Second Guessing My Financial Decisions

Summary

Jill on Money with Jill Schlesinger

Episode: Second Guessing My Financial Decisions
Date: July 20, 2026
Guest Caller: Marie from Idaho

---

Episode Overview

In this episode, Jill Schlesinger takes a listener call from Marie in Idaho, diving deep into the complexities of post-retirement financial planning, especially after an inheritance and major family changes. The discussion explores how to structure account allocations, whether to convert traditional retirement accounts to Roth IRAs, strategies for helping family, and the emotional side of managing inherited wealth. Jill and Marie candidly discuss the long-term implications of these decisions, emphasizing personalized advice and caution around shifting circumstances.

---

Key Discussion Points & Insights

1. Listener Background: Marie’s Financial Journey

• Marie, a retired teacher, and her husband, a retired soldier, have been navigating financial decisions following inheritances and family losses.
• They discussed the transition and allocation of inherited investments, recalling Jill’s previous advice on consolidating a complex portfolio.
  • Marie trimmed down her inherited holdings from 25 different funds to 7, citing some tax complexity ([04:22–04:49]).

Quote:
"I got down to seven, but... because of some tax stuff. It was weird." — Marie ([04:42])

• Both have modest pensions and Social Security, with total after-tax income of about $9,300/month—far in excess of their $5,000/month budget ([05:53–06:29]).

---

2. Current Financial Structure & Strategies

• Housing:
  • Debt-free, own $500,000 home in Idaho, no second property ([06:56–07:08]).
• Accounts:
  • Brokerage: Inherited investment split mirroring a "bucket" approach:
    • “Working money” ($170k): 20% stock, 80% money market; for use through 2035.
    • “Long-term money” ($170k): 80% stock, 10% money market, 10% private equity—cannot be easily liquidated ([07:22–08:11]).
  • Retirement Accounts:
    • Marie: $120,000 Traditional IRA (50% ETFs, 50% CDs)
    • Husband: $40,000 Traditional (to be drawn down soon)
    • Marie: $160,000 Roth (50/50 split, some in ETFs, some in CDs)
    • Husband: $110,000 Roth (kept in money markets due to prior bad experiences with the stock market) ([08:42–09:17])

Quote:
"He's played along for a long time, but now... he's like, you know what, I had it with the risk thing." — Marie ([09:24])

• Cash Flow Management:
  • Large monthly surplus, most goes into “sinking funds” for travel, hobbies, house maintenance, and regular 529 college fund contributions for six grandchildren ([09:55–11:19]).

---

3. The Central Questions: Conversion & Allocation Doubts

Marie’s primary concerns:

• Did she make the right move splitting her inherited brokerage into “working” and “long-term” funds?
• Should she continue converting traditional IRA assets to Roth, or focus elsewhere ([11:53–12:20])?

Jill’s Evaluation:

• Conversion pros and cons depend on tax brackets: Idaho is favorable tax-wise, but their income pushes the couple into the 22% federal bracket.
• With Marie’s income structure, converting could be done to stay in 12% bracket, but larger conversions trigger higher taxes ([13:06–14:46]).

Quote: "If you really want to play the game of staying in 12%, you won't be able to convert as much." — Jill ([14:44])

---

4. Hidden Risk: Pension Loss Impact

• Critical Factor: If her husband predeceases her, Marie’s income drops from $9,300/month to $3,000/month ([15:03]).
  • Jill’s revised recommendation is to stop further Roth conversions and preserve traditional assets for future living expenses given the risk of drastically reduced income ([16:10–16:26]).

Quote: "Until I heard that little detail about the pension, I was saying, well, why not?... I want to hang on to the money." — Jill ([16:25])

• Jill advises to:
  • Hold off on further conversions;
  • Build up more reserves in long-term investment buckets rather than over-funding 529 plans or "sinking funds" ([16:26–17:13]).

---

5. Portfolio Structure: Cash vs. Stocks

• Discussion of whether too much is sitting in money market accounts vs. invested for growth; Jill suggests adjusting so more is built in long-term, depending on Marie’s comfort ([17:27–19:13]).

---

6. Other Considerations

• Geographic Flexibility: They plan to stay in Idaho until one spouse passes, then possibly relocate (supported by home equity if needed) ([17:27–17:44]).
• Estate Planning: Documents recently updated, earning Jill’s approval ([19:37–19:39]).

---

Notable Quotes & Memorable Moments

• On Spousal Longevity and Income:
  "So you better find a new husband... Sorry. Sorry, soldier." — Jill ([15:03])
• On Inheritance Philosophy:
  "We were given a lot, so that, yeah." — Marie, on gifting to grandchildren ([11:41])
• On Changing Personal Advice:
  "I think I'm switching around. I'm switching my advice." — Jill ([17:03])

---

Important Timestamps

| Timestamp | Segment / Topic | |-----------|------------------------------------------------------------------------| | 03:29 | Marie reconnects, updates Jill on changes since last call | | 04:22 | Details of inheritance and reduction from 25 to 7 funds | | 05:56 | Household income and budget breakdown | | 07:22 | Account breakdown: brokerage, retirement, Roths | | 10:19 | Where does surplus monthly cash flow go? | | 11:16 | Support for grandkids: 529 college fund contributions | | 12:20 | Marie’s central question: continue conversions? | | 13:06–14:46 | Tax bracket and conversion analysis | | 15:03 | Key risk: Household income collapses if husband passes | | 16:25 | Jill reverses course: stop Roth conversions, build more cash reserves | | 17:02 | Advice to direct surplus into long-term investments | | 19:37 | Estate documents completed |

---

Actionable Takeaways

• Don't Over-convert: Stop Roth conversions for now to preserve flexibility should household income fall in the event of one spouse’s passing.
• Rebalance Surplus Savings: Direct more surplus into long-term investments rather than over-funding short-term “sinking funds” or 529s.
• Portfolio Structure: Ensure enough growth-oriented investments in long-term funds, but maintain adequate cash for near-term needs.
• Estate Documents: Keep estate plans up to date, especially when family and income arrangements shift.

---

Final Thoughts

This episode exemplifies Jill’s nuanced approach—she reminds listeners that financial plans are living documents that must evolve with life’s changes. The importance of considering “what if” scenarios is brought sharply into focus, as is the value of flexibility over optimization in retirement. Marie’s journey is relatable for many retirees who receive inheritances and must balance helping family with securing their own future.

---

Listen to more “Jill on Money” for practical, jargon-free financial advice on navigating real-life complexities.

Transcript

[A]

Growing up, money was a topic of conversation in my household, but for many it is taboo, and in those households it often leaves people overwhelmed by finances when they become adults. But money stories can change, and one way to change them is to use Monarch. Monarch gives you the ultimate clarity by tracking all of your accounts, investments and savings goals in one place, completely lifting that heavy mental load off of your shoulders. Unlike other apps that only show you what you've already spent, Monarch actually helps you plan for the future. You'll love using their AI assistant to ask specific questions like can I afford this vacation without touching my savings? Plus, the AI weekly recap automatically flags spending spikes and net worth shifts before they become an issue. Monarch can truly simplify your finances and empower you to hit your goals with total confidence. Write your own money story with Monarch. Use code Jill [e-mail] to get your first year of Monarch Core Half off. At just $50, that's 50% off your first year at monarch.com with code jillonmoney when a child faces a serious medical challenge, a children's hospital quickly becomes a family's entire world. Whether they're helping a child recover from a sudden injury or helping them manage a long term condition, these hospitals provide an irreplaceable community resource. Children's Miracle Network is dedicated to supporting this specialized care by securing the crucial funds centers depend on daily. Children's Miracle Network is a leading charity impacting the health of all kids. They raise funds for one hundred and seventy children's hospitals across the United States and Canada, protecting healthcare access for millions of families. Their fundraising network brings together corporate partners, local grassroots programs, and everyday donors like you and me. Your donation directly empowers your hometown hospital to use those resources and exactly where they are needed most. Wherever you see the Children's Miracle Network balloon, you're helping a local child receive care. Visit cmn.org today to learn more and make a donation to your local children's hospital. Welcome to the Jill on Money show. It's Monday, July 20th and we are here trying to help you make the best possible, the least bad, the best, I guess, decisions financially for you, for your family. And if you are wondering how some of the things that we're talking about with others would apply to your situation, give us a holler. All you need to do is go to our website jillonmoney.com jillonmoney.com and in the upper right hand corner there is a Contact Us button. When you click that button, a form will pop up and when you get that form. The coolest thing is you just click tell us what's going on. If you would like to join us on the air live, all you need to do is check the box and Mark will do everything else. While you're on the website, we encourage you to check out all the content that lives there. We've got a blog, we have videos, we've got resources. We always have our free weekly newsletter. You should absolutely subscribe to that because it's free. Right? It comes out on Fridays. That will actually automatically get you our blog as well. So check that out. Just bookmark our site. Okay. Today we are talking to Marie, Marie from Idaho. Hello Marie. What can we do for you?

[B]

Hello Jill and Mark. It's good to talk to you again. I really love your new show.

[A]

Oh yeah, I do.

[B]

I've watched it several times now.

[A]

What do you think is it. It's different watching versus listening. We're going to do a focus group right now.

[B]

It is different watching versus listening more because now I see what you look like. So when I'm listening to you, I still listen to your podcast. Uh huh. Now I can imagine you standing there sitting there.

[A]

Oh, I know we're getting new chairs. That's our newest thing. We need new chairs. But we'll, we'll attend to that. So. Well, thank you for that and everybody who's listening, you should absolutely subscribe to and follow our sister broadcast which is called Money Moves. You can find it on YouTube. And you can also of course subscribe for the audio on Odyssey or wherever you get your podcast. Okay. Thank you for letting me do that, Marie. Now let's talk about you. What should we do for you today?

[B]

Well, I spoke to you a couple of years ago when my mom passed and her financial company had put me in all kinds of, of ETFs and stocks. And you suggested I trim down to three from like 25.

[A]

That sounds already. I like my advice on that. How did it go?

[B]

I. I got down to seven, but.

[A]

All right, that's not bad.

[B]

Yeah, because of some tax stuff.

[A]

It was weird.

[B]

And then two years ago I called you, I wrote you and I was about to. I was about a week from going on with you again but my, both my brother and my sister in law passed away.

[A]

Oh my God, this is horrible.

[B]

It was like three weeks. It was very fast moving cancer. It was unbelievable.

[A]

Oh, I am so sorry.

[B]

But we made it through.

[A]

Oh my gosh.

[B]

I went ahead and did what I was calling you about but now I'm now I'm questioning myself. So basically, I just want to know, you know, if you see anything that I'm missing, what I didn't think of. We're a teacher and a soldier who never cleared more than 90,000 a year, but got a great gift from our parents. And should I convert more traditional. Should I invest more stocks?

[A]

All right, well. Well, let's. Let's go back to you guys now. So are you currently teaching?

[B]

I am not. We've been retired about 10 years.

[A]

Okay, so how old are you?

[B]

I'm 69, and my husband's 76.

[A]

Okay, and you both receive pensions, right?

[B]

My pension is very small. My husband is a very good pension.

[A]

How much is his. His pension?

[B]

Well, altogether with our pensions and Social Security and everything, and we're about 9,300amonth.

[A]

When you say everything, are you also including any money that comes out of accounts?

[B]

No.

[A]

Okay, so like, pension, Social Security, all tolls up. 9,300 bucks. Is that enough to support you guys?

[B]

Oh, yes. We really. Our budget is about 5,000.

[A]

Oh, gosh. So you're net savers, and you're, you know, 69 and 76. Goodness gracious.

[B]

I would like to say we're net savers. We're net like plane and funding grandchildren and.

[A]

Okay, meaning your current situation for you guys. Not every. All the money. I'm sure you're spending the money. I'm not doubting that. So. But you got plenty of cash flow. You own your home in Idaho?

[B]

We do.

[A]

How much would you say it's worth?

[B]

It's about 500,000.

[A]

Okay. And there's no mortgage?

[B]

None.

[A]

Is there any other property that you guys own?

[B]

We do not.

[A]

Okay. So you've got this pension money. It sounds like you also have accounts that have not been taxed yet, so you're talking about conversion. So let's talk about some of those traditional retirement accounts. What do you have?

[B]

So we have a regular sinking fund of about 20,000. And then we have brokerage, which is mostly our inherited stuff. And what I did is I broke it into two, so I made half of it working money of about 170,000.

[A]

Okay.

[B]

And the working money is 20% stock and 80% money market. And I figure until 2035, we'll be working out of that, I guess, bucket. Okay. And then I moved another section to long term and started in 2036 of another 170,000. But that one is 80% stock and 10% money market, and then 10% private equity that I cannot get out of.

[A]

Wait a Second, I'm kind of intrigued by this. You just did it because you wanted to have almost like a brokerage operating account where you could draft on that money market account if you needed stuff. Is that right?

[B]

Right. And really to force us to go ahead with some of the more fun things I see. So I could, we could think. Okay, don't worry. This section is, is safe for later.

[A]

Okay, I got you. I got you. So that's your taxable. What else do you have in traditional,

[B]

I have about 120,000 and that's 50% ETFs and 50% CD. And my husband has 40,000, but he's. We're going to empty that out in the next couple of years. A roth, I have 160. That's about again the same type of split. 50, 50. And then my husband has 110 and, and then he's just leaving that in money markets.

[A]

Why is he leaving that in money market?

[B]

Because he, we got, we got pretty burned in the 80s and he's played along for a long time, but now

[A]

he's like, you know what, I had it with the risk thing.

[B]

He's just done. Yeah, he just.

[A]

So I kind of feel like that's fair. Right? You know?

[B]

Yeah, I, I've come to peace with it.

[A]

Okay, so just so I understand this, the 9,300 bucks comes in, you're only spending 5ish. Let's say that the 9,300 after taxes, let's just say it's like 7,500 or something like that. So you have like 2,500 bucks a month in surplus, is that right?

[B]

Right. And actually that 9300 is after tax.

[A]

Oh boy. Okay, so when you get that extra money, where are you putting that? You know, few forgetting about the kids for a second, but like where would it go immediately? Like, okay, we have all this extra money every month. Let's say it's three or four grand. Where is that going? Into the brokerage account number two, the long term one.

[B]

It's going into the sinking funds.

[A]

Oh, it's going. So it's to that 20 grand. Right. Okay, so. And do you know about how much you really are putting in there every month?

[B]

Probably 3,500amonth.

[A]

Okay. And the sinking fund is what you are tapping to help out. Like when we talked, when you just said like, yeah, like we have all that money but we're spending it. So let's talk about who you're helping. And is it, is it some fixed amount every month or is it like, you know, every now and then it changes or we help when we can. So what is the, do you have a system right now?

[B]

I sort of do. Really. It's about travel because I'm going back and forth to see our grandchildren on the east coast. We're in the west. We have some pretty good hobbies.

[A]

Okay.

[B]

Upkeep for the house. And then the grandchildren each have a 529.

[A]

Oh, nice.

[B]

That's so great stocking that one.

[A]

Okay. And how many 529 plans do we have?

[B]

Six.

[A]

Six plans. And you're, are you putting a fixed amount every month or are you just kind of throwing it in at some, you know, at the end of the year it's gifting.

[B]

I throw it in every month and then at the end of the year it's gifting.

[A]

Wow, you are so nice. That's great. Okay.

[B]

We were given a lot, so that, yeah.

[A]

Well, it's nice that you're continuing that process. So it sounds like you're in great shape. So when you said I did something, what was it that you did?

[B]

So I, I, I broke those two in half. Working money in one and the long term money in the other.

[A]

Okay.

[B]

And, and so in turn, I basically stopped investing in the working money.

[A]

Okay.

[B]

I just, it's basically in money market.

[A]

Okay.

[B]

And then the other part is that I don't know if I should continue to move some of the traditional into my Roth.

[A]

I mean, you have this, you know, like you have whatever it is, $140,000 in money market in that, in that working account. So if you, I mean, I, like you said, you're going to probably end up taking the money out of your husband's. That 40 grand. You'll just kind of dribble it out. Right. And in your, in your account. I'm just looking at the, what's the, what's the tax situation in the state of Idaho, Just so I have a sense of that.

[B]

Incredible.

[A]

Incredible good or incredible bad?

[B]

Incredible good.

[A]

Oh, okay, Good. Okay. So right now, because you have all this income, which you said 9,300 is after tax. So what's coming in Pre tax, like 11, 12.

[B]

I hate to admit that I have no idea.

[A]

That's all right. Okay. I'm just trying to get. So you're basically your top bracket right now is the 22% is what I'm

[B]

assuming it's between 12 and 22. I mean, it fluctuates whether or not I convert a Roth. But my husband was military, so a good portion of that is not taxable.

[A]

Oh, I forgot about that. Oh, well, how do you feel about paying at 22%? I mean, you could kind of dribble it out yourself. You could just do a little bit like if you want to stay in 12, which is, you know, 100,800 this year, it seems to me like you could say, you can look at your tax situation like you look at your last year's return. Right, right. And you could say, you know, I'll do 10 or 15,000. That'll put me to the top of the 12. Right. At 100,000 ish and do that. Or you might say, oh, you know what, I've got longevity, or I feel good. I want to convert some of the money. And you can do it in larger chunks, but that will obviously put you in 22. So it kind of depends how you're feeling about it. I guess the other question is because you have all this money in money market, in this brokerage account, it's generating some interest income. So that's kind of adding to the liability. I don't think it's terrible. It's not so much money that's in those, that $120,000 in that traditional account that I would go nuts. But if you wanted to, I'm all game. It just kind of depends. If you really want to play the game of staying in 12%, you won't be able to convert as much.

[B]

Right. I, and I guess we've always thought of the Roth as our long term care insurance.

[A]

That's fine. Listen, you're not going to worry too much about long term care insurance because you got a lot of pension and Social Security income.

[B]

Right. But when, if something happens to my husband, I go down to $3,000.

[A]

So you better find a new husband. Sorry. Sorry, soldier. You know, I'm not nice. You really, you know, this is just showing my, my real subtle side. Yeah. I mean, how much Money's in these 529 plans right now? About.

[B]

About 15 in five of them. And then my oldest grandson was, is six years ahead of everybody else and he's. So we're doing his freshman year, so there's about 30 in his.

[A]

I'm gonna ask Mark Tularcio what his feeling is about the traditional retirement account money. This 120,000, Mark. I mean, I guess. Okay, wait. So there's two things to consider. Think about this, Mark. Like we could convert it. Maybe they'll be in the 22. If you lose your husband's pension and you go from 9300 to three grand. Then we'll just use that money and you will be. You just pull the money out and live on it. Basically, that traditional money.

[B]

Yeah.

[A]

So maybe we should. Mark, do you think convert or not convert? Now I'm leaning away from convert. Until I heard that little detail about the pension, I was saying, well, why not? I mean, they had the cash flow, but knowing what happens, God forbid, if something happens to him, I think I

[B]

want to hang on to the money.

[A]

Me too. So I think we, we know. I say don't convert anymore and keep him healthy, obviously. I also want to make sure that like, especially because of that extra fact which is losing that money, I don't want you to be overly aggressive on the 529 plan funding. It's not like you have a lot of cash flow. Now. I would not mind it, my friend, if instead of you putting $3,500 a month into your sinking fund, like you might want to build that up a little bit. But gosh, I'd like more money going into the long term fund.

[B]

Oh, okay.

[A]

I really would. I mean, again, until you gave us that last bit of information, I was kind of all in and like, let's rock and roll and do whatever you want now, you know, he is seven years older, he's a man. And so men's life expectancy and all that, like, I want to, I want to bolster your situation a little bit right now. I mean, do you have any kids around you in Idaho?

[B]

No.

[A]

Do you think staying in Idaho is long term is the thing or not?

[B]

Yes. Well, we'll stay here until one of us passes.

[A]

Okay. And then the other one is going to go move in with the kid who's kissing their tush the most. Well, right.

[B]

There are, there are lots of apartments in their area, so.

[A]

Okay. So in, in some respects that's good news for me because if I'm worried about stuff, then I can say, oh, well, there is a half a million dollars of equity that could flow to one or the other. I mean, obviously if you were to predecease him, he would lose some of yours, but he'll be okay. Right. It's the other way that is more precarious, right? Correct. Yes. Okay. Yeah, I think I'm switching around. I'm switching my advice. I mean, I guess the other thing is like sinking fund aside and splitting that 170,000 like stocks, 20% stocks, 80% money market. Do we really need to leave that much money in money market? I know that like when we put them together is not that bad. Right. Because you have 340 or $350,000 and you really think about it, you know, you do have probably a balanced portfolio, right? Like half stocks and half cash. I'm not worried in that respect. But if you, if it's easier to manage your money that way, that's fine. If you're really not doing anything with that money market money and it's just sitting there, then maybe I would want it to be invested, but kind of up to you. Does that make sense?

[B]

It does make sense. I was actually looking at investing all the rest of the long term money market into stock as well.

[A]

You could do that.

[B]

But I like the idea of going ahead and taking some of the sinking funds and buying stocks into the long term.

[A]

Yeah, I just think you should have. You need a little supplemental account, whatever we're calling it, you need a little extra money that's building up just in case. And we hope we don't need it. We hope everything's great. But at some point when you lose that income, we want you to be able to fall back on something, and that's what you would fall back on. And the proceeds of the house. So last question for you, Marie, do you have your estate documents done?

[B]

We just finished them.

[A]

Thank goodness. Thank goodness. See, Mark, another happy person. Because I don't get to yell at them. All right, well, then we'll talk to you every. I guess we have a few years from now we'll talk to you again. But so far, so good. Thanks for getting in touch with us, Marie, if you like. Marie, have a question about either allocation or how to think about accounts and what's used for what. Should you convert? Should you not? I mean, we love converting, but it's not every single person. So make sure you get in touch with us by going 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. Remember, you can subscribe, follow and promote us and our sister broadcast, Money Moves. Wherever you find your favorite podcast might be on Odyssey. And Money Moves is on YouTube also, so check that out. And please leave us a rating and review. Wherever you listen, lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. 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.