to, you know? So, it’s like having that conversation is, what’s the goal? Is it just to keep working to, because you’re supposed to and because the age says you’re supposed to? Or is it to save more money to leave behind? Is it to be more charitable? Is it to just have a sense of purpose? So, there are so many, I think at SHP, even though the dollars and cents are all we feel super strong about just the whole planning aspect of how our team is built out.

Like you said, you have your team. My team, I have myself, I have Natalia, I have Laura, Katie, Paul. We have a team, but beyond that, we have our operational team, making sure all the appointments are scheduled for our reviews and meetings. They’re setting up awesome events for clients, some fun, some educational, just making sure we’re keeping everyone in the loop there. We have our portfolio team who are handling all the portfolio decisions, alternative investments, regular portfolios. We have the planning team that are helping decisions around taxes, looking at tax returns. And so, all that is we can control. We can do a really good job of controlling as much as we can control for our clients around those important areas.

But beyond that is these conversations. Healthcare? Where are we going to live? How much are we going to spend? Where are we going to spend our time? Where are we going to spend our daily activities? Are we golfers? Are we beachers? Are we church people? Are we all the above? You know, those are things that I find so many folks don’t even talk about until they’re in the meeting with us, and we’re like, “Hey, by the way, have you ever thought about this?” And it’s like, “Well…” And they look at each other. “Something we should probably talk about.” And they’ve had 50 years together, 40 years together, but never talked about that.

Aidan Arone: Yeah, because it’s wake up, go to work, and do the next day, and take care of the next item on the to-do list.

Derek Gregoire: Exactly.

Aidan Arone: And, I mean, a lot of times, you see spouses are totally different. It’s pretty rare to sit down with two spouses that have the same exact mindset on 10 out of 10 topics or 10 out of 10 retirement ideas. So, it just really is so extremely important to have these conversations, and really what my situation brings it back to is you don’t really get to pick when life makes a decision for you, whether it be retirement, right? Some people get forced out of jobs. You don’t really get to pick that, which is exactly why having these conversations up front is important.

Derek Gregoire: Yeah, and I think, Aiden, kudos to you. I know you’ve been here a couple of years, but I know you were working before that, but I know you’re not too old. We won’t disclose ages. But what’s really cool is I know you just got your CFP this year, which is really good. That’s awesome. Congrats again. And Aiden works on Keith’s team, but it’s amazing that you’re already working with high-net-worth clients, and you feel comfortable in that role, and you thrive because you know all the different areas. And, again, even having these conversations, when I was your age, I was, even though we owned SHP, I wasn’t having those conversations. To be honest, when I was 20… How old are you? 25?

Aidan Arone: 25.

Derek Gregoire: So, when I was 25, let me think about that. We’d started the company when I was 23, and the company was like nowhere near. I always joke around people with clients, like good thing you weren’t with us back then. We did a good job. We just didn’t have the team to be able to execute on what we can now, right? You learn. You start out at one place, and you learn. We’re still growing and evolving and adding value all the time, but I was definitely at that point all about the numbers. “Hey, you make this. Here’s your Social Security. Here’s how much you can take out of your portfolio.” Figure it out the rest on your own.” That’s what it was in 2004-2005, when I was your age.

And fast-forward now, I think our world in general, like you mentioned with AI, all the advancements, it’s such a different world than what we came into, in a better way in a lot of instances. Obviously, some things are scary with people, are afraid of AI this, and technology that. But if you use it to your advantage, there’s a lot of enhancements that, like… I always look at where we are now compared to then. It’s like, wow, the value we’re adding is so much different than it was 20 years ago. And so, I bet in 20 years when you’re doing this, and you’re my age, you’ll probably talk about how far we went from 2026 until 2046. You know what I mean?

Aidan Arone: Yeah. That’s a long way out. I don’t want to think about it yet.

Derek Gregoire: I know. I mean, it goes fast. Like I said, I remember Keith, Matt, and I working here in 2003. And then in 2005 or 2006, we hired Giselle. She’s still with us today. And that was I think she was like, “Who are these knuckleheads?” You know what I mean? But over time, I think just hiring good people, growing the team, and it is where it is today. But back to the subject, any closing thoughts around like things? Anything else we left off the table of like… I guess, to bullet point it or to bring it to a conclusion, it’s like almost have some of the awkward conversations. No one likes to talk about: if I get sick, who’s going to take care of me? Where do we want to go, right? No one wants to talk about, well, how much money do you want to spend versus me as a spouse?

Or can we afford to do everything we want to do and not to worry about it? Like, these conversations you have to have instead of just going to work, coming home, going in your separate areas, never having these conversations with your family, spouses, kids.

Aidan Arone: Yeah, I think that’s a great point, and I think one thing that’s really stuck with me is Julie and I, we run the Hingham Road Race every year. And her cousin, 85 years old, or upper 80s, she’s like the happiest woman that I’ve ever met. And she still works as a crossing guard.

Derek Gregoire: Really?

Aidan Arone: Yeah, because she found that purpose in life, and she loves to run over and say hi to us every year on the 4th after we finish. And what she had said to me this year, because I had asked, I was like, “How are you still doing this after all these years?” Like, still active, still lighting off fireworks, which is just incredible.

Derek Gregoire: That’s so cool.

Aidan Arone: And she said, “When you retire, you rust.” And she doesn’t mean when you retire and step away from work as a whole. But it’s like, hey, if you retire and just step away from purpose and doing things that you like and building that community, that’s when you “rust.” But that was just so powerful to me, and that again kind of leads me back to this conversation is you have to have plans for a community or what you want to do after your working years.

Derek Gregoire: I remember, when I was younger, to close it out, my great-grandmother, my memories of her, she had Alzheimer’s, and she was probably in her 80s at that point. She probably passed away in her early 90s. But I remember my dad always said when she worked, worked, worked. She was sharp as a tack. And this is a little old, so this is back many years ago, but as soon as she turned 65, she retired, and as he said, she kind of just sat in her rocking chair. And her mind went like, unfortunately, super quick. She didn’t have purpose. She’s like, “I’m retired. I’m just going to rest.” And then it went really quick after that in terms of like she lived a long time, but her mind wasn’t there. And so, I think just having that purpose after work is important.

And obviously, like I said, the goal isn’t always about just having this big number and growing this number. It’s actually about having a family that’s ready, that’s together, that’s on the same page, that’s had these hard, maybe awkward conversations to not only get them through this year, but God willing, through the next 30, 40 years of an awesome retirement. So, these conversations you have, you mark, you put them down, you check it off, you have it, and then you can move on because you’ve kind of planned it out. And you have to revisit it once in a while, but just think about just have these conversations beyond the numbers because retirement… Let us worry about the numbers.

But have those conversations so we know what your goals are, so we can match the numbers with your goals and give you the retirement that you’ve always dreamed of. So, Aidan, for your first time on the podcast, great job.

Aidan Arone: Appreciate it.

Derek Gregoire: And I’m sure we’ll have you back on many more. And thank you, everyone, for tuning in on the Retirement Roadmap podcast. We’ll talk to you soon.

[END]