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Policygenius Narrator
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Jill
If that hits you close to home.
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Jill
People you love and feel good about the future.
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Jill
Welcome to the Jill on Money show. It's Tuesday, September 9th. Okay, you got through that first week of work after Labor Day. It is now for real. Now we're in it. There are four months, essentially a little less than four months to go before the end of the year. Things are going to happen very quickly in your life and so if you would like a little assistance before some crazy thing occurs, maybe it is the time where you say it is finally the moment where I'm going to send a note to Jill and Mark. I'm going to go to jillonmoney.com, i'm going to click that contact us button and I'm going to start to work through whatever financial anxiety, whatever financial issue, whatever maybe a life goal is and you're going to run that past us and we are going to try to help you out. And it doesn't have to be big. You don't have to have a lot of money, you don't have a little money, doesn't matter, whatever. Wherever you are, Mark and I are Going to meet you there. So if something's going on with your money, with your financial Life, go to jillonmoney.com, click the contact Us button, write us a note and check the box if you'd like to come on the air live. If you're shy, don't worry. We do email shows. We do. And while you're on the website, don't forget to sign up for the free weekly newsletter and subscribe to Jill on Money Live. That is our exclusive. All right. It's not that exclusive. That is a service where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content, all for $45 for the next 12 months. And our next live webinar is this week. As a matter of fact, it is exactly one day away. We are focusing on estate planning and we are not going to be messing around here. We've got a amazing estate attorney and we also have a CFP who is also. You ready for this? A shrink. It's amazing. It's like having the best of every world involved in this most emotional process. So please, if you have any estate issues and you want to join us, you can subscribe to Jill on Money Live up until I know Mark usually cut it off at like 3 o' clock on the day of, right?
Mark
Yeah, usually right around there.
Jill
Okay, so 3 o' clock by tomorrow at 3 o', clock, sign up. This is going to be a really important session and if you miss it, don't worry. If you sign up and you want to watch it after the fact, that's fine too. So check that out. It's really going to be fun. I know it's going to be fun for me. Okay, today we are going to do some emails and we are going to start with Jane who writes, my husband passed away in December of 2024. He handled our finances. Although I was kept informed of what he did. I should have listened more. We watched CNBC daily. Oh, well, that's, that's your first problem right there. But she did say, always love seeing you on CBS mornings. My husband always told me that when he passed away, I would not have to do anything to our portfolio as it would rebalance itself. We are with a well known brokerage firm and the CFP I talked to said the accounts would not rebalance themselves. I decided to talk with him about handling the accounts for me. I have received a plan that he worked up. Currently I have 59% in stocks, 29% in bonds and 12% in cash he wants to do, meaning the broker, I guess, is suggesting 40% in stocks and 60% in bonds. The portfolio value is $2.5 million. I have no debt other than the usual bills, utilities, taxes. I want to have enough to maintain our home, buy a car when needed, and travel occasionally in the US I'm terrified of turning our portfolio over to someone else and losing all of our hard earned dollars, although I know the market goes up and down. Can you ease my anxiety level? My pensions and Social Security cover my expenses. I currently have $60,000 in a checking account, $146,000 in a money market account, which earns a little bit of interest at the bank. I would appreciate any advice that you can give me. Thank you. Jane. Here's how I'm going to ease your anxiety level. The most important thing of your whole note had nothing to do with your portfolio. Here is the, as we like to say in the business, the nut graph. Like, the most important thing that you wrote is my pensions and Social Security cover my living expenses. Jane, because of that, you don't have to be so nervous about what happens next. I know that you don't want to lose a lot of money and I think that probably you didn't say how old you are. But you know, I'm not sure that you need to have a big change in the allocation. But you know, if you've articulated this to the person, the cfp, then that's probably why this guy said we should reduce the stock portfolio from around 60% to 40% and then move into some bonds. I think you probably are going to be a happier camper if you have four 40% stocks, 50% bonds, and 10% cash. I get the sense that you're going to want some cash around because that's going to make you feel secure, you know, in terms of like where you go next. You have to be terrified. I don't want you to worry about being terrified, but what I do want you to think about is you have direction and you have agency with this person. And you say to this person, to the cfp, and you say, hey, I don't necessarily want you to rebalance every year because that will create some tax liability for you. But you don't have to worry too much about what happens. You're not worried about making more. $2.5 million is going to keep growing. You don't have to take on tons of risk. Again, I don't know how old you are, but it seems to me that this is a very good Outcome. Don't forget to ask Jane how much this person is charging you on this account. And then if you want us to hold your hand a little more, you can get back in touch with us. But I don't think there's any problem here. Again, the way you can ease your own anxiety level is to highlight this sentence. My pensions and Social Security cover my living expenses. That's the most important thing you wrote. So I think you're going to be fine. I really do. All right, deep breath. It's going to be okay. Okay, next question. This is from someone with a very. Let's call her Mary because I think she has an identifiable name. Dear Jill, My husband and I are both 49 years old. We have an 8 year old daughter. We're in good health. I currently have a PPO health plan through my employer that covers the three of us. I do believe it would be beneficial to switch to a high deductible health plan for the upcoming year and start utilizing the benefits of a health savings account. However, my husband is not convinced that this is the best option. My question is, can my daughter and I enroll in the HDHP while my husband continues with the PPO plan? I don't think so. I don't think you can do this. I think the only way you could do this, Mary, would be if he got insurance through his own company and then you guys were on the plan yourself. You think that's right, Mark? I think that if she's on a family plan, he can't do it. They all have to do it, right?
Mark
You are 100% spot on, Jill.
Jill
Thank you very much. I remember a few things every, every now and again. Give us a holler if you need anything else. I like, I like HSAs. If your husband wants a little hand holding about why this could be a very good thing for you guys, why don't you come back on the air with us. We'll do a little extra health care coverage.
Mark
Triple tax free, baby.
Jill
Triple tax free. The money that goes in there, you don't pay tax on the money that grows. You don't pay tax on. You pay you the money that comes out when you, you have a health expense in the future. Now we're in the future. No tax, triple tax advantage. Okay. Steve writes, we're in our early 70s. We own some real estate. We've got pensions and investments. We have no children and we need someone to take care of our estate when we are no longer able to do so or die. We have trusts and wills and we're going to have an attorney take care of this, but that's no longer an option. A new attorney wants us to work with a nonprofit organization. We would appreciate your advice. Hmm. Okay. I don't know if you're asking me like, what happens, like who's the executor? There's two different issues that I, that I'm hearing in, in this one is that you need somebody to potentially or an organization to be the trustee of the trust, like to administer this. So let's just say that you die first, your wife survives you, then when she dies, who's taking care of all this? And that, that would really require you to either name an individual or a trust company to do it. Now, I don't know how much money you have. Maybe it's not even necessary. Maybe there's a niece or a nephew who can take care of it. If you're asking a somewhat different question, which is you have no children and you want someone and you want an ability to give money away, then I think that you can do something called a donor advised fund, or you can work with a charity to, to create a trust whereby when the, the survivor passes away, that all the residual of your estate passes to that charity. But I don't know if you're charitable or not. So I need a little bit more information. But it's an interesting question. I think there's a lot of people who don't have someone close in their lives, Marc, who they need like a point person, let me be clear. As somebody who's been served as a, as an executor for family and for friends. It's a pain in the neck, you know, my friend, someone, a friend of mine called it big death. Like, it's not like big tobacco, it's not like big alcohol, but it's, it's a lot to deal with. And so you need to have the kind of person who has administrative patience. That's what I would say. It doesn't need a lawyer, but it needs somebody who's going to stay on top of this. Okay. All right. Shannon writes. Hello, Jill and Mark. I live in the high cost state of Washington, where buying a house really feels like out of reach these days. The median sale price in Seattle is $885,000 according to Redfin. The median sales price for a condo, 630 grand. These numbers are so daunting to many first time home buyers like my 28 year old daughter. She's currently single. She doesn't think she can afford a house in the area. But she has a good paying job and a good savings habit. And I think she should try to shoot for a condo. My thought is to work with a reputable real estate agent, figure out the cost, the down payment, save for it, wait till interest rates come down, and then just do it. What's your thought on the strategy with this housing market trend? Some say that renting makes more economic sense. But I still think having your own piece of a roof over your head gives you so much leverage in the long run. Meaning building equity and wealth. Maybe I'm just old school. This is what Shannon's saying. Anyway, if you could please review the numbers and guide a 28 year old to strategize for her future housing and retirement. Okay, so here's what the 28 year old has. She has income of 5850 bucks. Monthly income, her expenses are 3500. So this allows her to contribute the maximum to a Roth and a 5, a Roth IRA and a 5%, and she contributes 5% to her 401k to get the match. Okay, and then she has, listen to this kid's 28, $57,000 in a brokerage account. Her Roth is 31,000, her 401k is 11,000. She also has a 403, 3400, a savings account with 40 grand, a checking account with $16,000. And she also wants to know about are there first time homebuyer programs? How do they work? Would she qualify? Love the show. Keep up the great work. Marc, let me bring you onto the microphone for this because I think this is an important question for us to explore. There are so many parents who are really worried about their kids ever being able to afford a home. So I love the idea of figuring out the costs and running the numbers. Right. I think that if your daughter is inclined to want to do this, I think some of these numbers actually make some sense. What do you think, Mark?
Mark
Yeah, I mean, I have a couple of thoughts. Yes, if she wants to do it, if the daughter's on board, and I don't want to oversimplify it, but run the numbers. And if she can afford to do this without decreasing the Roth contributions, without decreasing the 401k contributions, then yeah, it always comes down to the numbers. If you can do it, if you can pull it off and not have to pull back on any of the other stuff, go for it. But on the other hand, you know, if she doesn't want to do it, she's only 28 years old. It's not the worst thing in the world. I look at myself. I didn't own my first piece of real estate until I was 39.
Jill
Yeah. And also, I mean, I think that my. I'm underscoring this, that if she, she wants to do it.
Policygenius Narrator
But I also want to point out.
Jill
That your daughter is an amazing saver. So the thing that I think is hard for a lot of people. I don't know how old you are, Shannon, but I'll just say that people who are, say, 50 years old and older who own their homes. Okay. We all came of age at a time where the real estate market was a wonderful way to build some wealth. But maybe today, if she has a good job, considering she's already got almost $60,000 in a brokerage account and almost $50,000 in retirement already. She's 28. She is kicking tush, kicking butt on her saving and investing. Maybe that's also a valid way for her to actually accumulate wealth. So I think the, that if she wants to do it, I think she'll be able to do it. Run the numbers. You'll see for yourselves. But if she doesn't want to do it, I really would refrain from nudging her into it because it has to be something she wants and maybe renting is a good lifestyle for her. Okay, so we'll see. But I think it's doable. But don't push too hard. Just let it be. Okay? This is from Donnie. I never hear people name Donnie anymore. I have an Uncle Donnie. Okay.
Mark
Where's Marie?
Jill
Nice. Very good. Mini convention. Hi, Jill and Mark. Have you guys considered having a mini convention or conference in New York at a venue with some speakers of your choice? Your fans and listeners could stay at a nearby hotel of your choice and make a nice NYC trip of it next year sometime I would be among the first registrants of. Love your shows. Have a great vacation and have a great Mark. I like this idea. What do you think about that?
Mark
I would actually really enjoy that.
Jill
Well, we have to be able to. We have to figure this out. This could be a fun thing to do. How much would we charge for that?
Mark
I don't know. Because you know, these people are going to be footing the bill to get here, so that's a tough call. I don't know.
Jill
Like I would want to make it affordable, you know, I don't know. It's very interesting. I don't. I'm very excited to, to consider this. This could be the next expansion of Jill on Moneyland conferences.
Mark
We would hold it at Books Are Magic.
Jill
Oh, that's an excellent idea. But I don't know, like, it depends how many people there are. That could be a good idea. So Books Are Magic is a wonderful bookstore in Brooklyn. There's two of them and my friend is one of the partial owners. But I wouldn't want. Wouldn't you want it to be in Manhattan? Oh, wait, that's me. I'm going to look into this. I think having a live event would be fun. Here's another message. Hi, Jill. I just wanted to say how much I appreciate your show. I start most mornings listening to you, usually with my 10 and 12 year old boys in the car or playing in the background at home. They always grow. No, not Jill again. It's become a running joke in our house. I've been really intentional about teaching them financial literacy. It cracks me up when we're talking about money and they chime in with, I don't think Jill would advise that. Or is that what Jill would say? It's wild to hear kids casually talking about 401ks and IRAs, but here we are. And your voice has absolutely been part of that learning. You and Mark have such a great chemistry together. You definitely got fans in our house. One grown up, two very opinionated little ones. If you ever do a meet and greet in New York City, let us know. We'd love to come. Here we go. Mark, two emails. You're amazing. And if you ever need some kid voices for a segment, we got a couple ready to go. Oh, that's so nice. That is such a lovely, lovely note, Mark. I think that we have a message here, don't we?
Mark
Sure sounds that way.
Jill
I'm going for this. I'm going to talk to somebody. This is, this is exciting to me and the girls like it also. My girls like it here. No, not Jill again. Okay, sorry, that's just me. Okay, so listen, gang, love these notes, love your suggestions and I think that this is something that we are going to take seriously. But you know when I think about like what people say to me, like, well, why did you do this? Why? And I said, well, I think the audience really wanted that. Someone just interviewed me on a podcast and I was talking about, well, financial independence. New or next endeavor came about because the audience came back with those ideas. I didn't come up with those ideas. So we are forever grateful for everything you do for us and love your suggestions. And yeah, let's get some 10 and 12 year old super fans. Rocking and rolling. All right, gang, what a wonderful show. Thank you so much. If you have any questions, something bubbling up in your life, or suggestions for us, go to jillonmoney.com click the contact us button. Let us know if you'd like to come on the air. Don't forget, all of our content lives on the jillonmoney.com website and you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Don't forget to lift someone up. You guys lift us up every single day. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.
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Judge Dan Mentzer
Three judges, one bench, zero room for nonsense. I'm Judge Dan Mentzer. Joining me are Judge Rachel Juarez and Judge Yodit Towelde. And on Hot Bench, we don't just hear cases, we debate. What she's asking for is for the payments that she made on his car.
Jill
But there's still payments to be made.
Judge Dan Mentzer
Correct and we deliver justice. That is the verdict of the court. Follow and listen to the Hot Bench podcast on the free Odyssey app or wherever you get your podcasts.
Date: September 9, 2025
Host: Jill Schlesinger, CFP® | Guest: Mark (Producer & Collaborator)
Podcast Theme: Tackling real people's money issues and offering practical, empathetic financial advice.
In this episode, Jill Schlesinger and producer Mark answer listener emails on a variety of personal finance topics: portfolio management for widows, health insurance options, estate planning without heirs, and—taking center stage—the question from a listener about whether her 28-year-old daughter can realistically hope to buy a home in today’s housing market. True to the show’s mission, Jill approaches each scenario without jargon, demystifying the process and providing actionable advice.
(03:58–08:50)
“The most important thing you wrote is: my pensions and Social Security cover my living expenses. That’s the most important thing... So I think you’re going to be fine. I really do.” — Jill (08:21)
(08:50–09:45)
“If she’s on a family plan, he can’t do it. They all have to do it, right?” — Jill (09:23)
“You are 100% spot on, Jill.” — Mark (09:26)
(09:45–12:55)
“My friend called it ‘big death’…It’s a lot to deal with.” — Jill (12:41)
(12:55–16:43)
“If you can do it and not have to pull back on any of the other stuff, go for it. But if she doesn’t want to do it, she’s only 28 years old. I didn’t own my first piece of real estate until I was 39.” — Mark (15:15) “She is kicking tush…Maybe that’s also a valid way for her to accumulate wealth.” — Jill (15:24)
(16:43–19:20)
“I think that this is something that we are going to take seriously.” — Jill (19:04)
This episode underscores Jill’s philosophy: Successful financial planning is driven by self-awareness, flexibility, and realism—tailored to your needs, not societal pressure or nostalgia. Listeners leave empowered, whether they’re navigating widowhood, debating home purchases in tough markets, or just getting started. And through it all, Jill and Mark’s warmth makes even tough topics feel safe and approachable.