Estate Planning for My Parents

Summary

Jill on Money with Jill Schlesinger

Episode Summary: Estate Planning for My Parents

Date: October 27, 2025
Host: Jill Schlesinger
Guest Caller: Michael (from California)

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Overview

This episode centers on a listener, Michael, seeking guidance for helping his aging parents with estate planning. Jill and her producer Mark walk Michael through crucial steps, share actionable advice, and discuss the emotional and practical challenges families face when tackling estate and future care decisions for elderly parents. The conversation highlights real-life hurdles, best practices for family communication, and key legal/financial moves everyone should consider in similar situations.

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Key Discussion Points & Insights

1. Opening the Conversation with Parents

• Michael’s Dilemma: His parents are in their mid-70s with minimal estate planning in place. His mother’s health is declining, prompting urgent dialogue about their financial affairs and future care.
• Resistance: Michael describes resistance and discomfort from his parents about discussing money and mortality.
  • Quote:

    “Yes, yes and yes. Yeah, all the above.” (Michael, 03:30)
    On whether there was resistance to having these tough conversations.

• Family Dynamics: Michael is the youngest of three children; one sister has passed away, leaving minor children. This adds complexity to inheritance and guardianship concerns.

2. Understanding the Parents’ Financial Picture

• Assets & Income:
  • House paid off, worth $300k–$350k.
  • Investments: Father alludes to $500k, but exact asset allocation is unclear.
  • Monthly income: Around $5,600 from Social Security and a small pension.
  • Expenses: Lower than income; mainly insurance, taxes, basic needs.
• Bank Accounts & Titles:
  Michael is uncovering whether accounts are jointly or individually owned.

  “Do they have other money in other accounts? Possibly.” (Michael, 07:08)

3. Estate Planning Basics and Legal Guidance

• No Wills in Place:
  The parents haven’t written a will, at least not in the past 30 years.

  “I assumed they had one from 30 years ago... but they both said no.” (Michael, 07:26)

• Engaging an Estate Attorney:
  The family is reconnecting with an attorney who handled the grandmother’s estate, which will help structure and clarify their plans.
• Preparation for Attorney Meeting:
  Jill emphasizes bringing all financial documents—account statements, insurance policies, home deed, mortgage documents, etc.—to the first attorney meeting.
  • Advice:

    “You’ve got to bring an account statement for every account you have, every investment account, every retirement account, every bank account, you need to bring a copy of your insurance policies...” (Mark, 08:35)

• Physical Presence:
  Encourages at least one child to attend the meeting with parents, as it helps with understanding and accountability.
  • Quote:

    “It’s like going to the doctor with them.” (Mark, 08:17)

4. Special Considerations: Loan to Family & Guardianship

• Mother Holds a Mortgage:
  Michael’s mom holds the mortgage for his deceased sister’s husband and children, with about $100,000 outstanding.
  • Situation: This creates complexities if his mother passes or if she needs the capital for care.
  • Quote:

    “If something happened to your mother right now, I’m not sure what happens to that mortgage.” (Mark, 11:10)

• Guardianship:
  The deceased sister’s kids are minors and live with their father; the family relationship is good, but inheritance and trust structures need careful attention.

5. Housing Decisions & Future Care

• Staying vs. Moving vs. Renting:
  The siblings are encouraging their parents to sell their longstanding house for easier living arrangements, possibly renting to simplify.
  • Emotional Barriers: Resistance to the physical move/downsizing and sorting through decades of belongings.
    • Quote:

      “For years now, my mom said, I can’t imagine packing this house up and moving. And we said, you’re not the one doing it. We’ll be doing it.” (Michael, 06:34)

  • Financial Upside: Selling would free up $300k+, providing more liquidity if care is needed.
  • Renting Considered: For flexibility and to avoid the burdens of homeownership in older age.
    • Logic:

      “If they rent something in their area…there’s things that they wouldn’t have to deal with—upkeep of house, property taxes, homeowner’s insurance. It might be [worth it].” (Mark, 14:20)

6. Long-Term Care Planning

• The risk is that increasing care needs may deplete investments rapidly, so more liquidity (via sale of the house) and clear documentation (via estate planning) are crucial.

7. Family Communication and Guilt-Tripping

• Addressing Guilt & Avoidance: Jill and Mark encourage Michael to communicate frankly about the family’s loss and the need to avoid future chaos by planning now.
  • Quote:

    “It’s going to be horrible when something bad happens. Let’s tidy up what we can now.” (Jill, 17:37) “We’ll be able to focus on just feeling grief as opposed to freaking out about money.” (Mark, 17:39)

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Notable Quotes & Memorable Moments

• On the emotional difficulty:

  “Oh, we’re here for dinner. Let’s talk about your death.” (Mark, 03:32)

• On avoiding family drama:

  “The horribleness will be with us. And we’ll be able to focus on just feeling grief as opposed to freaking out about money.” (Jill & Mark, 17:37–17:43)

• Encouragement to listeners:

  “Every situation is very fraught when it comes to estate planning. I understand that. So let us know how we can help you out.” (Jill, 18:25)

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Timestamps for Key Segments

• [02:50] Michael introduces his family’s estate planning predicament.
• [03:30] Discussion of parental resistance and broaching difficult topics.
• [04:33] Sibling dynamics and impact of sister’s passing.
• [05:07–06:29] Assessing parents’ assets, monthly income, and expenses.
• [07:26] Confirmation that no wills exist; beginning steps.
• [08:35] Preparing for the estate attorney—what to bring and why.
• [11:07] Details about the intra-family mortgage.
• [13:09] Sibling cooperation and possibility of helping with future care.
• [14:20] Pros and cons of renting versus buying for aging parents.
• [17:37] Addressing emotional labor and family obligations; importance of planning now.

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Conclusion & Action Steps

• Michael is proactive and following the optimal order:

  1. Start estate planning with legal counsel.
  2. Collect all financial and legal documents.
  3. Address housing and liquidity for potential care needs.
  4. Maintain open, honest family communication.
  5. Follow up with Jill after attorney meeting for tailored next steps.

• Listener advice: Have these conversations sooner rather than later. Bring in professionals, stay organized, involve your siblings, and “tidy up” logistics so you can focus on each other—not just the money—when difficulty strikes.

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This detailed breakdown offers listeners a roadmap for navigating sensitive estate planning topics, highlights the emotional realities involved, and distills practical wisdom from Jill and her team.

Transcript

[Jill]

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[Mark]

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[Jill]

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[Jill]

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[Mark]

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[Jill]

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[Mark]

Welcome to the Jill on Money show. It's Monday, October 27th and we are here answering your financial questions. Now if you have one. If something's going on you want to run a scenario by us, get in touch with us. Go to jillonmoney.com and in the upper right hand corner, click the Contact Us button. Write us a note and if you'd like to join us live, check the box. Mark will do everything else while you're on the website. Sign up for the free weekly newsletter and get ready gang. We've got our next Jill on Money Live webinar that is going to be on Wednesday, November 19th where we are doing tax and financial year end planning and it's going to be great. You can only join us for that live webinar. If you are a subscriber to Jill on Money Live, you'll have access to this live webinar. Three more after it the entire back catalog of our webinars bonus audio and video content, all for 45 bucks for the next 12 months. Pretty good deal. So check it out. Okay, let's get to you. Today we're talking to Michael, who joins us from California. Hi, Michael, how are you?

[Michael]

Hi, Joel and Mark. I'm good. Thanks so much for having me on.

[Mark]

What's shaking? What can we do for you?

[Michael]

Well, I'm hoping you can help me and my family. We're going through the process of getting my parents affairs in order in terms of their estate planning docs. We realize they don't have much in place already. So just as they're getting into their older years, into their mid-70s, we're trying to see what we need to do. We've started the conversations, but just feels like there's a lot to navigate and wanted one of your set of eyes and ears on this to see what you can suggest.

[Mark]

You're a good child if you are doing this.

[Jill]

We're trying, right? Is it a little.

[Mark]

So how did you approach it? Where and were they. Was there resistance to the conversation?

[Michael]

Yes, yes and yes. Yeah, all the above.

[Mark]

What did you do to open up like, oh, we're here. It's, it's, you know, we're here for dinner. Oh, let's talk about your death. I mean, like, how'd you met? How'd you do that?

[Michael]

And that's kind of how it's come up for years. The main thing we've been talking about for a long time is getting them to move into a home that's more conducive for them. Um, it's been the house they've had for 40 years. We grew up in. We just want something that's maybe single story less to manage. So they've been kind of hemming and hawing on that. So that's kind of been the main focus. But now more recently, it's what are your affairs? How much money do you have? Are you good? My mom's health isn't the best and hasn't been. So the concern is, do they have money to help her if she needs advance care in the future? So kind of for years I've joked with my dad, who's very financially savvy, always handled their money. I said, you could have $10,000 or 2 million, which is it? And he would just laugh. I said, no, really? Where in the middle are we? Are we good? Are you taking care of. So.

[Mark]

Okay. Amazing that you're having these conversations. So that's number one. Are you the only child or do you have siblings?

[Michael]

I have siblings. So they. My parents had three children. I'm the youngest. I have two older sisters and sadly, one passed about three years ago. Pretty young with children. So that kind of adds another layer here as we talk about not just what their needs are, but in the future, where they want their state to go, what they want to happen. So that's kind of another, another thing to navigate here.

[Mark]

I'm so sorry about that loss. That's a lot. I mean, of course, it's also a reason to make sure you get your parents to do whatever they want to do.

[Michael]

Right, exactly.

[Mark]

So what have you found out so far?

[Michael]

So my dad now has been a little bit more forthcoming in terms of kind of where some money is kind of bulk, bulk amount. I know what their monthly income looks like, so I know enough to feel better. Where it's like, all right, their cash flow seems okay. They have some money for a rainy day fund, but just don't know how much more they may use or where it's all invested.

[Mark]

During their 70s, mom's health is not great. Is dad managing the money on his own or does he have a broker or an advisor?

[Michael]

I think it's all on his own at this point. Yep.

[Mark]

What's the monthly income? Is it Social Security, pension? What is the basis of their income exactly?

[Michael]

So it's my dad's, Social Security, my mom's, and my dad gets a small pension from a previous job.

[Mark]

Okay, and how much is that total?

[Michael]

It looks like it's around 5,600 total.

[Mark]

And what are their expenses right now?

[Michael]

Got to be less than that. The house is paid off. They have two cars that I don't believe they have payments on. So it's really just insurance, property taxes, groceries, medical appointments, all those types of things. So I don't know the exact expense, but I believe it's less than what they're bringing in.

[Mark]

Did your father tell you how much money he has invested and more importantly, whether it's in retirement or non retirement accounts?

[Michael]

The first part he's alluded to. The second part, I'm still trying to figure out where everything is. He says he's close to the 500,000.

[Mark]

Mark and the house is paid off. What do you think the house is worth?

[Michael]

It's between 300 and 350.

[Mark]

Are they on board with selling this and moving?

[Michael]

I do think they're both on board with it emotionally, but the physicality of them taking action and I mean, for years now, my mom said, I can't imagine Packing this house up and moving. And we said, you're not the one doing it. We'll be doing it. You just have to say what goes and what gets thrown away. So I don't know what it will take to kind of get them over the hump and take the action to do it.

[Mark]

In the 500,000 in investments, the fact that they're in their mid-70s and mom's health is not great is not a ton of money. Are we sure that's the actual number, or do you think that there could be more?

[Michael]

I think that's what he said. In terms of what's invested, do they have other money in other accounts? Possibly. I've been getting more out of my mom. Does she have any accounts just in her name? What has both their names on it.

[Mark]

So.

[Michael]

So there may be some more hanging out there. I just don't have exact numbers.

[Mark]

And do they have wills right now? No.

[Michael]

I assumed they had one from 30 years ago when we were children, but they both said no, we don't think we've ever done that.

[Mark]

Are they willing to sit down with an estate attorney?

[Michael]

They are. So that's kind of the conversations we've just had. So we were involved with my grandmother's estate almost 10 years ago. So the same attorney who helped with that is able to kind of get back on track, and she has the kind of history, knowledge of issues from that that now are kind of are not creeping up, but part of our consideration now. So we've just gotten those conversations going. I've reinitiated that interaction, so we're kind of moving forward. But I feel like this should have happened, obviously forever ago.

[Mark]

Okay. But now it has happening. It is happening. So you're going to get that process going. Now here's the good news for you. If they're comfortable with you sitting in on this. Are they living local or are you near? Are they somewhere else?

[Michael]

They're local to my sister, but I'm further away.

[Mark]

So either you or your sister has to be in this meeting. It's like you need another set of ears and eyes. It's like going to the doctor with them. But the good news is that the process of sitting down with an attorney will force the issue because they're going to have to say, because what's going to happen ahead of time? You can tell them this before we meet with a lawyer, before you and Cissy meet with the lawyer, here's what you're going to need. We need. You've got to bring an account statement for every account you have, every investment account, every retirement account, every bank account, you need to bring a copy of your insurance policies. You need to have, you know, make sure that the house like you have the deed somewhere so we know where it is. There's no mortgage documents, obviously they need a list of everything. And so chances are your parents don't know this off the top of their head. So it's going to force them to go get that account statement. And that's a good thing because you and your sister need to get all that contact information. They.

[Michael]

Exactly.

[Mark]

You're going to need to know like the names and the addresses and the contact information for all these institutions. Right. And it's going to be, that's part of the process. So this is one of the reasons why I think going to an attorney is very helpful because they have to get, they have to get organized. Right. And then you can say to them also before you get to the meeting, you should see like there may be some jewelry, there may be something you want to go to someone like you need to have, you'll have stuff and you'll want to know if that should go to someone. If it's like, oh yeah, you know, your mother's like, I want my, my engagement ring to go to my surviving daughter. Maybe that's something important to her. Maybe she's like, I'm going to give, split it up with, you know, between the two. So your deceased sister's kids, are they minors or are they older?

[Michael]

All under 18? They're all minors.

[Mark]

Is it your sister's husband who now is taking care of them? The survivor?

[Michael]

Correct.

[Mark]

And your parents have a good relationship with him?

[Michael]

They do. I mean they live very close by too. And that's kind of one other consideration here that I didn't know if you had input on. But the house that my brother in law and those three nieces, nephews live in, my mom actually holds the mortgage to the house that all that all happened during my grandmother's estate. So that's kind of a, not a sticky situation. It was all done legally. There's documents which I've just re obtained to know what's what. So at least now I know what the mortgage amount was when it started, how much time's left. But that was actually kind of the impetus of me kind of getting some of this going, thinking, what if mom does need a lot more care? What if they need more money? Her money's tied up in this mortgage. Which she thought when my sister was alive, hey, that's Great. It gives them a low interest rate. I get a little money on my money and it works for everyone. But now it's kind of like years later. Doesn't make the most sense for her.

[Mark]

Right. And how much is the outstanding balance?

[Michael]

Right now it should be about 100,000.

[Mark]

So here's what I think. There's a few things here. So I think, like in this pro. And by the way, you'll bring that. Your sister will bring that document also. And estate attorney is going to want to know, like, are you holding any mortgages? Are you. Is there any money due to you? And now there's this hundred thousand. And so. And if something happened to your mother right now, I'm not sure what the. What happens to that mortgage. That's.

[Michael]

That's kind of my question. So I think it was done just in her name. So we're talking about what documents should be done now to get my dad on there, too.

[Mark]

Right.

[Michael]

If my mom. Yeah. So.

[Mark]

Right.

[Michael]

All those. All those details.

[Mark]

So an attorney will certainly walk you through that. So I think that you're doing exactly what you should be doing here, Michael, because at this point, you need to get a sense of, like, everything that's there. Like, listen, for all we know, your father's like, oh, I have a half a million dollars investments. Oh, I also have a half a million dollars in the bank, which changes. Right, because that's sometimes say, oh, that's not investments. That's like, you know, my safe money. But I think it's important to get this part of the process done, which will then guide you towards the next part of the process, which is, what do we do if mom needs more care? Right. And I mean, I think if you. Right now, their expenses are less than their income, which is great, but if she were to need more care, obviously, you'd start to eat into that half a million dollars of investments. And so the issue to really consider right now is, well, you know, depending on what mom needs, could she plow through that half million dollars, leave dad with nothing? And it wouldn't be nothing. There'd be some amount of money. But, like, we do have to. There has to be a plan for this, is what I'm saying. And I don't think we have enough information to create the plan, But I do think you're about to have the information, because once they go through this process, if you and your sister are on board, then you will be able to kind of get a sense of really where they stand. Now, are you and your sister are you guys close.

[Michael]

Same page with all of this.

[Mark]

Okay, great. Are you both in similar financial situations? For example, if something happened, if mom's health went south and you started eating into this, would either or both of you be able to help them out?

[Michael]

I think that's certainly a possibility. We'd want to be available to do that. So my sister has three kids, all going through college, so she definitely has more of a strain. But we would both obviously do what we could and needed to do.

[Mark]

Okay, got it. I mean, that's important. So I think we need more information. And when you say that mom's health isn't good or going into a different place, are you thinking right now that they need to not just go into a house but go into more like an assisted living? Or is that not yet the place? The place where they are?

[Michael]

So it's all potential. So I mean, she has a setback and we think maybe that's the case. But then she kind of improves and we think, no, she just needs a better living condition. So it really kind of goes up and down.

[Mark]

I wonder, would they be open to instead of buying another place, renting for a while?

[Michael]

I don't know. I mean, I've thought there's definitely places nearby to say even get a two bedroom, something nearby. So you're close to everybody, make it easy, easy access in and out.

[Mark]

I thought that because also then you free up this money from the house, right? The three to 300 grand. If they rent something in their area, I don't know how much it would cost them, but there's, you know, there's things that they wouldn't have to deal with, which is like upkeep of house, which costs money. Property taxes, which cost money. The homeowner's insurance, which is going to be more than renters, insurance, you know, all of these things. It might be. And again, I'm not sure we can do this all at once. I think like number one is like, let's get this estate plan started. And then you start to really try to focus on like, well, what would it cost you to rent something? And maybe, I mean, nobody wants to move twice. I get that, like, certainly you don't want to do it in your 40s, your 50s, but in your 70s, it just gets harder and harder. My fear is that if you don't do something soon with them, then you're done. Because once they're in their 80s, it's really hard. It's just really hard to get them out. And so now's the time When Dad's feeling okay and he is kind of savvy about the money, and you say, dad, look, something happens to mom and she needs some care, you need some help. If that happens, we're going to plow through this half a million dollars. So we've got to get the money out of the house. And one way to do that is for you guys to move and rent for a while and get your sea legs and see where things stand, and let's see if she's better off in a place that's easier. And I don't know, let's. Let's make it up. Let's say that the rent is, I don't know, three grand a month for. What do you think it is? I'm like, I don't know where they are. So give me a rental number that we think is reasonable.

[Michael]

Think probably less. It could be, I'd say between two and three.

[Mark]

All right, so if it's three grand a month, even then that is a very nice price to pay for the flexibility of if something else had to happen for Mom. If something happened and we needed to bring some money in. Like now, you no longer just are confined to 500,000. Now we have 300,000 on top of that, so now we have 800,000. They're in their mid-70s. He's not drawing on this money anyway right now. And if we needed to pay for some care for mom, it was 1,000 or $2,000 a month, you'd have a pile more money that you could draw from, and I think it would. What really has to happen at this point is while you're doing. I think you're exactly doing the order in the correct way, which is, let's do this estate plan. This is going to reveal a lot because then you're going to have the actual numbers. If we're, like, shockingly surprised and it is $2 million, then the urgency is not nearly as necessary. But still, we just got to get a sense of what it is so we can plan. But if it is that 500,000 and some money from the house and some from the proceeds of the house, and then you can create a game plan that makes sense for them. I think you're doing what you need to be doing. And, you know, how do they deal with guilt? Should we guilt them into some of this?

[Michael]

Believe me, that's been my challenge. I'm saying, hey, we're going to have to deal with this now or in the future in terms of cleaning up the house, getting rid of stuff, make it easier on us. Now. Let's work together and make some progress.

[Mark]

Now, obviously you have had dealt with pretty significant death in your family with you losing your sister. And you can say, like, you know, remember how horrible that was. Like, it's going to be horrible when something bad happens. Let's tidy up what we can now.

[Jill]

Because the horribleness will be with us.

[Mark]

And we'll be able to focus on just feeling grief as opposed to freaking out about money.

[Michael]

Exactly right.

[Mark]

It's a very sticky situation. Okay. And I completely understand that you feel a little anxious about it, but I think you're doing exactly what you should be doing. You're a good boy. You're a very good son. Let's, let's do one step at a time. Why don't you get back in touch with us after they see the estate attorney? You might have to, like, make a trip to go there also for this so that they don't blow it off, right. If it's like, oh, Michael's coming all the way in from California and he's going to be there for the appointment. Can't blow it off, right?

[Michael]

Hopefully. Hopefully not.

[Mark]

So, Michael, thank you so much. We so appreciate it.

[Jill]

If you are trying to help your.

[Mark]

Parents out or you're just trying to help yourself out, then please, please, please get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note, and if you want to come on the air, we can talk it through with you. Every situation is very fraught when it comes to estate planning. I understand that. So let us know how we can help you out. You can subscribe to us on the Odyssey app or wherever you find. Find your favorite podcast and don't forget to lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

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