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Visit dafgiving360.org Today's episode is supported by what Should I Do With My Money? An original podcast from Morgan Stanley and Like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries and dreams, asking questions like can I retire early? Like really early? How do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and and it's shifting how I think about my money. Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player and feel empowered and supported when it comes to managing your life and finances. Welcome to the Jill on Money show. It's Tuesday, November 18th and you know what that means. It means that it is tomorrow we when we are doing our Jill on Money Live webinar. It's so exciting. So it is tomorrow night where we are going to be doing a very deep dive into year end tax and financial planning with Jana Davis. She is a certified Financial Planner Investment Advisor. She works at a company called Abacus big firm out on the west coast and she's going to help me and Mark field your questions about what what to do before the end of the year. Now if you'd like to join us, you must be a subscriber to Jill on Money Live and that will cost you 45 bucks for the next 12 months. So you'll get this webinar tomorrow night and in addition you will also get three more and the back catalog of webinars, bonus audio and video content again, 45 bucks for the next 12 months. I have a feeling we're going to be able to help you out and either save or make 45 bucks. I don't know, I'm not guaranteeing anything because that would be bad, but I had a feeling we can help you out. So join us, Jill, on Money Live. It's so exciting. I love the year end planning. I feel so like it's like crossing things off on my list. I love doing it. Okay, what else is on the website? Well, you can sign up for the free weekly newsletter. You can check out our other podcast which is called Money Watch. You can check out our radio show videos resources, all there right on the front door of the website. Okay, so we are going to do some emails today. So let's dig in here. This is from Ann who writes. Hi Jill and Mark. Love the show. Ann, we love you. I have a question about pensions. Here's the background. I'm 61 and retired. My husband is 54 and still working. We've got twins in high school. My husband will plan on working until they're through college at least seven more years. We're pulling money out of our savings to supplement our income, but we're trying to keep to that 2 to 3% per year for the next several years. And by the way, this is so wild because Mark and I were just, just laughing because we seem to be getting like a flurry of messages from people who are in their late 50s and 60s who have kids in high school. And it's like a lot of complications, man, it's crazy. Okay, so Ann has two pensions from two different companies. Boy, that's an embarrassment of riches. The first pension, remember she's 61. The first pension is available when she turns 65. She can take a lump sum of 220 grand or a monthly benefit of, of $1,226 with a 75% survivor benefit for the husband. The second pension is available right now. $125 of lump sum or payments of $650 a month that has a 100% survivor benefit. Okay, now thankfully Ann gives us a lot of detail because part of the pension conversation and decision has a lot to do with what other money you have saved. Do you hear Mark give that whistle? I didn't even see the non retirement stuff. Okay, so here's what we got. We have retirement accounts, $4.4 million. Those are traditional. There's About a half a million in Roths, a little bit of money in HSAs, and then $2.8 million in non retirement, 400 grand in 529s. Okay, here's the thing. My husband and I, we're in good health. Based on our parents. However, we are not likely to live into our 90s or anything crazy like that. He'll also get a pension when he retires, but I don't have amounts on that and it's a ways away. Okay, here are the questions. She says she's inclined to take lump sums, investing the money. And she says, I think we'll do better that way. And on the off chance that both of us die earlier than expected, you know, when we choose, if you get a pension benefit, the kids get nothing. So do we agree with. I agree you should definitely. I'm leaning towards taking the lump sum also because who needs the stream of benef of payments? It seems to me like there's like they're in great shape. Should we be doing Roth conversions? Let's see how the kids end up and where they go. Maybe it might be worthwhile doing. I don't know. It really does depend on how much money you're spending. I would totally do it, but I don't know how much you spend. You know, you've got all this money that is out there. You have money to pay. You know, you could use those lump sum amounts and you know, you can put those into your retirement accounts. But you've got a big number here where you're going to be forced to take money out and you could do conversions. I just, I don't know how much you spend. I really don't. Okay, here's the other thing. Last thing. I want to find a fee only advisor. I don't even know where to start to find one. How do you go about doing this? Okay, so the way you can do that is you can go to the national association of Personal Personal Financial Advisors, N, A P F A Napa, and you can do that. But just because you told me where you live, I'm going to recommend a few people that you check out because I think that I might have some help for you. Okay, so that's it for Ann. I think all. But if you, if you spend a ton of money, we would have maybe a different conversation. So we'll figure it out. Christina wants to know, should I pay off a rental property early? Here's what she says. My siblings and I are managing my dad's rental property. It's a Small house with an ADU in the back. We will eventually inherit it, and one of my siblings will keep the property and live there in retirement. I'm managing the mortgage payments right now. We are cash positive with three grand in rent monthly, and all of the leftover money after mortgage and expenses goes into savings for maintenance. There's about $85,000 left on the mortgage, and it runs through 2034. The adjustable interest rate, 6.8%. She says that bugs me, but it's down from 8%. Should I pay off the loan early with bigger payments so I can cut how much interest we are paying for the rest of this loan? We have a pretty small maintenance fund for the property, two grand. But I consider myself a backup, and I can fund any big emergency repairs. I'd rather have the money going toward paying off the loan quicker than sitting in the bank. I'm considering increasing the payment from 1300 to $2000 a month. Does this seem like a sound idea? Well, I mean, it's cash flow positive of three grand a month, and I'm not sure, like, is dad's rental property. Does he need the money? Maybe just use that money and, you know, use that extra 7 or 100 or 1000 bucks a month to pay off the 6.8% loan. It's a sound idea. I just don't know whether or not, like, the cash flow is necessary for dad or not. I don't have a huge problem with that. Do you, Mark? No. I mean, 6.8 is a real number. And, you know the fact that she says if something comes up, she could cover it. Yeah. I mean, I don't know. I need to know a little bit more about, like, the money's going in, but, like, does dad really need the cash flow or not? It's not a terrible idea, but it's also, like, you know, that you, you know, you can do this, which is fine. It's like, kind of up to you and the siblings as to whether or not this makes a ton of sense. But I, I, I get it. When you have that high interest rate, boy, it does sort of like blink a blaring red light of, like, pay me down. Okay, next question is from Holly, who says we are close to 70, and we retired three and a half years ago. That was due to health issues, but we're doing better now. Oh, that's good. Okay. They've got about a million bucks at Schwab. 70 stock, 30% bonds, cash. They moved to a different location a year ago, and they're Going to be meeting with a new rep from Schwab and she says we've got two large balanced funds from Vanguard, the Wellington Admiral fund and a balance fund. By the way, Wellington is balanced. I thought so. It looks like you have two, you know, two things that duplicate one another. But okay, you. Can you recommend a just bond fund also? No international bond. She writes. I don't. I mean, all these bond funds are like, just like an intermediate. This is. She asked me about a Dodge and Cox income fund. Why not just take like some sort of boring, you know, intermediate term bond fund index? That's what I would think. Okay, here's another one with a high mortgage. Mark, this is so weird. So Holly's like, next, I've been doing conversions to Roths and taking distributions to pay down a 6.4% mortgage. And when we moved to a new location, had to take out a mortgage and now I have it down to $20,000. And over the next three years, more Roth conversions and distributions before required minimum distributions kick in and likely of 65 grand a year. Okay, so the question is just. The bond fund is the question. So I like the idea of the bond fund. I would be just careful on the Roth conversions, making sure you have plenty of cash to pay the tax that's due. And of course, when that mortgage is all paid off, you're going to be so happy and you'll have your cash flow and that should all help. All right. Mary says, I've been listening to your podcast for several years. You've helped me develop a clear financial path to retirement after procrastinating for too long. Now I find myself at another fork in the road. I'm hoping you can help me choose the right path. My husband is 83. I am 68. We are still working full time. I am a caretaker to my 93 year old mother. And unfortunately, my husband was recently diagnosed with a terminal disease. Oh, brother. All right. She had planned to retire at 70, but now maybe she's going to step down to provide full time care for her husband. My only sibling is disabled after a stroke a few years ago. Her sibling is unable to help with her mother. Mom has a $1 million trust and a federal pension that nets her $3,000 a month. She's in a senior living facility that's close to me. She's doing well. Her expenses are about $7,000 a month. She wants to keep all of her assets in a credit union checking account, money market also, and some CDs averaging 3.6. Mary says I'd like to keep this money as safe as possible, but we are spending down her investments about clip of four grand a month. How can I preserve and grow as much of mom's assets while keeping them at the credit union? I'm now planning for being single in my retirement. This is so sad, Mark. Oh my God. I'm looking at selling our home, purchasing a smaller home in a 55 plus community for about $450,000 when my husband passes away where I could also care for my mom in the new home. Our current home has no mortgage. We've got no debt. All of our investments are with Vanguard and being managed through their personal advisor Service. It's a 7030 allocation. We spend about $6,000 a month. Is my plan possible? I think with mom you can ask the credit union if they have any investments available there. I don't know if you're going to be able to. I wouldn't mind having some small amount, you know, maybe going out farther on the cd, like out to six or seven years just to see what's available. You know, she is 93. We want to make sure we, you know, batten down the hatches and make sure she doesn't have any risk. But, you know, I would certainly go and look into what products they might have to help her out. But again, liquidity, access to the money is really important and you're going to have to spend this down. And Mary sent us a bunch of numbers for herself and it's kind of great because she has about a half a million dollars socked away in retirement accounts and Vanguard accounts. She's got a house that's worth a lot of money. So if she downsizes, she should be able to grab basically like an extra million dollars. And so, you know, between her Social Security and small pension and this money she socked away, the $6,000 a month spend, I think that the plan is possible for sure. I really do. I think that we'll have to see like how you do with this house and where you really can downsize. Let's see where you land. But I think this is a good game plan. And sometimes life will dictate something that is much more important than maximizing your finances. That's what I really think. All right, this is from Joe. He's got 529 plans for his two kids. They're both in college. He's, he says, but I've been cash flowing their expenses and leaving the 529 intact. So my original idea is that if I cash flow, I can gift the 529 to them. Is that a mistake? Should I use the 529 for their college expenses and just give them money after they graduate? Yes, you should use your 529 and you know, because I think that that money is there for them, which is why you saved it in the first place. And you can use that cash flow for other stuff. And you know, you might want to leave 35 grand each to or 30 grand each for them that you can eventually put into a Roth ira but use the money you saved. I definitely think that's a better idea. That's how I would certainly do it. So that's it. That is the program. If you have a financial question and want to join us, go to Jill on money dot com, click the Contact Us button, write us a note and if you want to join us live, just check the box. Mark will do everything else. Don't forget to check out our other podcast which is called Money Watch and we also have videos on the website. We've got resources, all sorts of fun stuff. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. We really do encourage you to lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. Foreign. Is everything that shows what your business is about, from what customers see to what they don't see, like operating agreements, meeting minutes and compliance paperwork. Get more for your business, more privacy, more guidance and more Free resources with Northwest Registered Agent Northwest Registered Agent has been helping small business owners and entrepreneurs launch and grow businesses for nearly 330 years. They're the largest registered agent and LLC service in the US. Build your business identity fast with Northwest Registered Agent and get access to thousands of free resources, forms and step by step guides without even creating an account. Don't wait, protect your privacy, build your brand and get your complete business Identity in just 10 clicks and 10 minutes. Visit www.northwestregisteredagent.com jillfree and start building something amazing. Get more with Northwest registered agent@www.northwestregisteredagent.com Jill Free what's up world?
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Is Von Miller, super bowl mvp, chicken farmer, and now host of Free Range. This is a show where I go off the field and off the script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet deep dives the conversation. This is your podcast. Join me every Wednesday. Follow and listen to Free Range with me, Von Miller everywhere. You get your podcast.
Date: November 18, 2025
Host: Jill Schlesinger, CFP®
Show Description: Jill answers listener emails on complex, often sensitive financial topics with her trademark jargon-free, practical approach—aimed at helping listeners make the most of their money.
In this listener-focused episode, Jill Schlesinger addresses a range of nuanced financial dilemmas sent in by listeners. Topics include pension decisions, Roth conversions, managing family real estate, coping with changing retirement plans, and strategies for multi-generational caregiving and wealth management. Jill emphasizes practical, emotionally intelligent financial advice, especially when personal circumstances intersect with major money decisions.
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Jill provides concise, jargon-free explanations, always returning to each listener’s real-life context. The show’s tone is warm, supportive, and occasionally laced with humor to balance heavier subjects. Jill’s responses exhibit empathy—particularly for those facing family stress, health challenges, or the complexities of intergenerational wealth transitions.
This episode underscores Jill’s commitment to practical, emotionally intelligent money advice—always putting listeners’ whole lives, not just their accounts, front and center on the path to financial health.