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Jill Schlesinger
Need contract help for those workload peaks and backlog projects.
Mark
You're not alone.
Jill Schlesinger
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Jessica
Hi Jill. Well, thank you for taking my call. Excited to talk to you here. I just really kind of want to know if I can retire. My husband did recently retire and we are just weighing our options here. Year I am willing to hold on but I would sure hope I don't have to. So that's kind of where we're at.
Jill Schlesinger
Okay. How old is your husband?
Jessica
He is 59 and a half.
Jill Schlesinger
Oh I love the half. So good. And how old are you, Jessica?
Jessica
58.
Jill Schlesinger
Okay. Does he receive income from a pension because he has retired, or is he just counting on you to float him for a little bit here?
Jessica
No, he was in a unique position about. I guess it was a year and a half ago now, where a lot of changes with his company and so kind of some looming layoffs happening, and he was given the opportunity to take a severance. So he took the severance. And that for us will be done as of October 1st, I believe.
Jill Schlesinger
So October 1st of this year of 2025. Okay, got it. By the way, I'm talking to you on August 7th, when CBS is supposed to complete the sale of the company, Paramount Global, to another entity. And I have a feeling I'm gonna field about a million questions from people just like you and your husband about severance and when it ends and all of those things. So I will now turn around and use you as practice for all the conversations I'm gonna have at work. Now, you receive your medical and healthcare through your position, through your workplace.
Jessica
That's correct.
Jill Schlesinger
Okay. And how much do you earn right now, Jessica?
Jessica
I actually reduced my income quite a bit in the last year because I took a different position within my company, thinking it would be less stressful. But. Yeah, in reality it has not been. And then the other factor for me is back in the spring, it was announced that work from home option is no longer. So I have been working from home for about five years, and really, that's made it somewhat tolerable. But to think that I now would have, you know, almost an hour commute starting in January, I just.
Jill Schlesinger
No, yeah, no, no. We're going to make. We gotta figure this out. Okay. So how much do you earn now?
Jessica
So now I'm down at 125.
Jill Schlesinger
Okay. Do you guys have kids?
Jessica
We do. We have twin boys.
Jill Schlesinger
And how old are they?
Jessica
23.
Jill Schlesinger
And they're on their own. Okay.
Jessica
Well, one, they both just graduated from the university. One got a job from his internship. They offered him a position. So he. We consider fully launched. He has the health benefits.
Jill Schlesinger
He's great.
Jessica
He's good to go. The other one is graduated, as I mentioned, but going on to graduate school. And we have covered their undergraduate tuitions and housing and everything, but we kind of feel that this would be up to him and doing loans or what it takes. However, I guess he probably will be going to a bigger city with higher cost of living. So. One of the things that my husband and I have talked about is having about 25,000 earmarked for him just to help him with cost of living, rent, that kind of thing, for the next two years.
Jill Schlesinger
25 per year or. Okay. Okay. So $1,000 a month for two years?
Jessica
Yeah, if possible, if we can do that.
Jill Schlesinger
What have you guys saved based on this? These multiple decades of work.
Jessica
So, yes, we have in cash, 100,000.
Jill Schlesinger
Okay.
Jessica
We have in a brokerage account, 135.
Jill Schlesinger
Invested in just stuff. Like, anything in particular?
Jessica
No. Stocks? Yeah.
Jill Schlesinger
Individual stocks or exchange traded funds or mutual funds.
Jessica
I think individual, but I think. I'm not 100%. That would be probably more detail that my husband would be aware of than I am.
Jill Schlesinger
Okay. I'll be in touch with him shortly. Okay. What else?
Jessica
We have Roth 140,000.
Jill Schlesinger
Okay.
Jessica
We were not really eligible for that for many years, so until the 401k option came in. So now I'm kind of looking at this as I was preparing, realizing we don't have a lot in Roth.
Jill Schlesinger
Okay. It's okay.
Jessica
We have an IRA for 2.1 million.
Jill Schlesinger
Okay. That's a huge number. Is that the rollover of his old plan?
Jessica
Yes.
Jill Schlesinger
Okay. So he's got a.
Jessica
A combination of both of ours.
Jill Schlesinger
Okay, gotcha. What else?
Jessica
401K, currently at 140,000.
Jill Schlesinger
Everything's 140. It's amazing. Okay. And that 401k, that's the traditional. Or is that a Roth?
Jessica
I think it's Roth.
Jill Schlesinger
Okay, got it. Okay, keep going.
Jessica
We have another brokerage account with 60,000 in it.
Jill Schlesinger
Okay.
Jessica
And then another brokerage account with 971,000.
Jill Schlesinger
Oh, my God. You saved the best for last. Oh, did I mention my million dollars in the other brokerage account? Okay. All right. That's big money, baby.
Jessica
Okay. Now, my husband did lose his father about two years ago, and so he has an inherited roth valued at 24,000 that I know we do need to use within 10 years, but you don't.
Jill Schlesinger
Have to pay tax on it because it's a Roth. Got it. Okay.
Jessica
And then he also has another inherited IRA that. Is that the $192,000? $192,000.
Jill Schlesinger
Okay. Same thing. We got eight more years to get that out.
Jessica
Yeah. And then he has an annuity, and I don't know a lot about this. I just have a note next to this that he took a five year withdrawal option. So I.
Jill Schlesinger
This is his dad's annuity, in other words.
Jessica
Yes. He split it with his sister, so.
Jill Schlesinger
Okay, I understand. And so three more years on that.
Jessica
Yes, I believe that would Be three years, his bottom line.
Jill Schlesinger
And do you know how much he's getting each year?
Jessica
I just know the total value, which is 55,000.
Jill Schlesinger
All right, this is great. You got a bunch of money. Good saving. Rock and roll. Jessica and husband. Okay, Any other assets, any rental income? Rental homes, anything like that? Okay, how about your primary residence?
Jessica
Yes, we do. We have only 50,000 left on the mortgage. Toying with the idea of paying that off, but.
Jill Schlesinger
What's the interest rate?
Jessica
3.05.
Jill Schlesinger
No. Okay, let's continue. What's the house worth?
Jessica
650,000.
Jill Schlesinger
And you want to stay there for now?
Jessica
Yes.
Jill Schlesinger
Till your twins move to far reaches of the universe and you have to move near them because you want to be a granny. Okay, so that's it. We got the assets, right?
Jessica
Yes.
Jill Schlesinger
The most important question. Are you ready for it?
Jessica
Can you.
Jill Schlesinger
Can you get ready for it?
Jessica
Yes.
Jill Schlesinger
What do you guys spend forgetting about. Don't tell me about the 25,000 for the kid for a second. Just like, what do you spend? Not the bare bones. What do you need to continue living the life that you want to live?
Jessica
Yeah, I've done a lot of drilling down on the monthly expenses in the last year, and so kind of realizing, wow, higher than. Than I really anticipated.
Jill Schlesinger
I hate when that happens. Right?
Jessica
Yeah. We're at about 14,000amonth.
Jill Schlesinger
Okay. You mentioned that your husband's parent just passed away. Do you have parents that are still alive?
Jessica
Yes.
Jill Schlesinger
And how are they? Do you think you'd have to take care of them? Okay, so your parents are alive. Do you think that you might inherit money in your future?
Jessica
No, I don't, but they're okay.
Jill Schlesinger
You're not going to have to help them out?
Jessica
No, I think they're good. My sister and I do have a handle on their finances, and they'll have enough. Okay. I will say that, you know, when you asked about moving or anything, we do plan to keep our home, but we do live in North Dakota, so it is cold.
Jill Schlesinger
I've heard that we do.
Jessica
We would like, if this is possible, to have an additional maybe $15,000 a year earmarked for travel. And so our thought is that we would take a few big trips.
Jill Schlesinger
Yeah.
Jessica
And. Or we have a lot of family in the South. We would like to rent a condo possibly maybe two months out of the year or three months out of the year. So just knowing that is there is something that.
Jill Schlesinger
Wouldn't it be more than $15,000 a year to do that for a couple, three months?
Jessica
Possibly. I mean, I Guess. I don't know.
Jill Schlesinger
I mean, you could be grifters, which I fully endorse, like mooching off of your family and staying with them. But, I mean, I think that if you. I think that if you want to do that, that you should get a sense of really what it would cost to rent. That seems very low to me. I don't know where they live. Maybe it's in a very cheap area. But that seems like a low amount of money to have for rental for a couple months.
Jessica
Oh, did I say 1500?
Jill Schlesinger
You said 15,000 a year.
Jessica
Oh, yes. Okay. That. Yeah, that's what we were kind of thinking, but okay. Yeah, we can do more research on that.
Jill Schlesinger
Yeah, do some work on that. All right.
Jessica
Oh, and then one additional thing that we were thinking to have earmarked is we would like to possibly gift our two boys, total, a hundred thousand dollars in the next five years. So 50,000 each. And that would be for either a wedding or a down payment on a home. It would be their choice, but we just thought that would kind of.
Jill Schlesinger
Don't you mean 25 for your graduate school son? Since you already will have gifted him 25 for those that year. Are you going to make it even, Steven, or. Not really.
Jessica
I guess we have to be fair.
Jill Schlesinger
I mean, you don't have to be. I'm happy to have. I won't tell if you don't tell.
Jessica
Okay.
Jill Schlesinger
No one has to know this. Okay, I got it. All right. So you have to work. You're going to work through this year, Correct. By the end of this year, will you be 59? Are you turning 59 next year? So you'll be 59 and a half next year?
Jessica
Yes.
Jill Schlesinger
So you've got all of this traditional money, this $2 million which we can tap, right? Not Maybe not this second. Because it seems to me that we know that you have to get this money. If you were to stop working, then I need to give you 15 grand a month, because I'm just. I'm adding in that extra thousand dollars for your kid or for something, you know, just for the travel, blah, blah, blah. So it's 15 grand a month. Right. Mark, how do you think this looks for. For the traditional IRA being able to support $15,000 a month? You know, we have no pensions. We'll have Social Security. What's your full retirement age? Social Security benefit.
Jessica
Full age being 67, correct?
Jill Schlesinger
Yes. Yep.
Jessica
Both of ours are very similar at 3500.
Jill Schlesinger
So seven grand will be from that. Okay. And you guys are both in good health.
Jessica
Yes, my husband does have some health issues in his family. He is healthy, but there has been some disease in his family.
Jill Schlesinger
Okay. I mean we need 180 grand a year. Okay. And you know you have money and I'm really just kind of first looking at the big $2.1 million. And you have this million dollars. So you know, you have the 2.1 is into all yours. Right. You own a. Uncle Sam owns a piece of it. Right, Right. So you know, you, you have let's say two and a half million dollars once we get paid. Done. You know, you're with your million dollars in your brokerage, it's really like 1, 1, 1. It's really like 1.2 that's already been taxed in the brokerage account. And then it's the 140 in the Roth actually 280,000 because one's the Roth IRA, one's the Roth 401. And then we've got a bunch, you know, another couple hundred thousand. 250 in the retirement assets from your in law. So Mark, how do you think these numbers line up so that we can give Jessica some reprieve? Do you think that this is possible or what do you think?
Financial Advisor
Well, you know, I can tell you that we're going to get feedback. Three and a half million dollars. Of course she can retire, they can do whatever they want. They're just looking for a pat on the back. But I gotta say, you know, given how much they spend per month, three and a half million dollars, it's not a slam dunk. It's probably doable, you know, they just gotta get to Social Security. But it's not a slam dunk. It's more like it's like a three point shot.
Jill Schlesinger
Yeah, I agree with that. Now let me ask you a different question, Jessica. Would you or your husband be willing to do some part time work maybe for the few years now, like in between this moment and say age 65. I mean one thing is, you know, we'll need health insurance for you. So it would be wonderful if you guys could figure out how to cobble together enough income at an employer to get health insurance. And the other is that it, it would be nice not to have to eat into all these assets. So would you be willing to work?
Jessica
No.
Jill Schlesinger
So, okay, I'm going to spend down so here so you. So then I'm going to be dream maker and crusher at the same time.
Jessica
Okay.
Jill Schlesinger
Okay, here's what I would tell you if I were you. I wouldn't re. I would not retire. I would not retire.
Jessica
Okay.
Jill Schlesinger
I would keep taking that money for another couple years. I'd see how things go. I tell your son who's going to grad school, we can give you this money for grad school as a loan. And when you're done, we need to be repaid because you cannot gift to them. You cannot gift to them. Absolutely cannot. Okay. How much were you making when your husband. How much was your husband making also?
Jessica
Well, combined, we were about 350, 380.
Jill Schlesinger
That's why you spend so much.
Jessica
Yeah. Yeah.
Jill Schlesinger
You know, and so, I mean, which is not like, if you're spending 14 grand a month and you're making 350 grand, fine, right. You have a choice here. If you told me, jill, I could take that 14 grand, I could take a hatchet to it, and I can make it nine grand, ten grand a month. We won't travel as much in the first few years. We'll figure it out. But we're going to go down to 10 grand a month, hardcore. Then the numbers look better. 14, 15 grand a month is a lot. And so what I can say is that Mark's right. I think you've got a lot of money. It's great. But you spend a lot. And so something has to give to make this plan. Give yourself a little padding. So the choices are if you want to really retire at the end of this year because you're spent, you have a nice long sit down with your hubby, and you say, I think we can make these numbers work, but we're going to have to spend less money. We can't spend, like, we're making 350 a year. We just can't.
Jessica
Mm.
Jill Schlesinger
Okay. So that's one choice. Second choice is you're like, you say to your boss, I love you. I there, you know, if there's no way that I can work from home, I'm gonna have to think about doing something else. Really? That's like, it's impossible, right? Or you can suck it up and just keep doing it and, like, have your horrible hour commute. That seems like the worst idea to me. Or you can basically say to your husband, like, if we want to keep spending at this level, then one of us has to be working part time at least for another three to five years so we don't blow through this chunk of money. I could easily see you blowing through $2 million in the next 10 years at a $14,000 a month spend. It's 180 grand a year. So we can do the math, and you cannot be invested as aggressively if, you know, you have to live on the money. You know what I mean? So that's the situation that you find yourself in. Could you, you know, is there another job out there where even if you made honestly, if you said, I got a work from home opportunity, I can make 80 grand a year, I'll get health insurance, I can bang that out for a couple years, even that would be preferable to just stopping and eating through all these assets. Okay, I'm sorry.
Jessica
No, that's. I mean, this was in the back of our minds as well, so. And I think expenses could be looked at as well because we really haven't, you know, cut much back.
Jill Schlesinger
Right. Why would you cut back if you're used to making 350 grand a year? You wouldn't. Right. And so, you know, just to. If I wanted to safely produce $180,000 a year, I would really be looking at more like five million mark. Is that about right? Three and a half? Yeah.
Financial Advisor
Five to six.
Jill Schlesinger
Yeah, five. I'd want five saved up. So if all of a sudden, you know, a year from now, you're like, I sucked it up for another year, now my million is worth a million and a half. And my traditional. See, you're getting closer, but every year you can prevent yourself from invading that chunk of money is a year that will look better for the game plan. It's just hard. You got a lot of years left, girl. You know, 58 years old, you could live for 40 years, right? And I don't want you to make the decision today and run out of money in 30 years. That's what I don't want.
Jessica
Do you think if we were closer to the 160 a year, this would be a bit different?
Jill Schlesinger
I mean, in terms of expenses? Yeah, I mean, it would help, but 160 is a big nut. You know, the other thing that you could consider, which may be nutty to even think about this, but you might consider, well, maybe what we would do is we like our house, but maybe we don't like it that much. Maybe we would rent in North Dakota, rent in the south, and have 400, $500,000 extra in our brokerage account from the sale of the home. Now, you're, you know, you would increase your expenses a little bit, but you wouldn't be maintaining a home either.
Jessica
Right, Right.
Jill Schlesinger
So all of these things are possibilities. Have you guys ever thought about working with an advisor, with a certified financial planner or somebo who can help us?
Jessica
Yeah, we do have a woman that we do work with.
Jill Schlesinger
What did she say? She said, you can do it or you can't.
Jessica
We could do it. We're a little on the fence, but we could do it.
Jill Schlesinger
Yeah. I mean, I'm very conservative, so I'm going to tell you that right now. But Mark is usually less conservative than I. I think having him say it's a three point shot, not a layup, that's a great way to think about it, especially if you like sports. If you don't like sports, then this may have just not been helpful at.
Jessica
Yeah, no, that's good. That's good advice.
Jill Schlesinger
All right.
Financial Advisor
But a lot of, A lot of it's, you know, within their control. You know, like you said, if they could take a hatchet to that monthly spend and really figure out where the money's going, you know, it might. The odds might improve.
Jill Schlesinger
Exactly. It might be like, you know what? I don't like eating. I may not need. First of all, you know what happens when you're really miserable at work? You start doing stuff that's like, I know it's joke, but it's like, true. It's retail therapy. You spend money on things. You're like, I'm eating out all the time because I can't deal with having to cook a meal because I'm working so hard or I need a really expensive vacation because I am so miserable at work. So all of these things argue for me is just a way to say some of this is in your control. Some like. And when I say, like, oh, you're not going to gift to your kids, like, you don't have to give 50 grand to your kids in the next five years. Is anyone engaged yet?
Jessica
No. No.
Jill Schlesinger
Okay, let's put that on the back burner. Don't even put that on there. Like, don't put that on yourself. For grad school, I think you can have a really honest conversation with your son and say, we would love to help you with grad school. And depending on what, you know, where you're going to go and what you're going to do, you know, we'd like to toss you, you know, a thousand bucks a month for the next two years, but we're not signing up for that automatically. That's what we hopeful that we could do. But this is also. If you stop working, I wouldn't want you to do that. If you want to work for your kid again, by the way, because you've obviously been doing that for 23 years, then that's your choice. But if that's even on the, if that's also out there, then, you know, you keep working. And between the two of you, I think you can do this. But I don't want you to think it's like, no biggie. It's a biggie. And I'm glad you got in touch with us and didn't just do it. But, you know, if it's three years from now, I think there's a lot. We have a lot more flexibility. That's my best guess for you.
Jessica
Okay, well, thank you so much. I really appreciate it.
Jill Schlesinger
All right. Don't forget to do your estate planning because you know a pain in the ass and going to tell you to do that on top of everything else. All right, I wish you all the best, Jessica. Thank you for getting in touch with us. Hey, gang. You hate your job? Do you love your job but you hate the circumstances? Now you can't work from home. These employers, Mark, they're so dumb. Like, you have this great employee who's pretty loyal and now you're actually going to say, you must come into the office. I still don't understand for a veteran who's 58 years old, why you would force that person into the office. I think that's the dumbest thing I've ever heard. I really do. I don't understand these organizations. I think it's a power play. Just saying. Okay, if you are in a situation that is changing, work wise, anything, get in touch with us. Go to Jill on money dot com. Click the contact us button. Write us a note if you'd like to come on the air. Just check that box. Mark will do everything else. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review. Wherever you listen and try to 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 tomorrow.
Mark
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Jill Schlesinger
I host a podcast called the C Word with my dearest friend and historian of bad behavior, Alyssa Bennett.
Jessica
What is up?
Jill Schlesinger
It's a chat show about women whose society is called Crazy.
Jessica
We're going to be rediscovering the stories of women's society dismissed by calling them mad, sad, or just crazy.
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Episode Summary: “Can I Retire at the End of This Year?”
Introduction In this episode of Jill on Money with Jill Schlesinger, host Jill Schlesinger delves into the challenging question many listeners face: "Can I retire at the end of this year?" Released on August 7, 2025, the episode features a detailed consultation with Jessica from North Dakota, who seeks guidance on her and her husband’s retirement plans amidst significant financial and personal considerations.
Caller Profile: Jessica’s Financial and Personal Situation
Age and Employment Status Jessica, aged 58, reaches out to discuss her retirement options as her husband, aged 59 and a half, recently retired. Her husband accepted a severance package due to impending layoffs at his company, which will conclude on October 1, 2025 (02:36).
Income and Expenses Jessica has reduced her income to $125,000 after shifting to a less stressful role within her company. Despite this, her monthly expenses have unexpectedly risen to $14,000 (09:34). She and her husband previously earned a combined income of approximately $350,000 to $380,000 annually (16:26).
Family and Dependents They have twin sons, both 23 years old. One has secured a job post-internship, while the other is pursuing graduate studies, prompting Jessica and her husband to earmark $25,000 to support him over the next two years (05:00).
Financial Assets Breakdown
Cash and Investments
Real Estate
Retirement Goals and Lifestyle Aspirations
Desired Expenses Jessica and her husband aim to maintain their current lifestyle with an additional $15,000 annually earmarked for travel, including renting a condo in the South for a few months each year (10:16). They also express a desire to gift their sons a total of $100,000 over five years for weddings or down payments on homes (11:27).
Financial Analysis and Expert Advice
Assessment of Retirement Feasibility Jill Schlesinger, along with a financial advisor, evaluates whether Jessica and her husband can sustain their desired $180,000 annual expenses through their current assets and expected Social Security benefits. Jessica’s Social Security benefits are estimated at $3,500 each monthly when she reaches full retirement age (67) (13:14).
Key Insights and Recommendations
Spending vs. Savings: Jill emphasizes that their high monthly expenses ($14,000) relative to their current income and savings pose a significant challenge. “[...] you spend a lot. And so something has to give to make this plan,” Jill advises (16:33).
Potential Solutions:
Financial Advisor’s Input: The advisor characterizes their situation as “a three point shot” rather than a “slam dunk,” highlighting the uncertainties involved (14:41).
Final Recommendations Jill Schlesinger advises Jessica and her husband to carefully reassess their spending habits, consider delaying retirement, and explore opportunities to increase their income or reduce expenses. She underscores the importance of not solely relying on their current savings and investments to sustain their desired lifestyle without adjustments (17:31).
Conclusion The episode underscores the complexities involved in making retirement decisions, especially when high expenses and reduced incomes intersect. Jill Schlesinger provides actionable insights, urging listeners in similar situations to conduct thorough financial assessments, seek professional advice, and consider multiple strategies to ensure a secure retirement.
Notable Quotes:
Tags: Retirement Planning, Financial Advice, Personal Finance, Retirement Challenges, Expense Management, Social Security
Transcript Hyperlinks: