Does My Plan Work, or Should I Be Worried?

Summary

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Podcast Summary: Jill on Money – "Does My Plan Work, or Should I Be Worried?"

Host: Jill Schlesinger, CFP® | Date: July 15, 2026
Listener Guest: Mary from New York

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Episode Overview

In this episode, Jill Schlesinger fields a financial planning call from a listener, Mary, who is evaluating her family’s retirement readiness and considering providing financial support to her adult daughter saddled with significant student loan debt. The episode dives deep into practicalities of retirement planning, intergenerational assistance, risk tolerance, and estate planning. Jill provides actionable advice and reassures Mary's anxieties about outliving her assets, offering step-by-step strategies for the next four years and beyond.

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Key Discussion Points & Insights

1. Listener’s Situation and Goals

• Mary (61) aims to retire at 65.
• Husband (63), already retired, collecting a pension and will receive railroad retirement benefits at 67.
• Considering:
  • Buying a car in the near future.
  • Helping her daughter pay off ~$45,000 in student loan debt (interest-free), with a repayment plan.
  • Assessing whether these moves threaten her retirement security.

Quote:

"I would love your feedback on whether that would work. I have some expenses coming up, possibly... probably will need to buy a car... and interested in maybe helping out one of my kids." – Mary (05:36)

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2. Family Financial Picture (06:00–13:00)

• Current Income:
  • Mary: $90,000 salary (contributing $100 biweekly to a 403(b), some Roth, mostly traditional).
  • Husband: $3,100/month pension (pre-tax), will add $4,900/month railroad retirement at 67.
• Assets:
  • Husband's IRA rollover: $660,000.
  • Husband's 457 plan: $260,000.
  • Mary's IRA: ~$19,000.
  • SEP IRA: $120,000.
  • High-yield savings: $115,000.
  • CDs: $24,000.
  • House: ~$550,000 (paid off, low property taxes/insurance).
• Expenses: ~$7,500/month ("break even").

Quote:

"We’re breaking even... basically, we’re breaking even. Even with planning trips or whatnot, we seem to kind of just break even." – Mary (09:42)

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3. Student Loan Help and Family Dynamics (10:45–14:00)

• Daughter has $45,000 in grad school loans; payments just spiked.
• Plan: Parents will loan daughter money (interest-free) to pay it off with an expectation of repayments.
• No need to "make it even" with other child (already supported equally for undergrad).
• Jill suggests a repayment schedule, possibly with a nominal interest rate, but parents prefer interest-free.

Quote:

"My thought is I would like to loan her the money to pay that off interest free." – Mary (06:32)
"Let's do it based on not charging interest." – Mary (14:05)

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4. Retirement Income Planning (12:00–17:00)

• Jill crunches numbers for their post-retirement fixed income:
  • Husband’s pension & railroad retirement = ~$8,000/month (pre-tax).
  • Mary’s Social Security (at 67 or delaying to 70 for higher benefit).
• Advice on drawing down taxable retirement accounts ahead of higher income years to optimize taxes and Medicare surcharges (IRMAA).

Quote:

"In four years... you have his railroad retirement, $4,900. We have his pension, which is $3,100. So there we have eight grand, pre tax... I think this is doable. This is totally doable." – Jill (12:38)

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5. Drawdown Strategy & Tax Optimization (16:00–19:00)

• Take systematic withdrawals from husband’s IRA/457 plans before higher retirement income kicks in (stay in the 22% tax bracket, avoid IRMAA surcharges for Medicare).
• Open a brokerage account for excess withdrawn funds (Fidelity, Schwab suggested).
• Pay student loan support and next year’s car from cash/CDBs, then replenish liquid savings via withdrawals.

Quote:

"Tell the accountant that you’re planning to take money out over the next four years from your husband’s account... we just want you to help us figure out how much we can take out... so we stay in the 22% bracket." – Jill (16:06)

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6. Investment Risk & Asset Allocation (19:20–22:00)

• Mary is more risk-averse than her husband, who is unbothered by market volatility.
• Portfolio: ~40% bonds, ~60% stocks (Vanguard, Schwab, dividend funds) – fairly standard.
• Jill recommends rebalancing, possibly increasing bonds if risk tolerance is low, especially in taxable brokerage accounts (suggesting up to a 50/50 allocation for liquidity and lower volatility).

Quote:

"If you’re uncomfortable with risk... just make sure you’re rebalanced." – Jill (21:23) "In a brokerage account, you might just want to grab the money. So maybe it’s a little less risky, more like 50/50." – Jill (21:31)

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7. Estate Planning & Final Concerns (22:25–23:36)

• Current wills and healthcare proxies are outdated (from when kids were minors).
  • Jill: Update documents to match current family structure and wishes.
  • Option to include stipulations about the student loan support if desired.
• Final validation and emotional reassurance: Mary’s plan is solid barring major lifestyle inflation.

Quote:

"You’re in great shape. You’re in great shape." – Jill (23:36)

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8. Broader Notes and Resources

• Jill references new, stricter federal student loan rules (capped borrowing, higher costs).
• Directs listeners to her website’s blog for a guide on the changes: jillonmoney.com.
• Invites more diverse financial questions beyond retirement planning for future episodes.

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Notable Quotes & Memorable Moments

• "Oh my God." – Jill’s genuine response to the daughter's 700% loan payment hike (06:22)
• "If that's too much, then... you tell me how many times you can get to a live event for 15 bucks a pop, you know what I'm saying?" – Jill, candidly addressing audience feedback about subscription prices (05:06)
• "I want to make it better." – Jill, empathizing with Mary’s anxieties (22:26)
• "Change your work, change your wealth, change your life." – Jill, closing encouragement.

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Key Timestamps

• 05:31 — Mary joins the show, outlines her retirement target and upcoming expenses.
• 06:32 — Mary details her daughter's student loan situation.
• 08:02–09:20 — Discussion of pension, Social Security, and retirement assets.
• 10:01 — Family's monthly expense breakdown.
• 12:35–14:03 — Jill summarizes projected retirement income and affirms feasibility.
• 16:04–17:00 — IRA/457 drawdown plan and tax bracket strategy.
• 19:20–22:00 — Risk tolerance discussion, asset allocation, and brokerage strategy.
• 22:41–23:36 — Estate planning: wills, power of attorney, and healthcare proxies.

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Conclusion

Jill assures Mary that her retirement plan is on track, even with helping her daughter and a car purchase on the horizon. The episode is a reassuring, rational walk-through of family financial decisions, focusing on smart withdrawals, risk management, and up-to-date estate documents. Jill’s empathy, clarity, and practical frameworks provide not just answers for Mary but a valuable playbook for listeners facing similar crossroads.

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Transcript

[A]

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[B]

Hmm.

[A]

$45 feels very, very doable for most people. I think that kind of anything that's like 60 or less seems pretty. Somebody. Somebody the other day on YouTube was saying, it's way too much money. Really?

[B]

Yeah.

[A]

Okay, well, then they shouldn't do it. That's what the other people basically responded

[B]

and said,

[A]

if that's too much, then that's. You tell me how many times you can get to a live event and for 15 bucks a pop, you know what I'm saying? Okay. Anyway, we digress. Let's get to you. We are talking to Mary, who joins us from New York. Hello, Mary. How are you?

[B]

I am well, thank you.

[A]

What's going on? How can we help you out?

[B]

Well, I recently turned 61. My plan hopefully is to retire at 65. And I would love your feedback on whether that would work. I have some expenses coming up, possibly

[A]

also really something fun or something less than fun.

[B]

Probably will need to buy a car in the next few years and interested in maybe helping out one of my kids.

[A]

When you say helping out because the kid is struggling or because the kid got married or like, is what. What's the.

[B]

My daughter. Both of my kids are launched and doing nicely.

[A]

Okay.

[B]

My daughter has quite a bit of student loan debt right now from grad school. She just got notified that her payment is going up 700%.

[A]

Oh, my God.

[B]

Which she has worked down to a better rate. But my thought, I don't know if you want me to jump into this.

[A]

Yeah, let's do it.

[B]

My thought is I would like to loan her the money to pay that off interest free.

[A]

Okay. How much is the outstanding amount for her?

[B]

About $45,000. Okay.

[A]

Just so we got that. Okay. In your mind, if you paid off this loan for her, would you want to make it even Steven, with the other kid?

[B]

No.

[A]

Okay, good.

[B]

Paying it back. He doesn't have that debt. Okay. We've helped them both out evenly in terms of what we helped them with for undergrad and we gave at one time. So I feel like we've been even Steven. And this is a separate thing. And she. There would be a plan. She would start paying us back. She'd be paying us instead of paying her student loan.

[A]

Who's the U.S. in this? Who's the U.S. are you married?

[B]

My husband.

[A]

How old is he?

[B]

He is 63.

[A]

Will he plan to retire at 65? Is he still working?

[B]

He is retired. He's currently Collecting a pension.

[A]

How much?

[B]

$3,100.

[A]

Okay, great. Fantastic. Okay.

[B]

Does he collecting retirement?

[A]

Not. Not Social Security yet.

[B]

He will be getting railroad retirement and.

[A]

Oh, when? What Railroad retirement at what age?

[B]

67. Our plan is right now.

[A]

How much will that be?

[B]

That will be 4900.

[A]

And is his health care paid for? When? Right now. And he goes, then goes to Medicare. How does that work?

[B]

Yeah, he's paid for till Medicare and I am as well.

[A]

Oh, nice. Will you be entitled to a pension?

[B]

A $250 pension from an old.

[A]

$250 a month. It's like your coffee budget.

[B]

I know. We won't count that.

[A]

How much do you earn right now, Mary?

[B]

Right now I take home. Well, my. My salary is $90,000.

[A]

And do you contribute to a retirement plan?

[B]

I do. I'm putting in a hundred dollars every paycheck, every two weeks. Okay. Which is now going as a Roth, but that switched recently.

[A]

Okay, how much is in traditional money? Right now?

[B]

It's a 403B and it has about 65, $66,000. Great.

[A]

Fantastic.

[B]

4,200 of that is Roth, but most of it is not.

[A]

Okay, wonderful. And does your husband have an old retirement plan kicking around in addition to the pension?

[B]

Yes.

[A]

What's he doing?

[B]

He has an IRA rollover with 660,000.

[A]

Great.

[B]

He has an 457 plan with 260 in it.

[A]

I'm sorry, I missed the number. Say that one more time.

[B]

260,000.

[A]

260. Got it. And this is. None of this has been taxed yet.

[B]

Exactly.

[A]

Got it.

[B]

Okay. And then I have a contributory IRA that has 18, 19,000.

[A]

Great.

[B]

And then another SEP IRA which has 120,000.

[A]

Did you work for yourself?

[B]

Yes.

[A]

But not anymore.

[B]

Not anymore.

[A]

Okay. How are you doing right now on your 90 and his pension?

[B]

We're breaking even. Okay. Pretty much breaking even. You know, I might dip into the savings a little one month. I might put a little savings one month. So, okay, basically we're breaking even. Yeah. Even with planning trips or whatnot? We seem to kind of just break even.

[A]

Okay, how much do you figure that you spend?

[B]

About 7,500amonth.

[A]

Is that being lean or. Or is that like. Oh, you know, that captures everything.

[B]

I think that captures everything.

[A]

Okay, good. Do you guys have any savings or brokerage accounts?

[B]

Savings? We have a high yield savings with 115.

[A]

Okay, good.

[B]

We have some CD ladders that together are 24,000. And then in our savings account we

[A]

have 104 oh, terrific. So we're gonna buy a car. No problem.

[B]

Alrighty.

[A]

Don't you. I mean, what kind of car? I say that no problem. Something reasonable.

[B]

I'm not.

[A]

You're not one of those?

[B]

No. And we drive them, you know, into the ground. Okay.

[A]

So then you buy a new car and you drive it into the ground.

[B]

It will be our last car. Don't.

[A]

Don't say that. My God, you're not gonna drive a car. Well, I mean, I guess hopefully you're gonna drive for 20 years maybe, but maybe you never know. I know where you live and it's not great to be on the highways in that area. So. Okay, when you look ahead and you look at, you know, the. We want to do. You want to do the student loan part of this right now, is that correct?

[B]

I would like to, if she lets us.

[A]

Well, she'd be silly not to. And. And I think that maybe what might make sense is that one way that you can have her feel a little bit less weird about is don't give it interest rate. Just give it at like a normal interest rate. It doesn't have to be 6%. I'm just saying, like you, we can get a schedule together. You can take. And the car thing, when is the car gonna happen? Like now or soonish?

[B]

I. I think we could wait a year at least. Okay, so we can wait on that. I'd rather get this done first. Yeah. And then do the next year.

[A]

Okay, that makes sense. So, and the savings account, are you actively putting money in there or is that just old money or not?

[B]

Like I said, we're kind of breaking even. So one month I might get lucky and put a little in so that the next month, if we're a little short, I can take a little out. But basically breaking even right now.

[A]

How much is your house worth?

[B]

About 550,000.

[A]

Is there a mortgage that remains? No mortgage, that's why.

[B]

And very reasonable taxes and insurance.

[A]

Okay, So I think that this is certainly doable because you're talking about retiring in four years, first of all. So that's like you already have a huge, huge, like jump that you're not saying. I want out right now. So in four years what?

[B]

You'll have four years. We can collect his.

[A]

Right? That's what I'm going to say. I was just about to go through this. So in four years you have his railroad retirement, 4900. We have his pension, which is 3100. So there we have eight grand, pre tax. Right. We have not figured in Your Social Security. What's your Social Security at 67.

[B]

At 67, it's 3,100, but it's 70. It's 39.

[A]

Yeah, that would be nice to wait till 39, till that. How's your health?

[B]

Very good, very.

[A]

Oh, look at you. Very good. Okay, I think this is doable. This is totally doable. Okay, so let's now talk about the mechanics of this.

[B]

Okay?

[A]

So you keep working, you're doing your thing, it's fine. And you don't have to, you know, squirrel away so much money in the retirement account you're doing. It's just fine what you're doing. Okay. Mark, I want to pay off the $45,000 student loan debt, but I think. How old, how old's the kid who's got the debt?

[B]

28.

[A]

Maybe we should do it on an amortization, like a 20 year amortization at 20, at 3%. I can't believe you're charging interest. I am. I'm charging interest because she said no, no, I'm not saying she has to. I'm just saying if the kid box right, then one way around it is to be like, oh, well, we'll charge you some interest. That's all.

[B]

Let's, let's do it based on not charging interest.

[A]

Right? Not charging. Okay, that's fine. I mean, that's the way to get around it. Just to say, hey, your interest rate jumped on you. Right. And then you can always come back to that. Okay? So you take the 45 grand from your savings, the 104, or as the CD ladders come due, just use that. I don't know what you're, what the time horizon, but as the CDs come due, you're going to pop that into your high yield savings anyway. Okay? And because we asked it to replenish your savings so you have enough to pay for the car. And so you take the money out of savings you get, you pay off the 45, you know, she'll pay you back on some schedule, you know, you might. Whatever she can afford. Right, right. And that's fine. I think that's totally fine. And the next year you buy the car. Fine, same thing. Out of savings, you're going to deplete your savings a little bit. I guess the next thing is that, you know, we have this chunk of money that he has in his combined rollover and his 457, and you're going to start to pull some money out of that because we'd like to try to do that. Maybe even in the next four years before that pension kicks in and everyone listening. If you have forgotten your tax 101, it's, you know, a chunk of money gets taxed at 10%, the next chunk of money at 12%, the next chunk of money at 22%. You might even be nudging up into 24%. But, you know, the top of the 22 is 211,000. So you make 90. We know he has his $3,100 a month pension. And so maybe you just take out whatever the difference is, and you stay under 211 and you take that much out. Now, if you find that, gosh, I need some money and, like, I'm tapped out, or you can go up, you can pay a little bit at the 24% bracket. It won't kill you. But if you stay under that 211, I think that's good. Do you work with an accountant or a cpa?

[B]

You do have an accountant? Yeah.

[A]

Tell the accountant that you're planning to take money out over the next four years from your husband's account and tell them that you're still helping the kids so that they don't, like, bust your chops. Oh, why are you doing. They always. Accountants hate paying taxes. But you need to get some of this money out anyway. So even if it ends up being, let's see, 90, 120 maybe, if it's like 80 grand a year. And again, I'm not. And just say to the accountant, we just want you to help us figure out how much we can take out of hubby's rollover 457 plan. So we stay in the 22% bracket. So let's say it's another 80 grand a year. Okay? You take the money out, you pay the taxes, you make sure that you replenish your savings and everything is good. And then you put the rest of it in the brokerage account and you say, what brokerage account? I don't have a brokerage account. We're going to open one. We're going to open up a brokerage account for you. Where is that rollover?

[B]

Everything's in Schwab. Okay.

[A]

You can open up a brokerage account at Schwab, by the way, and whatever is excess, once you get these two big things done, the car and the payoff of the loan, you can open a brokerage account. And so if you're going to take 80 grand a year out for the next four years before he starts collecting his railroad pension, and then you put it in the brokerage account, you've got some money that's available and you know what else you can do. You can then continue to take money out when even though he is, you know, collecting this money and the Social Security just going to take less out. And you should be good when you retire at 65.

[B]

Right.

[A]

He's 67. You got your money and you've got replenished your cash, you've started a brokerage account, you've helped the kid out. You know, all these things are great. This is amazing. I don't think there's any problem. Mark, is there any problem here for Mary and the benevolent mother that she is? No, they're good. I mean, their fixed income numbers are real numbers. They're big numbers. Yeah. So I mean, and you know, for you, it may be that one of the things you do in between that the time you retire and you're claiming at 70 is you too, you can continue to put more, pull more money out of your, out of his retirement account. I'm only going to his because he's got more money that hasn't been taxed yet and he's older. That's why we're going to look to that. And the only other thing is, you know, of course I dare I mention this, but you may have heard of us talk about something called irmaa. Have you heard about that? This is when you're claiming Medicare, it looks back a couple of years. So if you take money out and you're earning over. Let me just look at this. If you're over, if you're $218,000 or less in income, you will not pay any surcharge. If you go above 218,000, there is a surcharge that you will have to pay as part of this Medicare. So it's another reason that if we keep you under that 200 or 215, 211 rather, it'll make it a little bit easier for your Medicare planning as well.

[B]

The market scares me.

[A]

Yeah.

[B]

As you get older, doesn't scare me. He's like, everything's fine, we have plenty of money. It'll last forever. And I'm not that way. I'm worried we're gonna run out. Income looks good or, you know, I

[A]

don't think you're gonna run out of money. But if you're uncomfortable with risk, then you can say to him, I'm a little uncomfortable with risk and I don't really want to sustain a huge loss. I, I agree with him. I don't Think I don't see a scenario that you're going to run out of money unless you start spending a lot more money. You know, if all of a sudden you're like, we're not spending 7,500, it's $13,000 a month actually then. But you know, given these numbers, is most of the money in that, besides the CD ladders, is most of the money that you have invested in stocks or stock indexes and bonds?

[B]

Okay.

[A]

If you looked at like the, the portfolio, like, just like in a, as an example, if you looked at say your SEP ira, do you know what percentage is in stocks or higher, higher risk stuff?

[B]

We went through this at one time and really looked at it and tried to balance it a few years ago.

[A]

Okay.

[B]

It's 40% in a Vanguard interim term. 40% in a Schwab US broad market.

[A]

Yeah.

[B]

And 10 each in a Vanguard total world and a high end dividend.

[A]

Okay. So you have 40% in an intermediate bond fund, which is fine. That's fine. I don't think you're going to be. So if all the accounts kind of look like that, 60 equities. Right. Then I think it's fine. The one thing you may want to do is that since you're feeling like a little queasy and you're worried about the market, you can say to your husband, can we just look at the accounts? Can we just rebalance? Because maybe we're really not 60, 40 anymore. Maybe we're more like 70, 30, because the stock market's gone up by a lot.

[B]

Right.

[A]

So just make sure that you're rebalanced. But I think, I feel, I don't think that's outrageous. I really don't.

[B]

And if we open up a brokerage account, do similar.

[A]

Yeah. I mean, I would probably do more like 50, 50 in a brokerage because in a brokerage account you might actually need to grab the money for something. But this is money, you know, the, the highest risk can be in the Roth. Then after that traditional IRA rollover SAP, all that stuff, the, the old 457, all that stuff. And then in a brokerage account, you might just want to grab the money. So maybe it's a little bit less risky, more like 50 50. But it doesn't have to go, you don't have to go crazy either.

[B]

Right.

[A]

If, if, especially if it's like you, you have rebuilt and replenished the savings and CD and all that stuff and you've gotten these two big goals, these short term goals that have, you've accomplished, which is pay off your daughter's school loan and then buy a car, and then you've replenished the cash and you're good to go. Then I think you're in great shape.

[B]

All right.

[A]

You're so nervous. I want to make it better.

[B]

I am. No, I. I look at it on paper and I feel good, but I. I'm a little nervous, but I feel good. I feel. I feel great that you're validating what my. My plan.

[A]

Okay. All right. Now I'm going to ask you a question. Like the. To make you feel even more anxious is do you guys have your estate documents done?

[B]

We have will, living will, power of attorney, and health care proxy, but they were done when my kids were child children.

[A]

When you were talking about guardianship. Go do them again.

[B]

Being written that it would still work once they were of age. But I feel like you should revisit it all.

[A]

I mean, you should revisit it. Just have a set of eyes on it. It may not be that important. If you want to. If you want to make an adjustment where you say, the 45 grand that we've paid off in, you know, one child's student loan, like that kid gets an extra 45 later or whatever. If you want to put that in there, you could do that. That's where you would do it. Otherwise, if you really want to do it, then you can just, like, make it up to that other kid later. You know, it's up to you, or you don't even have to. I'm just giving you options.

[B]

Yeah. Yeah.

[A]

You're in great shape. You're in great shape.

[B]

Oh, that's good to hear.

[A]

You're good. All right. Very well done. Go off and make sure you rebalance your accounts. If you're like Mary, and you're looking for a way to help your kid, you know, there. There's a whole new student loan regime. I wrote about it on the website. So you should check that out under the blog [e-mail], it's getting a lot more expensive to manage student loans. A lot. And whether you agree with that or not, that's now I'm just telling you that is the way of the world going forward. And as parents, if you're saving for college, just know you cannot borrow as much money lifetime for through the federal loan system for your kids. The numbers are capped now, and there are really significant changes. So do check out the website jillonmoney.go under the blog section. You'll see that or just get in touch with us. Go to Jill on Money and then the in the contact us button, click that button, write us a note, check the box. Mark will do. Everything else you can find us on the Odyssey app and you ought to. You should subscribe there. You can also check out our sister broadcast. It is called Money Moves. You can find it wherever you get your favorite podcast or on YouTube. So check that out. The Jill on Money, Money moves channel on YouTube. And of course, we just always hope that you try to put your hands metaphorically on someone's back. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. This is the sound of captivity. This is the sound of rescue. And this is the sound of freedom. Give Armenia's captive bears a second chance by supporting International Animal Rescue. Call 508-826-1083 or search the Great Bear Rescue to learn more. Hey there, it's Jill Schlesinger. I'm launching a new show. It's called Money Moves. And your money is going to move. We're going to help you make better financial decisions. We're going to call out the B.S. you're finding all over social media. We're going to give you actionable guidance to make your financial life clearer, less stressful. We're going to answer your financial questions and take the mystery out of your financial life. Follow and listen to Money Moves with Jill Schlesinger. Wherever you get your podcasts.