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Jill Schlesinger
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Jill Schlesinger
Welcome to the Jill on Money Show. It's Tuesday, October 28th and we are here answering your financial questions. And Mark, I just want to bring you on because we're sort of relieved here at Jill on Moneyland because as we were recording Yesterday, not the 27th, but really yesterday, a week ago, the Amazon Web services system kind of blew a hole through a bunch of different websites. And so there we were recording happy go, lucky that we are. And at the end of the day, Mark's like, I can't get any of the things. We literally were doing like two and a half hours of recording. Mark's like, I have nothing. What happened? Mark? And it was there.
Mark
Yeah, little did we know that we would be impacted by this AWS outage. But yeah, the program that we use, I mean they had a lot of problems. A lot of problems. I'm just glad that we record in advance and I didn't need something that had to go out like that day because we would have been screwed.
Jill Schlesinger
We totally would have been. And we are very much recording in advance most of the time. Not like in the old days, Mark, in when we were doing the pandemic, you know, every day at the end of the close that day and waiting till the bitter end. Sometimes we do that, but thankfully not too often. But I want to thank Mark, as always, for being the very best executive producer in the world. So before we joined today and recording, I said, are we, are we going to be doing five hours of recording today? He said, thankfully, no. So, hey, were you impacted by that outage? Are you freaking out? I did a segment on CBS Mornings and I thought it was going to be like a dumb segment because I was like, oh, big deal. Was out for three hours. Meanwhile, when I was affected, of course I was like, oh, my God, big deal. But a lot of people were kind of freaked out because Robin Hood went down. And you know what I have to say to that? If you're such an active trader that you cannot, like, deal with three hours of being incapable of executing a trade, go open another account someplace. Really, it's not that hard. One good reminder that I will say about this, there are certain documents that you should have dupes of both in the cloud, electronic and physical. Can I just give that public service, Mark? I think it's important to have estate documents, both digital and hard copies, wills, durable powers of attorney, healthcare, proxies, trusts, and I think all of your insurance documents, you should have both electronic as well as physical. You know, I remember when those Palisades fires were raging and people were like, my insurance documents were in a quote unquote, fireproof safe, which was not fireproof because it's kind of hard when you have like a complete meltdown of everything. So I think that's good. So remember that, gang. Digital and hard copies, estate documents and insurance documents. Okay, that's it. That's your public service. If you've got a financial question, you want to know what documents you need to keep and have handy, of course. Give us a holler. Good. Jillonmoney.com Click the contact us button. Write us a note. If you'd like to join us live on the air. Check the box. Mark again, the best executive producer in the world. He'll do everything else. Today we are joined by Scott, who is listening to us in Delaware. What's going on, Scott? What can we do for you?
Scott
I'm 66. My wife is 61. I retired four years ago and my wife is still working part time. And I just had some questions about how I'm doing and I have some debt I'd like to clear up. A couple other questions. Social Security.
Jill Schlesinger
You drill through it. So tell us the story of your life. You retired four years ago. Are you happy? Retired?
Scott
Oh, yeah.
Jill Schlesinger
Love it. And. But you make Your wife still work? Why is that? Because she wants to.
Scott
To support my lifestyle.
Jill Schlesinger
I like that. I like that you admit that. I just. We need a few extra bucks for me.
Scott
She likes it.
Jill Schlesinger
That's good. Is she. Is she or you claiming a pension? No, no pension.
Scott
Neither one.
Jill Schlesinger
And part time income for your wife is how much money?
Scott
Last year it was 38,000.
Jill Schlesinger
All right, great. And so will she continue doing this for a while or she want to quit? What's her time horizon?
Scott
She wants to continue. She's got to cut back her hours to three days a week starting in January.
Jill Schlesinger
And what will that mean for income for her?
Scott
Probably looking at closer to 30,000.
Jill Schlesinger
And how are you guys supporting yourself? Not just on 30,000. So what is the other source of income for you?
Scott
My retirement 401k IRA.
Jill Schlesinger
So what's in your 401k right now?
Scott
So in my pre tax I have 1.85 million.
Jill Schlesinger
Okay, great.
Scott
Then $213,000 in a Roth, 68,000 in an HSA. Then my wife has $112,000 in an IRA.
Jill Schlesinger
And is that pre tax?
Scott
Yes.
Jill Schlesinger
Okay, so your Roth, you got one Roth and her pre tax IRA.
Scott
Okay, and then she has another small IRA for 47,000.
Jill Schlesinger
Okay, you mentioned a brokerage account. So tell me about that.
Scott
Probably one of the mistakes I made. Yes, I spent most of that down in the first two years.
Jill Schlesinger
Okay, all right, what about just plain.
Scott
Old just in savings? I have probably about 10,000. And then I have a home equity line for about a hundred thousand.
Jill Schlesinger
How much is your housework?
Scott
About 570.
Jill Schlesinger
And is there a first mortgage or just the home equity?
Scott
First mortgage is 355.
Jill Schlesinger
What's the interest rate on that one, Scott?
Scott
2.85.
Jill Schlesinger
And the home equity? Just give me the amount again.
Scott
Well, the actual credit line is 100,000.
Jill Schlesinger
What's outstanding for you?
Scott
12.
Jill Schlesinger
What's the interest rate on that right now?
Scott
7.75.
Jill Schlesinger
Oh, that'll catch your attention, right?
Scott
Yeah, that's the highest.
Jill Schlesinger
Any other debt besides the mortgage and the home equity line of credit, Scott?
Scott
I'm still paying for some of my kids student loans. That's a big one.
Jill Schlesinger
Oh boy. Okay, so how many kids do we have? They're grown, right?
Scott
They're grown and launched.
Jill Schlesinger
Okay, not really. Because you're paying for their loans.
Scott
Well, they're paying for some loans too. A lot more than I am.
Jill Schlesinger
All right, what's the outstanding student loan balance?
Scott
85,000.
Jill Schlesinger
And what's, you know, I know they may have lots of different interest rates associated with that. But what is approximate?
Scott
So you know, I, they were parent plus loans, but I refinanced them to private and they're 3.81 and then two car loans.
Jill Schlesinger
Okay, so what's car loan number one?
Scott
That one is 20,000 at 5.24% has two years on it.
Jill Schlesinger
Okay, great. What's the second car loan?
Scott
That's 26,000 at 3.99% and that's good. Three and a half years left.
Jill Schlesinger
Do we have your balance sheet taken care of. We've got your assets, we've got your liabilities. Anything else that we should know about? Any they, you know, you're retired, so you probably live in a very nice place. But any rental property or any other real estate we should know about?
Scott
No.
Jill Schlesinger
So, so as you look ahead, what is your strategy going to be for Social Security?
Scott
Right now originally I was planning on taking it at 70. I'm thinking about taking it my full retirement age, which will be August.
Jill Schlesinger
At age 67, what would that be?
Scott
66. In 10 months, that will be 3451.
Jill Schlesinger
34. What would it be? If you could, we could get you to 70.
Scott
43. 25.
Jill Schlesinger
How's your health?
Scott
Great. Best type of shape I've been in my life.
Jill Schlesinger
Oh my God, amazing. I can't wait to retire. I'll be in such good shape. What about your wife's Social Security? Do you have those numbers?
Scott
Yes.
Jill Schlesinger
So it at 62, you know that. Give me 67 and 70.
Scott
Okay. 67 is 1942.
Jill Schlesinger
Okay.
Scott
And 70 is 24. 32.
Jill Schlesinger
Okay, got it. And she also. Good health, Happy, good jeans. Okay, great. All right, so now we are where we are debt wise, all this stuff. What is it that you. Is there some. Are these loans keeping you up at night?
Scott
No, actually not at all.
Jill Schlesinger
You feel good?
Scott
Yes.
Jill Schlesinger
You know you can afford this, right?
Scott
I just was trying to decide whether to take withdrawals and pay them all up. I mean, I have a possibility of a small inheritance.
Jill Schlesinger
How small?
Scott
Could be anywhere between 150,000 to 300,000.
Jill Schlesinger
And is that like imminent or like someone has already passed away and we're waiting for that or.
Scott
No, it's. My father in law's in assisted living.
Jill Schlesinger
And so but he might spend it if he lives.
Scott
Thankfully he's got long term insurance at least for the first five years. So he's.
Jill Schlesinger
Let's not count on that though. Maybe.
Scott
No, I know Right.
Jill Schlesinger
Okay. But you got this pot of moolah, this, you know, essentially $2 million between your 401k and your wife's IRA. So let's do start looking at that. Now. Your tax bracket must be quite low. Is there any old tax situation that I need to know about or is this just straight up, like if I take $100,000 out of your 401k, it's the hundred thousand. I'm talking about next year. 100,000 plus your wife's 30,000. That's the only income, right?
Scott
Correct.
Jill Schlesinger
All right, I'm good. Mark, do you have any questions for Scott from Delaware?
Mark
Just to spend.
Jill Schlesinger
Aha.
Scott
Well, that was my philosophy.
Jill Schlesinger
Okay, so Scott, ready to come clean? What do you spend? What are your expenses?
Scott
Probably $11,000 a month.
Jill Schlesinger
Okay. Not terrible.
Scott
You know, been trying to take a couple of trips a year.
Jill Schlesinger
Okay.
Scott
This year.
Jill Schlesinger
But you have a lot of stuff to. I mean, you have a lot of payments. So it would be $11,000 a month, but for, you know, inclusive of, sorry, all of those loans. So here are the loans that I'm circling on my little piece of paper here. I want to pay off the home equity line of credit. Right. That I want that one done. I'm thinking also, just because it's not huge money, but I'm also kind of thinking about the first car loan, our five and a quarter percent loan.
Scott
Right.
Jill Schlesinger
All I need is to get 32 grand out of to do that. So I got to take 50 to clear the 32. Right. I got to pay some tax. Right?
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Right.
Jill Schlesinger
So if I took 50 grand out, the other question then is what else do I need to take out? So I got, I have 50 to take care of the loans, but then I need to do your expenses of 11 grand a month. And so the question is whether we take out. Essentially maybe what we do is we take out 200, we make sure you stay in the 22% bracket. Okay. Take out that 200 and the first thing you do is you pay down the home equity line of credit. The second thing you do is you make sure we have money set aside to pay taxes. And then maybe we'll just, we'll chop a year off of your five and a quarter percent. We probably can pay that off also. But if you needed more money, do you have an aversion to jumping into the 24% bracket? What were you up to earning when you were. Before you retired?
Scott
Last few years, about 120.
Jill Schlesinger
Okay. So I think that maybe staying in 22 is probably what we'd want to do. So let's say you took out 200 this year, you took out 200 next year. Now, the thing is, what this will require, Scott, is you being able to tolerate spending down the money in the 401k. Is that going to freak you out?
Scott
No, I don't think so. So that's the 200 includes my regular spending, so really I'm taking it an extra 80,000.
Jill Schlesinger
Correct. I'm, I'm willing to just make sure that you have, you don't have a lot of cash on hand, so I'd like you to have some cash on hand.
Scott
Right.
Jill Schlesinger
So let's say that this year, you know, if you look at the, where your wife comes in at 44, let's say this year you just take 100 out. Okay?
Scott
Right.
Jill Schlesinger
And you've already done most of your spending for the year, but you take 100 out before the end of 20, 25. All right? Now don't go crazy with anything just yet. Just like, just pay off the home equity line of credit. That's it. Then January rolls around, take out another now take out 200 or not even. Like, we'll have to see what she's making. But let's say, you know, 170. Take out 170 and live this year, see how it goes. And then let's see how long she's at three days a week. Because, you know, we could alter the amount if she's like, oh, I'm done. I, you know, then we can go back to 200. But I'd like you guys to stay under the 22% bracket. And if we ate into your 1.85 over the course of, say, you know, three years, I think you're still left with a lot of money. Right. And we leave your wife's IRA alone for now. Let that keep going. We clean up your balance sheet, which is eventually you'll either pay off these car loans, the, the heloc you pay off this year, next year you maybe pay off the first, the five and a quarter percent car loan and then everything else. Maybe I just leave alone. I don't know if there's anything really that we need to accelerate on the debt pay down, whereby I just want you to live on the money that we're pulling out of the 401k. Once we clean up those little bits on the balance sheet and you, you know, wait until 70, claim Social Security. Now you'll pull out less money every year once you claim Social Security at age 70 and then it'll be even less when your wife also gets to her age 70. So I think that kind of gets you there. And as long as you're not freaking out about the small. I mean, everything is going to get paid off. You know, essentially those student loans, the car, it's going to be gone. You know, by the time you're 75 years old, it's going to be gone. So at that point, you are left with a chunk of money, not as much in your 401k. You're going to have to start taking money out anyway. You know, it's going to be forced out because of the required minimum distributions. And I think it's. They'll make it. Mark, do you feel comfortable that they'll make it, or is he going to have to. Is Scott going to have to force his wife to make all of this money for the family until, you know, further notice?
Mark
Well, I mean, that'll certainly provide some wiggle room. You know, the retirement account is going to have to serve as the bridge to fill that gap between now and Social Security. But, you know, that's what it's there for. You're spending $11,000 a month. You can't be going crazy and it turns into 15,000amonth.
Jill Schlesinger
Right. And I think that once we get rid of some of the debt, you'll be able to actually clamp down on some of the spending. Right. So, you know, listen, you know, the Social Security in today's dollars, you know, it's 6700, so it's about half of what you need. So I think that under, you know, most circumstances, I would imagine that this is going to be okay. I think that I will put this out there, you know, in a year where the market stinks and there's a real fall off, I would to like, like to believe that most people would use a little more caution in their spending. So maybe if we're in like some deep bare market, I do think, Scott, it would be better for you guys to be like, okay, instead of two nice vacations a year, we're doing one this year. Because I think when you have to invade that account and the account value has dropped dramatically, that is a tough thing to swallow. And it's. It's going to make you feel a little bit less secure. So if I have a pinky swear with you guys, that you can do that. Amazing. Amazing. But I do. I like the idea of cleaning up the home equity line of credit and that first car loan over the course of the next year. Get it cleared up. Your cash flow should improve. Don't just spend the money you were putting down on that either. You know, I want those expenses to be down at like $10,000 a month in today's dollars. Once we clean up your balance sheet.
Scott
Right. Would it make any sense to use some of that HSA money?
Jill Schlesinger
No.
Scott
I have at least $35,000 in receipts that I could.
Jill Schlesinger
Oh, I mean, yeah. I mean, if you have that. I thought you were just saying, like, pull it out. I mean, you have money that you can actually use to pay bills for medical and health.
Scott
Yeah, because I've been paying those out of pocket and saving the hsa. I think my wife is on my former company retirement insurance plan. That's how she's paying, getting her health insurance. I'm on Medicare.
Jill Schlesinger
Right.
Scott
I mean, I didn't know if it would take part of that to pay off maybe one of the car loans or.
Jill Schlesinger
Well, it's not like, I mean, if you use some of the money for the HSA for a real medical expense and that freed up $12,000. Okay. That you could just pay off the home equity line of credit, then I would do that. No more than that, though.
Scott
I have.
Jill Schlesinger
Oh, well, I mean, as long as you can get the money, then yes, but I would definitely get 12. Don't do more than 12. That HSA is going to be quite valuable. Right. And the longer we leave it, you're both young and healthy, but like in your 70s, you're going to be like, oh, you know, this account is actually worth a lot to me.
Scott
Right.
Jill Schlesinger
So I think that's. I would maybe do like if you have 12 grand of receipts and you say submit it and you get 12 grand out tax free, pay off your home equity line of credit. Boom, done.
Scott
Right.
Jill Schlesinger
Okay. And then if you're going to take some money out of the 401k for expenses, so again, you pull 150 out right. @ the. By the end of this year and you pay off the $20,000 car loan at five and a quarter percent. And the rest of the money you put in your cash account. Account. And you are actually going to be, I think, vigilant about that. 11 grand a month spend. Right. Okay. And then let's see where we are by the end that. Now let's see how you do. You know, I think it'd be interesting to see, like, how you spend when you're paying attention to it.
Scott
I'm paying attention.
Jill Schlesinger
Yeah, I got your attention. Well, you know what I mean, when it's a little bit less like we're young and let's spend our money and we got 2 million bucks and you know, you can see how 2 million doesn't feel like so much hasn't been taxed yet.
Scott
Oh yeah.
Jill Schlesinger
So right. So that's a critical part.
Scott
I sort of subscribe to the, the go go years, no go years, slow.
Jill Schlesinger
Kind of thing where I, I'm with you. My friend Christine Benz from Morningstar is very much into that. I agree that, you know, 65 to 75 go go 75 to 85 slow go and 85 plus is no go. However, I don't know how healthy you're going to be. I don't know what's going to happen. So I'd like you to be go go ish. How about that? Does that seem reasonable?
Scott
Yes.
Jill Schlesinger
All right. If you are like Scott from Delaware and you are in retirement and you are now focused on how to make sure your money lasts and what is the best way to withdraw assets to fund your go go years, get going. Give us a Holler. Go to jillonmoney.com Click the Contact Us button. Write us a note if you'd like to join us live on the air. Check the box. Mark will do everything else. Hey, don't forget to sign up for the free weekly newsletter which also entitles you to our blog. And and and you can subscribe to Jill on Money Live, our quarterly live webinars and that is also on our website. Our upcoming webinar is on Wednesday, November 19. We are doing year end tax and financial planning. There is stuff to do so you will get access to that webinar. Three more after that. The back catalog of webinars. Bonus audio and video content. 45 bucks for the next 12 months. Check it out. It's Jill on Money Live. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. We'd like to remind you that to lift someone up, change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.
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Scott
Hey everyone, I'm Josh Radner And I.
Jill Schlesinger
Am so excited to tell you about.
Scott
How We Made youe Mother a rewatch.
Jill Schlesinger
Podcast looking back at How I Met yout Mother.
Scott
And I'm here with Craig Thomas, who.
Jill Schlesinger
Co created the show along with Carter Bayes.
Scott
Hi Craig.
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Hey, Josh. Somehow it has been 20 years since the show premiered that seem I'm going to check the math on that. Ten years since it went off the air and we thought that made this a perfect time to look back, see what the hell we did and why the show still seems to resonate with fans around the world today.
Jill Schlesinger
Follow and listen to How We Made.
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Youe Mother wherever you get your podcasts.
Date: October 28, 2025
Host: Jill Schlesinger, CFP®
Listener Guest: Scott from Delaware
In this episode, Jill Schlesinger takes a listener call from Scott, a 66-year-old retiree from Delaware. Together, they dig into his retirement finances, debt situation, and strategies for optimizing withdrawals from retirement accounts—especially with an eye on eliminating certain debts. Jill offers straightforward, jargon-free advice, focusing on actionable steps and real-life decision-making.
"There are certain documents you should have dupes of both in the cloud, electronic and physical. … Estate documents, both digital and hard copies, wills, durable powers of attorney, healthcare, proxies, trusts, and I think all of your insurance documents…"
[02:49]
Scott's Profile:
Assets
Liabilities
No other real estate or significant assets.
"If you have 12 grand of receipts and you say submit it and you get 12 grand out tax free, pay off your home equity line of credit. Boom, done. No more than that though." [19:14–19:13]
Jill reassures Scott that his plan—a controlled draw-down of retirement assets to clear the highest-interest debts, stay within a reasonable tax bracket, and bridge to Social Security—is sound. The bulk of the episode centers on making strategic, phased withdrawals and being vigilant about spending. Jill recognizes the value of the “go-go years” in retirement, but emphasizes flexibility and caution, especially in rough market years.
Anyone in a similar situation—approaching or in retirement with diverse debts—will find actionable steps and clear reasoning in Jill’s advice. The show stands out for its empathy, humor, and real-world application.
For further questions or to appear on the show:
Go to jillonmoney.com and click "Contact Us."
Newsletter & Webinar Info: See Jill’s website for sign-ups and event details.