Navigating Single Life in My 50s

Summary

Podcast Summary: Navigating Single Life in My 50s

Podcast Information:

• Title: Jill on Money with Jill Schlesinger
• Host/Author: Audacy
• Description: Host Jill Schlesinger, CFP®, delves into often uncomfortable and controversial financial and investing topics, stripping away the jargon to focus on what’s crucial for listeners. Each week, Jill engages with callers and guests to uncover surprising insights and provide actionable advice to help listeners make informed financial decisions.
• Episode: Navigating Single Life in My 50s
• Release Date: July 30, 2025

---

Introduction

In the "Navigating Single Life in My 50s" episode of Jill on Money, host Jill Schlesinger addresses the unique financial challenges faced by single individuals in their fifties. The episode features a detailed conversation with Jean from Texas, who seeks advice on long-term care planning amidst concerns about future financial stability and singlehood.

Key Topics Discussed

1. Long-Term Care Insurance Concerns:

   • Jean's Situation: Jean, in her early fifties with no children and being single, is contemplating the need for long-term care insurance. Her concerns stem from her father's experience with hospice care and managing an aging mother.

   • Host’s Insight: Jill Schlesinger explains the complexities of long-term care insurance, highlighting the high costs and limited providers. She mentions that many insurance companies have exited the long-term care market due to mispriced risks, making such coverage expensive and often not worthwhile for individuals like Jean.

     Jill Schlesinger [04:21]: "Care is more expensive and costs keep going up, people are living longer... There aren't a lot of providers. It's really expensive, and it's hard for these companies to quantify that risk."

2. Jean’s Financial Status:

   • Income and Savings: Jean earns approximately $110,000 annually, has a pension promising $5,080 monthly starting at age 62, and diligently maxes out her Roth 403B. Her savings include a Roth IRA ($163,000), a brokerage account ($125,000), certificates of deposit (CDs) totaling $22,000, and savings of $4,000.

   • Expenses: Currently, Jean's monthly expenses are around $3,000.

     Jean [05:54]: "About 110."

     Jill Schlesinger [07:12]: "Do you have any other money set aside?"
     Jean [07:37]: "I have a Roth at 162,800... brokerage about 125."

3. Retirement Planning:

   • Pension Details: Jean's pension will provide $5,080 monthly in five years without cost-of-living adjustments (COLA).

   • Social Security: Jean anticipates receiving $3,367 monthly at age 67 and $4,300 at age 74.

     Jean [10:11]: "It depends. So far, I look at the longevity of both sides of the house here..."

     Jill Schlesinger [10:26]: "Do you know what your Social Security benefit looks like either at 67 or 70?"

4. Evaluation of Long-Term Care Needs:

   • Projection and Analysis: Jill and her co-host Mark analyze Jean’s financials, considering inflation and future expenses. They conclude that Jean’s anticipated pension and Social Security will sufficiently cover her expenses, even factoring in potential long-term care costs.

   • Decision Against Long-Term Care Insurance: Given Jean's robust financial standing and single status, both Jill and Mark advise against purchasing long-term care insurance, as her existing assets and income streams provide ample coverage.

     Jill Schlesinger [15:02]: "I'm leaning towards no."

     Mark [15:04]: "Yeah, absolutely. Just given the guaranteed income that's going to be coming in and the low expenses right now... I don't see a need."

5. Handling Retirement Incentives and Lump-Sum Payments:

   • Jean’s Concern: Jean expresses anxiety over the tax implications of a lump-sum retirement incentive.

   • Advice Provided: Jill advises investing the lump sum in a brokerage account and maintaining disciplined savings and investment strategies to manage future financial needs without panicking over immediate tax burdens.

     Jill Schlesinger [18:07]: "What do you think? Give me an idea of what you think your lump sum might be."

     Jean [17:41]: "Let's do 80."

     Jill Schlesinger [17:16]: "There is no magical way to not pay tax on that. But what you can do is... put in the brokerage account. Keep putting your money away."

Insights and Conclusions

• Financial Independence: Jean’s comprehensive financial planning, including her pension, savings, and investments, positions her securely for retirement, minimizing the immediate need for additional insurance products like long-term care insurance.

• Investment Strategies: Maximizing contributions to retirement accounts, such as the Roth 403B and Roth IRA, and maintaining diversified investment portfolios can lead to significant asset growth through compounding, easing future financial pressures.

  Mark [12:05]: "She's got a million dollar in assets."

  Jill Schlesinger [12:36]: "That's how compounding works, gang. It's incredible."

• Long-Term Care Planning: For single individuals with substantial financial resources, long-term care insurance may not offer additional benefits, whereas for couples or those with dependents, it might be a prudent consideration.

• Tax Management: Handling lump-sum payments thoughtfully by reinvesting and avoiding impulsive financial decisions can mitigate the stress associated with tax obligations.

Notable Quotes with Timestamps

• On the Rising Costs of Care:

  Jill Schlesinger [04:21]: "Care is more expensive and costs keep going up, people are living longer... There aren't a lot of providers. It's really expensive, and it's hard for these companies to quantify that risk."

• On Financial Security:

  Jill Schlesinger [08:08]: "You're putting money away in your brokerage, in your savings. Like, you're definitely saving money."

• On Long-Term Financial Planning:

  Mark [12:05]: "She's got a million dollar in assets."

• On Compounding:

  Jill Schlesinger [12:36]: "That's how compounding works, gang. It's incredible. It really is."

Conclusion

This episode of Jill on Money provides a comprehensive analysis of financial planning for single individuals in their fifties, emphasizing the importance of robust savings, retirement planning, and strategic investment. Jean’s scenario illustrates that with diligent financial management, the need for additional insurance products like long-term care insurance may be unnecessary. Jill Schlesinger and her co-host Mark offer practical advice, empowering listeners to assess their own financial situations and make informed decisions for a secure and comfortable retirement.

For personalized financial advice or to discuss your unique situation, listeners are encouraged to visit jillonmoney.com and reach out through the "Contact Us" button.

Transcript

[Jill Schlesinger]

Need contract help for those workload peaks and backlog projects. You're not alone. Robert half found that 67% of companies surveyed said they will increase their use of contract talent. That's why their recruiters leverage their experience and use award winning AI to quickly find the skilled candidates you want. Learn about their specialized talent in finance, accounting, technology, marketing, legal and administrative support at Robert Half. They know talent. Visit roberthalf.com talent today wouldn't it be.

[Mark]

Great to manage your portfolio on one platform? Well, now you can trade all in one place on Robinhood. That means you can trade individual stocks and ETFs and also buy and sell crypto using seriously powerful and intuitive tools at one of the lowest costs on average without needing to manage multiple apps. Robinhood makes withdrawing and depositing crypto seamless. Send crypto to your Robinhood account or send crypto from your Robinhood account to other wallets with without deposit or withdrawal fees from Robinhood Trade all in one place. Get started now on Robinhood Trading. Crypto involves significant risk. Crypto trading is offered through an account with Robinhood Crypto llc. Robinhood Crypto is licensed to engage in virtual currency business activity by the New York State Department of Financial Services. Crypto held through Robinhood Crypto is not FDIC insured or SIPC protected Network fees may apply to crypto transfers. Crypto transfers may not be available to all customers. Investing involves risk, including loss of principal. Securities trading is offered through an account with Robinhood Financial LLC member sipc, a registered broker dealer.

[Jill Schlesinger]

Welcome to the Jill on Money Show. It's Wednesday, July 30th and we are here trying to help you make better or maybe just more considered financial decisions if there's something going on in your life, some big issue, some small issue. Maybe you're trying to figure out, hey, am I on track to retire? Maybe you're trying to say, hey, I hate my job. I really want a new job. Is it okay for me to take a job where I'm making less money? Is it something about maybe real estate? Because you know when you have a big chunk of money that's locked in your home, right? It is very difficult sometimes to come up with a game plan to extract that equity. Oh, and by the way, I did just get a note from one of these smarty pants economists who said that when the labor market when you look at something in the labor market, it's really interesting. Remember back during like that Covid boom where oh my God, we need workers and there was a big premium if you Switch jobs when you know, when the labor market is hot, it's like you get a lot of money for switching your job. Right. And today, I just want you to be clear, wage growth for job switchers is lower than wage growth for job stayers. That means that the labor market is cooling down because people are not just moving around. That said, maybe you can afford to take less money. Maybe that's okay for you. If that feels like something that is potentially in your, your sight line, give us a shout. Go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the air live, check the box. Mark will do everything else. Hey, while you're on the website, don't forget to sign up for the free weekly newsletter comes out every Friday. So it's a great way to kind of figure out if you missed anything during the week. So check that out. Okay? Today we are talking to Jean who joins us from the Lone Star State of Texas. Hi Jean, how are you?

[Jean]

I'm good. How are you?

[Jill Schlesinger]

Great. What's going on? How can we help you out?

[Jean]

So I've been listening for a long time and I've said since a year ago, I'm going to write in and do this. And it really is easy. I didn't believe how easy. And the reply was before I could turn around.

[Jill Schlesinger]

Yes, Mark, that's right. Mark's the best. So what prompted the outbound reach to us?

[Jean]

Thinking I'm in my early 50s, thinking about long term care. Had a father that helped through hospice and an aging mother. And now I'm thinking about, is that me in 18 years, I have no children, I'm single. And I'm thinking reaching out to these companies to assess costs for long term care. And it's pretty outrageous.

[Jill Schlesinger]

Yes. Oh my God, Gene, I'm not, I'm not kidding when I say that. Like I, I remember looking at long term care when I was a financial advisor, which is now basically 20 years ago. Okay, so it's been a long time. But I remember we would look for policies and you could find there were a lot of insurance companies that were in the long term care business. But what ended up happening was that a lot of those companies mispriced the risk of long term care for the same reason that you are looking at long term care right now. Those companies got out of the business of long term care. So what we know is, and you're experiencing this firsthand, that care is more expensive and costs keep Going up, people are living longer and women especially. It is true. This is a more of a woman issue. Statistically, we tend to be sicker in our lives and men die sooner. So that's the difference between morbidity and mortality. And it's the real crux of the matter with long term care. There aren't a lot of providers. It's really expensive and, and it's hard for these companies to quantify that risk. So Jean, let's figure out actually if you need long term care insurance because it is expensive. But I know your experience with your parents makes you very sensitive to it, right?

[Jean]

Yes, very.

[Jill Schlesinger]

I got you. Okay, so you're in your early 50s, you say no kids, you're single. Are you working full time?

[Jean]

Yes.

[Jill Schlesinger]

Okay. How much do you earn?

[Jean]

About 110.

[Jill Schlesinger]

Great. And do you have a retirement plan through work?

[Jean]

Yes, I do.

[Jill Schlesinger]

What is in that retirement plan in terms of the amount, not the actual assets or the investments?

[Jean]

Oh, well, I. The number I wrote down is the future monthly amount which would be.

[Jill Schlesinger]

Oh, wait, do you have a. You have a pension?

[Jean]

Yes.

[Jill Schlesinger]

Oh, okay. So the pension, what will your pension be?

[Jean]

$5,080.

[Jill Schlesinger]

$5,080 a month. @ what age does that start, Jean?

[Jean]

It's in five years. But I'm holding out for a retirement incentive that. Okay, it's going to be a lump sum.

[Jill Schlesinger]

So that would mean you'd have to hold on till age 62, right?

[Jean]

Yes.

[Jill Schlesinger]

Okay, so we got 10 years to go and it'll be about $5,000 a month. Now with that pension, is there a cost of living adjustment? Is there an inflation increase every year?

[Jean]

There was two years ago and that had never been done. So it's pretty rare.

[Jill Schlesinger]

Okay. All right. Now do you save money besides the pension? Do you put money away in any sort of deferred comp or an IRA or a Roth IRA?

[Jean]

A Roth 403B. I'm Max every year.

[Jill Schlesinger]

Oh my gosh. How much is in there?

[Jean]

About 102. But I feel like I started late. I should have done that.

[Jill Schlesinger]

Yeah, but you're maxing out now, so that's great. Fantastic. Any other money that you have set aside, savings wise or investing or other old. Anything else that's that I would include with how I would think about you financing long term care if you needed it.

[Jean]

So I have a Roth at 162,800.

[Jill Schlesinger]

And then I'm going to call it 163. Don't be mad. Okay. Roth 163. Okay.

[Jean]

And then I have brokerage, about 125.

[Jill Schlesinger]

Great, that's fantastic. Money in the bank, savings, checking, CDs, anything boring like that out there.

[Jean]

Yeah, about 22, just in a CD.

[Jill Schlesinger]

Okay.

[Jean]

And then savings is about 4,000.

[Jill Schlesinger]

Now you. You make 110,000. You said you max out your Roth 403B, right?

[Jean]

Yeah.

[Jill Schlesinger]

You're putting money away in your brokerage, in your savings. Like, you're definitely saving money. Do you have an idea how much your expenses are right now?

[Jean]

3,000.

[Jill Schlesinger]

And that's what I am, really. Okay, so essentially what you're saying to me is, hey, if. If you. If you never had. If you never got sick a day in your life, God willing. Right. That 5,000amonth is going to cover your needs. Not even a question, even before you claim Social Security. Right.

[Jean]

I'm relieved to hear that from an expert.

[Jill Schlesinger]

Yeah. I mean, it does it, you know, if your expenses are three grand a month now, I mean, in ten years, when you. I'm going to just. I'm pretending you're 52. You said early 50s. And 10 years, when you're 62, you've got this $5,000 a month. Those expenses grow over the next 10 years, you know, with, you know, there is inflation applied, but it's not going to be more. But then the money you get from your pension should basically cover your expenses, and that doesn't even include Social Security. How is your health currently?

[Jean]

I'm good. I'm just a former athlete, so my knees, my hip kind of situation.

[Jill Schlesinger]

Dude, me too. Me.

[Jean]

It's going to be a robot.

[Jill Schlesinger]

Mm, me too. I'm with you. What sport did you play? What's your aging athleticism?

[Jean]

Anything at the gym? If it didn't hurt, then it wasn't worth doing.

[Jill Schlesinger]

Oh, my God. This is how, you know what I say. I have a very dear friend of mine, she played squash in college. I played soccer in lacrosse. And I say to her, I said, you know all of our friends who sat in the dorm and like, smoked pot and partied their butts off for four years, their bodies are in great shape. We are breaking down, like day by day breaking down. Okay, so you're in good shape. Are you planning to take Social Security at 67? Is that the game plan for you?

[Jean]

It depends. So far, I look at the longevity of my both sides of the house here, and yeah, I think I'm going to surpass have a mother. She's about to turn 85, and she's sharp. Nothing passes her. Her memory's sharp.

[Jill Schlesinger]

Do you know what your Social Security benefit looks like either at 67 or 70?

[Jean]

I do. 3,367. And then at 74,300.

[Jill Schlesinger]

I mean, there's no problems here, really. No problems. When you retire, what happens for you, health care wise?

[Jean]

We've got an option that it's. We pay out of pocket, 200 to continue.

[Jill Schlesinger]

That's it. Oh, you're in good shape. Okay. This is great. Okay, now let's play devil's advocate for a second, okay? You look at your life and you say, this is. I've got the money I need. Jill says I'm cool. Let's just even pretend that by, you know, the time you're 67, you've got like 8,300, $8,400 a month in expenses. Hey, Mark, can you just do me a quick calculation of $3,000 a month? Can you inflate that for. For 15 years at a 3.5% inflation rate? So $3,000 a month in 15 years is going to be in. What is the dollar amount in 15 years future value?

[Mark]

Roughly like 5100.

[Jill Schlesinger]

Okay, so 5100. So now here's what you can think about, Gene. Let's pretend your pension doesn't really move. But it will a little bit. But let's just say you've got $5,100 a month from your pension. Then you had $3,300 a month from your Social Security. And your future expenses are about 5,100 or $5,000 a month. You got plenty of money to cover you.

[Mark]

Oh, yeah. Oh, yeah. She's got a million dollar in assets.

[Jill Schlesinger]

What do you mean a million dollars in assets? How did you figure that?

[Mark]

What she has right now, what does she have? 300.

[Jill Schlesinger]

Oh, I see. I see what you did. Okay, so I was like, what do you mean? So, so then what Mark also did was he took the $100,000 in the Roth 403, the 163 in the Roth IRA, the 125 in the brokerage account. He took that, you know, 380, $390,000. And then what he did was he presumed that it earned some modest rate of return.

[Mark]

And I assume that she continues to.

[Jill Schlesinger]

Max out and that you max out until you're 62 and all of a sudden there's a million dollars also in the kitty. Okay. Yeah.

[Jean]

Those people.

[Jill Schlesinger]

Yeah, you are, you're a millionaire. Sorry, babe.

[Mark]

No, a jillionaire.

[Jill Schlesinger]

You're a jillionaire. As we like to say on this show. So that's how compounding works, gang. It's incredible. It really is. Right. So one of the things that you're. But why you're calling is, well, what happens if I need long term care? So there's something that's interesting in your situation. Okay, let's say that you did need care. Okay. You own a home.

[Jean]

No.

[Jill Schlesinger]

You rent?

[Jean]

Yes. I prefer that because it's just me.

[Jill Schlesinger]

Okay.

[Jean]

Yeah.

[Jill Schlesinger]

Okay, so how much is your rent?

[Jean]

575Amonth.

[Jill Schlesinger]

575Amonth. Okay. So what would happen if you needed care? Well, there's two different things. One is like, do I need care in my apartment? Do I need to pay someone to come in and take care of me? Do I need to be in a facility? Let's pretend you needed to go to a facility because that's usually the bigger expense. Right? Okay. So you say, you know, do you have siblings?

[Jean]

Yes. Older brother.

[Jill Schlesinger]

Older brother. I don't want to be a burden to my older brother. Nieces or nephews or anything like that. What would happen? Okay, you'd go into a facility and it would cost money. Right. But you would still be getting that $8,000 a month. You would be able to pay for care to be in a facility of some sort. Now, it may be that you'd have to spend down some of your million dollars at the time, but it's highly unlikely you would spend all of it down. And it's just you. What if you did spend it all down? What if, if you spent it all down and you could then basically ride out whatever long term care would come about. Now, you know, of course, given the current changes to Medicaid, I can't say this with like absolute certainty, but there will be some sort of program for Medicaid where we have nursing care. It'll probably be tested in some way, so you'll probably have to spend down a bunch of your money, but chances are you're going to be covered. So the question that you come on the program asking, do I need long term care insurance, should you buy that coverage? I'm leaning towards no. Mark, are you also leaning towards no?

[Mark]

Yeah, absolutely. Just given the guaranteed income that's going to be coming in and the low expenses right now, and the fact that it's just. It's just her by herself. Yeah, I don't see a need.

[Jill Schlesinger]

You know, when we would think about long term care, Jean would be if you were partnered. Okay. And now let's just pretend it's the exact same Scenario and you're like, I have a wife, I have a husband, I have someone who's relying on me. And it's the exact same scenario where the two of you as a couple have, you know, instead of maybe 8,000amonth, maybe it's $10,000 a month. Okay. And it's a million dollars that you will have saved if one person were to get sick and go through the million dollars that could leave the surviving and healthy spouse in a precarious situation. And that's when we start to think, maybe there's some sort of insurance product. It may not even be long term care. Maybe it is a hybrid product where there's some long term care, we take some of the money and we pop it into some sort of an annuity or life insurance product that has a long term care rider. And that might be something worth considering. But because it's just you, I don't think you need to do this. I'm just wondering about your mom. So tell me, you said she's sharp as a tack. Is she living on her own?

[Jean]

She actually lives with my brother. But she could live alone. She just doesn't drive. We know that. We're gonna get her one of those self driving cars. Then she.

[Jill Schlesinger]

Oh yes. Did your father's passing leave her with some money or not really.

[Jean]

Yes, my father's pension and she's got Social Security, so she's, she's independent, she's okay.

[Jill Schlesinger]

That's great. I don't think you have anything to worry about here. I really don't. I think that, you know, listen, if you call me back in a month and say I hate my job and I have a new boss and I'm done, that might be a different, that's a different situation. But given the facts that you have laid out, seems to me that buying long term care insurance would be an extra expense that is probably not worth it for you.

[Jean]

I have one more question, so.

[Jill Schlesinger]

Okay.

[Jean]

The incentive retirement incentive.

[Jill Schlesinger]

Yeah, tell me about that.

[Jean]

That they're like, man, Uncle Sam took a majority of it. And I was thinking, since I like to listen to these podcasts, I'm like, you should have had an ira.

[Jill Schlesinger]

You should.

[Jean]

I was thinking to myself, I was trying to be you. I'm like, if I were chill, I would have recommended. But I researched it and I'm like, well, if once I'm there, I'm going to have the deer in the headlight. Look, what do I do? What's the proper way to take care of that money?

[Jill Schlesinger]

Well, it depends the money that is given as part of a retirement incentive is often given in a lump sum. Right? And what they're complaining about with everybody. I love when people complain that they make money. What they're complaining about is, I got this chunk of money, and, holy smokes, I was taxed on it. So what do you think? Give me an idea of what you think your lump sum might be. Just give us a ballpark and I'll give you the example.

[Jean]

Let's do 80.

[Jill Schlesinger]

Okay? So you make 110. All right. Right now, which means as a single filer, you pay a bunch of tax at the 12% rate and a bunch of tax at the 22% rate. If we now assume you were to get 100, if you were, then on top of your 110, get an $80,000 extra incentive bonus. Now, that 80,000 is on top of the 110,000, and it means that you've crept up into a tax bracket of 24% on that extra money. So what they're probably reacting to is, Uncle Sam took a quarter of my money. No kidding. You just had a big chunk of money as instead of paying tax along the way for another year, you just got it in one lump sum, and that's what you're paying tax on. You cannot make that money go away, by the way. There is no magical way to not pay tax on that. But what you can do is whatever your tax is for you, if you got that 80 grand, and you'll, you know, hopefully we'll be here, God willing, in 10 years. When you're doing this, if you got the 80 grand, you give us a holler and you say, okay, well, my 80 is now 55. What do I do? And I say, put in the brokerage account. Keep putting your money away. Keep investing it. Don't mess with it. That's wonderful. Good for you. That's it. Unless you needed a chunk of money up front for something. Unless you said, well, I've cleared 55,000, but I need a new car. Okay, so buy a new car with it. But it's a. It's a good problem to have, Gene. It really is. That's what I. That's why I laugh about these people. Oh, I have to pay so much tax. Okay, let's pretend you don't have to pay tax and you don't get the money either. Is that better? I don't think so. Do you? That's not good. All right, Gene from the Lone Star State, we are letting you go. Thank you for joining us. Hey, if you gang are thinking about long term care insurance or, you know, you've gone through a tough time with your aging parents, this is what happens is that we go through these periods with our own parents or grandparents and it kind of puts you on alert. Maybe you need it, maybe you don't. It kind of depends. Long term care is tough, right? It's a really thorny issue. So get in touch with us. And of course, if there's anything else going on, get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the air live, just listen to Jean. She said it was very easy. Check that box. Mark will do everything else. While you're on the website, check out our subscription service called Jill on Money Live. That's where you have access to quarterly live webinars, the back catalog, bonus audio and video content, all for 45 bucks. For the next 12 months, you can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.

[Brian]

Hey there, cats and kittens. It's Brian from the commercial break, the mediocre comedy podcast where my best friend Chrissy and I attempt to make sense of the world. We talk about the absurd, the ridiculous and the stuff no one asked for, like Internet weirdos, pickup artists, and why everyone is obsessed with crystals and colonics. It's all got to stop. The show is free, it's frequent, and it's probably not for everyone. You can go to tcbpodcast.com [e-mail] the commercial break, or check out the show wherever you listen to podcasts. We'll see you on the next commercial break. And best to you.