April 2026
In this episode of Couchside Conversations, Wealth Advisors Stacey McKinnon and Chris Galeski unpack the realities of midlife: a chapter in which responsibilities stack up and time becomes more limited than ever. Through personal stories and honest reflections, they explore how priorities shift from achievement to relationships, why energy matters just as much as time, and how small mindset shifts can make a meaningful difference.
Tune in if you're interested in…
* Navigating the “sandwich generation” while balancing kids, parents, and career
* Why time, not money, becomes your most valuable resource
* How to manage the mental load and avoid burnout
* The power of “pre-deciding” your calendar and priorities
* Why investing in yourself is essential to showing up for others
Watch previous episodes here:
How Different Generations View Wealth | Morton Wealth
A Family Meeting: Creating Shared Understanding Around Wealth | Morton Wealth
Welcome to another episode of Couchside Conversations. I'm very excited because today we've recruited Chris Galeski, host of The Financial Commute, to switch teams for a moment to talk about a non-financial topic: the messy middle, which is basically a reference to the fact that we're getting older and life is getting harder. I think that's how that's defined.
I turned forty this year, and Chris is in his mid-forties. What we've realized is that as life continues to evolve, we just keep adding more and more to our lives, and we tend not to take much away. And so we're going to talk today about how we're dealing with this.
Yeah, I think some people call it the sandwich generation, which I had never heard about before, but it makes so much sense. And it's more than just peanut butter and jelly in the middle. There's a whole lot of stuff that's sandwiched in between two pieces of bread.
I'm so curious from your perspective, when did you know that you were in the sandwich generation or the messy middle at all, however you want to call it?
You know, I don't think most people can pinpoint it to the day. I actually can. So I'm forty-six, and this is going to be like a therapy conversation. About eight years ago, my grandmother was in her mid-eighties and running out of money. And we're like, we need to keep grandma in her home. So my wife and I stepped in.
We weren't planning on having kids. We stepped in. We bought a condo. We made sure that she had a place to live. And then you fast forward to the Fourth of July, two thousand nineteen. We were visiting some friends in Colorado. We've got about six couples we're friends with. All the guys went out to play golf that morning. We said we'd be home at a certain time.
We were late, and it was not good. So we're rushing back because we thought the girls would be upset about people in my life are and how I invest in those relationchallenges, and that whole mental, you know, positive energy thingshipswhat surprised me most was that, at this point in my life, I wouldn't be focused on building us running late. So I come into the house, if eighty-five percent of my time is spent having energy and investing in relationships and people, but fifteen percent of my time is dedicated to, rip off my shirt to take a quick shower, and Brianna comes into the bathroom and says, "I've got some news for you." We're pregnant.
And I was like, my whole world just got flipped upside down because we weren't planning on having kids. We had five nieces and nephews.
We were like, hey, you were always going to be just like uncle and aunt of the year.
Yeah, exactly. I mean, we did a lot of cool things with our nieces and nephews, but that day our lives got flipped upside down. And it wasn't that day that it all of a sudden became the sandwich generation. But if you fast forward to the next few years, we raised our oldest daughter.
We lost a pregnancy in between. Then we had our second child. Then my mom started going through cancer. That was a three-year battle. That was just kind of brutal. And I think I pulled a muscle just trying to get out of the shower and dry off my back one day, and I'm like, man, I'm forty-six.
I'm no longer invincible. It all of a sudden just hits you in the face.
It's so hard to get older because you feel like you can still do all the things that you could do when you're younger. And then, in addition to that, you've waited a little bit longer in life to have kids. And so now you're a little older, and you're like, I'm not twenty-five picking up these two girls anymore.
Like mentally you feel twenty-five, but physically you're not. And what's interesting, I think about it from our perspective, is when my parents were forty-six, I was like twenty-three. And so we're in a much different stage in life than my parents were when they were raising us.
And I don't think anybody had the ability to kind of warn us about what was going to happen when you're in your forties, and you're no longer going to weddings and baby showers. Unfortunately, you're dealing with the issues that come with getting older. You may be having some physical issues yourself or dealing with other family members. It's a very interesting time.
And then you compound that with toddlers. So you're just, yeah, you're in the thick of it. I can feel it.
Lots of big emotions are going on. But, you know, it's fun. You're not in a situation that's too different. I mean, what surprises you most about life today that nobody warned you about?
It was funny because I was reflecting on us having this conversation today and on my early twenties and where I was mentally and emotionally. My husband and I got married when I was twenty-five. And then at twenty-seven, I started working at Morton, and I remember that phase of life being so career-driven.
I was just excited to work, but I also needed it for survival, right? It was like a needs-based decision, and everybody in my life knew I had to work, and that was what we were growing in, and that's our career. And then slowly, through my early thirties and even my late thirties, to me turning forty later this year, things just kept getting added to the plate.
More and more relationships, more and more people in my life. And I think it kind of snuck up on me. The times were actually very simple when I was building my career. Now I'm faced with many other complexities. So we have sixty people at Morton that we have to maintain relationships with. I have about forty clients that I work with.
I speak at conferences and events, and people always ask me to serve as a mentor to women in the financial services industry. I have dozens of friends that I want to engage with. I have my parents. I have my husband's parents. We have both of our siblings. All of those relationships happen. I think the thing that surprised me the most was that at this point in my life, I wouldn't be focused on growing a career. I'd be focused on growing relationships and maintaining relationships.
And I think that's the thing that I would say maybe has even been kind of the hardest part, is that there's only so much time that we have. We can't invent time. It's not like a resource in that way. And so at this phase, the messy middle to me actually feels a little bit more like, where do I invest my time in relationships, and how do I maintain all of these?
And I think that's something that you do really, really well. And you're very conscious about it. I mean, when you show up at the office, there are people who need your time, either inside or outside this organization, or other companies looking for your thoughts and advice. And so you structure your days in a way that, when you're here, you're able to be there for everybody else.
And then when you're not here, you're working on the things that you actually need to. And it's impressive because you can't create more time.
Well, I appreciate that. I don't always feel like I do a great job of it, but I am very conscious of, like, who the relationships in my life are and how I invest in them. Yeah. How do you deal with that mental load? Kids, parents, family, all of it.
Oh man, I wish I were great at it. It's something that I'm continuing to learn and evolve in. My life wasn't too different than yours. I mean, in my late twenties and early thirties, it was all about building a career, and I only had to worry about myself and my wife. Now I'm worried about, you know, grandma clicking on links she shouldn't and having to change her usernames and passwords.
And then you look at the relationships that you have in life, and all of a sudden, they're a little bit different because so many people need something from you. And I wish that I had sort of leaned into therapy and having somebody to talk to who was independent earlier. And I don't think anybody really talks to you about the importance of that.
We have our friends, our family, our relationships, and it's very natural for us to rely on them. But you get to a stage in life where everybody has something that they're dealing with and going on, and having a therapist or somebody that can be that independent person to just listen, help you work through problems and emotions.
I've got two little girls. We just got back from Hawaii. Lots of big emotions. And so you really have to be conscious about that. And, I think, having a therapist helps.
I'm so glad that you touched on this, because something that has evolved over time is just positive energy around having a therapist. Like, I think if you were to rewind to when we were growing up, twenty or thirty years ago, people didn't talk about having a therapist or didn't want one. And I think something that's changed, especially, and I would say in the last five years, is everybody kind of wants that coach.
They want that third party to come in, and I find that even with my husband and me, we sometimes suffer from groupthink. Like whatever we feel is the thing that we feel, and we have big feelings around that. You have a third party come in, and they're like, you're exaggerating that, or rethink that, or you didn't hear their angle on this.
And I think just a coach, somebody that can help you to see the things you can't see in yourself, it's so healthy to probably, back to the relationships thing I'm struggling through, maintain all those relationships. I think you sometimes need somebody to coach you through that.
Yeah, without a doubt. You know, I was lucky at a very early age. I had a sports psychologist help me when I was in my golf career, so I at least knew the benefits of talking through your goals and your challenges, and that whole mental, you know, positive energy. You talk a little bit about that boomerang effect, the emotions that you throw out there, what comes back in this world. How do you best deal with that?
Well, I think I do it through that. There's something that happens, I think, in life where you get to the point where you realize how your feelings affect other people. You talked about your toddlers when they have big feelings. Your reaction to that oftentimes is a reflection of their feelings. When I think about all the people in my life and where I need to spend my time, I often think about how I show up and the energy I bring, and how that will directly impact their energy.
So there was even a day this last week when I was just in a bad mood, and I told everybody so they knew it wasn't about them. But then they also knew I was actually depleted, and I couldn't bring the best energy to the workplace that I normally try to.
Mostly, it was because I flew to Washington, D.C., on Tuesday and back on Wednesday, and it was way too much to do that turnaround in such a short time. So I was just tired. But I often realize that in marriage, in life, whatever I bring to the table is what I get back. And so understanding that and having a mindset around, like, what do I actually want out of this day?
What do I want out of my relationship? If I go home and I'm cranky with my husband, he's going to be cranky back with me. Nobody really wants crankiness. And so I think I'm just acutely aware of how my emotions affect other people. And I think that actually helps with the mental load of it all. And then, on a personal note, I'm very thoughtful about understanding my big feelings. Like, what are my big feelings and how do I manage those?
For example, I have booked a weekend in Tahoe every month for the rest of the year. A long weekend, because I know that I need that. I need that escape. I need that moment. I need that peace and serenity to bring my best self back to work. And so if eighty-five percent of myself is having energy and investing in relationships and people, but fifteen percent of my time is dedicated to the rest and reset, I can show up as my best self. But I had to work through that to figure out that's what I really needed and then basically make it a non-negotiable in my life.
Yeah, setting those, not boundaries per se, but knowing what you need personally to be able to show up as your best self. A couple of weeks ago, I had to go to the grocery store and pick something up, and I was stressed. Long day, had to get home, make dinner, deal with kids, and all that stuff.
And I don't know if I was in a good mood or a bad mood. I wasn't in a great mood. And I'm walking out of the store, and I'm trying to hurry up to get home. And this woman, as I'm walking by, just gives me the biggest smile, and I couldn't help but smile back. And she goes, I got you.
And that boomerang effect, I love the fact that you brought that up, because how you show up and what you kind of throw out there in the world, it's going to come back to you. And I love the fact that you brought that up.
It's not a widely known concept, and I feel like more people should know it because I think it would actually create a better life. Because if you're boomeranging positive energy, you're going to get it back, right?
Okay.
Tell me a little bit about how you're balancing the upper half of the sandwich generation, which is parents. You mentioned your grandmother, whom you helped take care of. This has been a big part of your life, to not only raise young kids, grow your own career at Morton, you oversee a big team here as well, all of our advisors, and now also your parents.
So share with me what that's been like.
You know, it's an evolution. I think that one thing that doesn't get talked about is, as you age in life, you all of a sudden mature and grow up and you get to a point where you're used to relying on certain relationships or certain things, but then you're forty-six and they're relying on you to show up differently, and you have to deal with that mental shift of like, wow, I can't rely on my parents the same way that I used to.
I actually need to show up differently for them, all while managing a team, growing a career, and dealing with two amazing, big-emotions little girls at home. And so finding personal time and focusing on what you need, I think, is important. I used to be able to get those breaks from driving in a car, and just having a little bit of a break.
My commute is five minutes long now, so I don't have that.
A blessing and a curse. A curse.
And, you know, as much as I love golf, and golf is a huge part of my life, it's not convenient to take four or five, six hours to myself, to be away from my family and everybody else that needs me. So I've had to find little ways to do it. Maybe it's at the end of the day, sit here for an extra fifteen to twenty minutes, and then get in the car and go home.
But sort of pre-deciding, like, what is it that I need, and then sharing with others that day or that you're close with, like, hey, you know what, I really need this, and then I'll be there in an hour. I think that's important.
I think it's so important in that way too, and that our relationships change over time, right? Sometimes you have to put a lot of energy into certain aspects of your life, and sometimes you don't. And we kind of just accept it, and we do it. But I think if you have to pivot in that way, you also have to make sure you get what you need in the end, right? You just can't give to everyone else forever and then not give to yourself.
Well, that's what ends up hurting me. My love language is words of affirmation. So I love doing things for people because then they're like, okay, thank you. Thank you so much. And then I get energy. I also get energy from being around people. But that's just not healthy. And so setting boundaries is something that I'm trying to get better at.
But how do you set boundaries?
This is a funny conversation because I actually feel like I have the ick at the word boundary. I just don't know why. I just don't love it. I feel like it's this word that somehow has a negative connotation and has also been weaponized a little bit. But I love the concept of boundaries. I just don't like the word.
It's like you're building a wall.
Yeah, I'll give you an example. If I have a client who wants to meet with me at four p.m., I'm not going to say to them, well, I have a boundary to be done at four-thirty. That's silly. You can't say that to people. Instead, you could say, "I have an appointment at four-thirty," "I have to pick up my kids," or "I have something I have to do at four-thirty," and explain. Sometimes we use the word 'boundary' when we should just explain the 'why'. Just tell people why, and then communicate with them, and they'll be better.
So that's my inner monologue on boundaries. But I think the concept still stands, right? So when you think about what you need in life, whether that's your extra fifteen minutes before you commute home or something else that feels like a need of yours, somehow making sure that you've pre-decided, you used that word earlier, that you're going to be doing those things.
So for a lot of my friends, I already have weekends planned throughout the summer to spend time with them, because I want to have something to look forward to. Or when I go to Tahoe and see my parents there, they know when I'm coming back and when we're going to spend time together again.
I think knowing those things in advance helps you to prioritize your life, but then it also helps to get out of sticky situations, because I think where we end up in sticky situations is when we just run into life and then we just pivot, pivot, pivot, and we don't talk to the people in our life about what we're doing and why we're doing it.
We just end up in a situation where we disappoint a lot of people. And so I find that I have boundaries, but they're mine, the ones I know about. And then I micromanage my calendar to make sure I'm attending and present to everyone in my life. Yeah, for their sake, but then also for my sake, because I love these relationships and I want to spend that time. But it takes a lot of work to do it, which is why this concept of pre-deciding, I think, is something you and I talk about a lot.
Pre-deciding is actually a very magical thing because if, let's say, you're up in Tahoe with your family and you're having a great time and you don't tell them that you're going to be back in a month or two months, and it's just sort of left out in the open, your relationship with them, when are they going to see you next, when are you going to do that, you had such a great time. If you don't pre-decide, your relationship dynamic shifts.
But if you pre-decide, say, hey, in a month I'm going to come back, and we're going to do x, y, z, you all of a sudden have something to look forward to. You know, Briana, my wife's family did this around Thanksgiving many years ago.
We've been together twenty-one years now, and her family pre-decided so long ago that their Thanksgiving is on Saturday. It's not going to be on Thursday like everybody else's. So that way you don't have to worry about going to this family thing, that family thing, just the stress around it. Nope, Thanksgiving's on Saturday. We get two Thanksgivings. It's fabulous.
It's a lot less stressful, and pre-deciding can be a great life hack.
That's genius. I feel like I'm going to steal that. I mean, why not? And now we don't have conflict between, like, oh, you did this family this year and that family this year. Yeah. You've eliminated the conflict, making it much easier.
But because you pre-decided and it's not something you did yourself, you actually communicated that to your family, your friends,, and the people around you. It makes things so much better. It's sort of like sharing the why.
Yeah, totally.
This has been a really fun conversation. Do you want to play a little game we like to call 'this or that'?
Yeah, it's my favorite game.
Right, Stacey, this is one of the coolest things that you do on Couchside Conversations. You play a little game called this or that, and I don't get an opportunity to do it very often. So I'm excited.
It's my favorite, so I'm excited too.
Would you rather make more money and work longer hours or have more time and make less money?
Me? More time. I think that that's something that people don't always think about, and it's also probably something that happens in the messy middle. If you asked me at twenty-five, I might change my answer, but at almost forty, I think I value my time more.
Yeah, I like that. I think there, you work out of necessity, and then all of a sudden you get to a place where you're like, wow, the one thing that I really have in life is limited, and that's time. Yeah. And so I'd rather have more time to create experiences than miss out.
Yeah, totally. You have to evaluate that a little bit differently. Okay, question for you. Would you rather spend your day helping a friend move or be the solo parent with two kids?
How hard am I moving? Do I need to help carry the couch?
No, you're carrying couches.
I'll probably spend time with the kids. As stressful as solo parenting can be, sometimes you create amazing experiences: you can be the grandparent for the day, give them ice cream at noon, and have some fun. To me, if you fast-forward 20 years, the only people who will know I wasn't there are the kids.
And so I would choose the kids, even though it's a lot more stressful than maybe carrying a couch. Plus, I'm forty-six, and I don't know if my back's going to be okay.
I think you made the right decision in my case there.
All right. Now I have one for you. Stable, more predictable career, or more flexible with time but less certainty?
I think I would take more flexible time but less certainty, and then I would micromanage my calendar to create certainty. I cheat. I feel like I just cheated on my question.
I just know that you can do that.
Yeah.
I don't dislike the flexible time and the uncertainty because you and I aren't afraid of growth. And so, like, stable, there's something about the word, kind of like your whole thing with boundaries. Yeah. When I see stable, predictable, I'm like, ' Well, then I'm not growing. ' Then I may be bored.
The word stable gives you that?
I feel like that does that to you. You're like, no, I want to grow, but I want to control my time.
Exactly. So, last question for you. Would you rather be the person your family always calls, or deal with the possibility that they may be disappointed you didn't show up for them the way they wanted?
That's a very hard question to answer. I think, for the majority of my life, I've been the person people call, and I've had to learn to grow in order to have a healthier relationship with my wife and to let people be disappointed from time to time.
I think it's extremely important that you can show up as your best self when you can, but you have other things going on in life, and sometimes you need to set boundaries, share the why, and just accept that you can't make everybody happy all the time.
My grandmother has this really cool magnet on the fridge. It says I can please only one person per day. Today is not your day, and tomorrow does not look good either. And I feel like I need to really embrace that.
And she is strict about boundaries, yeah.
Ninety-two, you can just sort of be like—
Whatever you want.
This is who I am. Deal with it.
Oh, that's so—so thank you so much for this conversation. Thank you for joining us for another episode of Couch Conversations. We'll see you next time.
Wow.
Disclosures: Information presented herein is for discussion and illustrative purposes only and is not intended to constitute financial advice. The views and opinions expressed by the speakers are as of the date of the recording and are subject to change. It should not be assumed that Morton will make recommendations in the future that are consistent with the views expressed herein. These views are not intended as a recommendation to buy or sell any securities, and should not be relied on as financial, tax or legal advice. You should consult with your finance professional, accountant, or tax professional before implementing any transactions and/or strategies concerning your finances.
