April 2026
In this episode of Couchside Conversations, Morton Wealth advisors Stacey McKinnon and Chris Galeski talk candidly about what this chapter actually feels like and what it takes to navigate it without burning out.
These are the questions people in their 30s and 40s are genuinely asking. We've addressed them directly below, and the full conversation is available as a transcript further down the page.
What is the sandwich generation, and what does it mean financially?
The sandwich generation refers to adults, typically in their late 30s to mid-50s, who are simultaneously raising children and caring for aging parents. Financially, this creates layered pressure: college savings, elder care costs, mortgage, and retirement contributions all competing for the same dollars at the same time. The risk isn't just the expense; it's that people in this phase often underfund their own retirement to meet the needs of others.
When should someone in their 40s hire a financial advisor?
The honest answer: before you feel like you need one. The midlife financial squeeze, caring for parents, funding education, and managing your own career transitions rarely announce themselves with enough warning to plan reactively. A wealth advisor helps you model competing priorities before they become conflicts. If you're already feeling the pressure of the sandwich generation, that's a strong signal that it's time to have the conversation.
How do you balance caring for aging parents without derailing your own financial plan?
This requires planning in two directions at once. First, get clear on your parents' actual financial situation. Many families avoid this conversation until a crisis forces it. Second, understand your own numbers: what can you contribute without compromising your retirement timeline? Decisions made out of emotional obligation rather than financial clarity tend to cost the most in the long run. A good advisor helps you hold both conversations at once.
How do people in midlife manage the mental load alongside their finances?
In this episode, both Stacey and Chris point to two things: pre-deciding your priorities before you're in a reactive moment, and having an independent person, whether that's a therapist, a coach, or a financial advisor who isn't emotionally entangled in your situation. The mental and financial loads aren't separate problems. They feed each other. Managing one well tends to make the other more manageable.
What does 'pre-deciding' mean, and why does it help with financial planning?
Pre-deciding means making key choices about your time, money, and relationships before the pressure hits rather than in the middle of it. In financial terms, this looks like automating savings, setting spending parameters in advance, and deciding what you will and won't fund before a specific need arises. It removes the emotional decision-making that tends to derail plans. Chris uses the example of his wife's family moving Thanksgiving to Saturday, a simple pre-decision that eliminates an annual conflict entirely.
Is it normal to feel like time is more valuable than money in your 40s?
Not only is it normal, but it's also a meaningful financial signal worth paying attention to. When asked whether they'd prefer more money and longer hours or more time and less income, both Stacey and Chris chose time without hesitation. This shift often reflects a deeper truth about midlife: the constraints on your time are becoming real in a way they weren't in your 20s. A financial plan that ignores this and optimizes only for accumulation, without accounting for how you want to live, tends to lead to regret.
The midlife financial picture is more complex than most standard financial planning conversations acknowledge. At Morton Wealth, many of our clients come to us in exactly this chapter, managing competing priorities across generations, trying to make decisions that honor everyone in their lives without compromising their own future.
We work through questions like:
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If any of this resonates with where you are in life, we'd be glad to have a conversation. Reach us at hello@mortonwealth.com or mortonwealth.com/contact
Time becomes the scarce resource, not money
Both Stacey and Chris note that the shift from 'building a career' to 'managing relationships' happens gradually until one day it hits you. Planning your financial life around this reality, rather than just income and assets, changes the decisions you make.
Pre-deciding is a form of financial discipline.
Whether it's calendar commitments or spending parameters, decisions made in advance before the emotional weight of the moment tend to be more aligned with what you actually want. This applies to financial choices just as much as personal ones.
The 'sandwich generation' squeeze is real and under planned for
Most people don't anticipate the financial complexity of midlife until they're in it. The families that navigate it best have usually had honest, specific conversations about their parents' finances, their own priorities, and what they're willing to say no to.
Energy management matters as much as time management.
Stacey's practice of pre-booking Tahoe weekends isn't just self-care; it's recognizing that sustainable performance requires planned recovery. The same logic applies to your financial plan: what you protect matters as much as what you grow.
"If you're boomeranging positive energy, you're going to get it back. It would actually create a better life. — Stacey McKinnon"
Watch previous episodes here:
How Different Generations View Wealth | Morton Wealth
A Family Meeting: Creating Shared Understanding Around Wealth | Morton Wealth
TRANSCRIPT
Stacey: Welcome to another episode of Couchside Conversations. Today I've recruited Chris Galeski, host of The Financial Commute, to switch teams for a moment and talk about something very real: the messy middle. 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 plates and we tend not to take much away.
Chris: Some people call it the sandwich generation, and it makes so much sense. There's a whole lot of stuff sandwiched in between two pieces of bread.
Stacey: When did you know you were in it?
Chris: I actually can pinpoint it. About eight years ago, my grandmother was in her mid-eighties and running out of money. My wife and I stepped in, bought a condo, and made sure she had a place to live. Then on the Fourth of July, 2019, we were visiting friends in Colorado. We came back late from golf, I'm rushing to shower, and my wife Brianna walks in and says, "I've got some news for you." We're pregnant. We weren't planning on having kids. My whole world flipped upside down that day. Fast forward a few years, we raised our oldest daughter, lost a pregnancy in between, had our second child, and then my mom went through a three-year battle with cancer. And one day I pulled a muscle just trying to dry off my back in the shower and thought, I'm forty-six. I'm no longer invincible.
Stacey: It snuck up on me differently. In my twenties, life was career-driven and relatively simple. Now I'm managing sixty people at Morton, forty clients, speaking at conferences, mentoring women in financial services, and maintaining relationships with dozens of friends, both sets of parents, and my siblings. The thing that surprised me most is that at this stage of life I'm not focused on growing a career anymore. I'm focused on growing and maintaining relationships. And there's only so much time. You can't invent it.
Chris: That's so true. And you do that really well. You structure your days so that when you're present, you're fully there for everyone. How do you manage that mental load though? Kids, parents, family, all of it.
Stacey: Honestly, I wish I were great at it. It's something I'm continuing to learn. I think the thing I'd tell my younger self is to lean into therapy earlier, having someone independent to talk to who isn't emotionally entangled in your situation. We rely on friends and family naturally, but you get to a stage where everyone around you is dealing with their own things too.
Chris: Without a doubt. I feel the same way. And the conversation around therapy has changed so much.
Stacey: It really has. Twenty or thirty years ago nobody talked about it. Now people want that coach, that third party who can come in and say, "You're exaggerating that," or "You didn't hear their angle on this." Even in my own marriage we can suffer from groupthink. Having someone help you see what you can't see in yourself is incredibly healthy.
Chris: I had a sports psychologist early in my golf career, so I at least knew the benefits of talking through goals and challenges. You talk about the boomerang effect a lot, the energy you put out and what comes back. How do you use that in your own life?
Stacey: Whatever I bring to my relationships is what I get back. There was a day recently when I was just depleted after a quick turnaround trip to Washington D.C. and I told everyone around me so they knew it wasn't about them. In marriage, in life, if I go home cranky I get crankiness back. Nobody wants that. To protect my energy I've booked a long weekend in Tahoe every month for the rest of the year. It's non-negotiable. If eighty-five percent of my time is invested in relationships and people, that fifteen percent of rest and reset is what allows me to show up as my best self. I had to work through that to figure out what I needed and then make it non-negotiable.
Stacey: And then there are these small moments that remind you. A couple of weeks ago I was stressed, running errands after a long day. Walking out of the grocery store, a woman I didn't know gave me the biggest smile. I couldn't help but smile back. She said, "I got you." That's the boomerang effect in real life. What you put out there comes back.
Stacey: I love that story. Tell me about balancing the parent side of the sandwich. You mentioned your grandmother, and now your parents are relying on you too, all while managing a team and raising two girls at home.
Chris: The shift nobody warns you about is that the people you used to rely on start relying on you. At forty-six you can't lean on your parents the same way. You have to show up differently for them. The commute used to give me a mental break. Now it's five minutes. Golf takes too many hours away from everyone who needs me. So I've found smaller ways, sitting at the office for an extra fifteen minutes at the end of the day before I drive home, just to transition. The key is pre-deciding. Figuring out what you need, communicating it, and protecting it in advance rather than reacting in the moment.
Stacey: That concept of pre-deciding is so important. And I think where we get into trouble is when we just run into life and keep pivoting without communicating to the people around us why we're doing what we're doing. We end up disappointing people not because we meant to but because we never set the expectation.
Chris: Pre-deciding is honestly one of the best life hacks I know. My wife's family moved Thanksgiving to Saturday years ago. No conflict over whose family to see on Thursday, no last-minute stress. Everyone has something to look forward to. We get two Thanksgivings. It's fabulous.
Stacey: That's genius. I'm stealing that. And it works because you communicated it, you shared the why. Which brings me to something I think about a lot. I have the ick with the word boundary. It feels like you're building a wall. But I love the concept. The reframe that works for me is just telling people why instead. Not "I have a boundary at four-thirty" but "I have to pick up my kids." When you explain the why, people respond so much better. We reach for the word boundary when what we actually need is honest communication.
Chris: That makes so much sense. Okay, let's play This or That.
Stacey: Yes, my favorite.
Chris: More money and longer hours, or more time and less income?
Stacey: More time. At twenty-five I might have answered differently. But at almost forty, time is the one resource that's actually limited. I'd rather have more of it to create experiences.
Chris: Same. You work out of necessity and then one day you realize the thing you actually can't get back is time. Okay, stable and predictable career, or flexible with time but less certainty?
Stacey: Flexible time with less certainty and then micromanage the calendar to create my own certainty. Stable and predictable sounds like not growing. That word does something to me. I want to grow but I want to control my time.
Chris: Last one. Would you rather be the person your family always calls, or let them be disappointed sometimes?
Stacey: For most of my life I've been the person everyone calls. I've had to learn that letting people be disappointed sometimes is part of showing up as your best self the rest of the time. You can't make everyone happy all the time. My grandmother has a magnet on her fridge that says, "I can only please one person per day. Today is not your day, and tomorrow doesn't look good either." At ninety-two she's earned the right to live by that. I'm still working on it.
Chris: Thank you so much for this conversation. Thank you for joining us for another episode of Couchside Conversations. We'll see you next time.
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. 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 financial professional, accountant, or tax professional before implementing any transactions or strategies related to your finances.
