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Welcome to the Jill on Money show. It's Thursday, October 23rd 3rd and we are here helping you make better, sometimes less bad, sometimes more considered financial decisions. If something's going on in your life and you need some guidance, it doesn't have to be that there's a black and white answer. But maybe you're just thinking about something and you want to know what options are available for you. Get in touch with us. Both Mark and I are certified financial planners. And no, we don't do it for a living. However, we love talking to you guys and we love having these conversations that maybe make you a little less stressed. Sometimes it is stressful when I tell you you can't do what you want to do, but it shouldn't be. It should just be giving you a framework to think about these big events in your life and maybe transitions that you're considering. So if you would like our assistance, just go to our website, jillonmoney.com, click the contact us button, write us a note, and if you'd like to join us on the air, then just check the box. Mark will do everything else. Hey, don't forget to sign up for the free weekly newsletter comes out every Friday. Mark does a great job with that. And check out our subscription service. It's called Jill on Money Live, where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content, it's all for 45 bucks for the next 12 months. Our next webinar is just around the corner. Wednesday, November 19th. We are going to do some year end tax and financial planning. And you know, some of the new tax bill will go into effect next year. So maybe there are things you need to do this year. If you want to know what those things are, you're going to have to join Jill on Money Live. Okay, enough of that. Today we are talking to Annabelle, who listens to us in Washington state. Hello, Annabelle, how are you?
D
I'm doing well. Hi, Jill and Mark. Thank you so much for taking my call. And we love your show. Thank you for creating such a wonderful show.
C
Oh, aren't you sweet. We appreciate that. Tell us what's going on, how we can help you out today.
D
So my partner and I are calling to get a little checkup about our retirement plan and where we might be able to improve. We also have a couple of questions about withdrawal strategies and savings and all that.
C
Cool. How old are you, Annabelle? I'm 55. And partner?
D
61.
C
61. Okay. And are you guys both working full time right now?
D
Yes, and I have a second job.
C
Oh yeah? One's not enough for you? Okay, I got it. And you guys are partners, not married. So. We are married. Oh, you are married. You're just saying partner to be very hip and cool.
D
Pretty much.
C
Okay, well, I'll just say married. Okay. So you have a spouse. I was about to ask you if you have done all sort of different kind of estate planning because of that, but because you're married doesn't mean you're off the hook. It just means there is a methodology for creating an estate plan. Okay, so let's go through this. You have two jobs. One is one like the more dominant. Let's start with that one.
D
So my salary combined is about 170,000.
C
Okay.
D
And spouses, $150,000.
C
How is that for you guys? Living on the combined income of $320,000. Good. Yeah. You feel comfortable?
D
We get to have fun and you know, we can't go too crazy, but we, we get to have fun.
C
Okay. Do you guys have kids?
D
No.
C
Have you both been saving in retirement accounts?
D
Yes.
C
Tell me about those accounts. Are they mostly in traditional or some Roth or a little bit of both. Where. Where do you guys stand there?
D
They're all in traditional accounts, and combined we have about 900,000.
C
Are either of you going to be entitled to a pension?
D
Yes, we both will have a pension.
C
Wow. Tell me about those pensions.
D
So at 65, my partner wants to retire in about four years. Her pension will be $4,800, and that includes, like, a survivor benefit for me.
C
Okay, and does that pension have a cost of living adjustment?
D
It does not.
C
Okay, so straight. Okay. $4,800 a month, and that's with a survivor benefit. Okay, tell us about your pension.
D
My pension at 60. So again, that's in about four years. At 60, my pension will be 6,000amonth. Ooh, it does have a COLA of 2% annual.
C
That's amazing. Okay, so when you look at having that 10,800 bucks a month, how does that compare with your spending needs?
D
We spend about 12,500amonth.
C
Okay.
D
That includes fun money and, like, savings, too. Right.
C
Okay. And will you got when you retire, Annabelle, at 60, will you have health coverage or will you have to go purchase that?
D
Yeah, I will not, at 60 have health coverage. I actually won't have any health coverage at all. When I leave my job. I'll have to get. I mean, I have Medicare.
C
Right. You'll have five years where you have to buy coverage.
D
Right. Okay.
C
Okay. So when you look at that 12, 5. Can we add a little bit to that in terms of accounting for some health insurance? Yes. Okay, so maybe we. Are you a healthy person?
D
I am.
C
Yeah. So even if we said it was, let's just add 1000 for the heck of it, and we'll say 13. 5 is like fun money, you know? Listen, when your spouse goes on Medicare, there's also expenses that pile up there because you have to buy these weird supplemental policies. So let's say $1,000 extra a month for your total need, and you'll be bringing in 10,800, which is taxable. So I know that. What's your game plan on the Social Security claiming? Do you have a game plan?
D
We do. And my partner also does get a supplemental health plan. Oh, she won't need to buy a supplemental. She'll get one. And when I turn 65, I can take advantage of that supplemental as well from her work.
C
Oh, so maybe we really only need 13amonth. Okay. Doesn't matter either way, Ab. Okay. I know you're going to be great. Okay, so Social Security, what do you got? What do you think?
D
So at 65. We just checked. And at 65, when my partner retires, she'll get 3,150amonth.
C
Okay, but we shouldn't just. Shouldn't we just wait till 67? So that's a full retirement age. Sure. Yeah, I think. Is she in good health? Yes. I. I mean, it's. It is good to wait to wait to get that full retirement age benefit. It's just you take a tiny haircut when you claim early, even if it's 65. Not that it's going to make a big deal for you guys, but if, if you. Since you looked at your age 65, can you give me what your age 65, Social Security was?
D
I didn't look at the 65. I looked at. Mine's much smaller because I currently do. I'm not paying into Social Security and I haven't for a long time. So I looked at the 67 number and it was 1100.
C
Okay.
D
And then at 70, it's 1389.
C
You can see, by the way, her numbers would go up dramatically also even if she just waited till 67. So obviously you know that between your two pensions and your Social Security benefits, everything should be fine. Right. What else do you guys have saved besides the retirement accounts? Any other money? Is there a brokerage account? Is there a fun money cash account? Anything that else that's out there in terms of an asset?
D
We have a house.
C
Okay, what's it worth?
D
The house is worth about $1,600,000.
C
Wow. Welcome to Washington State. Is there a mortgage on it?
D
There is a mortgage on it. It's a big one. It's 855,000.
C
And this is a house you want to keep?
D
Yeah.
C
Okay, what's the interest rate on that? $855,000.
D
$3,010,000.
C
Oh, that's good. Okay, so that's a keeper. Any other real estate rental, vacation, anything like that? No. Okay, what about a brokerage account or a cash account?
D
So we're just kind of getting started with that. So I have a small HSA that I contribute to monthly that has about 7,000 in it.
C
Okay.
D
And we have. We just started contributing to a brokerage account and that we contribute $1,000 a month, and that has 7,000 in it.
C
So 7 and 7. 7,000 to the in the HSA and 7,000 in the brokerage is what you got.
D
And about 2,000 in a high, high yield savings. You know, I think that's it. The only other thing I would say is that I have this second job I'm pretty sure because I've just kind of been a workaholic my whole life. I think it's better for me not to just go cold turkey on work. And I think it'd just be better for everyone's sanity if I worked a little bit. Oh, I'm going to work when I turn 60, keep working part time probably until I'm, you know, even into my 70s.
C
When you say part time, what do you think that means for you in terms of income? How much?
D
Yeah, I think about not much. 2,500, 3,000.
C
Okay, but that's great. It's something. Would that amount, wait a minute, would that amount allow you to claim health insurance through that?
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No.
D
Okay.
C
It was a good try, wasn't it? I was hopeful, but. Okay. All right. But that's all good.
D
Just.
C
Okay. You pay for your, that does pay for incidentals. So the big number that you have saved up is this chunk of retirement savings, this $900,000. I think that the game plan, what.
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It sounds like is in four years.
C
You start collecting your pensions. And then what I think would be kind of cool is at that time when you're going to pull back. She, she's going to pull back. So now instead of being in a higher tax bracket, you really are in a lower tax bracket for real. Right. I mean, because you're only going to make whatever, 25, 30 grand a year, but of course you have the taxable income from the pensions. Not that that's a bad thing. It's a good thing. I don't want you to think that's a bad thing, but it does mean, I think that you have an opportunity to get some of the money out of that retirement account and use that to live on before you claim Social Security. Right. And so you could essentially take out, I don't know, like you need 13 grand. You're going to have 10 or 10, eight, let's say 11. You'll have some part time income. I mean, I don't think you'll probably need much more than three or four thousand dollars a month coming out. Basically you're going to pull the money out, pay tax on it and fund the gap. Right. Because the money that you, the 10,800 that you receive in pension will be pre tax. So we do need to get some more money in the door in addition probably to your part time income. But you don't have to go crazy. It's just that it seems to me that you'll be in a low tax bracket. Washington State has No state income tax. So I'm kind of like, let's keep pulling money out. As long as you stay in a tax bracket that's reasonable. 22, 24. I think that you should be trying to get as much money out. And even if you take out more, more than you actually need to live on, let's say that, you know, maybe when, when all said and done at age 60, you're like, you know what? I am working more than 2,500 or $3,000 a month. I'm making more money. You could potentially pull money out, pay the tax that's due, and just pop that money that whatever you don't use into your brokerage account. Which is fine. It's fine.
E
I will say these guys do have aspirations of buying a rather large property.
C
What do you mean? I didn't know that. I thought we just had a house. We have a 1.1 bigger.
E
They want another house.
C
What you. Wait a minute, Annabelle.
D
What do you. Keep the question section.
C
Okay, let's do the question section. So anyway, all was well and good until you blew up my plan. Now let's tell me about this.
D
Well, we did have a couple of questions about making some purchases.
C
So which ones?
D
The main, the main question is we, we need to replace one of our cars because we have a camper and our vision is that we're gonna, you know, travel around in our camper.
C
How much? Stop messing around with me.
D
So, you know, the, the, the cars that, that pull a camper could be, you know, even used can be 60 grand, something like that.
C
So what's my dream car? What's my dream car? What do I have to. What do I got?
D
We're probably like a Toyota Sequoia, you know.
C
And how much is that? Knew.
D
They're like 85.
B
What?
C
Mark, I am so behind. Who knew? 80 grand. Geez.
D
It's crazy.
C
Toyota.
D
I know.
C
My God. Okay, so the question is, can we pull 80 grand out of our retirement account to get that Sequoia?
E
Well, this would be the small purchase.
C
What? What are you talking about? So I was so ready to grant. I was ready to grant that wish right away.
D
Is it better to take it all out at once or just to make a payment? What do you think?
C
What's the interest rate on the loan that you could get?
D
I'm not sure because we haven't started looking. We're not really going to do it for a couple years. But, you know, let's just, let's just say that.
C
Let's say that in a Couple of years, we look at whatever the interest rates are. And if you've got a 4 or 5% car loan, yeah, you know, you can just take the money out as you need and pull it out of your retirement account. But if for some reason, I'm not sure how it could happen this way, that it was like an 8 or 9% loan, then we would just pull the money out of the retirement account, pay the tax, and buy the car. Okay, so you're gonna have to pull some money out of that retirement account. Are you guys both fully funding retirement accounts right now?
D
I mean, I wouldn't say fully funding, but we put in about $1,400 a month between the two of us.
C
It's time for you guys to start looking at building up your brokerage account and that high yield savings account in anticipation of this car. Like, yes, of course you can pull money out of the retirement account, but, you know, it would be nice if you didn't have to, like, yank it out all at once. So if it would give you more flexibility to have a little bit more in the brokerage account, you say you're started. You've just started it anyway, so that's good. So I think it would depend when you're ready to do the car. It will either be some combination of just adding to your monthly payments. So I don't know. Car payments are so freaking expensive now. So it'll be something like 8 or 900 bucks a month or $1,000 a month. So then our $13,000 a month question of, like, our expenses would turn into $14,000 a month. Okay, so far, so good. I feel comfortable that we can make that purchase happen, and there's no downside. Now you're about to hit me over the head with a second larger purchase, which I am sure is some sort of, like, weird vacation home in Hawaii or some crap like that. What is it?
D
But, you know, we've kind of been rethinking it, but we do have a dream of possibly having a small vacation house somewhere. And we thought maybe, you know, in about five years, we could take a larger withdrawal from our retirement monies to fund, but we're kind of rethinking it.
C
How much would I have to pay to actually own the dream house that you would think is worth it for you guys? Yeah, I mean, it depends.
D
You know, originally we were thinking maybe like, upstate New York, Adirondack area. And if it's that area, maybe 350, 400,000.
C
That seems like the low end because I bet you're again, you're about to whack me over the head with what's the real dream house.
D
The problem with that is that if we had a place like that, then I would probably stop working because, you know, that's far from where we live.
C
Yes, you're West Coast. This is easy.
D
Yeah. So you know, then if we're like, well, if we bought a place on the west coast, then I could continue working and we could just go up there, you know, on the weekends or my time off or whatever. But of course, west coast real estate is more expensive than upstate New York. So, you know, looking at like maybe like a townhouse or something like that.
C
It'S like, how much?
D
700, 750, 800, that kind of thing.
C
So in your mind you're saying, I just want to make sure I get this right before I crush your dream house. Yeah, like the wicked witch that I am coming in. So in your mind it would be like, hey, we got almost a million bucks in retirement. We're good. We have this great income. We would take a chunk of money out of the retirement accounts, 400, 500 grand out of these retirement accounts. We'd finance the rest and we'd have this dream house and that's how. That's the real dream. Is that right? Yes. What do you think I'm going to say, Annabelle?
D
Well, I think you're going to say it's better to have the money in the accounts is what I think, Mark.
C
What are you going to think? What do you think I'm going to say?
E
Well, I mean, I know the thought process is that, you know, the pensions and the future of Social Security more than covers their expenses. So they're really not going to have to dip into the retirement money. So why not use that money and.
D
Purchase their use summer? Right.
C
Because it's still on the books. Here's what I would. I would. Here's what I would prefer. Ready? The answer is absolutely not. You guys are being so much nicer than I would be to you guys now. I'm just kidding. No, I think no, because that's your nest egg. You are young, you are 55, Annabelle, you could live for 40 more years. And so a couple of things about that. One is that 4800 of your 10,008 has no cost of living adjustment, zero. So we know that's going to be a flat line. Your expenses will continue to rise and yeah, you will have a cola on the six grand and on the Social Security. But actually even Those your two streams of income and two Social Security checks. That'll be fine. But we still have to bridge the gap between these two years. Here's how you can do your dream house. You want to know how you got to sell your primary?
D
Yeah.
C
That's the way to do it. So if otherwise, I have a better game plan for you. Rent in a vacation area, and then you know what you got in a place that, like your 750 or $800,000 townhouse. Go rent there for a while. See if you like it. Maybe this is someplace where you would want to end up, you know, Maybe it is. Maybe you say, like, you know what, it's a pain in the neck to own two houses. It is. Okay. I don't think this is doable. Based on the asset level and even with the pensions, I would be very nervous about plowing through 4, 500 grand of your retirement, paying tax on it. By the way, don't forget, we have to pay tax on this. So that 900 is not 900. You are what? You know what Ed Slott says you're a joint owner in that account with Uncle Sam. So that 900 is like 700. So do we really want to spend half of it, 350, 400 grand, putting that into the dream house, I don't see that working out and having you guys feel the freedom that you want to feel. You know how that would work if you said, I'm 51, my partner's 61, we're working for 15 more years. That's how it works. If you're working full time making 320 a year, sure, go buy yourself a dream house. But if you want to retire in four years and have flexibility, I don't think so. I think that doing the second home, I'm okay. You had me at the $80,000 Toyota that I can. We can stomach that. But the $800,000 house, I mean, it would really. Things would have to have been very different in four, maybe five years. Now, let's pretend just crazy thought here. Let's pretend you rent and you try something out. And then you say, you know what? We love where we were renting. We're retired, we're selling the house. Then we're in a whole different ball game. Then you may be able to do this. I just don't think you could have, you know, something like $2.3 million of your net worth tied up in two illiquid assets, the primary house and the new one. So, Barbie, get your dream van and don't worry about the dream house. What do you think about that, Annabelle?
D
Outstanding.
C
I think it's great. It's not so bad. You still got great. You have so many options. So many options. All right, anything else that we need to worry about for you guys?
D
I don't think so.
C
You're in good shape. You really are. Two pensions, two Social Security checks, and both a million bucks in retirement in pre tax retirement. And you're going to live a great, happy retirement if things change. If something goes different than you had planned, then you played the lottery, you won. Who knew? Give us a holler and we'll figure out the dream house.
D
Okay, well, thank you very much.
C
It's a pleasure. Mark. Dream crusher today. They don't always work all the dreams, but it's good to have them. And isn't it nice to know that, like, you could replicate the dream simply by renting? Renting's okay. I think it's a really good option for people who want to try something out. So we'll see how it goes with Annabelle and her wife. Hopefully we'll get them back on. They'll tell us all about retirement and how great it is. If you are thinking about a dream and you want us to either cross crush it or make it a reality, get in touch with us. Go to jillandmoney.com, click the contact us button, write us a note. And if you want to join us live, check the box. Mark does everything else. Hey, don't forget to check out all the cool stuff that lives on our website. We've got a blog, we've got a radio show, we've got videos, and we've got resources. Everything is there. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Please leave us a rating and review wherever you listen and of course, lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.
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Hi, I'm Nancy Cartwright. You may know me better. As the voice of Bart Simpson on Simpsons Declassified, we're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers? The celebrity guests? Be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.
Date: October 23, 2025
Host: Jill Schlesinger, CFP®
Special Guests: Annabelle from Washington State and her spouse
In this episode, Jill Schlesinger tackles Annabelle’s and her spouse’s financial planning questions, focusing on their upcoming retirement, withdrawal strategies, big-ticket purchases (a new car and a potential vacation home), and the reality check involved in trying to make their post-career dreams a reality. The tone is supportive, realistic, and pragmatic, with Jill offering both encouragement and tough love as needed.
Quote:
"It should just be giving you a framework to think about these big events in your life and maybe transitions that you're considering."
– Jill (01:30)
Quote:
"As long as you stay in a tax bracket that's reasonable—22, 24 percent—I think that you should be trying to get as much money out. And even if you take out more than you actually need... just pop that money that you don’t use into your brokerage account."
– Jill (12:56)
Quote:
"It’s time for you guys to start looking at building up your brokerage account and that high yield savings account in anticipation of this car."
– Jill (16:02)
Quotes:
"You are young, you are 55, Annabelle, you could live for 40 more years... That 900 is like 700 once you account for taxes. So do we really want to spend half of it, 350, 400 grand, putting that into the dream house? I don’t see that working out.”
– Jill (20:23)
"Here’s how you can do your dream house. You want to know how? You’ve gotta sell your primary.”
– Jill (20:22)
Quote:
"I think that doing the second home, I’m okay. You had me at the $80,000 Toyota... But the $800,000 house—I just don’t think you could have something like $2.3 million of your net worth tied up in two illiquid assets."
– Jill (21:16)
"Renting’s okay. I think it’s a really good option for people who want to try something out."
– Jill (23:12)
On Retirement Flexibility:
"You guys are going to live a great, happy retirement. If things change... give us a holler and we’ll figure out the dream house."
– Jill (22:49)
On the Hard Truth:
"Mark, dream crusher today. They don’t always work out, but it’s good to have them."
– Jill (23:12)
This episode provides a thorough case study in practical financial planning for late-career couples with stable incomes but big dreams. Jill balances affirmation (“you’re in good shape”) with accountability, vetoing risky moves in favor of preserving flexibility, security, and future freedom. While Annabelle and her spouse can enjoy a well-earned, secure retirement and even upgrade their car, the allure of the “dream” vacation home simply doesn’t stack up against their long-term well-being unless their life circumstances (and housing situation) change. Renting remains a smart and liberating alternative.
Listeners with similar aspirations will find actionable guidance on how to weigh wants versus needs and keep their retirement dreams attainable and stress-free.