Loading summary
Jill Schlesinger
Support for today's episode comes from Square. Whenever I need a jolt in the afternoon, I head over to my local coffee shop and they use Square. It makes the entire experience effortless, from ordering online to checking out at the counter. When a business uses Square, you can just tell they've got their act together. And let's face it, running a business is hard work, and you're constantly juggling at payroll, online orders, and customer service. Instead of forcing you to manage multiple platforms that don't talk to each other, Square brings your entire operation into one. Smart Transparent with no hidden fees or contracts, it works in real time so you can focus on your passion instead of administrative headaches. If you're starting a business or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down. Right now, you can get up to $200 off square hardware at square.com go jillonmoney that's sq u a r e.com go jillonmoney run your business Smart Square get started today.
Mark
Growing up, money was a topic of
Jill Schlesinger
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.
Mark
Unlike other apps that only show you
Jill Schlesinger
what you've already spent, Monarch actually helps you plan for the future.
Mark
You'll love using their AI assistant to
Jill Schlesinger
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 onmoney@monarch.com to to get your first year of Monarch Core Half
Mark
off at just $50.
Jill Schlesinger
That's 50% off your first year at monarch.com with code JILL on money.
Mark
Welcome to the Jill on Money show. It's Wednesday, July 22nd. Hey, check this out, guys. It's video. And all of you people who've said, oh, we want you to do video, here we go. This is Jill. No makeup. This is not tv Jill. This is New York. Nick loving Jill. See that? All right, good Mark, say hi to the folks.
Mark's Co-host
Hello, everybody. Yes, this is truly an experiment in real time.
Mark
Yeah, we just decided to do it.
Mark's Co-host
This is not my bookshelf here, and
Mark
this is not and this is not New York City.
Mark's Co-host
I'm noticing that this bookshelf has Riverside placement all over it.
Mark
Oh, that's hysterical. I see it. That is so fun. Brilliant. Hey, gang. This is a program that takes the mystery out of your financial life. If you've got a question, go to jillonmoney.com, click the contact us button, write us a note, and if you would like to join us live, check the box. Mark will do everything else. All of our content lives@jillonmoney.com and we would love you to consume that content. Mark, we've got to come up with our next webinar. Remember, that's a. We got it. In fact, are you. Is there a topic you guys are interested in? Is there something we should be doing? I was sort of thinking like, should we do long term care? Because I feel like people really want to know more about that. But then again, it could be so depressing. I mean, it's not like, as depressing as doing, you know, estate planning, but I don't know. I'm ready to hear whatever you guys have on your minds. I could just do a fun guest anyway, you know, could be anybody. We'll see. Anyway, if you've got something going on, some. Some type, you know, we just did Social Security with Heather Schreiber. We have done Ed Slott. But, you know, if there's a epic, we can go find you a guest. It'll be fabulous. So go check that out. And if you would like to subscribe to the Service, Jill on Money. 45 bucks for the next 12 months. Very easy to do. You get the whole back catalog, you get bonus stuff. And, and, you know, It's. It's just 45 bucks for the next 12 months. I don't know. It's a pretty good deal.
Mark's Co-host
All right, Mark, what's going on with your microphone? It looks great. It looks a little nasty. What's on there?
Mark
I don't know, like fuzzies?
Mark's Co-host
Is that what it is? Fuzzies?
Mark
Yeah.
Mark's Co-host
Okay. All right, carry on.
Mark
All right. I can get a new mic if I. If I take that off, I'll, you know, I can get it as long as it's fuzzies. Okay, it's fuzzies. Why did you think it was like,
Mark's Co-host
dandruff, like, dried, like saliva?
Mark
No, no, no, no. It's just fuzzies. I'm sure you're gonna leave this in. Hey, Mark, let's do some emails, because I can read it on the screen and not have my eyes float around Too much. Is that good for you?
Mark's Co-host
Yeah.
Mark
All right, let's do it. Kate is saying this. Should I start doing Roth conversions? What account should I pull from to fund retirement? And so Kate goes on and says, I've been listening to your show since last year. I love them all. That's so nice. I've retired at age 59 and a half. And here are the facts. You're going to write this down, Mark. Two and a half million dollars in a 401k, 1.4 million in a brokerage account, 0.6. Is that supposed to be 60,000 or 600,000 in cash and cash equivalents?
Mark's Co-host
I'm going to say 600,000.
Mark
All right, 600 grand in cash and cash equivalents. Social Security at 67 would be four grand a month. At 70, it's almost five grand. Annual expenses are $96,000. Okay, here we go. Unsure whether I should start Roth conversions this year ahead of the Medicare lookup, which affects Medic. Medicare is irmaa, Mark. Irmaa. All I can say. I'm just going to say that IRMAA. We need a sound effect for IRMAA. Last year tax bracket was 10%. What? And dipped a bit. She doesn't mean 10%. How could that be? She said and then dipped a bit into 32. She must mean 22, 24. I mean, that's a typo.
Mark's Co-host
No, I would think so.
Mark
Because, I mean, the brackets only go 10, 12, 22, 24, 32. So I'm thinking, anyway, she's got a lot of money portfolio. 60, 40. Is it too aggressive? No. Where should she pull funds to? Okay, so 59 and a half with it. Sounds to me like the two and a half million bucks is in the 401k. So the question is, should she convert some of that and go into Roth? Yeah, why not? I would do that. I would convert as much as I could into the, let's say 24% bracket. And by the way, I wouldn't worry about Irma because, Mark, the IRMAA thing is it's like derails you from the larger issue, which is this massive two and a half million dollars. Right?
Mark's Co-host
Yeah. People get too hung up on what turns out to be kind of like a small drop in the bucket over the long term.
Mark
So I get it, like you don't want to pay this extra charge for Medicare, but I would definitely. I mean, you have cash, so I would go ahead and do that. I don't think your mix is too aggressive. So I think you should probably. Probably do some combination of money that you would pull from your 401k to live on, and then also take some money and convert it, stay in the 24% and so 24%. I think she's single up to 200,000, so seems like pretty good thing to do ahead of. Forget about irmaa. Ahead of your Social Security. So go ahead and do it. I think that's a good idea.
Mark's Co-host
Good job, Kate. All that money.
Mark
Amazing. Okay. Doug says I'm 47. My wife's 39. I work for a municipality. I make 76 grand. My wife makes 100 grand in a pri. In at a tax firm. I want to retire at 55 or 57. My wife at 47, 49. But wants to double check what the financial planner says. She thinks we're 90% sure to go at 57 and 49. Could you give us a second opinion? All right, you ready for the money? He's got a traditional IRA, 240 grand. He's got a Roth at 160. He's got a 457 at 54. So just think of it this way, gang. He's got like 300 grand that hasn't been taxed yet. 160 in Roth IRA. He's got a $1.5 million brokerage account. That's nice. Cash savings of 15 grand. Wife has a traditional accounts of about 220. And then cash savings. He gets a pension at 62. 2500 bucks a month. No cola. And then he says Social Security at 62 is 1800 bucks a month. Houses worth 685. 370. Mortgage left. Do we think we can do it at these ages? We would downsize in retirement in the future. There would be some inheritances. Exact figures are not known. Maybe one to two million. No kids. Estate planning is done so young. You know, Mark, it's like, can he get. Can he pull the plug in 10 years?
Mark's Co-host
Well, did he say what they spent?
Mark
He did not. He did not. Wait a minute. I'm gonna guess he's all right. You want. I think I know what he spends, but you tell me what you think.
Mark's Co-host
I'm guessing it's very little, but. Yeah, but he also talks about Social Security at 62, as if, like, that's for sure what he's gonna.
Mark
Why would you do that? No, I. Let's say he. Let's say between the two of them, right, they make 175 grand. They've saved a bunch of money. I'm guessing they probably spend. I don't know, nine, eight, nine, ten grand a month. That's my guess.
Mark's Co-host
At most.
Mark
At most. So they're going to be fine. I don't know what you're going to do with yourself, but if we've missed something here, let us know. It seems like you're on track. And if your financial planner and your wife, the accountant think that you are on track, you probably are. I mean, run the numbers.
Mark's Co-host
I think they're good. They have 2 million now. They're going to, you know, we're talking another 10 years or so, give or take. They're still going to be saving along the way. So. Yeah, that two is going to turn into four. Plus the pension. Yeah. Yeah. And I'm guessing it's that much.
Mark
I think they'll be okay. Emily wants some financial advice. You've come to the right place, Emily. We like to say guidance. I'm buying a new home using proceeds from selling off my current home to pay off all the debt. Listen to this. We moved into our house in 20, 23 and a half percent interest rate. But we knew that it was never going to be our forever home. We finished the basement and we could potentially make 200 grand if we sold. We're looking to get into a 650 to $700,000 home.
Mark's Co-host
I don't think.
Mark
Did they tell us how much the current home is? Let's just say they have 200. That they'll make rates, their VA. They're entitled to a VA loan. Little before below 6%. Were wondering if it's worth going from a $1900 mortgage. Mark, they're going to double it. What do you think about that? They got two cars, a home equity loan, a credit card to pay off with the proceeds, leaving us with 50 grand to pocket and reinvest. We've got a money market account, a Roth annual income is 200. I need to know more.
Mark's Co-host
I mean, how much debt do they have?
Mark
I'm not sure. I think that they need. If they were to sell their home. Okay, they have 200 grand. And it sounds to me that in order to pay everything off out of their $200,000 take from selling the house, they'd have $50,000. So they've got 150 grand in debt or is 150 grand include paying off the current mortgage?
Mark's Co-host
And then how are they getting into the new home?
Mark
Well, if it's an FHA loan, it could be 3% down, right? Isn't it as little as 3, maybe 5? I don't know. I don't love this plan. I need to know more.
Mark's Co-host
I mean, based on what I've read and all that I know, which is not a lot. I'm kind of, you know.
Mark
Yeah.
Mark's Co-host
Thumbs down type of thing, I think. I don't know.
Mark
I don't know. I want to hear more from you. But I'll tell you one thing about this that's interesting, Emily. I want to know why you guys got into debt considering you had a 3 1/2% interest rate. What happened here? Is it like, oh, we ran up the debt because of the basement and we were always going to flip it and. But then you got to get into this big house and you're going to. Can you afford doubling your mortgage? I don't know. You tell me. You tell me. Is it like Your income is 200 grand for, you know, 35, 4 grand? Mortgage payment isn't just where it stops. That's the mortgage rate. But you're in a bigger house. It's higher taxes, it's more homeowners. There's a lot to consider here. And also would you like be in the home and not be able to save any money for retirement? So I'm a little concerned about this. Emily, get back in touch with us. Jan wants to talk about student loans, big changes in student loans. Mark, Jan says, my daughter has 130 grand in student loan debt and she's in forbearance, meaning she doesn't have to pay right now. What do we do next? Who can help us get right? Okay, so Jan, I presume that we are talking about a federal student loan because you're in forbearance. So now the first thing you have to do is go to studentaid.gov and what you haven't told us is she's in forbearance, but is she now going to be able to pay any of it? There are generally three choices. One is an income based repayment plan. It gets you. It's basically like you pay off as much as you can. It's like 10% of your income for 20 years. You keep paying and if you paid it for 20 years, you've been a good person and done all that. They forgive the loan. The new plan, Mark, I don't know if you saw the details of this new plan. You pay 1 to 10% of your income. It's a 30 year payoff and you pay for 30 years and it can get let go. Or if she doesn't do anything and she gets kind of, she'll get slotted into the traditional Plan, which is expensive. So does she have a job? Can she afford it? StudentAid.gov is where you start. That's the portal. See what the options are and get back in touch with us. We need to know, like what are your choices and what she can actually afford to do. Okay, good. That goes for everybody, by the way. Okay, I love this. This is from David, who says, I'm 59, planning my retirement next year. And my husband wants to retire about the same time, but at 55 when his pension will be a decent amount. I've been tempted to contact your show to do a how am I doing check in. But I have one thing holding me back. I'm having trouble figuring out our monthly spend. My mom passed away a couple of years back. I received an inheritance including a brokerage account. That's done well. We only have now taken some money from that account to do some renovations. I. It's. I know it took like 30 grand from a half a million dollar account. Our financial advisor has been able to help minimize our tax hit, but we now have taxable events that we didn't have before the inheritance.
Jill Schlesinger
Oh, poor you.
Mark
I'm creating taxable income with my half a million dollar cap. Okay, monthly spend, do I include tax payments? Do I include the home renovations when there is brokerage money involved in. No, first of all, do not include one off events that you don't need to do that you've already done that. We're looking at what is the cost to carry the house? What is the cost for you to go out to dinner? What is the cost for you to live your life? Right. And Mark, what about tax payments?
Mark's Co-host
Yeah, Well, I was just thinking like if these are going to be consistently thrown off, you know, from that account, then yeah, I would probably factor that into the equation.
Mark
Yeah. He says I'm using a product, like an online product that shows everything. I would say the name, but they're not advertising right now. If they advertise, I'll say their name. I'm struggling with this a little bit. Sometimes I look at months when we don't have tax payments or a home reno and it looks like 7,500 bucks a month. Okay, so you want to smooth this out. So it's okay, you know that you have quarterly payments. So if you wanted to you could just sort of have a, you know, put that in as a dummy holder and you know, over the course of the year, you know what it was. Do we look at one to two years of spending and divide by the number of Months. Yes. That's good. He says it was easier when we were broke. Is that really true, Mark? Is that really true? Is it. Is it really easier when you're broke?
Mark's Co-host
I'd rather have the alternative.
Mark
You know, my father used to say, richer, poor, it's nice to have money. Okay, so here's what I'm gonna guess. If you're saying it's $7,500 a month, forget about the home renovation again. Add the taxes in and, like, don't go crazy. Like, maybe it's 10 grand a month, maybe that's fine. But come on anyway. We'll have fun. Don't worry. It's okay. Okay. Max writes. Okay, this is funny. Comment, not question regarding. This was supposed to be an episode supporting adult children or boomers. Coughing it up. Auntie Jill and cousin Mark, I listen to you every day and greatly appreciate you, your podcast and all that you've taught me, some of which I wish I had known earlier. Thank you. Sincerely, I feel compelled to comment on the frequent parents who support their adult children. So feel free to save time and delete this now if you'd like. No. Okay. First, I refuse to categorize people by age groups or designations any more than I would by race or sex. People are people. Everyone's an individual with their own concerns who deserve the same respect as everyone else. Also, everyone should spend their money in any way they want. They've earned it. That's so true. I roll my eyes when I hear people talking about how their adult children live at home and are supported by people trying to live their lives and save for or enjoy. You get what you tolerate. They're responsible for this situation. Okay, you ready for their situation, Mark? So he and his wife were in their late 60s. They came from nothing. My wife was born and raised in Europe, naturalized with English as her second language. We worked our butts off. I entered the military. I earned four degrees that did not cost me beyond my service, which was my privilege to give. We lived frugally until we had enough to send them to college. Then we lived frugally to save for retirement beyond my pension. And now we're enjoying the party called retirement. We have four children. My wife stayed at home, entered college in her late 30s, and had a full career in nursing. These were our family rules, which were understood from birth. Okay, Mark, you ready for the rules? We might have to. Should we adopt these rules? We could just call them. I mean, if we like them, everyone will. Maybe we'll just say, should we vote? Max's Rules we might have to post this. College is a non negotiable. We will pay all expenses for your 4 year not longer undergraduate degree at any school that does not cost more than in state resident tuition. We will not take or co sign any student loans. All four went to out of state public universities. They had in state tuition through scholarships or other programs. They graduated without any debt. This was our honor. Okay, ready? Number two. You have to major in something on the job highway. If you want to study 19th century literature, that's great. Do it as a hobby, take an elective minor in it, or even earn a graduate degree on your own dime. But the major in which we invest must be a subject that will result in a job. We will not invest in something that is awesome to study but results in you not being able to support yourselves. How do you feel about that one, Mark?
Mark's Co-host
I'm looking ahead. Number three is my favorite.
Mark
Okay, here we go. I see it too. When you leave for college. This is number three, guys. Mark's favorite. When you leave for college, we will sorely miss you. We want you to visit as often as you can, but know that you will not ever move back into the house to live. You just took the big leap out of the nest. Here's number four. I love this guy. Upon college graduation, we will all celebrate. And you are at that time off the payroll, that is you need to get your own cell phone plan stat because we will drop you within a month. Once you're off the payroll, we're focused on the next kid and then ourselves. We did keep them on my health insurance because that did not cost extra. Okay, ready? All four who are in their 30s and 40s, they're extremely, and I mean extremely successful, earning more than we ever did. Three completed graduate professional programs. I recognize this may not be the preferred method for many or most. When Auntie asks parents if their children want to attend private or public university, when it's obvious that any tuition will be challenging, it will be a challenging expense for them. I roll my eyes at that question. I can't help I have to ask that question. Don't you think, Mark? Like I have to find out what they want. Some of them can do it. Okay, so Max, don't come down hard on me. Nobody would even consider buying a Rolls Royce Specter. I don't even know what that is. On $150,000 salary, why would they even contemplate a private school that costs 100 grand a year and then tell an 18 year old it's okay? To major in a passion subject that will not result in a job. I don't get it. The fault is with the parents for not being parents. Providing guardrails, the US Higher education system that operates as a business rather than a higher educational system, and high school counselors, who, for the most part, are worthless in providing a reality check for high schoolers. Not you, Dean Diamond. You were great. That was my Dean. Okay, here we go. Max says my kids well know that our goal is that they inherit zero because it's our turn. We are responsibly spending money on travel and goods that we've always wanted but had to put on hold. I'm not coughing up anything because we did our job as parents. Our adult children don't need anything. Obviously, we'll leave something on the table that will be split amongst them in our wills. I feel better. Thank you. I've contacted you before each time you provided stellar advice that I adopted and from which we benefited. I again will be contacting you next year with a question that I have not ever heard during my seven years of faithful listening, with a hope that you'll once again provide helpful advice. We fi. We handle our financial affairs ourselves. We do not have a financial advisor. Thank you again, your loyal fan, Max.
Mark's Co-host
Okay, is it any surprise that Max was in the military?
Mark
I mean, it's awesome. I also want to say that it's very. One of the things that we kind of pride ourselves on when we're doing this show, when we're doing Money Moves, is that we don't want to be judgment. We really don't. And so for us, it's important that we are not being judgy, nasty, you know, what's. And so we're going to meet you where you are. So, Max, I get it. Thank you for that and for everyone listening. I hope you enjoyed your first. Your first email episode with cameras on, no makeup hat. The Knicks still won the WNBA championship. Mark, I don't know if you know. All right, gang, thanks so much for listening. If you have a question, go to Jill on money dot com, click the contact us button, write us a note, and if you want to come on the air, check the box. Mark will do everything else. Don't forget to subscribe to this show and our sister program called Money Moves on Odyssey, wherever you get your podcasts, and of course, you should subscribe to it on YouTube. Okay, gang, lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow. Room.
Maintain X Advertiser
When equipment breaks down, and operations come to a halt. Every single second counts. So why is your maintenance team spending 60% of their time doing anything but turning wrenches? Maintain X is the AI powered maintenance and asset management system that helps your team get back to actually fixing breakdowns. No more searching for manuals. No more hunting down parts. No more drowning in paperwork. With Maintain X, your team can access manuals from anywhere, create new procedures in minutes, and turn voice notes into clear and complete work order feedback. What used to take hours now only takes minutes. Keep your operations moving and your wrenches turning. Join over 13,000 maintenance teams that are already fixing more and filing lessons. Try Maintain X for free today. Go to maintainx.comai that's maintaininthelterx.comai hey there, it's Jill Schlesinger.
Mark
I'm launching a new show.
Jill Schlesinger
It's called Money Moves and your money
Mark
is going to move. We're going to help you make better financial decisions.
Jill Schlesinger
We're going to call out the B.S. you're finding all over social media.
Mark
We're going to give you actionable guidance
Jill Schlesinger
to make your financial life clearer, less stressful.
Mark
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.
Episode Title: How to Calculate the Monthly Spend?
Date: July 22, 2026
Host: Jill Schlesinger, CFP®
Co-Host: Mark
Episode Type: Listener Questions (Q&A), Financial Planning
In this lively Q&A episode, Jill Schlesinger and co-host Mark tackle a series of nuanced listener questions about retirement planning, Roth conversions, debt, buying homes, student loans, and—most centrally—how to actually calculate your monthly spending as you move toward or enter retirement. The hosts exchange practical advice, challenge financial assumptions, and read an engaging letter on setting firm boundaries with adult children. Their tone is approachable, humorous, and free of financial jargon.
(05:00)
Question from Kate: Retired at 59.5, with $2.5M in a 401k, $1.4M in brokerage, $600k in cash, and annual expenses of $96k. Should she do Roth conversions now, and from which account should she draw retirement funds?
(07:52)
Question from Doug: Doug (47) and his wife (39) hope to retire at 57 and 49, respectively, with a healthy mix of IRA, Roth, brokerage, and pension income. Are they on track?
(10:28)
Question from Emily: Sells current home (can net $200k), wants to use proceeds to pay off debts and buy a much more expensive house ($650-700k). Is doubling her mortgage smart?
(12:29)
Question from Jan: Daughter with $130k in student loan debt is in forbearance. What next?
(15:38 – 17:02)
Question from David: Nearing retirement, but confused about how to calculate the true “monthly spend,” especially with new taxable events and irregular large expenditures (like renovations).
(17:15 – 22:45)
Max writes in to comment on parental support for adult children, sharing the “rules” he and his wife used with their kids—sparked by previous episodes about generational financial support.
Jill and Mark’s Reaction:
Jill respects Max’s clarity but reiterates this show is not about being judgmental—every family situation is different.
"...we don't want to be judgment. We really don't. And so for us, it's important that we are not being judgy, nasty, you know, what's." (22:49 – Jill)
| Timestamp | Topic | |-------------|--------------------------------------------------------------------------------------| | 05:00 | Kate’s question: Roth conversions & pulling from accounts | | 07:52 | Doug’s retirement scenario and “can we do it?” discussion | | 10:28 | Emily’s move: Debt, home sales, and buying a bigger house | | 12:29 | Jan’s question: Student loan forbearance and new repayment plans | | 15:38–17:02 | Main theme: How to calculate your monthly spend (David’s question) | | 17:15–22:45 | Max’s listener letter: Financial boundaries with adult children |
Jill and Mark are conversational, warm, and sometimes playful, focusing on delivering straight talk without jargon or condescension. They encourage listeners to submit questions, highlight the importance of personalized advice, and repeatedly return to the theme of “meeting you where you are.”
This episode provides accessible, actionable advice on calculating essential monthly spending, addressing complex investment decisions, and handling intergenerational financial boundaries. Jill and Mark’s honest reactions, guest stories, and memorable listener feedback make it relatable and highly practical for listeners grappling with these money questions—as well as offering a few laughs along the way.