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Today's episode is supported by what Should I Do with My Money? An original podcast from Morgan Stanley. And like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries, and dreams, asking questions like, can I retire early? Like, really early. Hey, how do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and it's shifting how I think about my money. Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player. And feel empowered and supported when it comes to managing your life and finances. Welcome to the Jill on Money show. It's Tuesday, December. December 23rd. Ooh. It's getting down to it. Oh, my goodness. And if you are like most people and the holidays are approaching, you want to just like, shut down. You don't want to think about money or finances. I get it. It's okay. Maybe you're listening to this next week. I don't know. But we, Mark and I are always here ready to field any question you have about your own financial life. And that could mean a lot of different things. You know, sometimes people say to me, oh, this is only a retirement show. No, it's not. It's an everything show. It's just that, you know, we tend to get a lot of questions around retirement because there are so many people who are considering retiring. You know, 10,000 people a day are retiring right now. So the bulk of those people have things to do, decisions to make. But you may be younger, you may be just starting out. You may be thinking that you need to start planning for how you're going to send your kid to college. Maybe you're going to get one of those sweet new government accounts. Mark, don't you wish you had a baby now? Last year. God, you know, this past year for $250.
B
That's okay. I'll pass.
A
Yeah, I know. Well, wait a minute. The Dells are going to help you. Going to be a little bit more. We should do a deep dive on those accounts on our other show, on our Money Watch show for a little weekend dive on education funding. We'll do that, I promise. So we are here to help you out. If you're. If you've got a question, go to jillonmoney.com, click the contact us button. Let us know if you Want to come on the air live by checking the box. Mark will then follow up with you and nudge you and bring you on with us. And while you're on the website, you can check out all the content that lives there. We've got another podcast as I just mentioned, that is called the Money Watch show. We've got a radio show, we've got a blog, we've got videos, we've got resources, all there for you. And of course don't forget to sign up for the free weekly newsletter which comes out every Friday. Okay, Right now let's get get this party started. It is Dave who joins us from North Carolina. Hi Dave, what's going on? Hey Jill, what's happening? What can we do for you, sir?
C
So I AM in my mid-50s, my wife's a couple years older than that and we are have the questions about retirement. So I've got several questions around that. I also have two sons in their 20s. They're independent, financially independent. But I had started a 529 for one of the boys 20 years ago. He opted not to go to college. So I'm looking to see you know, what to do with that.
B
I'll take that.
A
Mark's gonna happy to help you out with that. No, we'll help you with that. That's easy. Dave, when you think about like just going forward, when do you think about retirement? Like what is the your age and your wife's age? Like what, what are we looking for? What's our game plan?
C
Yeah, I mean I have about 10 more years. I'm looking to retire around 65. My wife is self employed. She's again a couple years older. She's really kind of starting to wind things down. She's probably really only doing part time. So yeah, really, over the next 10 years I'd like to be able to retire.
A
Great, okay, I bet you can. That's good. First of all, congratulations on having two sons in their 20s who are financially independent. I feel like that's just like you buried the lead. That seems like the most miraculous thing of all right now. So well done for you guys. Amazing.
C
Still feels, yes, surreal.
A
Hopefully it lasts. So Dave, how much do you earn right now?
C
I'd say between my wife and I, it's about 350,000 a year.
A
If your wife were not working at all, what would the number be?
C
Probably 275.
A
Okay, so do you think she'll really wind down to nothing or do you think she'll keep doing the 75 for a while?
C
It Might wind down to half that, I think.
A
So should we just say the combined income is closer to like 300? Just so we. Are you both making retirement plan contributions?
C
Yes.
A
Okay.
C
Yes.
A
What are you putting into a 401? A 403. What do you got?
C
Yeah, 401 with the company I belong to. And maxing out also the catch up.
A
Contribution, how much is in there?
C
I have around, it's like 1.7 in. In my 401k. She has an individual 401k as well as a SEP IRA that somewhere around 650, 625 combined. Combined would be probably 2.3, 2.4.
A
No, no, I'm sorry. Her 650 is the SEP and her 401k combined. Okay, got it.
C
And then we have some IRAs and a couple of Roth IRAs that have been around for a while.
A
Okay, so lots of money. And the 1.7% that you have accumulated in your 401k that has not yet been taxed. It's traditional, right?
C
Correct. I just in this past year started doing some after tax contributions on top of my max out of my taxable or tax free contributions to do a Roth in plan conversion of those.
A
Okay. All right. That's great. I mean amazing dollars saved already. And what about non retirement savings? Any brokerage or savings accounts? Anything going on there?
C
Yep, probably a million dollars in just kind of mutual funds and brokerage accounts. And then also I have about a million and a half of company stock.
A
Oh, is it a publicly traded company? Don't say the name of it.
C
Yes.
A
Okay, this million and a half dollars is. Tell me about the tax treatment of it so we can really sort of figure out what it's worth to you. Like if we sold it all today, would it be taxed as capital gain or income?
C
Probably some of both, but mostly capital gain.
A
Okay, that's better. That's a better amount.
C
I'm buying an ESPP at a discount, so there's a small amount that would be income when I.
A
You love your company?
C
I do.
A
Okay, well maybe you don't love it so much. That's a lot. That's some big bet you have. You feel good about it though, right?
C
Yeah. And definitely starting to consider diversification with that actually. For sure.
A
Yeah. I'd say that again. That's a lot. So in just, you know, you said funds brokerage, but you also have some savings. Just boring money set aside.
C
Yep. I have a couple high, high yield savings accounts at roughly around 450.
A
Okay. Wow. Okay. You own Your home?
C
No, I have two mortgages.
A
I like. You're like, well, the answer is yes, and I have a mortgage. Not like, do you own it outright? So how much is the house worth?
C
650.
A
Okay. And then there's a mortgage amount. The primary mortgage that you originally took out, how much is left on that?
C
120. 120.
A
And what's the interest rate?
C
Roughly 3%.
A
And then you have what, a HELOC or a home equity loan?
C
No, I have a rental property that has a mortgage.
A
Okay, what's the rental, what's the rental property?
C
235 ish.
A
And the mortgage outstanding?
C
Yeah, 3% ish.
A
The rental property is worth 235 or that's what the mortgage.
C
That's the mortgage. It's also about 650.
A
Okay. Oh, okay. The rental property, how is the cash flow on it?
C
I've recently had a tenant leave and found some issues. So cash flow for it's going to be low for the next few months till we get some repairs done.
A
How much?
C
Past eight years, it's been. It's been pretty good.
A
How much does it deliver? Like in real terms? Like you pay for the mortgage and the. Whatever.
B
All the stuff?
C
Yes. I mean, 10, 10 grand a year.
A
Okay. Do you guys like where you live? Do you feel like your current primary residence is where you want to be?
B
Yeah.
A
Okay. That seems like a little hesitation, but okay. It was sort of like, yeah, well.
C
We have a beach property and we have a mountain property. So we split time amongst, you know, several different places. So.
A
Okay, wait a second. Big shot. So we now have four pieces of property. How much is beach worth?
C
So beach. I'm a 1/3 owner of property, so it's roughly 400 my share, mortgage or not?
A
No. Okay. And mountain property?
C
Mountain property today is just a plot of land. It's 100k mark.
A
All these people with like their various land ownings. My God, it's incredible.
C
Yeah. North Carolina is a short drive to eat, so it's, it's, it's really convenient.
A
Okay. But you want to keep everything, right?
C
Yeah.
A
Okay. And is the plot of land in the mountains something that you wish to develop? Yes.
C
Or potentially trade up if we find something that's already got a property, it's very expensive to build. We're learning.
A
Totally.
C
Yeah.
A
Yeah, I know. Such a drag. And the process itself, it's like open season on your relationship when you're doing those projects also. Okay, that's incredible. What, what did you want that for? Okay, what else do we need to know on your balance sheet. I'm going to talk about the 529s in a second. But just anything else in your names that shows up on the balance sheet.
C
That we should know about, I think that covers it.
A
It's a lot. Yeah, it's a lot, man. How much you guys spend?
C
I'd say, I mean roughly 11 to 12,000amonth.
A
Okay.
C
But then know that doesn't include some travel that we'll do periodically. So it probably averages.
A
How could you travel? You're either at the beach or on your mountaintop. I'm just kidding. So more like 13, 14 when you put it all together.
C
Sure, I think why not?
A
Right. Okay. There will be no pension for you. Yes, correct or no? Okay, no pension.
C
So my wife does have a small pension.
A
Oh, really?
C
She was worked for a corporation. I think it'll be 1500amonth. At 65.
A
Wow, that's actually more than I thought. And how old is she right now?
C
She's just about turned 60.
A
Okay. All right. So in five years she gets her. How many? You said 1500. Is that what you said?
C
Yeah.
A
Wow, that's more than I thought you were gonna say. How about. So for her, she's on your health benefits, right?
C
Correct.
A
So there's no big deal. As long as you're gonna be working, she's covered. Then she goes on Medicare. Okay, that's fine. What do you think at age, if you worked your butt off for 10 more years and you did all of your 401k contributions, you did all your catch ups, you did everything and you've got a lot of money that's in the brokerage account. Do you have extra money like that? Do you have extra cash flow that you're throwing into these accounts that we can just count on for the next 10 years?
C
I mean, I have significant dividends from the company's stock.
A
Oh, interesting. So you're in a pretty bad tax situation just in terms of that.
C
Correct.
A
Okay. All right, so what's your top tax break? If you're making 300 and you have dividends and you've got rental property, are you kind of finding yourself in the 32% bracket, like between 4 and 500 grand of income?
C
No, I mean, it's still 350ish, I'd say.
A
Okay. Yeah, all in with all that other stuff. Okay, so you're in 24. Okay, that's good. I'm happy you being in a lower one. So you got a lot of money. I don't think Mark do you, do you think that 1.7 million in traditional is Dave's? His wife's got 650. They got a million dollars in brokerage stuff and, you know, ETFs and mutual funds in a brokerage account. Then a million and a half dollars in this publicly traded company for which he is a fine employer employee. We've got residence, we've got rental property. That's cash flowing, 10 grand a year, all these other little things. Even his wife's even going to have a little pension. They want to spend 14 grand a month. What do you think, Mark, Yay or nay? Do we have a 10 year time horizon to build out that 14 grand a month for them and they can travel.
B
I don't even think you need 10 years, but if you want to do 10 years, knock yourself out.
A
Yeah, I was thinking the same thing. You sure you want to do the 10 years? If you want to go for it, but like, you're in great shape, you have a lot of money. I think your biggest risk is concentration in the company. Right. And I don't know how, you know, there are people who can help you manage that. I mean, you could either just say, I'm going to bite the bullet. I'm going to sell some every year. I'm going to, you know, take a couple hundred grand and it's. Is it in your, is it in the, in the ESPP right now? And then you have to like take it out, pay the tax, then do that whole thing, or is it already in a brokerage account for in your name?
C
I mean, yeah, it gets transferred into a brokerage account, but I haven't paid any tax until I sell it.
A
Okay. And so do you have a, an accountant that you work with tax time or not?
C
No.
A
You're going to need somebody.
C
I do have a tax advisor, but I have questions. Not a tax advisor, I'm sorry, a financial advisor that I've worked with.
A
Oh, and you like this person or not so much? You have questions. Questions like, I don't know, I'd like.
C
To start taking it back myself and really simplify things. I think it's really complicated. I transfer everything from all my accounts into Quicken and that has become now kind of not synced. And partly because of the number of transactions that they do, it just. Oh, it seems overly complicated for me. So I, I mean, I would like to put it in index funds and manage it myself. Make it much more simple over the next. I don't know if it needs to be short run, but Certainly by the time I retire.
A
Oh yeah, by the time. I mean, put it this way, if it's complicated, no financial advisor should be making your life more complicated. Should be less complicated. It should be like, here, here are the keys to the kingdom. Make my life less complicated. Sounds like you're very much on top of this. Maybe. This is an interesting idea though. If you're going to take it over yourself. Maybe you do want to grab the advice of a fee only advisor who can guide you about this, about the tax impact of doing this, or get yourself a really good accountant. The reason I'm thinking that is that if things are very complicated in the million dollar account and we're adding to the tax issue with a publicly traded company that you work for where you have stock, if you just blew everything out and made changes, it would be a silly tax hit to take all at once. There could be some smarter ways to do that and that. That may be helpful to have somebody to walk you through it. There's some planning that needs to be done and maybe you, you want to pay someone by the hour to help you.
B
Yeah.
A
You know what I mean? Like, it doesn't sound like you're saying, I don't want to pay. It sounds like you're saying, I don't know if I want to pay as much as I'm paying to the person I'm working with right now. Is that about right?
C
Yeah, I think working with somebody else would bring more energy at this point. I just feel like it's time to.
A
Yeah.
C
Take Take a fresh approach to it and, and really get it back under to where at least I understand completely all. Everything that's happening and, and I do to the most extent. It's just I'm very partial to my Quicken. I've done it so many years. I don't really want to lose that.
A
Yeah, you don't have to. We don't. Absolutely. I mean, there's no reason that you have to lose that. It's just working with someone who can help you game it out in a smart way more than some chick who's hosting a podcast. That would be me. I think the 10 year game plan is great. Do you like where you are? I mean, we know you love the company. You feel comfortable. Okay. So you're into it, so keep working. That's awesome. Yeah. Let's just do a quickie here about the kiddos. How much money is left over in the 529 account?
C
It's 105.
A
Okay. And he's how old?
C
25.
A
Okay, so, Mark, the most you can do so you can open up a Roth IRA for. If he opens a Roth IRA, you can contribute from that 529 plan the amount that you are allowed to contribute under the law every year until you get to $35,000 max. Is that right, Mark?
B
Spot on.
A
Okay, so that means that if for this year it would be $7,000. So what about the rest of the money, Mark? He's going to still have 70 grand in here. What should happen with that money?
B
Is by chance the other child's 529 plan still open or has that been closed altogether?
C
It's closed. He used.
A
And no grad school for him for other.
B
No.
A
And nothing for you or your wife. You don't want to go get an advanced degree? You're like, no, I'm done.
C
Yeah, not necessarily. I mean, cashing. It's not an absolute. I mean, if it just. We're going to, you know, we obviously have other cash available. And yeah, you know, to some degree we feel like our son, you know, that's his money and we'd like to be able to help him with it at some point. But it wouldn't have to be the exact same cash.
A
Certainly I would do the transfer up to the $35,000 limit. I mean, you could take some of it out and just give it to him and pay the tax. It's too big deal.
C
Yeah.
A
All right. That's one thing to do, but I would do that, certainly do the. As long as I can up to the 35 grand. I would do that every year for sure.
B
Is there a tax, is there a tax deduction that you get in your state? No, I was going to say if there is that, you know, they may recapture that. But if there hasn't been, then you don't have to worry about that.
A
And then I think what, what you can do is like test the waters a little bit with him. Like if he, if you think that he is, you know, he wants to buy a house and you'd like to help him out, like, so whatever. Take the money, I'm. Pay the tax it's due and move on. Give him the money. I mean, it sounds like a good kid. Right?
C
Right. Yeah.
A
You know, it's interesting. Let's just say that, you know, we leave 35 grand in there, but now we have $70,000 left in the $529,000. The money comes out. Does that get come to come out at like the tax hit? Does it come out for the kids tax rate or for Dave and his wife's tax rate?
B
No, I think it'll be for Dave and his wife.
A
Darn it. I was trying to find another way to save some money. Okay.
C
Yeah, that would be understanding. And I think in this, with this 529, there's a 10% penalty for not using it for, for qualified education.
B
Yeah.
A
So what? Yeah, so whatever. So pay it. Yeah, right. It's not a big deal.
C
Right.
A
So if the kid gets like, here's 50 grand here. Good. 60 grand. Good. Go. You know what I mean?
C
Absolutely.
A
All right. I think you're great. Do you guys have your estate documents done?
C
We need to refresh them. They're probably five years old.
A
Yeah. Because we have young men who are ready to spend your money.
C
Yeah.
A
And we want to make sure that they don't go crazy, but that they get it right. I mean, they are older now, so at least they're like, you know, they can manage it themselves. I think it's worthwhile that, you know, you really try to work through with, with somebody, a game plan for managing these assets and getting more diversification over the next group of years. Slowly, you know, you. No sudden moves, but with taxes in mind. So it's like a two. This sort of. You have a dual mandate like the Fed. On one hand you want more diversification. On the other hand you want to pay attention to taxes. And both are important. I mean, diversification is probably more important, but at this point, I don't want to ask for a tax problem if we don't have to.
C
Yeah. Thinking about taxes too. So my company is going to start matching my contributions in Roth contributions.
A
Oh, okay.
C
And I can also opt to do my contributions as Roth. So at this point, do I have enough taxable? You know, I've done pre tax contributions and I'm looking at switching now to just do post tax and put everything into a Roth for.
A
Yeah, I'm going Roth. Mark, aren't you going all Roth 100%.
B
Especially if you're going to be there for another 10 years. Absolutely.
A
Yeah. Definitely, Definitely, definitely. All right. We're wishing you the very best. Having a very happy holiday season for you and yours and enjoy all of your properties and all of your money and keep working hard and keep us posted and we'll look forward to hearing all about what the next move is for for you. It won't be 10 years from now. I have a feeling you're not going to make it 10 years. I'm just going to put it out there, give yourself permission. If it doesn't, once it stops being fun, then you will not need to be doing this. Okay? Truly. So pay attention to that. No reason to stick. You have plenty of money. You're going to have plenty of money. If you were like Dave and his wife and you got a lot going on, you're kind of thinking through what happens in the next phase. It's almost like the off ramp of how you get your financial life in order. Or if you're working with a financial planner or an advisor who seems to be complicating things more than you would hope for. 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 live, check the box. Mark will do everything else. And don't forget to sign up for the free weekly newsletter comes out every single Friday. You can subscribe to this program on the Odyssey app or wherever you find your favorite podcast. Hey, you can also find our sister broadcast called Money Watch on the Odyssey app, so check that out. And as always, we ask that you do something nice for someone else today. Change your work. Change your wealth, Change your life. Thank you for listening and we'll talk to you tomorrow.
D
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Jill on Money with Jill Schlesinger – December 23, 2025
Host: Jill Schlesinger, CFP®
Episode Focus: Financial planning strategies for a high-earning mid-50s couple looking toward retirement, optimizing their assets, and handling tax implications.
This episode centers on a listener call-in from Dave in North Carolina, who, with his wife, is navigating the complexities of retirement planning, asset diversification, and tax optimization. Dave’s questions span from handling leftover 529 college savings funds, managing concentrated company stock, and reconsidering his relationship with his financial advisor. Jill Schlesinger and her producer Mark provide actionable insights and reassurance, helping Dave streamline and strengthen his financial future, while keeping their advice jargon-free and pragmatic.
On Financial Independence of Sons:
On Over-Concentration:
On Advisor Complications:
On Switching to Roth:
On Time Horizon for Retirement:
On Life Satisfaction:
Jill’s signature approach is direct, warm, and no-nonsense, delivering complex advice in accessible language. The conversation is upbeat, supportive, and pragmatic, with gentle humor woven throughout.
Listeners can submit questions via jillonmoney.com. Jill highlights the importance of seeking help before making big moves, especially when it comes to taxes and asset allocation.
This summary covers all major topics, actionable advice, and memorable moments for listeners seeking to maximize their own assets and optimize their taxes, especially if they see themselves in Dave’s financial shoes.