Loading summary
Jill Schlesinger
You know, I always say to make smart financial decisions.
Commercial Voice
So let me ask you this.
Jill Schlesinger
What exactly is that old car in your driveway doing for you right now? Seriously, is it an extra car? Nobody drives anymore.
Commercial Voice
Maybe it doesn't run.
Jill Schlesinger
Do you keep saying you'll sell it
Commercial Voice
one weekend and suddenly it's been two years?
Jill Schlesinger
Meanwhile, it's taking up space, costing you money, and slowly becoming part of the landscape. Here's the easy solution. Donate it to Cars for Kids. And yes, it's that Cars for Kids. The the one with the jingle you absolutely know already. 1877 Cars for Kids here's why people love to donate to Cars for Kids. It's ridiculously simple. You go to carsforkids.org Jill that's cars with a K. Answer a few simple questions and you're done. They'll come pick up the vehicle for free, tow it away, handle the paperwork, and you'll receive a tax deductible receipt.
Commercial Voice
Done.
Jill Schlesinger
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. Hey gang.
Commercial Voice
You know, I used to think the hardest part of healthcare was getting the appointment. Turns out it's just the beginning. Waiting on those referrals, dealing with insurance approvals, trying to interpret test results, and then somehow making sure every doctor's on the same page. That's why I was so happy to learn about Solace. It's a platform that connects you with a dedicated healthcare advocate who helps you navigate all of that in a real hands on way. A Solace advocate can find the right doctors and schedule appointments, fight denied insurance claims to help get care approved and make sure your doctors stay coordinated so nothing gets lost in the shuffle. They can also join your appointments, remotely translate medical language into plain English, and break down test results and treatment plans so you actually understand your career. These are experienced healthcare professionals, often nurses with years of experience, and they've already helped tens of thousands of people get better care. Go to SolisHealth.com to see if you qualify. It takes about two minutes and it's covered by insurance. That's Solish. Health.com must be 18 or older. Advocates do not provide medical or legal advice.
Jill Schlesinger
Welcome to the Jill on Money Show. It's the Thursday, June 4th, and we are Here answering your financial questions. And it could be anything that's on your mind financially. So it could be something about retirement, it might be about switching jobs, it might be, what are you doing with your bust out kid who just moved home after graduating from college? I mean, I didn't mean bust out, I just mean dealing with that. It could be dealing with your aging parents, which I just think is, you know, because I have an aging mother, it becomes a very big topic of conversation among me and my friends. And, and so whatever it is that's going on in your financial life, I really would love it if you could get in touch with us because we're here to help you out. We're just gonna meet you wherever you are. We don't need to go back into the past. We just wanna know where you are today. Go to our website, jillonmoney.com. click the Contact Us button, write us a note if you wanna join us live. Check the box, Mark. We'll do everything else. And while you're on the website, check out all of the great content that lives there. And, and don't forget to subscribe to our new show. It's called Money Moves. And thank you, all of you who have told us that there are other programs named Money Moves. I didn't name the show, but all that being said, there's nothing called Money Moves with Jill Schlesinger, I'll tell you that much. How about that, Mark? Is that the distinguishing characteristic of like 25 shows with the same name?
Mark
So far? From what I'm seeing, yeah, that would be it.
Jill Schlesinger
You know, I told you I went to high school with another woman, girl then named Jill Schlesinger. It was oddly confusing. It was a very bad thing to have two kids named Jill Schlesinger in the same class, but it happened anyway. There's only one Jill Schlesinger who hosts financial stuff and that's me. So go to our website, check out our content. We'd love for you to make sure that you are subscribing to the Money Moves podcast and show. Are you a YouTuber? Everybody is, Mark. Except me. You have YouTube TV, don't you, Mark?
Mark
I did a long time ago. And then they dropped Tennis channel and then I dropped them.
Jill Schlesinger
Oh, because I'm thinking now of abandoning ship. You know, I abandoned cable, as everyone knows. I told this long, torturous story about how I was practically crying on the phone to like, let me cancel my cable subscription. I'm thinking about doing it in the city. I might be the last person in New York City to cut the cord.
Mark
It's possible you're no longer going to save money, but it's just more convenient. But yeah, it costs probably almost as much as cable now.
Jill Schlesinger
Well, what else do I mean? I guess so, because I'm going to. Well, maybe not. Because when my employer, Paramount buys Warner Brothers Discovery, I'll have HBO Max. That gets floated into my Paramount app. That'd be kind of cool. Maybe I'll wait for that. And I do get a discount on that, since it is Paramount. All right, let's stop talking about us. Hey, gang. If you have a question Again, Jill, on money.com, click the contact Us button. Let's go talk to Audrey, who joins us from North Carolina. Hi, Audrey. How are you?
Audrey
I'm well, thank you.
Jill Schlesinger
Tell us what's going on and how we can help you out.
Audrey
So I am completely burned out with my current job.
Jill Schlesinger
Dude, I want to tell you something. You're like the voice of a generation. Meaning I cannot tell you how many people are coming on the program right now. It feels like Mark. It feels like now, I don't know, six years after the pandemic. This is the moment. How old are you, Audrey?
Audrey
I'm 60.
Jill Schlesinger
Perfect. I understand it. Burnt out. Why do you think you're burnt out? Do you think that the job changed? Do you think you change? You think the industry changed? What happened?
Audrey
It's. For me, it's simply the workload. It's just awful. I'm doing the. I'm expected to do the work of maybe one and a half people, and it's just. It's just too much. I have no work life balance.
Jill Schlesinger
Oh, I'm so sorry for you. I just. It's so funny because you know how everybody's saying, like, oh, AI is going to take my job. I don't think that's exactly what's happening right now. I think that in this weird period where employers are like, I don't want to have a big headcount. But people like Audrey, we're just going to pile the work on. She knows how to do the work. We're just going to pile more on. She'll get more productive, and then by the time she's exhausted, we'll have AI to help out. That's my working thesis. But let's get back to you. How are we going to give you a work life balance? Are you thinking about, like, pulling the plug right now?
Audrey
Yes.
Jill Schlesinger
Okay. Are you married? Single? Partnered?
Audrey
Married.
Jill Schlesinger
How old is your spouse?
Audrey
65.
Jill Schlesinger
Working. Still or not?
Audrey
Yes, working.
Jill Schlesinger
Okay. Plans to keep working or will, like, if you, if you say I'm done, is Spousy going to be like, you're not doing this without me?
Audrey
Yes. He wants to throw in the towel as well.
Jill Schlesinger
I like that. I like that. Okay, so let's talk about the money you guys have saved and let's figure out how you can. Let's just figure out the way you can do this most efficiently. So tell us about the money you have saved first and then we'll go into spouse.
Audrey
Well, I have it all together. Is that okay?
Jill Schlesinger
All right, sure. Perfect. Give it to us.
Audrey
So for cash and CDs, we have 120,000.
Jill Schlesinger
Okay.
Audrey
Work. Roth is 134,000. Okay, we have a brokerage with 51,000.
Jill Schlesinger
Okay.
Audrey
Traditional IRA, 1,648,000.
Jill Schlesinger
Can I, can I just give you a 1,000,650? I'm going to give you two rounds. Let's round up. Okay. It's a bull market. I'm rounding up. What's next?
Audrey
Roth IRA for 223,000. Okay, I have an HSA with 23,000. I have some ESPP and RSUs.
Jill Schlesinger
That's what happens. Wait a second. What happens if you quit tomorrow? What happens to those? What's the value?
Audrey
Well, those, those are vested fully.
Jill Schlesinger
Oh, okay, so RSU is vested. What is it?
Audrey
40,000.
Jill Schlesinger
And employee stock purchase?
Audrey
Well, I have it all together.
Jill Schlesinger
Okay, so that's the four or 40s total.
Audrey
Total, yes.
Jill Schlesinger
Okay, gotcha. Okay. Is that it for those, you know, investment stuff?
Audrey
Well, yeah, but I have to. I have a question about. I have two stupid annuities. They're awful.
Jill Schlesinger
That's so good, Mark. Just clip that for me. I have two awful annuities. Okay, let's do stupid annuity number one.
Audrey
Number one is a non qualified indexed annuity.
Jill Schlesinger
Uh huh. How much is in there?
Audrey
The accumulation value as of September of 2025 is $231,000.
Jill Schlesinger
Okay, so everyone listening. Non qualified. Not a retirement plan. After tax dollar went in, the money that went in, whatever it's grown to beyond what you put into the contract. If you just blow out of the contract, essentially is taxable income, it's not capital gain. So that's just an important thing for everyone to know. Okay, so when did you buy stupid annuity number one?
Audrey
So they're 12 year annuities.
Jill Schlesinger
12 years.
Audrey
And they're up this coming September.
Jill Schlesinger
I love your timing. Okay, great. Okay, now let's go to stupid annuity number two.
Audrey
Number two is an inherited IRA indexed annuity.
Jill Schlesinger
Oh, God. Yeah, I. You know that this was. Someone crammed this down your throat.
Audrey
Okay.
Jill Schlesinger
How much is in there?
Audrey
105,000.
Jill Schlesinger
Okay, so this is from 11 and a half years ago, I presume?
Audrey
Yes.
Jill Schlesinger
Okay. We're going to get out of them anyway, so that's perfect. Fantastic. Okay, anything else in the balance sheet here? Anything else, like stuff you own? We'll get to the house in a second, but just. Okay, so how about your house?
Audrey
So our house is valued about $500,000.
Jill Schlesinger
Mortgage.
Audrey
Mortgage is $1800 a month.
Jill Schlesinger
What's outstanding? What remains on that mortgage, do you think?
Audrey
102,000.
Jill Schlesinger
Interest rate?
Audrey
2.875.
Jill Schlesinger
Stop it. Any other real estate besides the primary?
Audrey
No.
Jill Schlesinger
Okay. Do you want to stay in this home?
Audrey
Yes.
Jill Schlesinger
I mean, everybody's moving to North Carolina when they retire. You're already there, so good job on you. Okay. Any pension income that you might be due, either of you, I will get
Audrey
a whole whopping $430 a month.
Jill Schlesinger
All right, what should we spend that on? Is that. I'm going to call that your beverage allowance, which is you can have a lot of coffee and you can have a lot of booze for 30. That seems like reasonable. Okay, what about Social Security? What's the game plan?
Audrey
So my husband would like to take it now.
Jill Schlesinger
How's his health?
Audrey
His physical health is not good.
Jill Schlesinger
Oh, okay. That. That's a huge issue. Okay, what's his Social Security benefit right now?
Audrey
So his Social Security benefit at 65 to 70.
Jill Schlesinger
Say that one more time.
Audrey
I'm sorry, 2273.
Jill Schlesinger
2273. Okay, great. And for you, what about health insurance for you? Like, let's say you quit tomorrow. We have five years before Medicare. Do you have an idea about health insurance?
Audrey
Well, what I would do is I would do Cobra for 18 months.
Jill Schlesinger
Yeah.
Audrey
And then I guess I would have to go out to the marketplace.
Jill Schlesinger
Okay. All right. So we're going to deal with that when we talk about how much money you spend.
Audrey
Okay? Right.
Jill Schlesinger
Okay. So what's your Social Security benefit at what age? Let's do 67. What the heck?
Audrey
67 is 3624.
Jill Schlesinger
Yes. Yes, my queen. How's your health?
Audrey
Good.
Jill Schlesinger
All right. What do you happen to have? 70? Just out of curiosity, 70 is 45.
Audrey
72.
Jill Schlesinger
Ready for your hard question? Get ready, Audrey. Take a deep breath.
Audrey
Okay.
Jill Schlesinger
How much money do you guys spend?
Audrey
So I have a budget and I kind of cushioned in healthcare like cobra, the cost of sure. Insurance. And I put A little extra in for like travel. So I'm going to say 11,000.
Jill Schlesinger
11,000amonth. Okay. Seems reasonable. Okay. Do you have grown kids? Any kids?
Audrey
We have four grown kids that are launched.
Jill Schlesinger
Four kids?
Audrey
Well, between us, yeah.
Jill Schlesinger
Wow. Oh, second marriage.
Audrey
Yes.
Jill Schlesinger
Oh, okay. All launched. That's so nice. Congratulations. Thank you. How'd you guys do that? It was kind of lucky, huh?
Audrey
I guess we were just. Yeah, probably luck had a lot to do with it.
Jill Schlesinger
I would imagine. So right now, how much do each of you earn?
Audrey
So my salary is 124,000 and my husband's salary is 52,000. He was laid off from his job quite some time ago. And then being 65, it was very hard. Yeah, it was very hard for him to find, I bet, a job. So he's just. This is just a contract job for him.
Jill Schlesinger
Okay. But so what he's working, money's coming in, but you know, he's kind of spent is what it sounds like.
Audrey
Right.
Jill Schlesinger
Okay. I'm sort of thinking it goes something like this. What's your loyalty to like giving notice and when you want to do this, like really, what. What's your expectation about the year ahead?
Audrey
I'm thinking maybe September time frame.
Jill Schlesinger
Right. Like you're thinking what I'm thinking maybe like when those annuities are ready to be annuitized.
Audrey
Correct.
Jill Schlesinger
Uh huh. Great. That's what I'm thinking too.
Audrey
Okay.
Jill Schlesinger
Okay. The inherited ira, I know that there is no. You don't have to take the money out. I understand that when those annuities are up, these 12 years are up. What you could potentially do is annuitize the stupid annuity number one, which is the non qualified one. You could roll over the inherit because you don't have to take that money out. You. It'll take a little bit out every year, but you could roll it over into a more efficient. That's what I would say.
Commercial Voice 2
You could.
Jill Schlesinger
I'm not saying you have to, but we know that there's more money in the 231. Right. Because we in the non qualified. So what I would think is that when you say that you're 60, you say we try to annuitize this first one and I think you want to try to get the money out over. I'm just trying to look at your time horizon here. Do we want to get that money out like a little bit at a time till 67 or 70? How do you. I'm trying to figure out which way we're going to lean on this.
Audrey
Well, unfortunately I Have these and I don't really know a lot about them, but the fees are so high.
Jill Schlesinger
Yeah, but once you annuitize, the whole thing goes like, it's much better. So you'd rather just get out as quickly as possible.
Audrey
Yes.
Jill Schlesinger
Okay, so if we annuitize both of them, what happens is, you know, there's, there's going to be still taxable income because what's going to happen is the inherited IRA that's all going to be taxed. So we don't want to necessarily, we don't want to pull it out all tomorrow. You want to dribble it out. We really do. So maybe what we try to do is like you would want to get a quote on what it would be to annuitize each of these over a five year period.
Audrey
Okay.
Jill Schlesinger
All right. And I think that what happens is I'm not 100% sure about this, but I have to look at this contract. It could be that you could essentially say the fees might go down once you start annuitizing. On the other hand, if you just want out, there is also a case to be made where you say, okay, here's what you're going to do. You're going to take, come September, you stop working and we're going to take 50 grand out of the stupid annuity. Number one, the non qualified, just going to take 50 out. Then you're going to wait till the beginning of the calendar year and then you're going to take the whole inherited IRA and just going to take it out and you're going to pay tax on it. Could be $105,000 of taxable income, but you're going to use your, then you're basically saying, all I'm saying to you is that like, I don't know if I want to take the whole tax hit in one calendar year.
Audrey
Okay.
Jill Schlesinger
And then you can probably, I would you, would you want to find out about the first annuity is what is the tax liability? In other words, if I pulled the whole, if I did 50 grand out. Let's, let's in fact ask them this. What would happen if, if I pulled out the whole $231,000, you know, in December of this year, what's a tax liability? We know what the tax liability for the other one is. It's 105,000, that's all going to be taxable. But we want to use these two chunks of money for you guys to live on for the first couple of years.
Audrey
So the initial, the initial premium is 161,000 for the annuity.
Jill Schlesinger
161.
Audrey
Okay.
Jill Schlesinger
So I mean, it just shows you how bad these products are. Meaning that like, you know, because you're not going to have a huge tax liability. So 161,000. So it's 70 grand of taxable. So we have essentially about $175,000 of taxable income between the two annuities. Okay. So if you guys both stopped working at the end of this year, you may basically be able to just like delay it. You can take, don't take all the money out this year. Wait, okay, you can take some money out of the, the first one, but like I said, like 50 grand. Then in the, you know, January 2nd, get all the money out of both of them. Make sure you understand that you're going to have taxable liability, but it's going to be very similar to your current income.
Audrey
Right.
Jill Schlesinger
Okay. Now you're going to use that money to live on. So this gets us to. When's your birthday?
Audrey
October.
Jill Schlesinger
October. Okay. So you'll be 61.
Audrey
Yes.
Jill Schlesinger
Okay. So now we have, you have, we have you set for at least a year basically with that money. Now if you can kind of, you get the money out of the annuities, you live on that. Now you're 62 years old. Now we have to get you from 62 to 67. And then from the, for those five years, you start pulling money out of the traditional assets. Just to be clear, your husband's first, yours second.
Audrey
Okay, okay.
Jill Schlesinger
Because he's in poor health, we are going to get some assistance because you're going to get a couple grand from his Social Security. So that's going to start coming in. Now what then happens is you'll have his Social Security, your Social Security. And then, you know, once that kicks in at age 70, you're pulling less money out of your traditional account. I guess there's only, the only other thing is that if something comes up like, like a health issue for your husband, there could be a little pressure on you. Meaning, like if you had to dip into a lot of this money because you needed care in your home or something, you know, like, something like that. But I think we can deal. I don't, I don't think you're going to be able to afford long term care insurance. And I don't think it really makes sense at this point to do it. And he has bad health, so it's kind of like that's already done. But I just want you to be aware that if something were to Happen to him, you might not be able to spend $11,000 a month.
Audrey
Okay.
Jill Schlesinger
Or you're going to spend $11,000AMONTH. But part of that's going to be for care for him.
Audrey
Okay?
Jill Schlesinger
Fair?
Audrey
Fair. Yes. All right.
Jill Schlesinger
Um, what else do I need to ask you? How about estate planning? Do you have your wills and your powers of attorney and your health care proxies? Done.
Audrey
We have all of that done, yes.
Jill Schlesinger
Are you feeling okay? Are you really? Are you ready to do this? That's what I want to know.
Audrey
So what I was going to add is I really want to work part time.
Jill Schlesinger
You do? That makes this all. That's a no brainer.
Audrey
I don't want to not work. I think my brain would turn to mush. So my first thing I would ask my current employer, could I do that? But you know, it's a person and a half job. It's not a. So I don't know what will happen there. But even if that doesn't work out,
Jill Schlesinger
you can figure something out. You can hustle a little is what you're saying.
Audrey
Yeah. Yeah.
Jill Schlesinger
And when you work time, what do you think you would. You could earn like a couple, three grand a month?
Audrey
Yeah, maybe. Yeah.
Jill Schlesinger
Okay, that helps. If you're willing to work part time, then. That's amazing.
Audrey
Yeah.
Jill Schlesinger
That'll make it work. And I'll tell you what I do. I would. I kind of. So who sold you these annuities? Some insurance guy? Gal? Yes.
Audrey
Yes.
Jill Schlesinger
Okay. And the big chunk of money of those traditional assets, is somebody managing that or are you managing it?
Audrey
I'm in Vanguard. So we have advised. We have advisor.
Jill Schlesinger
Okay. One thing you could do with that advisor is just have them kind of pick apart the annuity and make sure that we're make. We are accounting for all the tax liability. That might be something that's worth. Because you have an advisor there. It's great. Just another set of eyes on this that's looking at the documents so we're not missing anything. Okay.
Audrey
Okay. I do have one more question.
Jill Schlesinger
Anything.
Audrey
The inherited ira, indexed annuity. Could I just roll that into Vanguard?
Jill Schlesinger
You can. It would be another inherited ira. They'd open it up for you. You could do that almost immediately and. And it would be, you know, under the same rules, but again, just make sure you have all the original, like here's the date of death certificate so they don't treat it as an inherited IRA that you inherited like last year. Okay, but you can do that. Absolutely.
Audrey
So do you recommend that I don't
Jill Schlesinger
Know, I sort of feel like you're going to want the money, but, you know, we'll see. But you could do that for sure. It depends. Kind of like, well, you know, if you're. All of a sudden you say, well, I said two or three grand, but I'm, you know, I actually went to my. My company, and they're like, how's five grand a month? You know what I mean? Like, if you don't really need it right now, you can roll it over.
Audrey
Okay.
Jill Schlesinger
Right. So it's. Some of this depends on, like, what you need.
Audrey
Okay.
Jill Schlesinger
Audrey, you're in very good shape. You guys have done a lovely, lovely job managing this. And if you need anything else, just give us a jingle. How's that?
Audrey
Thank you. I love your show.
Jill Schlesinger
You're very sweet. We love you. Thank goodness, Mark. We have the best audience. If you are like, Audrey and her husband, like, I'm tired. I don't know. Like, something's going on out there in the workplace. People are getting piles and piles of work, and they're exhausted. And I hear that. So if that's you or if it's more like you're in the early part of your career and just don't like where things are going and you want to make a different decision going forward, give us a Holler. Go to jillonmoney.com, click the contact us button, write us a note, and if you want to come on the air, check the box. Don't forget to subscribe to. Our free weekly newsletter comes out tomorrow on Fridays. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Hey, try to put your hands metaphorically on someone's back. Give someone a boost, would ya? Change your work, change your wealth, change your life. Thanks for listening, and we'll talk to you tomorrow.
Commercial Voice 3
Are you really buying a car online on Autotrader right now?
Commercial Voice 2
Really?
Commercial Voice 3
At a playground?
Commercial Voice 2
Yeah, really. Look at these listings from dealers.
Commercial Voice 3
Wow, your search can really get that specific.
Commercial Voice 2
Really?
Commercial Voice 3
And you just put in your info and boom, car's in your budget.
Commercial Voice 2
Mom needs a second.
Commercial Voice 3
Honey, you can really have it delivered.
Commercial Voice 2
Really? Or I can pick it up at the dealership. One sec, sweetie. Mommy's buying a car.
Commercial Voice
Mommy, look.
Commercial Voice 3
I think your kid is walking up the slide.
Jill Schlesinger
Kyle. Again?
Commercial Voice 2
Really? Autotrader? Buy your car online? Really?
Commercial Voice
Hi, this is Jill Schlesinger, CBS News business analyst, certified financial planner and the host of the Jill on Money podcast. Beginning, middle, or end of the year, it's always a great time to take
Jill Schlesinger
control of your financial life and the
Commercial Voice
Jill on Money podcast is here to help your questions make it possible for me to provide unconventional and entertaining insights
Jill Schlesinger
on your money and, more importantly, on your life.
Commercial Voice
Follow and listen to Jill on Money wherever you get your podcasts.
Episode Title: In Our 60s and Considering Retirement
Date: June 4, 2026
Host: Jill Schlesinger, CFP®
Guest: Audrey (Listener Call-In from North Carolina)
In this episode, Jill Schlesinger responds to a listener, Audrey, who calls in for guidance as she and her husband, both in their 60s, weigh the decision to retire. Audrey is experiencing burnout from her demanding job and wants to know if—and how—retirement can work financially, especially with health issues and complicated financial products in the mix. Jill provides a clear-eyed review of Audrey’s assets, walks through distribution strategies, and offers insight on pensions, Social Security, and annuity management. The episode provides practical retirement planning advice for listeners approaching or considering retirement, especially couples with blended families and modest pensions.
Timestamps: [05:21]–[06:59]
Timestamps: [07:14]–[10:23]
Timestamps: [08:19]–[09:44], [14:07]–[16:49]
Timestamps: [10:20]–[11:51]
Timestamps: [11:42]–[12:28]
Timestamps: [13:15]–[17:46]
Timestamps: [17:54]–[19:31]
Timestamps: [19:33]–[21:06]
Timestamps: [19:48]–[20:26]
Timestamps: [20:26]–[21:05]
Jill’s practical tone and supportive manner provide reassurance:
"Audrey, you're in very good shape. You guys have done a lovely, lovely job managing this. And if you need anything else, just give us a jingle. How's that?" [21:59]
Actionable wisdom: Retirement decisions should sync with financial product maturities, tax brackets, health, and life goals. A trusted advisor can add value by checking details and paperwork.
For listeners facing similar crossroads, reach out to Jill’s team via jillonmoney.com for personalized advice. And remember, even in transitions, a flexible approach and a willingness to adapt—like considering part-time work—can make all the difference.
"Change your work, change your wealth, change your life." – Jill Schlesinger [22:56]