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This message comes from Jill on Money sponsor Charles Schwab. Independent financial advisors focus on building a relationship with you that goes beyond your portfolio. As fiduciaries, they must act in your best interest always. The relationship they have with you will be based on transparency and trust, and they're committed to bringing you advice that fits your values. That's why Schwab is proud to support them. Visit findyourindependentadvisor.com whether you're hosting the whole family or keeping it cozy with friends, Whole Foods Market has everything you need to make Thanksgiving feel effortless and delicious. You'll find great prices on all your seasonal favorites. And the 365 by Whole Foods Market brand brings the trusted quality you love at prices that make every dish a little brighter. Start with a turkey, no antibiotic ever. Birds are just $1.49 a pound with prime or upgrade to organic for $2.99 a pound. Terms apply. Then stock up on pantry staples like condensed soups, instant mashed potatoes, and organic baking spices to make your favorite recipe shine. And for easy entertaining, something I love, grab three 65 brand frozen appetizers like the quiche Trio, butterfly shrimp or breaded calamari, ready to serve in minutes so you can spend less time in the kitchen and more time at the table. Enjoy. So many ways to save on your Thanksgiving spread at Whole Foods Market. Welcome to the Jill on Money show. It's Friday, October 31st, Halloween, one of my least favorite holidays. I like that Mark's already done the monster Mash. I guess I'll watch the Great Pumpkin Charlie Brown, which is, you know, maybe the only way that I honor most holidays is with peanuts. And I hope that you are having fun as you prepare for Halloween. Mark, what's your opinion of adults who get into Halloween?
B
Not a fan, not a fan, not a fan.
A
But we love it for the kids. Mark, this will be your second year of doing your trick or treating in the neighborhood, right?
B
Yeah, yeah, that's true. And I will say where I live in this, this area of Brooklyn, I mean they go all out. Some people wait all year for this one day and then they go all. I mean they shut the streets down.
A
It's like the Diker Heights of like that. Okay? It's Diker Heights, a neighborhood in Brooklyn where the very famous for their Christmas decorations. So your neighborhood being very famous for the Halloween. Well, listen, good for you, good for Theo. Happy Halloween to everybody. For everyone else, all this means is there's only two months left in the year. I Can't even Mark. So crazy. So that means you really have to focus. I'm guessing that there's probably about six weeks before the end of the year where you can hyper focus on something financial. Like the next three weeks, three and a half weeks before Thanksgiving, then it's the first couple of weeks of December and then you're done. You're shutting your brain down. I get it. But if you are really considering what kind of tax and financial planning moves to make before the end of the calendar year, I will encourage you to subscribe to Jill on Money Live. Our next quarterly live webinar is on Wednesday, November 19. We are going to do year end tax and financial planning with a wonderful certified financial planner named Jana Davis. And there are a lot of moves that you may want to consider before the end of the year. I will tell you one of the big ones that I've already made is charitable giving. You probably don't even realize this, but a lot of the charitable giving rules are going to change slightly next year, which means getting money to charities this year or inside of your donor advised fund this year is actually quite beneficial. So anyway, sign up for Jill on Money Live by plucking down 45 bucks for the next 12 months and you will be entitled to the next webinar. Wednesday, November 19th. So that's pretty cool. I'm very much looking forward to that. Mark. I do like the year end stuff because I was like, oh, you know, I don't want to wait till December 30th to do something. It's time now to do something. So listen, we have been a little bit remiss. We need to do a couple of email episodes because things are piling up. So today it is an email episode. So Mark and I will be yakking through all of your questions. If you've got one, go to jillonmoney.com, click the contact us button. And of course, if you'd like to come on the air, which I do love, just check the box. Mark will do everything else. Okay, this message is from Rachel. Hi Jill. Let me start by saying I'm so glad that I subscribed to Jill on Money and I listened on YouTube. I retired in 2024. I'm 60 years old, single, no kids. I need your help with a withdrawal strategy from my retirement account. She's got a federal pension of 71,000 bucks. Wow. Right now the pension is higher because she gets that supplement until age 62. So right now instead of her 71, she's getting about 100 grand. After 62, the pension drops down to 71. And then she writes at that time, at age 62, when she's receiving 71,000, I will need to tap into my thrift savings plan to bridge me until I take Social Security at either 65 or 67. My Social Security at age 67 is $3,800 a month. She's got $1.3 million in a traditional thrift savings plan. 75 stocks, 25 bonds, $8,000 in a high yield savings account. I own my home. The mortgage is $430,000. The interest rate is 5.6%. My monthly income is enough to cover my monthly expenses. So $5,300 a month, expenses she'd like a little more, like $1,500 a month more. She says I plan to tap into my retirement savings for major house repairs or a new car when needed. Okay, question. Do I really need to do Roth conversions? Can I simply withdraw 25 grand a year from my thrift savings plan and save whatever I don't spend? The exception would be the years when I need more for house repairs or maintenance or I thought about withdrawing $150,000 right now, paying the tax for three to four years in a row to create my own cash bucket. The hope here would be to reduce the amount of required minimum distributions at my age 75 and those taxes in the future. I. But if I make the withdrawals, where would I put the excess money that I don't need? What's the best withdrawal strategy? I feel like I should make some now before I start Social Security at either 65 or 67. Most financial planners would like me to roll over the majority of my thrift savings plan into an annuity or a structured note or allow them to manage it completely. And I'd like to manage my own money. Thank you very much. I added that. Thank you very much. Your thoughts? Okay. So, Mark, does Rachel need to do Roth conversions? I don't think so. What do you think?
B
No, I don't think so. I would just withdraw. I mean, maybe in the beginning, take out a little bit more than necessary just to kind of have some cash on the sidelines just in case.
A
I wouldn't mind that either. And by the way, why are we talking about 65 or 67 if you're in good health? I'm kind of thinking that maybe you can wait till 70, and then we can start taking some money out. And so when you said 25 grand, I would take. I'd probably take 50 grand. I would take 40, let's say 40 grand a year is what I would take out starting now. And, you know, have it available for you. You're going to, you know, you'll. You'll be in the, you're going to be in a high ish tax bracket if you want to. Only if you want to stay in the 22% bracket or the 24% bracket. You can take some money out. You can overdo it a little bit. You can take some more out. But I wouldn't, I wouldn't go above the 24% bracket. You are going to be there probably, you know, in the 22ish range. I guess that, you know, you have your, your pension right now, you know, till 62 is 100 grand. So it's going to be hard to stay in 22 with that. But I would take more like 50 grand a year. Not 25, 40. 50 grand a year. And I would really think, unless you are not in good health, I would think about 70. And I would take these withdrawals out, get the money out. I would manage it myself, the thrift savings plan, as long as you're comfortable with it. And I might reduce my allocation from 75, 25, maybe more, to 50, 50 as you start pulling money out, but kind of up to you. And I would get the money out and pay for the things you need to pay for, bridge the gap and open a investment account just in your own name. And you can do that at any of the big brokerage accounts and go to sleep at night. Seems good to me. I don't think I would do much. Would you, Mark?
B
No annuity.
A
No annuity. N A, no annuity. Okay. Lily says I have IRA accounts at both T. Rowe Price and Charles Schwab. The stocks that I own at T. Rowe are not being managed. My bonds at Charles Schwab are being managed. I've been advised to combine everything at Schwab. My question is, should I actually keep my IRAs in one place or is maintaining two accounts fine? I mean, look, it kind of depends on you, Lily. If you feel like you want to pay up to have Schwab manage the stocks that you have at T. Rowe. And you'll have to pay some fee on that. But if you're just fine managing it separately, then that doesn't seem like a bad thing at all. You don't have to combine. We always say combine because it's easier to manage. But if Schwab's just managing the bonds and you've got a bunch of Stocks and you're not really trading them and it's not costing you anything. We maybe I would just leave as is.
B
Who do you think's advising her to move that stuff?
A
Someone who wants the account. Thomas says hello. Jill and mark. I am 41. My spouse is 38 and I've got questions regarding our current investment strategy. Okay, so 41, 38. They work full time. Two kids that are 7 and 5, they make 250 grand. They have a bunch of money saved. 401k, 1.1 million. Brokerage account, 22 grand. Roth 50,000, HSA 30,000. Home is worth $1.1 million. They've got a mortgage at 6% interest. They've got 529 plans, about 30 grand. High yield savings of 80 grand. Okay, so here we go. We started the 401k about a dozen years ago. We've been maxing them out for the past eight years. We lowered our 401k and now only contribute up to the company match up to 5%. By doing that, we've freed up some money for our brokerage account into which we contribute $1,200 monthly. Our plan is to continue this and increase our monthly contribution to our brokerage to two grand starting next year. They both max out their Roths. They started doing that a couple years ago. We've always maxed out our hsa. Our goal is to have flexibility. We both want to retire from full time work in 15 years. They're so young. Fifteen years, my goodness. Okay, and earlier if they could, they're open to working part time and early retirement to cover insurance, health care. They spend monthly about 10 grand. They don't have pensions. They've got know Social Security at age 67. For him, 3500. For her, 3600. Are we on track to meet our goal of possible early retirement? Should we consider a Roth 401k? We contribute an extra $500 a month towards our mortgage. Is this a wise strategy or should their funds be invested elsewhere? Remember that the mortgage is 6%. Okay, Mark, here's a couple of things that I'm noticing. I would not put as much money into your brokerage. What about these 529s? These kids are not so young anymore at 7 and 5. Like if you really want to fund your their education, instead of putting two grand a month into the brokerage account, I would do like a thousand in the brokerage and 1,000 into 529. So that's my number one thing. I wouldn't put money 500 bucks on the mortgage. I would just free that up and either add it to the 529 or again split it between the 529 and the brokerage. They've got so much money already, Mark, in pre tax, I'm kind of considering the Roth 401K. What do you think?
B
Yeah, I mean that's a given. That's a given. And like you said, the 529s, if, if that's a priority, they need to get cranking on those.
A
Yeah, they really do. Are they on track to meet their goal of possible early retirement? Remember, they're spending 10 grand a month, which is not nothing. So 15 years. It's so hard for me to do this, Mark, because it feels like so much for someone who is 38 and 41 years old could change in 15 years. But do you think that for the 15 year time horizon they're kind of doing what they should be doing?
B
Yes, they're doing what they should be doing. Is that going to generate $10,000 in a month? In 15 years?
A
Borderline, yeah. I'm not sure. I think it really. I need more information. I'd love for you to come on the air with us because what I really want to find out is what is the priority on education and what is the amount of money we really could count on you being able to generate in a early retirement scenario. Would you be working from, you know, age. You said 15 years but like you know, 52 to 62. Would you be willing to work for from, you know, age 52 to 59? Like we need a little bit more information. I'm not exactly, I'm not sure, I'm not sure. So get back in touch with us. Okay. Samantha, 27 years old. Amazing. I love getting 27 year old. Questions? Okay. Samantha works in sales. 100% commission based based on my annual pay. I'm reaching the point where I'm feeling financially comfortable enough to explore personal purchasing a home. However, my monthly income is so inconsistent that it's really hard to figure out the kind of mortgage that she'd be comfortable with. She guarantees, she says I am guaranteed to bring home five grand pre tax each month. But then every four to six months there's a larger commission check. So it's 60 grand a year, but then essentially another hundred at least in commission. She said last year her income was 180. This year it's going to be 325. Oh my God. I've got 32 grand in a high yield savings account, 140 grand in stock market. Current rent, $2,200 a month. Oh, my God. How do you determine a monthly mortgage, home price, when my pay is so inconsistent? I don't feel comfortable taking my monthly average for the year because sometimes it's six months until I receive those commission checks. Am I better off continuing to rent and investing my commission checks in the stock market, which has been earning a 14% return, I'm sure, over the last five years? All the information out there is really focused on those with consistent pay. Any advice for saving, purchasing a home with inconsistent pay is helpful. Thank you so much. I love the show and your advice. Okay, love you. Samantha. 27 years old. I'll tell you where I'm leaning. I'm leaning, like, build up that investment account. Because what I really want to understand is, you know, what's the benefit right now for you to buy? It doesn't seem like it's so great. You know, you're a single person. It's fine. But, like, your life could change a lot over the next few years. And I love that you're channeling all this cash flow into the markets and being able to invest and be really prepared to buy when things settle in. I wonder if your income might become more range bound. I mean, the way that mortgage companies look at it is they're gonna say, what's the last three years been? And they will average it out. If you're dying to buy something, it doesn't sound like you are, but if you were, then what we would do is we would just make sure that you would have a year of mortgage and expenses set aside in a cash account before you actually started doing this and that every year you would make sure you had that to kind of bridge the gap for the draw spells. Mark, do you think Samantha should buy a house? $2,200 a month in rent?
B
I mean, I'm not gonna say she should, but if she wants to, I have a feeling that she can. I mean, I know her income is, you know, what she calls inconsistent, but she's consistently bringing in at least five grand every single month. There's a lot more questions I have. You know, I tried to get her on, but no go, no go.
A
Oh, we want you to come on so badly. I think you could, but I would delay it. Unless you're, like, stumbling on something and you're like, oh, my God, this is the greatest deal. Get back in touch with us. But we'd love to have you on be so great. All right, that's it Mark. You're ready to go trick or treating.
B
Everybody be careful out there tonight.
A
Everybody be careful. Be nice to each other. Don't forget, if you have any questions just go to jillonmoney.com click the contact Us button. Especially if you are one of those people who dresses up your dog in a Halloween costume. We did it one year. My dogs have never forgiven me. Hit the Contact Us button. Write us a note. Let us know if you want to come on the air. Sign up for the free Weekly Newsletter do check out all the other free content, the blog, our other show called Money Watch our radio show, videos, resources, all of it that lives@jillonmoney.com and of course you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. It's Friday and that means I do great. Thanks to our composer extraordinaire Joel Goodman who put our music together. Mark Telercio the best Executive producer in the whole wide world and the king of all things Web. We are distributed by the fine folks at Odyssey. We ask that you please do something nice for someone else today. Change your work, Change your wealth. Change your life. Thank you for listening. We'll talk to you on Monday. This message is from Jill on Money sponsor Charles Schwab. We all know what an IRA is, but how about an ria? Same three letters but but completely different meaning. RIA stands for Registered Investment Advisor. These folks operate under one of the highest standards in the business. Let's break each word down. Registered Every RIA is registered with either the securities and Exchange Commission or State securities regulators, which means they have a fiduciary duty to put your interests first. Always. It's more than a promise. It's a legally binding obligation to consider your long term financial well being above any short term transaction. RIAs are also independent. That means they typically have the freedom to choose from a wider variety of funds or products to select what's best for you. They look at the intersection of your money and your life and help you invest in what matters most. RIAs are the financial stewards you and your family deserve and they do way more than just help you invest your ira, do your homework, find an RIA you feel good about and get the attention you and your money deserve. Dive deeper at find your independent advisor.com hey everyone, I'm Josh Radner and I am so excited to tell you about How We Made youe Mother a Rewatch podcast. Looking back at How I Met yout Mother and I'm here with Craig Thomas who co created the show along with Carter Bayes. Hi, Craig.
B
Hey, Josh. Somehow it has been 20 years since the show premiered that seem. I'm going to check the math on that. Ten years since it went off the air and we thought that made this a perfect time to look back, see what the hell we did and why the show still seems to resonate with fans around the world today.
A
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Podcast Summary: "Buy a Home or Invest Instead?"
Podcast: Jill on Money with Jill Schlesinger
Airdate: October 31, 2025
In this episode, Jill Schlesinger and producer Mark Telercio dedicate the show to answering a backlog of listener emails, focusing on key personal finance dilemmas: how to approach retirement withdrawals, portfolio management, college savings, mortgage decisions, and—central to the episode—whether to buy a home or continue investing, especially when income is unpredictable. True to Jill’s style, the conversation is accessible, practical, and sometimes blunt, with a sprinkle of light-hearted banter.
[03:00 - 05:00]
[05:40 - 09:12]
[09:12 - 10:40]
[10:40 - 13:40]
[13:40 - 17:30]
If you haven’t listened to this episode, the key takeaway is Jill and Mark’s practical, cautionary approach to major financial decisions: Ask what truly serves your long-term goals, walk away from unnecessary complexity, and keep your options open—especially when life is likely to change.