Help! I’m Going to Be a Grandma

Summary

Episode Summary: Help! I’m Going to Be a Grandma

Jill on Money with Jill Schlesinger
Release Date: July 27, 2026

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Overview

On this episode, Jill Schlesinger takes a call from Joy, a soon-to-be grandmother in Northern California. Joy is contemplating a move to be closer to her son, daughter-in-law, and new grandchild, and she seeks Jill’s expertise on how to relocate without jeopardizing her long-term financial health, minimizing taxes, and maintaining her investing strategy—specifically regarding her significant real estate assets.

The episode evolves into a savvy consultation touching on leveraging assets, retirement planning, risk tolerance, and the emotional intersections of major life and financial decisions.

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Key Discussion Points & Insights

1. Joy’s Financial Background & The Motive for Moving

• Joy’s Motivation:
  Joy wants to move from her current home (45 minutes away) to be closer to her family, especially as she becomes a grandmother.
• Assets and Income:
  • Age 63, widowed, still working with high income.
  • Earns ~$235k/year from employment, ~$13.8k from a small pension, and ~$140k net rental income from three residential properties (owned outright).
  • Plans to convert her current home into a fourth rental property ($4k/month projected).
  • Real estate portfolio worth ~$2.3M (rentals), plus her primary home valued at ~$950k.

"I'm about to become a grandmother and I need to move closer to my son and daughter in law. Oh, I'm just trying to figure out the best way to do that while preserving my long term wealth, avoiding unnecessary taxes, and keeping my appreciating assets."
— Joy [03:46]

2. Evaluating the Move—Buy, Sell, or Leverage?

• Target Home:
  The desired new home near her family is estimated at $1.5M–$1.7M.
• Asset Snapshot:
  • $3.1M in traditional IRA/401k, $625k in Roth IRA, $1.4M brokerage, $111k in high-yield savings, $45k in checking.
• Potential Approaches:
  • Sell current assets versus taking a mortgage at current high rates (6.5%+).
  • Jill suggests selling assets to buy the new home, avoiding a high-interest mortgage and reducing overall tax burden by starting required minimum distributions (RMDs) strategically.
  • Alternative: Take a mortgage (interest-only) and pay it down over the next decade using IRA withdrawals, forcing annual distributions and staying ahead of RMD requirements at age 75.

"No, why would we get a mortgage right now? Six and a half percent. I don't think so. I'd rather sell one of the properties."
— Jill [08:47]

3. Real Estate Comfort vs. Liquidity—Understanding Risk & Personality in Decision-Making

• Joy’s Attachment to Real Estate:
  Joy does not want to sell her primary residence or rental properties—she prefers to keep her real estate holdings.
• Jill’s Perspective:
  Jill expresses her own preference for liquidity and diversification but recognizes that comfort and peace of mind are as important as optimal financial efficiency.
  • Jill underscores that sometimes, clients “just want what they want” and emotional comfort can trump theoretical best practices.

"You know what the upside and the downside is of all of this... it's really important to keep the mortgage really in a tight bound so you kind of keep yourself very accountable..."
— Jill [16:21]

4. Work/Retirement Transition and Income Flow

• Considering Part-Time Work:
  Joy is considering reducing her work to three days a week soon, which will lower salary but is balanced by strong rental and pension income.
• Retirement Income Plan:
  • Pension: $1,442/month (no COLA).
  • Social Security strategy: Claim survivor benefits first, then switch to her own benefit at 70 ($5,058/month).
  • Jill validates that Joy’s income streams—plus Social Security and pension—will comfortably meet her needs even as work income reduces or stops.

5. Tax, Withdrawal & Investment Strategy

• Tax Realities:
  • Acknowledges that pulling from retirement accounts and the brokerage will trigger taxes and capital gains.
  • Suggests using a combination of these sources (ideally emphasizing required distributions from traditional IRAs) to fund the purchase in either a lump sum or as part of a mortgage pay-down plan.

6. Value of Professional Advice

• Financial Planning Help:
  Jill recommends Joy engage a fee-only financial planner for tailored, holistic retirement and tax strategy, given the complexity and size of her portfolio. Joy manages most investments herself, with some assistance.
• Estate Planning:
  Quick confirmation that Joy’s estate documents are up to date—a must when making major life and asset changes.

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Notable Quotes & Moments

• On Doing What Feels Right Emotionally, Not Just Financially:

  "You know, sometimes, emotionally, people need to do what feels right for them, even if it's not the absolute most optimal way financially."
  — Jill [18:34]

• On Pressure from Family Opinions:

  "Funny, my son is advocating for doing exactly what you're recommending, not taking out a mortgage. So he'll be happy to hear this."
  — Joy [17:38]

• On Letting the Client Lead the Charge:

  "It's not my job to convince you otherwise... If that's the way you want to roll, that's cool... wouldn't be my way, but I'm a wimp and I don't like illiquid assets."
  — Jill [16:21]

• On Proximity to Family:

  "You're sure your kids want you to move closer, right? I'm just kidding. I'm sure they do... Close, but not too close."
  — Jill [19:58]

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Timestamps for Key Segments

• [03:42] – Joy introduces her situation and financial background
• [05:17] – Rental income and property value disclosure
• [07:54] – Retirement savings breakdown and purchase funding discussion
• [08:47] – Debating mortgage vs. selling assets
• [10:42] – Discussion of work reduction plans and expected retirement income
• [11:42] – Social Security strategies
• [13:05] – Concrete advice for paying for the new house: sources, taxes, and withdrawal strategy
• [15:44] – Role of professional financial advice and managing a complex portfolio
• [16:21] – Discussion of emotional comfort vs. optimal financial moves, and accountability in big financial decisions

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Tone, Takeaways, and Final Thoughts

The episode is characterized by Jill’s signature direct-yet-empathetic style, blending financial expertise with understanding of the real-life, emotional considerations behind major money moves. The conversation moves fluidly between technical details and human factors—respecting that sometimes, the “right” answer is the one that brings comfort and fits one's personality.

• Key takeaway:
  There is no one-size-fits-all in financial planning—especially at transition points like becoming a grandparent and making big lifestyle changes. Both the numbers and your gut matter.

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For Listeners

If you're facing a similar life transition and big financial decisions, Jill encourages reaching out at jillonmoney.com. Whether you want to talk through the nitty-gritty numbers—or just want a second, reassuring opinion—she and her team are there to help “lift someone up, change your work, change your wealth, change your life.”

Transcript

[Announcer]

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[Jill]

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[Announcer]

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[Jill]

Done.

[Announcer]

Cars4Kids has been doing this for over 30 years and has accepted more than a million vehicle donations. So if you've got a car you're not using, turn it into something meaningful. Go to carsforkids.org Jill that's cars with a K. And fair warning. Now that jingle's going to be stuck in your head for the rest of the day.

[Jill]

Welcome to the Jill on Money show. It's Monday, July 27th, and we are here trying to help you make more considered financial decisions. Or maybe we're just here to give you permission to do the things you know you probably can do. I feel like our Audience is so interesting and interested and we very much love hearing from you. But often you'll come on the air and I'm thinking to myself, this guy's got know he's in good shape or she knows she's in great shape. But if you just need another set of ears and eyes on a situation, a question, something else that's going on, just get in touch with us. Go to jillonmoney.com jillonmoney.com and click the contact us button. When that form pops up, that's an email. And we often will do an email episode every so often. And you know, if you'd like to come on the air, you check the box and Mark will do everything else. So by the way, speaking of Mark, also known as the handsome man, now that we have another program with video, happy belated birthday to him. So everyone should send him a note of belated birthday greetings. And if you got anything else going on and you have a question about maybe a guest you'd like to hear about or you've got a question even just about the economy, of course, get in touch with us. So again, jillonmoney.com, click the contact us button. Hey, while you're there, don't forget to sign up for the free free weekly newsletter. Okay? Right now let's talk to Joy. She joins us from Northern California. Hello, Joy. What's going on?

[Joy]

Good morning, Joe and Mark. How are you?

[Jill]

Great. What's happening?

[Joy]

Well, I'm about to become a grandmother and I need to move closer to my son and daughter in law. Oh, I'm just trying to figure out the best way to do that while preserving my long term wealth, avoiding unnecessary taxes and keeping my appreciating assets.

[Jill]

Oh, that's a lot that you want to do. How far away are they? Are they different state or same state?

[Joy]

Oh, no, they're in the same state. Okay, so 45 minutes away, but that's still too, that's too far for me.

[Jill]

Oh my God, 45 minutes away. Okay, so how old are you?

[Joy]

63.

[Jill]

Are you married, single, partnered, Widowed, you said? Oh, you're so young. I'm sorry, that's terrible. All right, so are you working or are you retired?

[Joy]

I'm working.

[Jill]

Can you work remotely like moving? Okay, so that's not. So you're going to continue to work, right?

[Joy]

Maybe, maybe not. I don't know.

[Jill]

How much are you earning right now?

[Joy]

So right now I earn approximately 235,000. I get a pension, I net a small pension of 13 point. 13,800. And I also get rental property income of 140,000.

[Jill]

Wait, what? That's a huge number.

[Joy]

Yeah.

[Jill]

Is this a commercial property?

[Joy]

No, it's residential properties.

[Jill]

Uh huh. And you're gonna keep that, like that's a nice chunk of money, right?

[Joy]

Yes, yes, it's residential properties that I own outright. And that's kind of my part of my question too.

[Jill]

How much is the property worth? Properties, how many are there?

[Joy]

There is three right now, but I plan to convert my residence into another.

[Jill]

So you will have four eventually. Okay, so let's do the three rentals separately. How much are those together worth?

[Joy]

About 2.3 million.

[Jill]

Okay. Are they owned free and clear or

[Announcer]

is there a mortgage?

[Jill]

Okay, so no mortgage.

[Joy]

Yes, I have no mortgages.

[Jill]

Okay. How much is your primary residence worth?

[Joy]

Oh, it's worth about 900 and maybe 950.

[Jill]

Are all three of these properties that, the rental properties, are they all kind of similar in terms of they're easy or hard to manage or one is better than the other or, you know, are they kind of similar in nature?

[Joy]

They're easy. I have a property manager.

[Jill]

And so when you say the 140,000 of rental income is that after the property manager is paid?

[Joy]

Yeah, that's net.

[Jill]

Okay, got it. And what do you think your primary, if you were to convert that, what do you think that could generate?

[Joy]

About 4,000amonth.

[Jill]

So we got a huge amount of income right now because you're working, you got the small pension, you got the rental income. So if you were to move closer to be near your kids and the grandkids to be, what would that mean in terms of like how. What would you need to pay to either rent or own something near them?

[Joy]

So you mean in terms of the price of the home?

[Jill]

Yeah, exactly.

[Joy]

Yeah. So they live in an expensive area, so too bad. I'm estimating 1.5 to 1 7.

[Jill]

Are you saying to, to me that essentially you have the ability to buy such a property with other money without having to sell your current property?

[Joy]

I think I do.

[Jill]

You think so? Okay, so let's talk about that. Let's talk about the money that you have accumulated so far.

[Joy]

Start. We'll start with retirement.

[Sally Helm]

Okay.

[Joy]

3.1 million in traditional IRA and 401K.

[Jill]

Okay.

[Joy]

I have 625,000 in a Roth.

[Announcer]

Great.

[Joy]

I have 1.4 million in a brokerage. I have 111,000 in the high yield savings and then I have about 45,000 in checking.

[Jill]

And so are you thinking that you Will be pulling some of the money out of the traditional plus the brokerage to buy the new place. Is that your general game plan?

[Joy]

Well, well, no. So that's kind of my question. I mean, maybe it's time I get a mortgage and maybe it's time I leverage some of my properties.

[Jill]

No, why would we get a mortgage right now? Six and a half percent. I don't think so. I'd rather sell one of the properties. Again. Let's just pretend if you had the primary residence, you sold it and you could not. You won't net 900, but you know, it's your primary, so you'll be able to exclude some of the gain. And you have that money, you put it down with a new one and then you use some money from brokerage and then retirement, Then you own something free and clear. Right. Or conversely, you might say, well, I'm not so sure that I actually want to do that. That way maybe I should rent for, I don't know, like a year to make sure you like where you are. Because what if you don't like it there?

[Joy]

Well, I've been looking at the area for a while now. Yeah, I looked into renting, but unfortunately that deal just kind of fell apart.

[Jill]

Okay.

[Joy]

So I'm familiar with the area and I've been going to looking at open homes. I'm not, I. I don't want to sell my primary residence.

[Jill]

All right, well, that's it. That's that. So you see what happened. You just shut me down. Mark, did you hear that? I am not. And you don't want to sell the rental, you don't want to sell the primary. I mean, you have a lot of money. You know, you've got a lot of money that is tied up in real estate. And so you will have even more money tied up in real estate. How much do you spend right now?

[Joy]

So, you know, it varies. I spend, I would say maybe 10 to 15,000.

[Jill]

That's a big variance.

[Announcer]

Give me a better.

[Jill]

Give me, give me a smart. Give me, give me the real number. Is it 15 is fine.

[Joy]

It depends. Like if I travel? Well, I would say let's bump it up then. How about 13? Lucky 13.

[Announcer]

All right, lucky 13.

[Jill]

Are you going to presume that you're working until some period of time? Like what, what do you think the work? You know, like a year, two years? Do you say like, oh, I want to. Just actually really want to be done, like anything in your mind.

[Joy]

I'm hoping to go down to part time, perhaps next year.

[Jill]

Ah, okay, so what would that mean in terms of income for you?

[Joy]

Well, I guess I would have to do the math on my current salary and.

[Jill]

But like, how much? Like 80%, 50%. What do you think?

[Joy]

Oh, I'm thinking I'd go down to like three days a week instead of five.

[Jill]

Okay, like that's possible where you work.

[Joy]

Yes. Oh, I forgot that I also get, I get a pension too.

[Jill]

Oh, tell me about that.

[Joy]

But it's, it's a lump sum or a monthly pension, so.

[Jill]

Okay, wait a second. What's the, what is the monthly pension?

[Joy]

1442.

[Jill]

1442. Okay. And no cola, you said?

[Joy]

Yes, no cola.

[Jill]

Okay, no cola. How's your health? How's your longevity? Like what? Tell us a little bit about you. Good. So were you planning on claiming Social Security at 70?

[Joy]

Yes.

[Jill]

Do you know that amount?

[Joy]

Yeah. Well, actually, so I think my strategy is first to collect survivor benefits and then convert to mine at 70, which will be 5,058.

[Jill]

So just. So we got this now. Now this makes me feel a little bit better about not selling any property because we left out a couple of pieces and now we got it. Okay, so let's presume you go part time. Let's Even forget about 3/5.

[Announcer]

Like if, even if you went half

[Jill]

time, like, let's just say you made 120 grand. You have, we know you have expenses about 150 grand, but. But in addition to that 120, you have 140 coming in from the rental property and maybe more.

[Announcer]

Right.

[Jill]

Because of the. Your primary. So you're looking good. Right. And then when you turn 70, you will have your 1442amonth. You'll have your $5,000. You'll still have your rental property, and you're all good. Like, it works. The question is what we do to pay for this new property. So, okay. I mean, you have a lot of income. It's such a weird thing. It's like you make good money. So when do we want to actually pull the trigger on buying something? Is that this year or is that a next year thing?

[Joy]

Well, that's this year.

[Jill]

Yeah.

[Announcer]

Okay.

[Jill]

All right, so.

[Joy]

Because with the mortgage broker.

[Jill]

Well, but why would you have a mortgage? I don't understand. I really don't see why you would do it. Okay, so let's just talk about what the facts are. Right now you got 3 million bucks that has to start coming out of your traditional account. We need to start taking some of that out.

[Joy]

Yes.

[Jill]

No matter what. Okay, so what we could do is Sell out some of your brokerage account. We could pull some money out of your traditional account, get this money out and buy yourself a place and be done with it. I mean, you're going to be in the high, you're going to be in a very high tax bracket for a while. I mean, you're in 35% already, right?

[Joy]

Right.

[Jill]

Okay, let's just pretend you're in a high tax bracket. You just say this is going to be a crap year for you for taxes because no matter what, when you look at what's happening, you're going to have a brokerage account where you're going to have to actually, you're going to incur some capital gains, I presume. And I don't want to deplete the brokerage account, but I might want to just take a whole bunch of money out of the retirement account, pay the taxes due and buy yourself your new house and use the, some retirement money, some brokerage money. Now, if you want to do the mortgage the way that you would do it is you would get your mortgage broker and say, I'm going to put a million dollars down from my brokerage account. I'm just making this up. Right. So you're going to need to get a mortgage for $700,000, right? You're going to get that mortgage and your expenses are going to rise pretty dramatically because you're going to have a $700,000, six and a half percent ish mortgage. Right. And what you could do is you could do an interest only maybe for 10 years and we'll put a gun to her head and make her pull the money out of the retirement account over 10 years, 7 years even, we could do like a 7 year interest only. So what would that would mean, Joy, is that whatever your mortgage amount is, seven, eight, hundred thousand, whatever you decide you have them do not a 30 year fixed. You say, I want to have a 10 year interest only mortgage. That's it. And then over the course of the next 10 years, you will pull money out of your retirement account. You will pay the tax that's due on that retirement account, and each year you will pay off some of this, this outstanding mortgage. Maybe it's like 150 grand a year. You do that and that's how you manage it. There are costs involved. And do you have someone who's managing your money, your retirement account, your brokerage account? Are you doing that yourself?

[Joy]

Well, I do have some people with a part of it, but I manage most of it myself.

[Jill]

Okay, and are they Doing any sort of financial planning for you?

[Joy]

No, I know I need to do that. I'm inclined to go with a fee only.

[Announcer]

Yeah.

[Joy]

I mean, towards retirement.

[Jill]

Yeah. I mean, I think it might be worth it for you. I'm happy to, you know, talk to you a little bit about maybe kind of people that you might want to consider. I'm just going to state the obvious for everyone listening. Joy came in with what she wanted to do. It is not my job to convince you otherwise. You know what the actual. How can I put this? Like, you know what the. The upside and the downside is of all of this.

[Joy]

Right.

[Jill]

Okay. So if you know that and it feels more comfortable for you to manage the. Manage the process by assuming a mortgage, knowing that it's costly, knowing that you're kind of, you know, you're kind of just buying yourself a pathway to own this house free and clear, and you'll be okay. If you do understand that, then I think it's really important to keep the mortgage really in a tight bound so you kind of keep yourself very accountable so that every year you're forced, and I mean forced. I would. Do not pull money out of the roth. Don't pull any more money out of the brokerage account. You're forcing yourself to pull money out of that traditional account. That $3 million is going to keep growing, so it's going to create this problem. So if we can manage that over the next 10 years before. Before you turn 75 and have to start taking money out, then I think you're in great shape. Then I think it'll work. So if that's the way you want to roll, that's cool. And, you know, wouldn't be my way, but I'm a wimp and I don't like illiquid assets. That's really what you are more comfortable with, real estate. And for me, I'm like. I like my liquidity. So it's like we both are. We're two sides of a coin.

[Joy]

Yeah. I mean, funny, my son is advocating for doing exactly what you're recommending, not taking out a mortgage. So he'll be happy to hear this.

[Jill]

Well, you're going to do what you want to do, whether, you know, screw me and your son. You know, we understand that. I'm sure he also understands that, so. But I get it. I get the difference. You know, it's funny. I was talking to. I was with a bunch of really smart financial planners a couple weeks back, and we were talking. These are the amazing women who have Done just like, they grown businesses. And we were talking about a case where we were just sort of talking about different cases and how people, like, emotionally deal with things. And so this one advisor said to me, you know, it's a fascinating thing, she says, you know, I have a client, and they make a lot of money. And she said, they're like, you know, 40s, 50. So, like, think Bay Area tech people. They got. They make a lot of money. They have a bunch of money.

[Joy]

And.

[Jill]

And the wife is very insecure about the financial market. She gets really nervous, even though they've done incredibly well. And so she's like, I want to buy a fixer upper Bay area, one of these crazy Victorian houses. Right. So it will cost a ton of money, and, you know, it'll cost a ton of money to actually own it outright. Okay. But it will be, at the end of it, an $8 million place. Okay. And she kind of wants to, like, pull all the money out of. Not the all, let's say, 60% of the money out of the investment accounts to do it. And the advisor's kind of like, I get just knowing her personality, I think she'll just be more comfortable having a big asset, this house that she owns free and clear, even though she's like, I don't think this makes the most financial sense, but I understand the emotion behind it. And if this is what my client wants to do, I'm going to figure out the best way to do it. And that's kind of what I'm hearing in you, Joy. It's like, here's what I want to do. And I think that you got a decent game plan one way or the other. It really. I mean, you're in great shape. You got a ton of assets, and, you know, I think that the only thing you need to really consider is, like, the. The method to get there.

[Joy]

Right, Right.

[Jill]

So, I mean, you're ready to go, girl.

[Joy]

Go.

[Jill]

Go get yourself a new place, and you have your estate docs done.

[Joy]

Yeah. Yes.

[Jill]

Okay. And you're sure your kids want you to move closer, right? I'm just kidding. I'm sure they do.

[Joy]

Yeah. Close, but not too close.

[Jill]

Mom, how about, like, not five minutes away, like, not 45, but not 5. 15. Maybe. 15 is the right amount. Well, thanks for getting in touch with us. Hey, if you, like, Joy, are considering moving closer to your family, whether it's your aging parents or your young kids having kids and all that, get in touch with us. It's such an interesting idea and how you manage it and how you get there is really dependent on what's going on in your life. So get in touch with us. Go to jillonmoney.com click the contact us button. Write us a note if you'd like to join us on the air live. Check the box. Mark will do everything else. Don't forget, you can subscribe to this show as well as our other broadcast Money Moves on the Odyssey app or wherever you find your favorite podcast. Maybe it's Apple, maybe it's Spotify. Spotify what ads you can find us. It's great. And of course, lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.

[Announcer]

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[Sally Helm]

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