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Featuring

Chris Galeski, Wealth Advisor and Partner, Morton Wealth

Kristin Dillon, Modearn® Advisor, Morton Wealth

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Overview

About 40 percent of couples do not share the same vision for retirement. And 53 percent disagree on how much they actually need to have saved to get there. Those are not small gaps. They are the kind of gaps that surface at the worst possible moment, when one person is ready to stop working and the other is not, or when the money runs out before the plan does.

In this episode of Financial Commute, financial advisors Chris Galeski and Kristin Dillon walk through the questions most couples never quite get around to asking each other before retirement. Not the financial logistics, though those are here too, but the deeper ones: what are you retiring toward, what happens if something goes wrong before you get there, and what is the cost of staying in a stressful job just a little longer than you need to?

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Key Takeaways

• 40 percent of couples do not share the same vision for retirement, and 53 percent disagree on how much they need to save. These are not abstract statistics. They are the source of real friction that tends to surface at or near retirement, when the decisions become concrete and reversible changes become harder to make. Having the conversation before you are in the middle of the transition is the point.

• What are you retiring to matters as much as when you are retiring. Identity, purpose, and the structure of your day are all things that work provides without most people realizing it. Chris has a client who is financially ready to retire but has not done so because he genuinely loves the impact he has on his team. Kristin notes that the loss of daily purpose is harder for many retirees than they anticipated. The question is not just when. It is what comes next.

• Retirement spending is almost always higher than people expect. The common assumption is that expenses decrease in retirement. Kristin says she has not seen that in practice. People have more time, they fill that time, and filling time costs money. Healthcare, travel, flying out to see the kids, family adventures: these are the categories that tend to grow, not shrink. A $300 hotel room ten years ago is $1,000 today.

• The cost of staying in a stressful job just to maintain health coverage may not be worth it. Chris walks through a scenario where someone in their early 60s is ready to retire but holds on until Medicare age. If there is a year and a half to two years between their desired retirement date and Medicare eligibility, the out-of-pocket health coverage cost is roughly $30,000 to $40,000. The question worth asking is whether the time and stress of staying in the job is worth that amount. For many people, once it is framed that way, the answer changes.

• Time is the scarcest resource that cannot be recovered. Kristin's framing is direct: we overestimate how much time we have on this earth with the people we love. The impact of stress on health and relationships is real and underestimated. For people who are financially positioned to retire, Chris and Kristin both push back on the assumption that working longer is always the right answer. The Die With Zero philosophy, which both reference, argues for spending at the life stages where you have the physical capacity and energy to actually enjoy it.

• A spending strategy is more useful than a budget. Chris frames it this way: rather than building a budget and asking whether retirement is affordable, the more useful starting point is to ask what the life you want to live actually costs. That number drives everything else: how much you need saved, what rate of return you need, what risk level makes sense, and how long you need to keep working. People retire with less than $1 million and are comfortable. Others with $10 million should probably not yet. The number is not the whole picture.

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Key Moments from this Episode

0:00 – Intro: municipal bond yields are at their highest level in 20 to 25 years
0:47 – Welcome: why muni bonds are suddenly back in the conversation
2:12 – The catch: duration risk and the inverse relationship between bonds and rates
3:36 – Taxable equivalent yield: how to measure a 4% tax-free return against other options
5:47 – The California muni bond ETF is down 4% this year despite the headline yield
6:32 – How to calculate taxable equivalent yield and what it actually means
8:00 – Private lending vs. munis: flexibility and short duration as an edge
9:57 – Lock-up periods matter: what you should expect in return for ten years of illiquidity
11:44 – Credit risk and California's balance sheet: why defaults are rare but real
13:29 – Morton's current stance: not no forever, just no right now
15:03 – When does a muni bond actually make sense for you?

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Questions This Episode Answers

What questions should couples ask before retirement?

Chris and Kristin work through several, but the most important ones are: What does your ideal retirement look like, and do your visions actually match? When would you each like to retire, and what if those timelines differ? What is the life you want to live going to cost, not as a budget but as a spending strategy? What are you most worried about financially? What happens if retirement comes earlier than planned because of a layoff, an illness, or a forced transition? And how will you each maintain purpose, health, and social connection once the structure of work is gone?

What does the 40 percent statistic about couples and retirement mean?

It means that roughly four in ten couples approach retirement with meaningfully different expectations about what that chapter of life will look like. That gap can show up as disagreement about where to live, how much to travel, whether to support adult children financially, how much time to spend together versus independently, and what counts as a successful retirement. The 53 percent who disagree on how much they need saved is a related problem: if two people are contributing to the same retirement without agreeing on the target, the plan is being built toward two different destinations at once.

How do I know if I can afford to retire early?

Chris's framework starts not with the account balance but with the spending strategy: what does the life you want to live in retirement actually cost? Once that number is clear, it becomes possible to work backward through how much needs to be saved, what return is required, and whether early retirement is viable. The health coverage question is often the biggest variable in early retirement scenarios. For people approaching retirement before Medicare age, out-of-pocket coverage for a year and a half to two years runs approximately $30,000 to $40,000. That number sometimes reframes the decision: is continuing to work in a stressful job worth that amount?

What is the Die With Zero retirement philosophy?

Die With Zero, the book Chris and Kristin reference, argues that the goal of financial planning should be to maximize life experiences at the stages of life where you have the physical capacity and energy to enjoy them, rather than accumulating wealth until very late in life and leaving it to heirs who are already well into their own adult lives. The practical implication is that there are things you can do at 55 that you cannot do at 75, and calibrating spending to life stage rather than deferring all enjoyment to later may produce a more satisfying outcome. It represents a shift from the FIRE movement's emphasis on frugality and early exit toward a more intentional approach to when and how you spend throughout life.

Should I be worried about running out of money in retirement?

Chris is careful to frame this as a planning question rather than a fear. He has seen people retire comfortably with less than $1 million and others with $10 million who are not yet in a position to do so. The number is less important than the relationship between what you have, what you spend, and how long you need it to last. The spending strategy, what the life you want to live actually costs each year in retirement, is the variable that drives everything else. The biggest risk most people underestimate is how much retirement actually costs: expenses do not typically decrease, and healthcare, travel, and family involvement tend to grow.

What happens if I have to retire earlier than planned?

Chris describes two versions of this. The first is a layoff or forced transition: not on your timeline, not on your terms, and emotionally more difficult because you did not choose it. The second is when a spouse or family member gets sick and you step away from work to become a caretaker. Both happen more often than people plan for, and both are more manageable when there is a financial plan in place before they occur. Kristin describes a client who was laid off before his intended retirement date and whose first call was to Morton Wealth. Working through the numbers together, they were able to show him he was okay, and help him figure out how to make his savings last until his next move. Having a planning partner before the event makes the event less disorienting.

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Why This Matters for Anyone Within Ten Years of Retirement

Most retirement planning conversations focus on the accumulation side: are you saving enough, what are your accounts invested in, when can you afford to stop working. This episode is about a different set of questions, the ones that determine whether the retirement you actually experience matches the one you imagined. Those questions are best answered before you arrive, not after.

• Couples in their 50s who have been saving diligently but have not yet had a real conversation about what retirement looks like day to day, where they want to live, and whether their visions are actually aligned
• Anyone considering early retirement or approaching the Medicare gap who wants to think through the health coverage math and whether the tradeoff is worth it

At Morton Wealth, retirement planning is not a single conversation. It is an ongoing one that evolves as life does. If you want to work through the questions in this episode with someone who does this every day, that is exactly what we are here for.

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Watch relevant content:

Navigating Different Retirement Timelines

Replacing Income in Retirement

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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 concerning your finances.

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