Reset Dilemma Advice

Summary

Jill on Money with Jill Schlesinger

Episode: Reset Dilemma Advice
Date: April 9, 2026

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Episode Overview

In this episode, Jill Schlesinger, joined by her producer Mark, takes on tough listener questions about complex life and money dilemmas, focusing on the emotional and practical aspects behind financial decisions. The main story is from a listener, Steph, who faces a “reset dilemma” after inheriting significant money in the wake of family losses and considering divorce and a major life change. Jill dissects financial moves, legal precautions, and the path to a safer, happier future. Later, Jill addresses additional questions about homebuying strategies, concerns over the national debt, and a listener contemplating costly long-term care insurance.

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Key Discussion Points and Insights

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1. Steph’s Reset Dilemma (02:56–10:42)

Steph’s Situation

• Background: Steph writes in after a decade of major life changes—moving to a rural area, losing several family members, and inheriting just over $1 million.
• Conflicting Goals: Steph’s partner wants to retire early and live off investment income, pushing to pay off their mortgage. Steph is more cautious, worried this is short-sighted given uncertain relationship and market risk.
• Considering Divorce: With no kids and diverging goals, Steph is considering separating, moving closer to friends, and renting while restarting her career.
• Financial Concerns: Post-divorce, Steph estimates she’ll have $500,000–$600,000 left and could return to a job making $35,000–$40,000. She asks if this is enough for a secure, modest retirement, especially if she needs to use some savings to support her reset.

Jill’s Advice

• Legal Caution on Inheritance:
  • “Did you co-mingle these assets? That’s what probably happened, right?” (05:59)
  • “If you’re the kid, make sure it’s separate and never commingle your inherited money ever, ever, ever.” (06:07)
• Do Not Pay Off The Mortgage:
  • “Absolutely do not do that. … You want to stay as liquid as possible.” (07:55)
• Liquid Assets Over Home Ownership:
  • “If he wants to stay in that house and use his half to pay off his mortgage, fine, have him buy you out. … Your whole reset is predicated on being as liquid as possible.” (08:35)
• Career and Retirement Confidence:
  • “You don’t have to worry about whether you’re going to [be] living under a bridge by 80. … You’re going to plug along and get where you need to go.” (09:33)
• Emotional Support:
  • “Your grandparent and your parents gave you a gift. … You risk actually having a life if you don’t move closer to friends and get out of this toxic relationship.” (09:43)
• Legal Strategy:
  • “You need a divorce attorney… Do not use any of your free cash flow, and do not. And make sure he doesn’t either, because if he does this behind your back, you’re screwed.” (09:55)
  • “You cannot make any big decisions until this thing is settled.” (10:08)
• Mark’s Take:
  • “If the rules are the rules and he’s entitled to whatever portion of this, half of it…” (07:41)
  • “All her relatives just passed away recently. If I’m him, like, in no way could I possibly take that money.” (07:48)

Notable Moment

• Jill’s Down-to-Earth Tone:
  • “[About the husband:] He sounds like a dummy.” (07:39)
  • “Get an attorney. … We’ll hold your hand through this process.” (10:42)

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2. Homebuying with Proceeds and Investment Strategy (10:42–14:09)

Terry’s Question

• Background: After selling a longtime family home ($800K value), Terry and her husband consider buying a townhouse ($500K), debating whether to pay in cash or leverage a mortgage and invest the remainder.
• Two Perspectives:
  • Husband wants a mortgage to invest the equity, hoping for higher returns.
  • Terry prefers paying cash, especially after missing out to a cash buyer.

Jill’s Response

• “It kind of depends about everything else going on in your life, Terry.” (11:32)
• “If you’ve got a lot of other money floating around and you want to pay cash for this, and you just don’t want to deal with a mortgage, that’s fine.” (11:37)
• “I’m sort of feeling like maybe you should rent for a while. Let’s see how that goes.” (11:52)

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3. National Debt Concerns (12:42–14:09)

Thomas’ Question

• Topic: Why isn’t the national debt a bigger public concern? Are we just going to keep increasing it for future generations?
• Jill’s Analysis:
  • Yes, debts are being pushed to future generations. The issue is often downplayed compared to previous decades.
  • Quotes Ed Slott (from a prior webinar): “With this level of debt, are we not probably guaranteeing that tax rates will have to rise in the future?” (13:23)
• Implications:
  • “It’s not so much the Social Security system, which is actually a pretty solvable problem... But it is about how do you pay for all the promises being made?” (13:36)
  • Cuts to federal programs or higher taxes seem inevitable. “Ed seems to think it’s the taxes going up that will be the more likely scenario.” (14:06)

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4. Long-Term Care Insurance Follow-up (14:09–14:54)

Katrina’s Situation

• Proposal: Insurance broker recommends a permanent life insurance policy with a long-term care rider (for half a million in coverage); high premiums (~$6,400/year her, $8,000/year him).
• Jill’s Verdict:
  • “The cost is incredible. … I’m saying no, I’m saying skip it. It’s a lot of fricking money.” (14:32)
  • “Self-insure is the deal.” (14:55, Mark)

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Notable Quotes & Memorable Moments

• Jill empathizing with listeners’ emotional journeys:
  • “We are all voyeurs. We love hearing your stories and we just want to always scratch beneath that question. The surface of that question is what’s bothering you.” (02:26)
• On mixing finances in marriage:
  • “Never commingle your inherited money ever, ever, ever. … I don’t care how solid your relationship is.” (06:07)
• On seizing a family-provided opportunity:
  • “Your grandparent and your parents have now provided an opportunity for you to live a different life.” (08:22)
• On economic reality checks:
  • “I don’t think it’s gonna submarine us, but … if you can’t pay for the stuff that’s been promised … you’re gonna cut that stuff or … taxes are gonna go up.” (13:46)
• Jill’s signature clarity and humor:
  • “He sounds like a dummy.” (07:42)
  • “Get an attorney. Pay for the attorney. Do not use any of your free cash flow, and do not. And make sure he doesn’t either, because if he does this behind your back, you’re screwed.” (09:55)

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Timestamps of Important Segments

• 02:56 – Start of Steph’s “reset dilemma” question
• 05:59 – Discussion of inheritance rules and asset commingling
• 07:39 – Jill and Mark critique Steph’s husband’s financial approach
• 08:35 – Detailed advice for structuring assets, legal steps, and moving
• 10:42 – Moving on to Terry’s homebuying and investing question
• 12:42 – Thomas’ concern about the national debt
• 14:09 – Katrina’s long-term care insurance question
• 14:55 – Recommendation to “self-insure”

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Episode Summary Takeaway

Jill Schlesinger tackles the deeply personal intersections of money and life change, emphasizing practical financial strategies while always centering the emotional realities of listeners’ situations—whether it’s untangling inherited assets amid divorce, rethinking homeownership after a lifetime in one place, or confronting daunting insurance decisions. Her advice is straight-talking, laced with empathy and wit: protect your assets, seek legal help when needed, and remember that having a financial “reset” can be an unexpected gift to shape a new, more fulfilling life.

Transcript

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welcome to the Jill on Money Show. It's Thursday, April 9th and we are here trying to answer your financial questions. If you've got one, please just go to our website jillonmoney.com jillonmoney.com you click the Contact Us button, you write us a note and you let us know if you would be willing to come on the air live by checking the box. And the reason why we like having you come on the air is that we are all voyeurs. We love hearing your stories and we Just want to always scratch beneath that question. The surface of that question is what's bothering you. But from our purposes, because Mark and I are both certified financial planners, hearing more of the emotional part of what you're thinking about and doing and contemplating is also very important. Of course we know that you are shy out there. There have been so many people who say to us, like, I could not ever come on, but we would protect you. We change names, we'll change locations. The only thing we can't do is we're not altering your voice. Although, Mark, I'm sure we could do that. I would like to make it like it's a. Like it's a 60 Minutes piece and we can protect the voice. What do you think? Can we do it?

[C]

I'm sure that ability exists. I haven't had it in 15 years.

[B]

I know, right? So anyway, we're going to do some emails today because I do want to help the shy folks. So Steph has got some big decisions and needs some support. Okay. The subject is reset dilemma advice. Remember, my book is called the Great Money Reset. It was about all of you who inspired me to write this. You know, before the pandemic, but even more so during the pandemic. So Steph says, I was in a totally different place 10 years ago, living paycheck to paycheck. Marriage provided some stability and the opportunity to leave an unfulfilling job. Okay. Since then, we moved to a rural, which is very hard for me to say, rural country. We moved to a rural setting, far from friends. I lost my last grandparent, both parents. Oh, my God. And I lost my last grandparent and then both parents over a six year period. A decade of grief, new perspectives, and unforeseen financial changes. That's tough, man. Oh, I'm so sorry. Okay. May I also just prescribe to you that you should listen to Anderson Cooper's podcast, All There Is, which is incredible. Okay, that's a totally separate issue, but you should do that. Okay, Steph. All right. So Steph says I received a little over a million dollars due to these premature and consolidated inheritances. We quickly tuck this away in the attached list of assets after a little crash course on smart investing. Now it seems my partner and I have very different goals for the future. He thinks we can live off the interest of the portfolio if he were to leave work at 55 or sooner. Yikes. He also wanted to pay off the mortgage since it's our last debt. This math and our relationship feels short sighted and risky at best. Further Motivating me to consider a big reset solo. We have no kids. Mark. I gotta tell you something. I already love this. Okay, question. Should I resist paying off the mortgage full or half? Not sure. If he would keep the house, I'm concerned that a sale would be hard in the next year or so. I'd rather rent to find a job and be closer to friends. A divorce would leave me with about a half a million to $600,000 of the inheritance.

[C]

Oh, man.

[B]

Wait a minute. This stinks. Did you co mingle these assets? That's what probably happened, right?

[C]

And they're married, right?

[B]

They're married. Okay, gang. I mean, that's bad timing. Also, I think what's really tough here is that this is very avoidable. Parents, people listening. Do not leave money outright to the kid. And if you're the kid, make sure it's separate and never commingle your inherited money ever, ever, ever. I don't care how solid your relationship is. Just don't. It's just so much smarter. Keep it separate. Okay, next. Here's what she says. So she's gonna have about half a million to 600 grand. It's going to be hard to start building a new life until I move. Based on location and opportunities, am I risking a comfortable retirement if I get stuck in a service job for a few years while I reset? Okay. I will most likely be returning to a career where I can earn 35 to 40 grand. It's not great, but if I work for 15 years or more, does this inherited money put me on track for a safe but modest retirement? Better off than 15 years ago, but still. What if I use $100,000 for a year of expenses and career investments? Would I be living under a bridge by age 80? I appreciate any insight or guidance. It feels like I only have bad choices at the moment. Let's take a breath. Let us take a breath, because here's the deal. You are, as you said, you're in better shape than you were 10 years ago. You were living paycheck to paycheck. Let's forget about this knucklehead guy. He's a dingbat. He.

[C]

By the. By the way, if I don't. I know nothing about this guy.

[B]

Yeah, we hate him.

[C]

And if the rules are the rules and he's entitled to whatever portion of this, half of it.

[B]

Yeah, yeah.

[C]

All her relatives just passed away recently. If I'm him, like, in no way could I possibly take that money.

[B]

Well, because you have a soul and you are not. This guy is like entitled. And he sounds like a dummy. But first of all, let's. So, okay, he's a dummy. You need a divorce attorney. So that's number one, which I hope you have. Okay? You have had so much go on in your life that. Just understand that your grandparent and your both of your parents have now provided an opportunity for you to live a different life. Okay? So what I think you should do is, number one, have this divorce attorney absolutely do not pay off this mortgage. No way. Absolutely do not do that. However, if you're going to have. If he wants to buy you out of this, of the house, then do that and go move closer. Do rent and find a job to be closer to friends. So when you say you're concerned that the sale would be hard, I would say you cannot pay off the mortgage. You want to stay as liquid as possible. Okay? In which case, if he wants to stay in that house and use his half to pay off his mortgage, fine, have him buy you out. Have him buy you out. Your whole reset is predicated on being as liquid as possible. You go back and you get 35 or 40 grand a year and you work for 15 years and you don't have kids and you don't know what's going to happen next. And you're renting and you keep your expenses low. You don't have to worry about whether you're going to living under a bridge by 80. You're just going to. You're going to plug along and get where you need to go. But you now have a gift. Your grandparent and your parents gave you a gift. And so when you have new perspectives and you're contemplating a reset like this, again, get an attorney. Pay for the attorney. Do not use any of your free cash flow, and do not. And make sure he doesn't either, because if he does this behind your back, you're screwed. Okay? So do not use that money. No way. Getting a lawyer. And what they'll do is they'll say, you cannot make any big decisions until this thing is settled. Right? And resist paying off the mortgage. Let him keep the house if he wants, otherwise, sell it. And if, even if it's hard to sell, just blow it out and get the money out of this house. I don't care. And then I don't think it is a problem. You're not risking a comfortable retirement if you just take a job, but you risk actually having a life if you don't move closer to friends and get out of this toxic relationship. So. Right.

[C]

Am I Right, Mark, We've got them divorced.

[B]

I'm done. This guy, as soon as he said that, I don't know. Anyway, I'm happy to talk to you more off the air. So get back in touch with us, and we're. We'll hold your hand through this process. Okay. All right. Terry says, my husband and I are selling our family home of 36 years. It's worth 800 grand. They're going to buy a townhouse. It's going to be a half a million. My husband would like to have a mortgage on the new home and use the equity we earned from the house that we sell to invest in the market. We missed out on a home that we really made an. That we wanted and made an offer on because the buyer paid cash. Therefore, I think we should pay cash, which is the best financial advice, considering interest rates, insurance, et cetera. Would we actually make more money using 600 grand for investments instead? We'd put 25% down on the new home with a mortgage. I mean, it kind of depends about everything else going on in your life, Terry. I mean, if you've got a hunt, a lot of other money that's floating around and you want to pay cash for this, and you just don't want to deal with a mortgage, that's fine. But I'd have to know, what other money do you have? What is your income that's going to be the retirement source of your retirement income? And what are my other options here also, if you're missing out? I don't know, gang. Everybody's, like, freaking out. Like, they want. They have to buy a house. They have to buy it. It's a terrible time to buy. Frankly, I'm sort of feeling like maybe you should rent for a while. Let's see how that goes. Anyway, Thomas says, quote, I'm old. I didn't say that, Thomas. You did. In recent years, it seems like no one is concerned about the national debt, or at least as much as they were a decade or two ago. Has something changed? Can we go on now? As we are now adding to the debt indefinitely, are we not indebted the future generations? Yes, we are indebted the future generations. No one does seem to care about it. You know, when we had Ed Slott on our webinar last month, that's always something that he always. It's sort of bubbling in the back of his head because he said, with this level of debt, are we not probably guaranteeing that tax rates will have to rise in the future? And that's one of the reasons he really does like the Roth ira, that when you look at the numbers, the math doesn't work. So it's not so much the Social Security system, which is actually a pretty solvable problem. But. But it is about, you know, how do you pay for all the promises being made? And yeah, no one seems to talk about the national debt anymore. I mean, I don't think it's gonna, it's not gonna submarine us. But it does beg the question if you can't pay for the stuff that's been promised either, you're gonna cut that stuff. So, hello, cuts to Medicare, Medicaid, those kinds of things, or taxes are gonna go up. And Ed seems to think it's the taxes going up that will be the more likely scenario. All right, last question from this is a follow up to somebody who was on the air with us, Katrina. We were talking about long term care insurance, and she spoke to somebody who is an insurance broker affiliated with a big bank. And interestingly, the. The broker was sort of like, hey, let me give you a quote on permanent life insurance that had a rider for a half a million dollars of long term care. It's very interesting. The cost is incredible. She's how old, Mark? Do you remember?

[C]

They're both, I think, like 54, 55.

[B]

Yeah, these are big numbers. Cost for her, 63, about 6400 bucks a year. The cost for him, eight grand a year. This is huge. The good news is that if you do not use the policy for long term care, half a million dollars will go to the beneficiary on the policy. They do have a lot of money. I'm. I'm saying no, I'm saying skip it. I don't want to do this. It's a lot of fricking money. And you'll have different choices to make. I think that I roll the dice. Nice of me to do that for your. Nice of me to contemplate that, but that's what I think. I would skip it.

[C]

Self insurer.

[B]

Self insure is the deal. All right, that is it. That's the program. Wow, we're gonna blast through this. If you've got a question, go to jillonmoney.com, click the contact us button. Write us a note, let us know if you'd be willing to come on the air live. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen. Hey, don't forget to sign up for the weekly newsletter. All that good stuff. Everything that we do is on our website, so jillonmoney.com should be a favorite of yours. It's a favorite of mine because Mark does a great job with it. Don't forget to do something nice for someone else today. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

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