Managing the Moving Parts

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Managing the Moving Parts
Air Date: January 12, 2026
Host: Jill Schlesinger, CFP®
Guests: Jane and Pat, listeners from Chicago

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Episode Overview

In this episode, Jill Schlesinger assists Jane and Pat, a couple from Chicago navigating the complexities of approaching retirement while addressing ongoing family responsibilities, particularly for their younger son with special needs. The discussion centers on financial reassurance, strategic retirement withdrawals, estate planning, and handling emotional aspects of this major life transition.

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Key Discussion Points & Insights

1. Family Background & Context

• Jane (61, stay-at-home mom) and Pat (64, local government worker) have two children:
  • 28-year-old, fully independent
  • 17-year-old, junior in high school with lifelong special needs requiring continued support (05:12)
• Pat continues to work full-time; Jane manages household and caregiving (05:53)

2. Current Financial Snapshot

• Income:
  • Pat earns $13,900/month gross (06:09)
  • Receives a pension: $7,850/month, guaranteed for his and Jane's lifetime; possibly transferable to their youngest son with special needs (06:47; 06:59)
  • Expecting a second pension: $49,000/year after full retirement (09:04)
• Savings & Investments:
  • Brokerage accounts: $55,000 (07:28)
  • HSA/HRA: $150,000 (07:29)
  • Pre-tax retirement savings: $1.9 million (07:53)
  • Roth retirement: $1.37 million (08:09)
  • Inherited IRA: $280,000, subject to lifetime distribution (08:23)
• Monthly Living Expenses: Approximately $15,000, possibly rising to $17,000 due to healthcare costs (08:38; 10:01)

3. Housing & Real Estate

• Current home value: $800,000 with $108,000 remaining on a 3.3% mortgage (11:01; 24:00)
• No additional properties
• Flexibility to relocate depending on youngest child's future education or the older child’s location (11:14)

4. Retirement & Income Planning

• Planned retirement age for Pat: Possibly 65, but open-ended; Pat expressed difficulty envisioning retirement after working since age 14 (10:18; 10:21)
• Combined pensions will generate ~$143,000/year gross (09:17 onward)
• Jane and Pat anticipate Social Security benefits ($3,000/month for Jane and $2,600/month for Pat at 67) (12:58–13:13)
• Strategy: Supplement any income gap with pre-tax retirement account withdrawals, rather than solely relying on pension/Social Security (14:18–18:27)
• Quote:
  • Jill: “One of the funny things is that you have all this money in pre tax retirement, right?... Maybe one of the things that we really decide to do is that... you start taking some money out of that pre tax retirement account and using that to supplement whatever you need.” (14:18)

5. Special Needs & Estate Planning

• Special needs trust in place and being actively updated; attorney involved (11:33–11:45)
• Main goal is to ensure lifetime support for their younger son; considering optimal estate and tax strategies for this outcome (10:52; 14:54)
• Quote:
  • Jane: “Probably [inheritance] would go mostly to the 17-year-old, but certainly the other one will, you know, will be considered as well.” (14:54)

6. Roth Conversions and Tax Strategy

• Debate on whether to convert pre-tax retirement funds to Roth now
• Mark (producer): Pulling from pre-tax accounts preferable to conversion at this stage, due to limited brokerage cash (15:19–15:25; 20:04–23:09)
• Consider withdrawing to the top of the 24% tax bracket annually for tax efficiency (21:43; 23:08)
• Quote:
  • Jill: “If you even thought to yourself, the most important thing that we can do is take as much money out of our pre tax retirement accounts to keep us in the 24% bracket, that is truly the best you can do, I think.” (23:09)

7. Mortgage and Home Equity

• Advised against paying off remaining low-interest mortgage given favorable rate and current cash needs (24:00–24:14)
• Quote:
  • Jill: “You should not [pay off the mortgage]. Do not pay off the mortgage. That's not a good place to use your cash.” (24:08–24:10)

8. Emotional Aspects of Retirement

• Pat admitted being a “workaholic” and struggling with the idea of stopping work; Jill acknowledged the emotional shift for long-time workers (10:21; 18:29)
• Jill’s reassurance: Financially, they’re in strong shape, need to give themselves permission to change their routine and approach retirement with confidence (18:29; 19:09)
• Quote:
  • Jill: “...At some point, you have to give yourself permission to not do that or to say, okay, you know what I'm going to do, I'm going to be a volunteeraholic or whatever you decide you want to do. Like you're going to use your time differently.” (18:29)

9. Takeaways and Final Reassurances

• Jill and Mark both strongly reassured Jane and Pat they’re well-positioned for a secure retirement, even under conservative spending assumptions (19:19–19:38)
• Encourage annual withdrawal strategy, consult with a CPA for evolving tax planning, and avoid impulsive Roth conversions (20:11; 21:43)
• Stay flexible for future changes in family or living situations (24:15)

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Notable Quotes & Memorable Moments

• On work & retirement:

  • Pat: “I'm a workaholic. I work, work, work. I've been working since I was 14. But the end is near...” (10:21)
  • Jill: “At some point you have to give yourself permission to not do that...” (18:29)

• On financial security:

  • Jill: “You’re not going to run out of money. I can tell you that right now...” (18:29)

• On estate planning:

  • Jane: “We have a special needs trust…but it’s being updated. You know, it’s constantly an updated type situation...” (11:43)

• On tax strategy:

  • Jill: “If you even thought to yourself, the most important thing…is take as much money out of our pre tax retirement accounts to keep us in the 24% bracket, that is truly the best you can do, I think.” (23:09)

• On mortgage payoff:

  • Jill: “Do not pay off the mortgage. That's not a good place to use your cash.” (24:10)

• Summing up reassurance:

  • Jill: “I don’t see any, I don’t really see any problem here.” (19:09)
  • Mark: “Zero problems. They got this huge income from the pensions...” (19:19)

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Important Timestamps

• 04:23–05:11 – Introduction to Jane & Pat and their situation
• 06:00–07:13 – Discussion of Pat’s income, pensions, and employment
• 07:28–08:23 – Review of savings and investment accounts
• 08:38–10:01 – Current and projected expenses, including healthcare
• 11:01–11:39 – Housing value, mortgage, estate planning
• 12:49–14:18 – Social Security and income strategy
• 14:54–15:25 – Legacy wishes for children, Roth conversion debate
• 18:29–19:09 – Emotional side of retirement, Jill’s major reassurance
• 20:04–23:09 – Tax strategies for retirement withdrawals
• 24:00–24:14 – Mortgage payoff advice
• 24:22–24:33 – Final reassurances and encouragement for retirement

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Conclusion

Jill on Money’s “Managing the Moving Parts” offers an in-depth, supportive session guiding a couple through the overlapping financial and emotional decisions of retirement—while planning for unique family needs and managing substantial resources. Jill and Mark provide clear, actionable advice, a strong sense of reassurance, and encourage seeking professional tax help as their situation evolves. Listeners in similar situations will find both the practical financial strategies and the compassionate approach to life’s transitions invaluable.

Transcript

[A]

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[B]

We are doing great. Yes. Lots going on. A lot of moving parts in our lives right now. So we're excited to have you help us sort through some of that.

[A]

All right, tell us what we can do. So first of all, what is, like the main reason that you got in touch with us?

[B]

We need some reassurance, I think, on the financial side of things. We're approaching retirement. Like many couples approaching retirement these days, we do have kids involved. So our moving parts are still around our kids a bit. And so we just need some help on the financial side to say give us reassurance that we're definitely financially okay and that we can focus on the emotional pieces of trying to manage through all of these moving parts.

[A]

How old are the kids?

[B]

We have a 28 year old who's launched and we have a 17 year old who Is a junior in high school not launched?

[A]

When you're a junior in high school. Gotta say that. Right.

[B]

That one is not launched. And when he was in kindergarten, we found out he has some special needs that are going to require that he has some sort of supervision and oversight for the rest of his life, including when we're gone.

[A]

Okay, understood. So it's just the two kids, right?

[B]

Correct.

[A]

Okay. And how old are you guys?

[C]

I'm 64.

[A]

Okay.

[B]

Jane and I'm 61.

[A]

And you're both working full time?

[C]

Yes, I'm working full time and my beautiful wife is a stay at home mom. Working full time. More than full time.

[A]

Oh, yeah.

[C]

Well, holding the kid.

[A]

Yeah. Unfortunately that pay sucks. But okay, Pat, how, how much do you earn, Pat?

[C]

So I make about 13,900amonth.

[A]

I like that. That's about, just about.

[C]

Just about.

[A]

Okay. And that's your. Is that your take home or is that your gross?

[C]

Oh, that's my gross.

[A]

Okay, got it. And has that been consistent income for you?

[C]

It has, but I also have, I've retired once but continued working. I'm in a local government and I've changed, change roles. And so I also have a pension that comes in on a monthly basis and that monthly pension has been very beneficial. That's about $7,850 a month.

[A]

Okay, so that's on top of my 13. Nine.

[C]

Correct.

[A]

Okay. And that will continue. So that extra 94,000, that will continue is that there's no period certain, it's just for your life?

[C]

Yes, for life. And then it's also for, for Jane, if or, or. And then potentially, we don't know yet. We're still searching if it would qualify for our youngest son with a special needs.

[A]

That's interesting. So how, how have you done in terms of saving? Let's get to that part of it. So you've had a couple of different careers. Let's start with retirement savings. What have you socked away?

[B]

So currently we have about 55,000 in our brokerage accounts, but those are pretty much earmarked for different aspects of our life. So we have an HSA HRA combined is 150,000. And most of that is Pat, since he's worked the longest. We have pre tax retirement accounts of 1.9 million.

[A]

Wow.

[B]

Most of that is.

[A]

Hold it, let's pause. That's great. That's amazing. So thank you. Tax retirement 1.9.

[B]

And most of that is mine at 1.5 since I worked in the public sector.

[A]

Okay.

[B]

Then we have our Roth Retirement accounts that are 1.37. 75 of that is mine, and 320,000 is PAT. And I have a inherited IRA of 280.

[A]

When do we have to get that out of the account?

[B]

Oh, it's lifetime.

[A]

Okay, gotcha. So it's an old one, inherited ira. Gotcha. Okay. How much do you guys spend on a monthly basis?

[B]

We're about at. I had originally thought we were about 13 to 15,000amonth, but given the price of things this year, I think we're probably close to 15,000.

[A]

Is there going to be any income besides the pension after Pat, you retire?

[C]

Yes. So I'll have a second pension. That will be about 49,000 a year.

[A]

Oh, my God. You're just a washing pension. My God.

[C]

Well, I've worked hard. I got 35. I got 35 years, and I'm probably going to do another year to 18 months if possible, or. Or maybe sooner. We'll see how the advice goes today.

[B]

We'll see what you have to say.

[A]

So. So wait, just so I have it set here. So you will have $143,000 in pension, right?

[C]

Correct.

[A]

Correct. Got it. And that covers. You know, I know that's gross, but let's just say that's. That's 12 grand gross, and you only need 15 grand a month.

[C]

Right. But we also then will have expenses of medical care that is not covered, that we'll have to account for.

[A]

How much more should we account for?

[C]

You know, right now, 100% goes back on the employees. So that's about. For a family plan is about 26,000 a year. If you stay on that, or if we have to look at the market prices.

[A]

All right, so if we said not 15, but we said 17,000, would that be fair? Yes, let's do that. Okay. And how soon are you thinking about retirement, Pat, in terms of like, actual, like, let's get done here.

[C]

Oh, I don't think about it.

[A]

You don't?

[B]

No, he doesn't.

[C]

And I think that's one of the dilemmas, is I'm a workaholic. I work, work, work. I've been working since I was 14. But the end is near. I'm approaching a stage where our youngest will be graduating in a year and a half. And then we have to make a decision. What's the next chapter going to be for him? And we're trying to leave all our funds available for him upon our passing, but unfortunately, we know Uncle Sam's going to take a big chunk of it.

[A]

Right.

[C]

Is trying to prep for that.

[A]

Okay, so can I just go, biggest picture, Is there anything else I need to know about? Like, in terms of, like, housing? Do you have a. You own your home. How much is that worth?

[B]

800,000.

[A]

And is there a mortgage?

[B]

Yes. 108.

[A]

And any vacation home or rental property?

[B]

No.

[A]

Okay. And you're going to stay in this house for the time being. Like, as far as we know, this is where you'll be. Right.

[B]

As far as we know, if our youngest decides to do a college type program that's out of state, we're going to have to move with him. So. And then our, our oldest lives on the other side of the, of the country, so there's that option as well.

[A]

Okay. Have you guys done estate planning?

[B]

I've done as much as I can on our own.

[A]

What does that mean exactly? You have your wills?

[B]

Well, we have, yeah, we have our wills. We have a special needs trust.

[A]

You do. Okay, that's what I was really going for.

[B]

But it's being updated. You know, it's constantly an updated type situation, so. So, yeah, okay, we're set with that.

[A]

Okay, so the. So you have an attorney who will be able to guide you on, you know, does this pension get to go to your, your 17 year old? Eventually, but let's say it doesn't. Let's just say it ends at the second death, which is what usually happens with most of these. Okay, let's just pretend that for a minute now we're in a situation where Pat, let's just pretend that you say, okay, I'm done when I'm 65. Just, you know, I think that maybe, you know, if you've been, if you've been working for 50 years, I feel like it's time.

[C]

You're like, okay, well, I do too.

[A]

You know, it's time. Okay, so at that point, you will have gross income between two pensions of $12,000 a month. This does not include any Social Security. Yet. I'm just saying $12,000 a month. And then let's. Do you happen to know what your Social Security benefit looks like at 67 or 70?

[C]

We do. And we're grateful that though the WEP program just changed that all of us in government are now going to be back entitled to Social Security. So.

[B]

So my Social Security at 65 will be around $3,000.

[A]

And 65. Do you mean 67?

[B]

I'm sorry, 67.

[A]

Okay, so 67. It's 3,000. And what about Pat?

[C]

I'm at 67. I'm at 2,006. Hundred dollars a month.

[A]

Okay. Although we could wait till you're 70 and the numbers get go up. Right. Are you guys both in good health?

[B]

I'm in really good health, I think.

[A]

Okay.

[B]

And Pat's in good health, but just he has some chronic things that he has to, he's gonna have to manage.

[A]

So maybe. So maybe what we do is we wait. Jane, maybe you wait till 70. What's your 70 number? You're claiming number 3,700. Okay, so let's pretend that Pat gets 2,600 at his age 67 in just a few years. Jane, you've got nine long years. No, everything is good nine years before you claim yours. And between the two of you, you know, obviously it's not perfect, but like your dollars add up just income wise it looks really, really good. I mean one of the funny thing is, one of the funny things is that you have all this money in pre tax retirement, right?

[B]

Yes.

[A]

So maybe one of the things that we really decide to do is that let's say Pat's done at age 65. Maybe you start taking some money out of that pre tax retirement account and using that to supplement whatever you need. But also you'll be in a somewhat lower tax bracket. Not a ton lower, but you'll be lower. And maybe we start to get some of that money out so you have access to it. I mean, I guess, I Wonder, is the 28 is launched, do you want most of the money to go to your 17 year old or do you want to split?

[B]

Probably would go mostly to the 17 year old, but certainly the other one will, you know, will be considered as well.

[A]

I'm wondering whether it's, it makes sense at this point to convert some of the pre tax money or not. Mark, what do you think? Should we convert or should we just pull some of that pre tax money out and have that available?

[D]

I don't think conversion is the best solution. I think pulling it out probably works better.

[A]

Yeah, that's what I think. You leave the Roth alone, you pull some of the money out of the pre tax account before you guys are forced to. Because remember, at Pat's age 75, he has to start and at your age 75, but you got some time. So now we're gonna pull some of that money out. We are going to be able to build up the brokerage account at the same time. And whatever you need income wise between now and your age 70, Jane is just gonna come out of that pre tax retirement account. The funny thing is that when you started the conversation, you said we need reassurance on retirement. Do you? Come on, you guys, you're in incredible shape. I don't see any situation that is a problem here. Even if we said oh no, we're wrong, it's not $17,000 a month, we need $20,000. Even then you're fine.

[C]

Oh, that makes me feel really good because that's been my fear and that, you know, it's given up the gap of what I'm making today to what my two pensions will cover us. And ultimately my, my mindset was to have our pension, my combined pension costs, or I'm sorry, revenue, cover all our expenses.

[A]

Why do. No, no, come on, hold on.

[C]

I know, I know, I know.

[A]

Get it.

[C]

This is, you know, the way I work and with having a special needs.

[A]

Child, I get that. But I think that you're putting the bar way too high. So what I think we, the way that I would approach this is to say, okay, 20 grand a month, let's just look at that as a number. We're going to be able to cover that. And whatever we can't cover, we're going to take out of the pre tax retirement accounts. That's what we're going to do. And maybe at the time, like when you retire, let's say again, let's say you're 65 years old and you say I'm retired, no big deal. So you take out five grand a month from that retirement account. That's what I would do out of your account. I would, I would tap yours first just because you're older. Take five or six grand a month out every single month. Don't even like that's the extra pay that you create for yourself. In other words, you'll have your income starting of your pension that is existing. You'll have that next pension, pension amount and whatever else it is. Maybe it's five grand, maybe it's six grand, I don't know, whatever you need. But when we get to that number, whatever it is, you take it out of your retirement account and you do it every single month. Now you're saying, you know how you just said like, oh, I just want my income to basically be covered by these two pensions. You don't make the retirement, the pre tax retirement account, your third stream of income, two pensions, one retirement account, or one stream from the retirement account and that will create your $20,000 a month gross. That's what you need to do.

[B]

Okay, that sounds great.

[A]

You're not going to run out of money. I can Tell you that right now, the details on the special needs trust and what you need to do with your 17 year old because you know he's young still. Right. We don't really know what's going to happen exactly. These numbers can change and, but they're not going to change so much that you need to alter your own retirement plans. I get it when you said Pat, like I'm a workaholic, but at some point you have to give yourself permission to not do that or to say, okay, you know what I'm going to do, I'm going to be a volunteeraholic or whatever you decide you want to do. Like you're going to use your time differently.

[C]

Correct?

[A]

I don't see any, I don't really see any problem here. Mark, I'm going to bring you on the air. Is there a problem for Jane and Pat at all?

[D]

Zero problems. They got this huge income from the pensions. Even if there is the $5,000 shortfall, Social Security will make up for that. When they get to Social Security, all they have to do is pull a little bit out of the pre tax, which as it stands, it's over $3 million. I understand it hasn't been taxed yet, but it's going to generate, you know, it could generate almost $10,000 a month.

[A]

So you're good, I think. Absolutely. So the thing that I want you to just give yourself permission to do is use a pre tax retirement account as another form of income. That is why you saved all those years.

[B]

Yes.

[A]

Right, yeah.

[C]

Do you have any advice on our tax? Because we know upon our passing that there's a term that I'm gonna look.

[B]

To because of the trust that there's accelerated tax brackets. So that's why we were looking at converting to the Roth.

[A]

So if we leave, I think that the problem is about the converting is that you don't have a lot of money in cash right now, your brokerage account. So that's why I said for now, if you want to, you could take more money out of the retirement account. Let's just say you took 100 grand a year out of the retirement account and you do that for 10 years, that's gonna help a lot. And then you can try to figure out how to accelerate and get that. I mean, the problem as you will see, is that you're sort of managing for two different outcomes. One is like, okay, we're alive, we're well and everything is good. And I want that to be good for you guys. And the other is for Our son. Right. And so I don't want to favor one versus the other. I think that if you can get money out of that pre tax account. And by the way, do not hear this Pat as like, oh, I have to keep working. So I don't hear that. What I'm saying is we can take more money out of that pre tax retirement account, pay the tax right now. And even if you end up like, let's say it's five years from now and the pre tax retirement account has grown or whatever, it's still like $1.3 million. We'll have more information then. And if you've built up your brokerage account at that point, maybe we would convert some. But I would not start converting this second. I'd first start to just try to pull the money out on an annualized basis. That's what I would start to do. Great. Now do you have an accountant or a CPA that you work with?

[B]

We do not.

[A]

And you manage your own money. I mean, you can look at this situation and maybe say maybe this is something we need to consult with a CPA about because I don't think, I mean, the big problem is that again, on one hand I want to make sure you get the money out of the account. On the other hand, you know, something bad happens too early in your retirement, it's not going to be good for your kid. So it is possible that, you know, you can consult with somebody or you can just kind of play with some of the numbers. But I got a good feeling that if you just, let's say that you retired next year, right. And you have the income coming in, right. You've got two different pensions and you say, all right, well we're in the 24% bracket. The top of that bracket, the 24% bracket, is $400,000. So you could just say I'm going to take out as much money up to the 24% bracket every single year and you could do it that way and instead of converting it, you just have a brokerage account and then that brokerage account would grow or you'd have cash on hand. And then maybe a few years later you might say, okay, now I can actually convert because you don't have a lot of cash on hand this second converting. I don't know if that makes sense. I want you to have liquidity too.

[B]

Correct?

[A]

Right, Correct. So I think that that's where I think you should go with this. I mean, I'm happy to talk to you more as you gain more information but if you even thought to yourself, the most important thing that we can do is take as much money out of our pre tax retirement accounts to keep us in the 24% bracket, that is truly the best you can do, I think.

[B]

Okay. Okay.

[A]

All right.

[B]

And there's never a time, Jill, where you use the money that's in that account to pay the taxes.

[A]

No, it doesn't. Conversion doesn't work that way.

[B]

Gotcha, Gotcha.

[A]

Okay. So it's much better if you have the money outside of retirement when you're doing a conversion.

[B]

Yes, of course it's much better. Okay.

[A]

Okay. So I think you're in great shape. So I don't know.

[B]

One last question.

[A]

One last question. Okay. Yes, go on.

[B]

You have it.

[A]

Sure.

[B]

Our house. Our home is only at 3.3. What? Typically I wouldn't pay off the mortgage.

[A]

Then you should not. You should.

[B]

Okay, okay.

[A]

You should not. Do not pay off the mortgage. That's not a good place to use your cash.

[B]

Okay, great.

[A]

Okay. And listen, if you sell the house and you move someplace else and some, you know, things change, you get back in touch with us, right? Okay.

[B]

Sounds good.

[A]

You guys are in great shape.

[C]

Thank you.

[A]

Mark, what are the odds that Pat retires next year? Mark?

[D]

I don't know. I think he's gonna do it. I do. I mean, he may do something else, but I think he's gonna do it.

[A]

Pull the trigger, Pat.

[C]

I. I know it's. It's coming really soon, so this helped tremendously and just reassurance and my wife's been giving me the advice and let me know how much I'm making as an hourly rage gang.

[A]

If you are like Jane and Pat and you need reassurance on retirement or reassurance on education, planning, or you are trying to. Trying to figure out what comes next for you in your financial goal making, get in touch with us. All you need to do is go to our website, jillonmoney.com, click the contact us button, write us a note, and if you don't want to come on the air live, check the box. Mark will do everything else. Don't forget to sign up for our free weekly newsletter comes out every single Friday and we always want to remind you that you can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Please try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[E]

Ringcentral will completely transform the way you work. It gives you built in, AI across all your business conversations. Your phone System has an AI receptionist that answers calls 24 7. Your video meetings have AI that takes notes instantly. Even your contact center has AI so you can help customers faster. It all comes together in one reliable platform for effortless AI communications. See for [e-mail] ringcentral voice of your Business hey, this is Richard Deitch, the host of the Sports Media Podcast.

[A]

If you're interested in what's happening with all the places where you consume sports, the Sports Media Podcast has you covered.

[C]

I've been turning down interviews all week. Kodakapi reached out. Oprah, George Stephanopoulos. So I said no. I was booked on the Deitch Podcast before the Taylor Swift phenomenon. I must live up to my responsibility.

[A]

Listen wherever you get your podcasts.