In My 60s and Feeling Concerned

Summary

Jill on Money with Jill Schlesinger

Episode: "In My 60s and Feeling Concerned"

Date: May 13, 2026

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Episode Overview

In this episode, Jill Schlesinger welcomes Susan from New York, a listener in her mid-60s facing classic late-career and early retirement decisions—how to handle the sale of a longtime home, manage pre-tax retirement funds, address credit card debt, navigate upcoming Social Security choices, and search for trustworthy financial advice. As always, Jill offers practical, clear-headed guidance, balancing emotional realities with the financial facts, all in her signature direct and empathetic style.

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Key Discussion Points & Insights

1. Susan’s Situation: Life & Finances

• Background:
  • Susan (65) and her husband (76), living in New York.
  • Susan is semi-retired, seeking freelance work; husband is retired and collecting Social Security.
  • Planning to sell their home and rent.
• Assets:
  • House with $600,000 net equity after expenses and debts.
  • Pre-tax retirement accounts: Susan ($1,300,000), husband ($188,000).
  • Brokerage account: $40,000–$50,000.
  • Little to no cash savings.
• Income & Expenses:
  • Husband receives $1,708/month from Social Security (after Medicare).
  • No pension income.
  • Renting will cost at least $5,000/month; additional expenses bring the monthly need to ~$10,000.
  • Credit card debt: $100,000 (to be paid off immediately after house sale).
• Other plans:
  • Susan hopes to delay Social Security for a higher benefit.
  • Anticipates a potential future inheritance ("several hundred thousand").
  • Wants to return to freelance work (~$2,000 per week potential, though uncertain).
  • Estate plan (wills and power of attorney) is in place.

2. Selling the Home: Strategy & Emotional Aspects

• Jill’s Guidance:
  • Strongly supports selling the home to free up liquidity for living expenses, especially given the high real estate appreciation ("House prices are up 50% in the last six years.").
  • Recognizes the emotional difficulty:
    • “It's hard, it's emotional. But the reality is we don't need it anymore...” (17:28)
  • Recommends renting as a transitional step:
    • “We want to go somewhere, catch our breath, consider what the options are.” (08:01, Susan)

3. Managing Cash Flow & Pre-tax Accounts

• Short-term (Before Susan Returns to Work):

  • Use proceeds from husband’s retirement account to cover living expenses, especially given his age and the mandatory Required Minimum Distributions (RMDs).
  • Move those funds into the brokerage account for greater flexibility.
  • Suspend withdrawals from Susan’s account if possible:
    • “Don't pull from yours, pull from his. … He’s older. We know we have to get the money out.” (13:13)

• Credit Card Payoff:

  • Priority is using home equity to clear $100,000 credit card debt immediately upon sale. (09:57)

• Income Bridge:

  • If Susan returns to work with even $60,000/year, it’s a “game changer” for the budget.
    • “Even if it were $60,000, not $100,000, that would be… a game changer for you.” (10:52)

4. Social Security: Timing & Maximizing Benefit

• Husband: Already claiming; no pension.
• Susan:
  • Planning to delay until full retirement age or age 70:
    • At 67: $3,280/month
    • At 70: $4,066/month
  • Jill encourages waiting, if possible:
    • “Everyone would agree that if you could wait till 70, that would be a great thing for you to do.” (18:50)
  • Emphasizes longevity (mother in her 90s):
    • “That's why I want to wait.” (11:20, Susan)

5. Roth Conversions: Not a Priority

• Susan's Question: Whether to consider Roth conversions.
• Jill’s Response:
  • Advises against using limited cash for Roth conversions in this scenario:
    • “You're done. Forget it. You're going to pull the money out of this account as you need it and you're going to pay tax on it.” (18:03)

6. Finding a Financial Advisor

• Susan: Has been "burned" before, wary of picking an advisor at random.
• Jill: Offers offline help with potential referrals, underscores importance of fee-based, fiduciary advice.

7. Estate Planning

• Susan: Wills and power of attorney are in place, no trusts.
• Jill: Recommends holding off on helping adult kids financially until Susan and her husband’s future is secure:
  • “We need to take care of you in the future. … We got to secure you guys first.” (18:50)

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Notable Quotes & Memorable Moments

• On Anxiety and Big Financial Decisions:

  • “First of all, Susan, deep breath. I hear the anxiety in your voice.” (05:11, Jill)

• On Selling the Home:

  • “Usually we’re like, sell the house. And people are like, no, we love it.” (17:20, Jill)
  • “It's hard, it's emotional. But the reality is we don't need it anymore and it's in great condition.” (17:28, Susan)

• On Work as Security:

  • “Even if it were $60,000... that's a game changer for you, I got to be honest.” (10:52, Jill)

• On Social Security Strategy:

  • “That's why I want to wait [to claim Social Security]. Especially if you’re healthy and you’ve got some longevity.” (11:20, Susan, with Jill’s reinforcement)

• On Managing Withdrawals:

  • “Don't pull from yours, pull from his. His is the one I'm more interested in. He's older. We know we have to get the money out.” (13:13, Jill)

• On Roth Conversions:

  • “You're done. Forget it. You're going to pull the money out of this account as you need it and you're going to pay tax on it.” (18:03, Jill)

• On Supporting Kids:

  • “If you want to do something like, okay, here's when you can be okay, I want to help my kids out. Sure. But we got to secure you guys first.” (18:50, Jill)

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Timestamps for Key Segments

• [04:31] Susan joins the show, begins explaining situation
• [05:36] Age and family status
• [06:07] Social Security and income review
• [08:25] Deliberating rent cost and move plans
• [09:46] Discussing credit card debt source and resolutions
• [10:34] Susan’s work prospects and budget impact
• [11:14] Social Security benefit figures by age
• [12:57] Expecting inheritance; support from mother
• [13:13] Withdrawal strategies for retirement accounts
• [15:40] Choosing and trusting a financial advisor
• [17:28] Emotional side of selling the house
• [18:03] Roth conversions and cash priorities
• [18:25] Estate planning status and kid support discussion

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Tone and Style

Jill is, as ever, deeply practical but compassionate—firm on numbers but gentle on anxieties. The conversation is warm, sometimes humorous, and always focused on actionable next steps, directly addressing listeners’ questions without jargon or judgment.

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Summary Flow & Action Steps

• Jill expertly walks Susan through confronting and calming her main financial worries, laying out a practical, actionable plan:
  • Sell the home to free up cash and clear debts.
  • Use proceeds and husband’s IRA withdrawal to bridge income until Social Security and/or employment boost budgets.
  • Wait on Susan’s Social Security for maximum long-term benefit.
  • Avoid Roth conversions for now; use resources for immediate living needs.
  • Seek a fee-based fiduciary advisor for ongoing support.
  • Secure their own financial future before considering gifts to their children.

This conversation candidly addresses the fears and technicalities of late-in-life transitions—showing that while the numbers matter, so do the emotions and hopes driving the decisions.

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For anyone considering retirement housing changes, balancing pre-tax assets, or wrestling with the timing of Social Security and work, this episode delivers both empathy and clarity—classic Jill on Money.

Transcript

[A]

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[B]

I'm good. How are you? Jill?

[A]

We are fantastic. What can we do for you?

[B]

I'm reaching out to you because we are in the process of considering, you know, what our next step is in terms of our lives and retirement. And we are currently in a home that we know we can sell and NET probably about 600,000 from the equity. My investments are all pre tax in my investment accounts. So I feel sort of like a deer in headlights right now. I feel like okay to make a move and would love your advice on how to find the right financial advisor in the past and just planning for the future.

[A]

Amazing. First of all, Susan, deep breath. I hear the anxiety in your voice. This is now How I've become my mother. Full on. Because my mother's like, I hate texting. I can't tell how you're really feeling. Which is kind of true. Right? You're a parent. You just said that before we came on the air. So I know that, like it's true. You hear this in someone's voice. So let's talk a little bit about kind of where you stand. Susan, how old are you?

[B]

I'm 65.

[A]

And you said a we. So you have a spouse?

[B]

Yes, I do.

[A]

And how old?

[B]

76.

[A]

76. Both are retired.

[B]

I'm semi. I'm just in between jobs right now. I've done some freelance and I'm looking to get back into it. But with this current situation, I'd like to kind of settle this and then move forward.

[A]

Okay, fair enough. So what are the sources of your income right now? Are you. He's got. He's receiving Social Security, right?

[B]

Yes, he is.

[A]

And what's his Social Security benefit?

[B]

It's after his Medicare payments. It's 1708.

[A]

Okay, great. And does he receive any pension?

[B]

No, he does not.

[A]

Okay. And are you receiving Social Security benefits or have you waited?

[B]

No, my. My real goal is to wait quite a while.

[A]

So now that's all the income. You don't have any rental property or anything like that? Right. So that we just have one Social Security check coming in at 1708amonth, right?

[B]

Correct.

[A]

Okay, got it. Pre tax retirement. Tell us what's going on there. What have you saved?

[B]

Mine is about 1 million 300.

[A]

Fantastic.

[B]

Sorry. And his is about 188.

[A]

Part of the way that you are supporting yourselves is in addition to his Social Security and your part time work, he's been pulling out of his retirement account. How much has he pulled out?

[B]

Oh, that's a really good question. I'm not sure. At least 20 to 25,000 for last year.

[A]

Okay. Okay. Let's presume you never work again just so we can like run some numbers here. So in addition to the 1,300,000 and the 188,000, do you have any other savings?

[B]

Just a regular brokerage account. And y. That is worth about 40 to 50,000.

[A]

Okay. And do you have safe money somewhere, like cash accounts?

[B]

Not really, no. That's where.

[A]

Okay, that's. Everything's pretty much in the brokerage. You've got grown kids, right?

[B]

Yes.

[A]

Okay, so we're not worrying about that. Presuming you sell this house and you grab that 600 grand, we still.

[B]

You have to.

[A]

Unfortunately you have to live somewhere. So what does that look like for you?

[B]

We are looking at rentals for the time being. We want to go somewhere, hold our breath. Not hold her breath. Catch our breath.

[A]

Yes.

[B]

Consider what the options are.

[A]

Great. Would you leave New York because you're one of those people who's like, oh, I hate the cold. We just talked to somebody who's like, I hate the cold, or like, I hate the taxes, or you want to hang around New York and pay up in taxes like the rest of us.

[B]

Yeah, we probably will hang around here for a while.

[A]

Okay. If you rented, what would you have to pay in rent?

[B]

Oh, at least 5,000. We've. We've already been checking it out. It's probably not going to be cheaper at the beginning.

[A]

I understand. But you'll have the money. But you'll have. You'll have all the money. What about your other spending? So in addition to. Let's just pretend it's five grand a month, what other spending are you doing? So what do we need to really think about for your total needs?

[B]

Yeah, we've considered that. I would say between an additional 4 to $5,000 more.

[A]

Okay, so 5 grant. So we were. Look, we're targeting 10 grand a month in need. Okay. All right. Now you're in good health.

[B]

Yes.

[A]

You're planning to claim Social Security at 70? Is that what I'm hearing?

[B]

I'd love to wait till then. It certainly would pay for me to do that. Or 67.

[A]

What's the 70 number, just out of curiosity?

[B]

Number is 4,066amonth.

[A]

When you said net 600, you did include paying taxes, like, do. Have you made more than a half a million dollars in gains on this house?

[B]

Yeah. We've spoken to our accountant, and he feels pretty confident. We've done a lot of work on the house.

[A]

Great. Great. Hooray. Yeah. Yeah. I mean, it sounds like it. Right? So that's. That's wonderful. Is there any other debt besides whatever is existing on a mortgage or anything else out there?

[B]

Well, I'd say on both of our credit cards, we need about $100,000 to just clear the deck.

[A]

When you said net 600, was that clearing the deck of the credit cards?

[B]

Yes, actually.

[A]

Okay. Okay. So the credit card is 100 grand. So you're really going to net 700, but you're going to pay off the credit card as soon as you sell, right?

[B]

Yes.

[A]

Did that credit card debt come about for some particular reason?

[B]

It's really the situation we've been in since There isn't a lot of cash coming in. You know, most of it for me is groceries and things of that sort. It's really frivolous stuff. So.

[A]

Okay, right now, if you were to go back to work, what would the amount of money be that you think you could bring in? And I would say be conservative on that.

[B]

Yes, I agree. I would say probably about $2,000 a week, and that's because I've been doing freelance in the past.

[A]

2000 a week, that's awesome.

[B]

Yeah.

[A]

Holy smokes. You could bring in 100 grand a year.

[B]

If I get solid work, yes. That's why I really want to get back to that, because I enjoy it.

[A]

Okay. Even if it were 60 grand, not 100 grand, I mean, that would be. That's a game changer for you, I got to be honest with you. So I would shoot like. Like, if you could do 60 grand, you're in good shape. Okay, so we know that in the interim, before you claim. What was your. I'm sorry, I forgot to ask one other piece of information. Social Security at your age. 67.

[B]

What was that, 3,280amonth.

[A]

Oh, it's a big difference, isn't it?

[B]

That's why I want to wait.

[A]

Yeah. Especially if you. You're healthy and you've got some longevity. Right.

[B]

I have a mom in her 90s, so.

[A]

Oh, and do you have to take care of her? Do you have to. Is that something that's like, you need to.

[B]

No, thankfully. She was one of those moms who worked full time.

[A]

Okay.

[B]

And I mean, I help her. I take her to appointments sometimes, but sure, sure.

[A]

Like daughterly things. Not like, financial things.

[B]

Self sufficient financially, thankfully.

[A]

Oh, my God. Amazing. Will you inherit some money when she passes away, do you think?

[B]

Yes.

[A]

A lot or a little?

[B]

Several hundred thousand, I believe.

[A]

Okay. Okay. That's a little buffer, right? The excitement. Jill, in your voice. Oh, my God, this is a problem. I've got to tell you something. I told you, Mark, what my mother said when I was on the air, and I evidently smiled when I was talking about my father's death on the air. And my mom's like, why did you smile when you were talking about Daddy? I didn't know I did, but I may have. I just want to say, because I was thinking about this period of time when. When my sister and I were dealing with my father's illness and we were like, share. We had this Google document that, like, took over the world. Like, we had every single, like, medication, every doctor's meeting Everything. So I was smiling kind of thinking about how crazy we were about it. But it did help anyway. Okay, I digress. So several hundred thousand dollars. Okay, here is what it sounds like. You sell the house, you clear the credit card. Great, fantastic. Until you make that 60 grand again. Did you make any, did you earn any money this year?

[B]

This year? 20. 26 or 20.

[A]

Yeah. Have you? Six. Have you earned any? No. And so right now the source of your income is just his Social Security and whatever you pay from his retirement account. Right.

[B]

And I've started pulling a little bit from mine as well.

[A]

Don't pull from yours, pull from his. His is the one I'm more interested in. He's older. We know we have to get the money out. You're gonna sell this house. You probably had that nice property tax, that salt deduction. You got the 40 grand this year, so that's good for last year. Your tax bracket is going to be pretty low until you get start working again. If you said to the accountant, look, we want to take all the money out of my husband's retirement account, all of it's going to come out at the 22% bracket. The 22% bracket ends at 211. 211. 4. You take all the money out, you pay it at 22%, just get it out and then you can live on that money. That money would simply go from your husband's account into the brokerage account and he would just fill it up just to give you a nice base. Then stop pulling from your account. You, you can live on that money. And frankly if the 188, I mean because you're in New York, so you are going to pay real tax. So let's just say that, you know, you end up with 1:25. That's being overly conservative on taxes. You end up with 125. There's your 10 grand a month that you can live on. Okay, right there. Next year we're going to find out whether or not you're really working enough so that you don't have to take any money out of your account. Because if you have that, we get the money. We know his money has to come out anyway, so you might as well just get it out while you don't have a lot of income. If all of a sudden your part time income is now $60,000 and he's got his Social Security, you pull a little bit of money out of your retirement account to fund the difference, you're okay, you're fine and you don't even have to. In fact, I, I would suggest that maybe when you sell the house, we use that. I mean the only reason I would put.

[B]

That's one of the reasons we were thinking about.

[A]

Yeah, I would, I would. I mean the thing is like let's not pull from your account at all. Let's hold on off on that. I was going to say we want, we want to get money out of your account, but you know what, forget it. We have plenty of time because you're young. So let's do this. Sell the house, get the money out of his account. Just because we know it's going to come out. You put that money aside and then the, the $600,000 that comes out of the house proceeds goes into the brokerage account. Do you work with an advisor or are you managing this yourself?

[B]

No, we've been doing it ourselves because I was sort of burned in the past and that was one of the questions I had for you. You know, I've gone on websites as you recommended for a fee based financial professional. But it's just, I want to just pick someone out of the sky. So I didn't know if you had any.

[A]

Well, we'll talk about this offline. I may have somebody that I know where you live, so I might know somebody who could help you out. So I think that what you would want to do is use that 600 grand plus your whatever years, your brokerage. I'm not even including the money we're pulling out of his account because that money's going to be spent. Okay? We're going to spend that money. That's what you're going to live on. We need 10 grand a month. You only need that for a couple of years and that's your Runway to see. Hey, can I make some extra money or not from my part time work? And you may still. And maybe you just keep stretching it out. Like even if you made 30 grand this year, 60 grand next year, it's just some money that comes in, you can tap into the brokerage account to pay and then by the time you're 70, you know, you still have $5,700 a month coming in at that time. So we do need to get more money out. But you will have the ability at that point, I hope it's 70, but you can take some money out very slowly from your retirement account because you know you're going to have to take it out anyway. So maybe we start using that a little bit to fund the difference if you need it, if you don't need it. And your part time income is amazing and you're just kicking butt and you're making 100 grand a year from age 66 to 72. You can just leave everything as is. It's fine.

[B]

Wow.

[A]

It's fine. But I think selling the house is a great idea because usually we're like, sell the house. And people are like, no, we love it.

[B]

It's hard, it's emotional. But the reality is we don't need it anymore and it's in great condition. So, you know, it's just finding a rental that's honestly the challenge now.

[A]

Yes, of course. I mean, and, and again, it's like we. When you live in a, if you live in a place where there is high cost of living and high housing costs, it is hard to find. But you would go, I assume you could go into like the neighboring area with the not so good schools so that you can hopefully get a somewhat cheaper rent. That's what I'm guessing.

[B]

But what about Roth? Like, is there any. No, nothing.

[A]

You're done. Forget it. You're going to pull the money out of this account as you need it and you're going to pay tax on it. That's how you're going to do it. You're not going to use your cash to, to, you're not going to burn up your cash to do a Roth conversion. What about your. Okay, let's do a few other things. What about your estate planning? Got it.

[B]

We do, we have our wills, not trust. Wills and power.

[A]

Good.

[B]

That.

[A]

Perfect.

[B]

I do want to figure out, and I guess maybe that's another conversation, you know, planning kids in the future.

[A]

No, come on, you have done such a good job. I know you have. I can tell from your voice. But what I'm going to tell you is that we need to take care of you in the future. If you want to do something like, okay, here's when you can be okay. I want to help my kids out. Sure. But we got to secure you guys first.

[B]

I agree. I agree.

[A]

Okay, that's good. So, Susan, go sell your house. Take a deep breath. Take the money out of his retirement account. Pay the tax that's due, use that money to live on. Take the money that the net proceeds from the house, roll it into the brokerage account and then you'll be happy to hopefully work with somebody who can at least walk you through what your options are. I think everyone would agree that if you could wait till 70, that would be a great thing for you to do. Okay, thank you. All right, Mark, are you satisfied with this? I feel like this is a good one because many times we're trying to tell people, just sell your house. We need the liquidity here as a case in point. Point. So if you are in that situation, you got a bunch of equity in your house. House prices are up 50% in the last six years. Maybe you want to extract that equity and do something with it. Then get in touch with us. Go to jillonmoney.com, click the contact us button. Of course, let us know you'd like to come on the air by checking the box. Then Mark will do everything else. Check out all the content that lives on the website. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Please do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. Hey, gang, you know I've changed my tune on Bitcoin. Meaning I know that a lot of you are bitcoin curious, and that's okay. I know you're not putting all of your money into this. If you've been curious about bitcoin, but haven't made the jump yet. Cash App makes it easy. You can set up automatic purchases with zero fees or buy larger amounts also with zero fees. Start small or go bigger. It's designed to be simple either way. So whether you're just learning or ready to try it out, it's built to meet you where you are for a limited time. New customers can get $10 added to their balance. Just use code CASHAPP10 when you sign up. And don't forget this part. Send at least $5 to a friend in the first two weeks. Terms apply. Cash App is a financial services platform, not a bank. Banking services provided by Cash App's bank partners. Bitcoin services provided by Block Inc. Brand for additional information, see the Bitcoin disclosures at Cash App slash Legal Podcast

[C]

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