Jill on Money with Jill Schlesinger

Realistic Next Steps for Living Life Now?

28 min
May 6, 202625 days ago
Listen to Episode
Summary

Jill Schlesinger discusses a major rebranding initiative at CBS where the Money Watch podcast will be reformatted as a video-first show targeting 30-45 year olds, launching in approximately one month. She then advises a caller named Andy, a 55-year-old earning $350k annually with her 58-year-old husband, on whether to maintain a grueling 1-2 hour commute for 8 more years to maximize pension benefits or sell their $850k home, rent closer to work, and improve quality of life.

Insights
  • High-income earners often overlook quality of life improvements they can afford, prioritizing long-term financial optimization over present-day wellbeing and health
  • Renting strategically during transition periods provides flexibility for life changes (family, relocation preferences) without locking into real estate at market peaks
  • Pension benefits and Social Security create a floor of guaranteed income that allows for more aggressive lifestyle choices and risk-taking in earlier retirement years
  • The shift toward video-first podcast content reflects audience preferences, though audio remains the primary revenue driver through ad downloads
  • Couples often have misaligned priorities on major lifestyle decisions; one spouse's willingness to change can unlock previously unconsidered options
Trends
Podcast networks pivoting to video-first formats to capture younger demographics (30-45 age group) despite audio being the primary monetization channelPost-pandemic reassessment of work-life balance among high-income professionals, particularly around commute burden and location flexibilityGrowing recognition that traditional retirement planning (maximize savings, work until full pension) may conflict with quality-of-life goals in mid-careerStrategic use of rental housing as a low-commitment way to test lifestyle changes before making permanent real estate decisionsIncreased focus on Roth conversion strategies and tax-efficient withdrawal sequencing for high-net-worth individuals approaching retirementHousing market normalization expectations after 45% appreciation since 2020, reducing FOMO-driven real estate decisions
Topics
Roth IRA and Roth 401(k) conversion strategiesPension benefit optimization and timing decisionsQuality of life vs. financial optimization trade-offsCommute burden and relocation decisions for dual-income couplesReal estate strategy: renting vs. buying in transition periodsTax-efficient withdrawal sequencing in retirement457 deferred compensation plans for public sector employeesBrokerage account funding for non-retirement savingsHousing market valuation and timing considerationsSocial Security planning coordination with pension benefitsCatch-up contributions to retirement accountsSecond home ownership and buyout financingPodcast monetization models and audience targetingMedia industry consolidation and rebranding strategies
Companies
CBS
Parent company (Paramount) mandating rebranding of Money Watch podcast to video format targeting 30-45 year olds; rad...
Paramount
Corporate overlord overseeing CBS media division; directing podcast rebranding strategy and format changes
People
Jill Schlesinger
Host of Jill on Money podcast providing financial advice to callers on retirement, tax strategy, and life decisions
Mark
Producer and co-host of Jill on Money; tasked with becoming video editor for new podcast rebranding initiative
Andy
55-year-old caller from Northeast earning $350k annually with husband; seeking advice on Roth conversions and quality...
Quotes
"What I say is that if you guys find work enjoyable and fulfilling right now, and you plan to work for eight more years, you know, you have, you know, you're going to have this big pension. You'll both end up having social security. Eventually you'll be able to pay for everything and you have a lot of money and there's not a problem."
Jill SchlesingerMid-episode
"You have got to do something different. Only eight more years. Just eight more years. Eight years of this? Are you kidding?"
MarkLate-episode
"Quality of life matters. It matters wherever you are, whether you're 23 or 43 or 83. So if you have an ability to change the quality of life, to improve it, and you know, what's really most important here is that we are listening to you, we are wondering what is it that makes you tick?"
Jill SchlesingerClosing remarks
"You can always buy something. So if you're renting and you stumble on something, you have assets, you'll be able to buy. It won't be a hardship."
Jill SchlesingerLate-episode
"The whole reason that your house is worth this much money is because the housing market exploded. So now you're just going to take advantage of it."
Jill SchlesingerLate-episode
Full Transcript
Welcome to the Jill on Money show. It's Wednesday, May 6th, and we are here talking through whatever is going on with you in your financial life. Now, it is different for each one of us. And I know some of you listen to this program every day and you feel like, oh, there's only this type of person or this type of person. If you want to reflect what type of person you are, then you should get in touch with us. Just go to our website, jillonmoney.com. In the upper right-hand corner, there is a contact us button. When you click that button, a form will pop up. That's the email that we receive. When you write that email, Mark responds to it and it's all great. And what he's going to try to do is see if you check the little box that says, yes, you want to join us on the air live. Why is that so much better? Because Mark and I are voyeurs. We love to hear your stories in your own voices. Of course, of course, we love to get the emails, but we can change your name. We can change your location. We can anonymize you. We like to have you on the program. We can ask follow-up questions. We can be nosy and, you know, we won't reveal anything that will expose you. I promise. Okay. So with that said, while you are on the website, you should absolutely subscribe to the free weekly newsletter, which comes out on Fridays. And that will also entitle you to our blog, which, you know, I write a blog every so often when this, when, you know, something strikes me, usually once a week, maybe I'll start blogging more, Mark, once the radio day is over. Maybe Monday will be my day. Maybe I'll do it one at the beginning of the week and one at the end of the week. I don't know. I could get into that. I need a little bit more writing. Big change is coming for me at CBS because the radio division is shutting down and we are going to be launching a brand new, brand new podcast. It's kind of not brand new. Yeah, not our third podcast. We're just rebranding. Can I just say something? Do we think that the overlords at Paramount are listening to this show or not? Zero chance. Okay. So then let us speak very openly. The overlords at Paramount came to us and said, we love your Money Watch podcast, but we want to put it out in a slightly different format and we really want to focus on 30 to 45 year olds. And I was like, that's good. We've been trying to do that. But, you know, sometimes like people who want to come on the show, it's different anyway. So then they say, how do you feel about rebranding Money Watch to a new name? And we'll drop it on Tuesdays and Thursdays. And it's going to be really focusing on people 30 to 45 years old. I said, you know what? That's awesome. Mark, are you just out of the demo? Poor you. But you seem younger. You do seem younger. Yeah, I am officially out of that demo. That's Oh my God, you're 45 plus. It's a terrible place for you to be. Really awful. Stuck with us. No, I think it's going to be fun for lots of people. If you have kids, if you know younger folks, 30 to 45, what we're going to do is we're going to really refresh the podcast and we are going to make it video because the kids, they only like video, I guess. Right, Mark? That's what the thesis is. By the way, when you think about like everything on video, the money is all made with audio. The model is really that the money gets made when you guys download the podcast and we can sell ads against it. So the more people who download the podcast, the better it is. Fine. They want more people listening. I want more people listening and they also want video, but you know, the video we'll see. Mark has been begging me to do video for a long time. So this is a good excuse. Now Mark has to become a video editor. So Mark, how are you feeling about that potential in the future? I'm just taking it in stride one day at a time. This is, I see this as an experiment. We'll see what happens. I know. But if you guys make it successful, then we'll keep doing it. Well, then it becomes more than an experiment. Exactly. So we got, I think we have six months to really test. So let's see. Of course, the overlords haven't approved our name yet. We're down to four names. We're testing all of them. And as soon as we have the name, we'll tell you. And then anyway, if you're a subscriber to this program, Jill on Money, I also encourage you to subscribe to Money Watch, which we're just going to change the name. The feed's going to remain the same, and there'll be new cover art, and it'll be very fun. So we're excited about that. It is starting, I guess, in a month, which is crazy because Mark and I are not really ready for it. But, you know, we're getting new mics. We're getting – what else are we getting? Cameras? Are we getting cameras? Yeah. We're getting cameras, mics, and what else? Backdrop, some sort of backdrop. Oh, yeah, backdrop. We're still waiting on all this stuff. I know. Anyway, that's what we were talking about right before we came on the air because Mark's like, they haven't ordered anything yet. Okay. Well, they'll get there because our first show is in less than a month. So anyway, this show is still the priority. This is the mothership. The other show is for them. This is for us. So today we are so blessed because we are speaking to Andy from the Northeast. Hello, Andy. How are you? Hi, Jill. I'm well. Thanks for having me. Of course. What's going on? How are you? What can we do for you? Well, first, I'd like to just get a sense of how we're doing. I have a few questions about Roth conversions, whether it makes sense for us. And just, you know, some general quality of life decisions, looking ahead and just, you know, due to just some, I think, life altering things that have happened and just kind of thinking about working to live versus working just to focus on retirement. Andy, I had the funniest conversation with an oldster who's like me, who was complaining about like, I don't know how old you are, but we'll find out in a second, who was saying like, you know, these kids, they really want an award for working and they don't work hard enough. And I said, I get it that like we came up a certain way. I'm 60. And there was a certain work ethic that was expected. But I also understand the idea that, hey, maybe that isn't the be all end all to do it like we did it. So I want to hear about these quality of life decisions because I think it so matters. I am way in your camp. First of all, Andy, how old are you? I am 55 and my husband is 58. Okay. And are you both working full time? We are. Okay. And you have kids? We have one who is launched. How did you do it? How did you do it? Tell the folks out there, what is the secret? There really isn't one. Luck. Truly. We were just lucky, truly. Okay. All right. But launched and out of the house. And you're both working. How much are you guys earning? We earn about $350,000 per year. Okay. And so you said there was a life-altering something. What happened There have just been some health issues over the past year just very kind of crazy things that have just come up And I think too just at our age we just noticed friends that have had some things happen. And it just it just gets you thinking. Totally. Plan. And I'm a planner. So I think, you know, life might have a different plan. So I think you can set goals and follow a certain path. But then you realize that it's not really up to you. Yeah, exactly right. And you can make plans that allow you the opportunity to make different choices. That's the other thing I think people forget about. It's like, well, why did you do all the saving and working in this? If you don't have to feel like you're a slave to it, now you have some choices. So Andy, when you put money aside into retirement funds, do you have money in a traditional or Roth? What's going on in terms of savings so far? It's a combination. Within our retirement accounts, we didn't always have the option for Roth. In my husband's accounts, we have a traditional IRA that has about $1.2 million in it. He has a Roth IRA that has about $20,000. And then for his employment at this point, he has about $310,000 in a Roth 401k. Okay. So that's Roth. Great. Okay. Perfect. Will he be entitled to any pension? No, he will not. Okay. Okay. So 1.2 traditional IRA work plan is the Roth 401k 310, Roth IRA 20. Now that's, that's just him. Now, how about you? On my end, I have a 403b that has about 650 in it, 650,000. And I have a Roth IRA that has 145,000. Will you be entitled to a pension? I will be. Tell us about the pension benefit, like when it kicks in or what your plans are for it. If I can make it till the end, the full benefit would be about $8,100 per month. And with the survivor benefit, it would be about $7,300 per month. And when you say the end, what does the end mean? That would hopefully be about eight years. Eight more years? Eight more years. Stop it. You already sound exhausted right now. There's no way I'm getting there for eight years. What happens if you left today and you let it percolate for eight years? What would the benefit be? Do you know? The benefit at this point would be a very low percentage, maybe 30% of my full-time income. But the little caveat to that is that there would be health insurance. What's your income? It would be based on $130,000 for me. I make a little bit more with other work that wouldn't be factored into the pension. Okay. But eight years does sound like a long time the way you just kind of prepped us for where you stand. No? Does it seem long to you? It sounded long like you sounded tired today. It doesn't. But it doesn't, it's in the big scheme of things, working doesn't seem, eight years doesn't seem like a big deal. But we live a good distance from where I work. So you got a bad commute? I do. And I can do it. I think I don't want to leave money on the table, but it's also just that juxtaposition of, it keeps us very solidly located in one region. And I think just given different family things, just different events, some of the appeal of maybe having a little bit of location independence wouldn't be a bad thing. Yeah. Okay. Well, okay. So you've given me your retirement assets. Do you guys have a brokerage account as well? We do not. We used that to help fund college. She drained you. She just drained you. God. Okay. What about bank accounts? Just boring, safe money. Yeah. We have $90,000 in a high-yield savings account. Great. And tell us about the house that is a long commute for you. How much is the house worth? It's about $850,000. And is there a mortgage that remains? There is, which is about $65,000. The interest rate is? 2.5%. Gosh. Any other real estate besides your primary? We have a share in a home in the country that my husband's from, and we would eventually like to buy that out. What percentage of it does he own? 50%. And what's it worth? The conversion is probably about $450,000. So he has to come up with $225,000 to buy out the other person? Exactly. Okay. What is the game plan with your husband in terms of how long he would like to work? I think we would both like to work as long as we could. And even if we phased out of the positions that we are in, we wouldn't we really enjoy working part time. I think we're both people that enjoy work and find it very fulfilling. So I think we both would be people that would like to work as long as we can. Um, that aside, I think that if down the road we were fortunate to become grandparents, we might want to make some changes based on that. Um, but that might be a ways down the road. Well, let me ask you this. If you're, you're both working, you're making a lot of money. I'm sure you're, you're probably both, um, you're maxing out with the catch-up contribution to retirement accounts. Is that right? We're not doing the catch-up contributions. We're maxing out. Um, and I guess that's one of our questions. Should we be putting more in that? Should we be putting more in a brokerage account, putting it in a traditional high yield savings account to be able to pay off this other property? You know, those are some questions. And right now on your 350, what do you spend? Per month, probably about 8,000 per month would be. Oh, okay. That's pretty, that's great. That's wonderful. So the most likely scenario is that you keep working for eight years and then you start phasing out. So right, you're at 63. At 63, you know, you kind of dial it back. But can we just pretend eight years and that's it just so we don't even have to worry about you working part time? Sure. Okay, good. And then at that time, you have this either $8,100 a month, your life, $7,300 with a survivor benefit. Kind of like amazing in terms of that that covers a big chunk of your need And then I guess the next question I have for you is in terms of making your life your quality of life better would it be possible to sell your current home and move closer to work or rent closer to work like, or is that like no way we love where we are? Well, I think that was one of our questions for you. Because if yes, we could sell from where we are and move closer, which would be more expensive. And as people who hate debt, and I have refrained on overpaying on the mortgage, although I did it before listening to you. Two and a half percent. You're killing me, girl. I know. So we could do that. And then we would probably assume more debt to do that. Why? Wait a second. Wait, wait, wait, wait, wait. I'm not suggesting you buy something. I'm saying that you rent for a while and see how it goes. Why do we have to buy something immediately? Well, I think our fear had been losing, you know, a share in the market. And if prices go up, I think that's probably everybody's fear. But do you think you want to stay in your general area for long term? Or do you think that you will be having some sort of split life between the second home and where you are now? More that. I think what we would like to do ideally is move someplace outside of this area and then split our time between the two locations. That would be like post-retirement though, right? Exactly. I see. So let's just play it out. Okay, so let's just pretend for all intents and purposes, you just want to put yourself last and you want to keep commuting and have a horrible commute and you stay where you are for eight years. Eight years is a long time of commuting. I'm sorry. It's a long time. I can't make so many more podcasts for you to listen to. Let's just say, so then you say, all right, then we sell. We move outside the area. We sell the house. We have whatever the proceeds are of our house. We'll use some portion of that to buy a condo or something cheaper. and we'll be able to buy out the other half of the house, generally. And then you're like, let's just say you spent no more money. There is no other mortgage. That's that. So that's one option, right? Option two, right? So option two is like sell now, start renting closer to your workplace and see how that goes. You can always buy something. It's an amazing thing. You can always buy something, but you don't really know where you want to be just yet. And I presume that there's some issue around, not issue, but there would be some idea around, like you said, if you're my daughter, had a baby or something, I might want to be closer to them, but that you would, you know, sell now, rent for a while, eventually buy, but you could certainly use whatever proceeds you have. And do you have a timeline on when you want to buy out the other person in the share of your second home? We don't, but I would assume that it would be probably in the next five years. So we definitely would have time to save up that money for sure. Okay. I mean, so there's a lot of options is what I guess I'm saying to you. So you could do, stay where you are. You could sell now, rent. You could sell now, buy something smaller, closer to work, and then sell that eventually. But something that is a different lifestyle. So now we are at this place where you say, you had a lot of different things you mentioned. I always take notes when people come on the air. We've had life altering issues, right? Nothing terrible. We want to make quality of life decisions. We're thinking what our options are. So what I say is that if you guys find work enjoyable and fulfilling right now, and you plan to work for eight more years, you know, you have, you know, you're going to have this big pension. You'll both end up having social security. Eventually you'll be able to pay for everything and you have a lot of money and there's not a problem. You will be able to buy half of the house. You'll be debt free in your own house. It'll all be great. It'll all be perfect. Okay. No problems. I think the biggest question you have to ask yourself is, you know, given these life altering issues, given you want to be thinking about quality of life, what are you willing to really consider to make your life better? And that to me is a decision on your end more than anything else. I hate commuting. Mark, well, I just want to be clear. Mark, come on the mic for a second. I had to get him to commit to leaving Brooklyn and showing up at the CBS Broadcast Center tomorrow. And he was like, oh. It's a one-off. He says to me, you know, you better tell them I'm not coming to the broadcast center. Like, I'm not, just to be clear. Like, I get quality of life. Mark, do you think that Andy and her husband should consider selling and getting closer? How long is the commute right now? On a good day in the morning, it's maybe an hour. Oh, forget it. Oh, my God. Listen to him. And it's never good. Yeah, on a good day. It's got to be a bad day is an hour and a half, right? Yeah. And I know you get up early, but I leave it in absurdly early hours. So I think that that helps the commute. On the way home, it can be anywhere from over an hour to two hours. Dude, you have got to do something different. Only eight more years. Just eight more years. Eight years of this? Are you kidding? No, you can't. I mean, all right. You can choose to do whatever you want. I, okay. You can afford to take this. You can afford to do this. All right. So I want to explain something. You, if you want to know how to enjoy your life more and have better balance, it's not spending three to four and a half hours in a car every day. That is not fun. and if you want to know how like you can be healthier and be able to instead waking up at five o'clock in the morning you can wake up at like six and go to the gym or do some take a nice walk in the morning and then go to work like that to me is how you extend your work life so if that's the idea I absolutely think that you should consider getting out of what you have and what would it cost me for you guys to rent something that you'd want to be in that's closer to work It doesn't have to be like in the same place, but closer that is like reasonable. And is your husband willing to do this with us? Oh, my husband's more than willing to do this. Oh, he's like, I'm out of here. Yeah, no, I'm the problem for sure. I think you know I think if it were it probably could be up to about per month All right So let say five grand a month See that I just did it Five grand Sell that house Sell the house Sell the house You have the equity Put aside like a little bit of money just so you have it Like you already have $90,000 in your high-yield savings account. So if you just want to make yourself feel better, like every year, make sure you have an extra $60,000 in the bank in the high-yield savings account just so you can pay your rent. The rest of the money can start a brokerage account. All right? By the way, you're debt-free. How good do you feel? You then have that brokerage account building over the next five years, not a guarantee, but it's going to grow by something over five years. And you're going to be able to buy out the other home, the other person in the in the second home. So you'll have that. And then you're going to learn about like, what do you like? You'll have the freedom and you'll buy something. What do you mean like, oh, I'm so worried the market's going to get the market's already gotten away. You are basically selling the top of the housing market in terms of values. it's already gone up by 50% in the last five years. It ain't going up 50% in the next five years. I can promise you that. And so what I see is give yourself a better quality of life. Rent, see how it goes. Maybe you find yourself like a little something. Maybe there's like a pied-a-terre that's like, instead of you spending, having 850,000, you're like, okay, I can do something for half a million or maybe not. Maybe you just say, I'm going to rent for eight years and then you'll figure it out. You can always buy something. Nothing is so terrible getting away from you. You've got a ton of money saved. You really do. And there's no problem. But your problem is a solvable problem, which is you have a terrible commute and you have the money to make it different. I say go for it. Do you think Andy's convinced? I don't know if she's convinced, to be honest with you. I mean, I'm convinced. And it would make the next, if she chooses to stay for eight more years, it would make the next eight years so much more easier. Then you get that pension and you guys forget it. Everything's, everything's. It's gravy. It's gravy. And by the way, you also mentioned something about Roth conversions. I wouldn't necessarily start converting this minute. I think in eight years, what you'll start to do is you'll start to then consider whether or not you need to convert. You can maybe just pull money out of the accounts. You're using the Roth retirement accounts right now for both of you, right? You're putting new money. New money going in is going into Roth or going into traditional right now. On my husband's end, it's going into Roth. My 403B, it's not an option. Although we do have a 457 Roth that I could perhaps start investing in. Yeah, I might do that. Do that and do the brokerage account or just focus on a brokerage account. Mark, I think doing the 457 Roth version makes sense, don't you? Yeah. If you're going to be working for the next eight years, if that's the game plan and you have a Roth option, I would use the Roth. I would too. And listen, all of this is to say that if something changed and you wanted to make a different decision, you've got plenty of money to make that decision. You really do. I'm able to do both the 403B and the 457. Would you do both or would you just do one? No, I don't think you need any pre-tax money. I agree. You have a lot of money that's already pre-tax, right? Because he's got the 1.2 million and you've got 650. We already are going to have to deal with that down the line, maybe not this minute, but we're going to have to deal with that. So I wouldn't put new money into traditional. But I think you're in great shape, Andy. And I take quality of life quite seriously. And I think commuting is a total bummer. Hey, I know people, you're all out there and you're like, oh yeah, but I do this, this, this. It's great if you can do it, but it gets harder and harder. And I think you're in such a good situation. You have the ability to do it. That's the thing that's amazing. And especially, I thought you were going to say to me, oh no, my husband loves the big house and the lawn and we can't do that. But it sounds like he's on board. Oh, more than on board. He's ready to rock. He's like, I'm done. All right. Well, let's go get you a spot. Go look into this. And everyone who listens, I know that many of us came of age owning, but I want to be clear, you can always buy something. So if you're renting and you stumble on something, you have assets, you'll be able to buy. It won't be a hardship. And what is the market going to jump by? Again, the market has gone up. Valuations of homes have gone up by about, let's say, 45% since 2020. Do I think that's going to continue? No, it's already slowing down, by the way. So I think you're in a good situation. The whole reason that your house is worth this much money is because the housing market exploded. So now you're just going to take advantage of it. Go find yourself a rental, make that commute shorter and, um, and be clear that you'll always have a chance to buy. You have plenty of money. You guys have done a great job. You really have. So take advantage of that and, um, get out of that car, do some stretching. Do you have a back pillow? I have a back pillow in my car? I don't, but I listen to a lot of podcasts. Besides ours, how dare you? You should just make sure. Just yours. All right, I thought. All right, Andy, good luck to you. And just be clear that we're here for you. And for everyone listening, quality of life matters. It matters wherever you are, whether you're 23 or 43 or 83. So if you have an ability to change the quality of life, to improve it, and you know, what's really most important here is that we are listening to you, we are wondering what is it that makes you tick? What do you want to do? And how can we help you take all the hard work you've done and translate that into different opportunities? That's what we just did with Andy. We could do that for you. You have to go to jillandmoney.com, click the contact us button and check that box to come on the air. I promise you, if we had had this question and we read it as an email, we would not have gotten to the nuance of this. I promise you that. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Don't forget to lift someone up, change your work, change your wealth, change your life. Thanks for listening. And we'll talk to you tomorrow. Hi, my name is Lloyd Lockridge, and I'm the host of a new podcast from Odyssey called Family Lore. In this podcast, I'm going to have people on to tell unusual and sometimes far-fetched stories about their families. I've heard my whole life that she invented the margarita. And then, We're going to investigate those stories and find out how much of it is true. He gets a patent one month before the Wright brothers. Oh my God. Please follow and listen to Family Lore, an Odyssey podcast, available now on Apple Podcasts, Spotify, or wherever you get your shows.