Pay Off My Mortgage Quickly?

Summary

Podcast Summary: Jill on Money — “Pay Off My Mortgage Quickly?”

Host: Jill Schlesinger, CFP®
Co-Host: Mark Tularcio, CFP®
Date: April 29, 2026
Episode Theme:
This episode of Jill on Money dives into timely personal finance dilemmas sent by listeners, with a particular focus on whether it’s wise to pay down a mortgage quickly—especially for those with limited retirement savings. Jill and Mark break down listener questions on high-yield investment options, Roth IRAs vs. traditional retirement accounts, protecting inheritances, and the long-debated rent vs. buy question.

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Key Discussion Points & Insights

1. Investing a Real Estate Windfall — Weighing “Safe” Yield

[04:00-05:30]
Listener Annette, ages 67 and 71, plans to cash out a real estate investment and seeks a high-yield but “safer than stocks” option for $639,000.

• Jill warns that chasing high yield usually correlates to higher risk; prior 8% returns were possible because funds were locked up long-term.
• Suggestion: Diversify with a blend of cash, CDs (1-3 year terms), munis or intermediate bonds, and modest stock market exposure.
• Memorable Quote:
  “If you reach for yield, the problem is if you say, ‘I want to earn 8% for the next six years,’ there’s going to be risk.” — Jill Schlesinger [05:12]
• Jill invites Annette to share more about her risk tolerance and financial goals for tailored advice.

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2. Roth vs. Traditional IRA — The Timing of Taxation

[05:31-07:40]
Listener Rich (63) asks if he or his kids are better off contributing post-tax to a Roth versus pre-tax to a traditional IRA, pondering the future tax implications.

• Jill clarifies that Roth and traditional both grow tax-deferred, but the key difference is when you pay tax—not if.
• With a Roth: you pay tax now; withdrawals in retirement are tax-free.
• With a traditional IRA: you defer tax now, but withdrawals are taxed later at rates you can't predict.
• Jill’s perspective: With decades ahead and tax uncertainty, paying tax today (via Roth) is often safer for the next generation.
• Notable Moment:
  “Both a Roth and a traditional account will be invested and make money without any current taxation. The big difference...is when you pay your tax.” — Jill Schlesinger [06:26]

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3. Should You Pay Off Your Mortgage Early?

[07:41-10:40]
Emily, 56, with $105K income, $4K/month expenses, $200K equity, a $146K mortgage at 6.125%, and “not a lot in retirement,” wonders if quick payoff is wise.

• Jill flips the typical logic: Since Emily’s retirement assets are modest, keeping liquidity is more important than burning them to erase a mortgage.
• Key insight: If you pay off the mortgage, “the problem is you don’t have the money either, and the money’s not growing. And if something bad happens, you don’t have access to the money.” — Jill [09:44]
• For listeners with substantial assets ($5 million+), paying off a mortgage can make sense. Otherwise, keep assets growing and maintain flexibility.
• Recommendation: Continue normal payments, stay liquid, and prioritize retirement saving.
• Context: If five years in a home is uncertain, it's even riskier to accelerate payments.

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4. Protecting Inheritances & Avoiding “Commingling”

[10:41-13:39]
Anonymous asks about inheritance commingling and the impacts of state law—how can parents ensure assets are protected for children/grandchildren?

• Jill explains: If you inherit and deposit assets into a joint account (e.g., with a spouse), that money often becomes marital property in many states.
• Protecting an inheritance often depends on state law—community property states are strict.
• To “lock down” inheritance for family lineage, consider trusts with clear beneficiary language.
• Memorable Quote:
  “When you look at your nest egg, if it passes to your kid…how you title that asset can have a real impact on their lives.” — Jill [11:21]
• Action Item: Open conversation with heirs and, for significant estates, consult a lawyer about trusts.

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5. Rolling Over a Variable Annuity: What Next?

[13:39-14:56]
Listener Susan, approaching retirement, wonders about rolling $156K from a variable annuity into an IRA or annuitizing for $9,300/year.

• Jill’s default: Rolling into an IRA for more investment flexibility.
• Caveat: The correct answer depends on broader context—other income streams, retirement assets, and cash flow needs. Jill asks for a follow-up with more detail.

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6. Long-Term Homeownership vs. Renting — Was Buying Worth It?

[14:57-17:10]
Dan, a longtime listener, questions whether four decades of owning a home were financially smarter than renting and investing.

• Dan reflects on the opportunity cost: maintaining a house (10–15 hours/week) vs. working a part-time job and investing earnings.
• Jill highlights the emotional, cultural pull towards homeownership and the tendency to underestimate non-financial costs (time, hassle, maintenance).
• “All the money you have…would that have not grown faster…being invested in a balanced portfolio? Maybe, maybe not.” — Jill [16:39]
• Takeaway: It’s a personal choice, but don't dismiss renting as a smart, viable alternative—especially in today’s market.

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Notable Quotes & Memorable Moments

• “If you reach for yield…there’s going to be risk.” — Jill Schlesinger [05:12]
• “The big difference [between Roth and traditional] is when you pay your tax.” — Jill [06:26]
• “You don’t have a lot in assets. Therefore, I don’t want to sink those available assets into a mortgage… If something bad happens, you don’t have access to the money.” — Jill [09:33]
• “How you title that asset can have a real impact on their lives.” — Jill [11:21]
• “I cannot convince people that renting is a good alternative. But here is somebody asking a smart question.” — Jill [16:13]

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Timestamps for Key Segments

• [04:00] High-yield investment options for real estate windfall
• [05:31] Roth vs. Traditional IRA tax timing
• [07:41] Mortgage payoff considerations with limited retirement funds
• [10:41] Protecting inheritances from commingling and divorce
• [13:39] Variable annuity rollover or annuitization options
• [14:57] The rent vs. buy debate, time & opportunity costs

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Overall Takeaways

Jill Schlesinger fields challenging listener questions with candor and practical wisdom, emphasizing the importance of liquidity, risk management, and long-term planning over chasing returns or zeroing out debt at the expense of flexibility. She continually stresses that personal finance isn’t one-size-fits-all: the right choices depend on individual circumstances and future uncertainties.

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For more episodes and to submit your own question, visit jillonmoney.com.

Transcript

[Jill Schlesinger]

Are you the kind of person friends turn to when they need help planning a trip? I know I am. That means you got to dig into the hotel options, figure out the best neighborhoods, track down that one hard to get dinner reservation. There's something really satisfying about turning a loose idea into a trip that feels unforgettable. And that's why Fora stands out. Fora is a modern travel agency built for people who already love planning their travel and and want to take that skill a step further. You get training, booking tools, and a community of experienced advisors who share real insights and support as you build your own travel business. Fora also provides flexibility. You're working for yourself on your own terms alongside whatever else life looks like for you. And with access to thousands of preferred partners, clients can get perks like upgrades and resort credits that make a real difference in their trips. With when you book travel, you earn commissions, and getting started can be as simple as helping people you already know. Now's the time to turn that passion into something more with Fora. Become a Fora advisor [e-mail] jillonmoney that's f o r a travel.com jillonmoney and make sure you tell them we sent you foratravel.com Jill Jill on money hey gang, when summertime rolls around, there's probably a lot of exciting plans. Maybe there's a big trip or you're doing something really fun. And if you're like me, sometimes this brings a heightened awareness of what you need to do to protect everyone in your life. Maybe you're wondering if something happened unexpectedly, how would that impact my family? Well, now you can stop putting off life insurance and check it off your list with Policy Genius.

[Mark Tularcio]

You.

[Jill Schlesinger]

It's an online marketplace where you can compare quotes from top insurers side by side for free. And their licensed team walks you through everything, coverage, pricing, all of it. So there's no guesswork. So instead of a summertime worry, it's a summertime win. You'll get that peace of mind knowing you've got the solid safety net in place. With Policygenius, you can see if you can find 20 year life insurance policy starting at just $276 a year for a million dollars in coverage. And head to policygenius.com to compare life insurance quotes from top companies and see how much you could save. That's policygenius.com. Welcome to the Jill on Money show. It's Wednesday, April 29th and we are here trying to provide you with unconventional and Entertaining insights on your money and your life. Yes, I wrote that 10 years ago, and it still holds. I am your hostess, Jill Schlesinger, and I am joined often by my compadre, Mark Tularcio. We're both certified financial planners, and we don't do anything with that except help navigate your financial journey. Let us take some of the emotion out of a lot of the decisions that you are facing. Get in touch with us by going to our website, jillonmoney.com. click the contact us button. Write us a note if you want to join us live. Check the box. Mark will do everything else while you are on the website. You've got to check out Jill on Money Live. That is our subscription service. Yes. That means we're going to charge you money $45 for the next 12 months. That's it, $45. You will have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content for the next 12 months. 45 bucks. And our upcoming webinar is a doozy. We are going deep into the Social Security system. We with Social Security expert, queen, princess, whatever you'd like to call her, Heather Schreiber. Heather has so much knowledge about the Social Security system that even Ed Slott says, oh, she knows everything about Social Security. That's how good she really is. If you want to join us for the webinar, please subscribe to Jill on Money Live. If you don't want to subscribe, you want to wait for the webinar to occur, you can always buy it at after the fact for 15 bucks. So you can always do a single purchase. We started that because Mark's so smart. He started that after the Ed Slot webinar. So if you want to buy Ed 15 bucks. You want to buy Heather, it's 15 bucks. But you can't participate live. And live is fun. Okay, let's do some emails. Here we go. This is from Annette, who Sundays, at age 67 and 71, we have a real estate contract maturing. We're going to receive. Oh, my gosh, $639,000 cash out of this. This real estate. This must have been one of those fixed real estate investments. They earned 8% for six years, but we feel like we should cash out. Where should we invest for a high yield that's safer than the stock market? Oh, brother.

[Mark Tularcio]

Tell me where, please.

[Jill Schlesinger]

Yeah, I mean, everything has risk, right? You earned 8% for six years because the money was tied up for eight for those six years. Right. So what you could do is it's not like a binary choice, cash or the stock market. What about some blended approach where you could say, you know what we're going to do, we've got some cash, we want to have some real safe stuff. So we're going to have some CDs, longer, you know, maybe one, two, three year CDs, maybe even longer. Some money in a diversified portfolio so that we don't have too much in the stock market. Some in, maybe some intermediate bonds or if you live in a high tax state, maybe municipal bonds, depending on what else is going on. But, you know, if you reach for yield, the problem is if you say, I want to earn 8% for the next six years, there's going to be risk. So, Annette, we want to know more about you. And when you find that 8% for the next six years, that's guaranteed. We'd love to hear about that. I'm just kidding. Okay, this is from Rich, who is asking. Hi, Jill and Mark. This may have been answered already in the Ed slot webinar, but I'm hoping you can help me understand this. Okay, here you go. You ready for your hypothetical? Mark, pay attention. Now, if somebody is in the 22% tax bracket, wouldn't the incremental 22% that is being invested and growing for decades be better than not investing that now by paying the tax? I don't really understand this question. I'm assuming there's a tax consideration at the end that makes the Roth so attractive. Oh, okay. Yeah. What you're missing is that when you take the money out, there's no tax due. And when you take your money out and it's invested, even if it grows, even it grows for decades. Both are growing for decades. In one scenario, you have to pay tax at the end and you don't know what the tax rate will be in the future. So rich says he's 63. I have two adult kids. I talk about personal finances with them. I want to understand it better. Okay, so the reality is both a Roth and a traditional account will be invested and make money without any current taxation. The big difference about the structures is when you pay your tax, right? So in the structure of a Roth, you say, I'm putting an after tax dollar in. It grows without any taxation. When you pull it out at the end, no tax due. With a traditional, the money has gone in, there has not been any tax paid on it. But. But when you pull it out later, there will be tax due for the kids especially. Especially if they're looking at the future decades down the line. It's far better to pay the tax today, not knowing what taxes will be like in the future. I hope I answered your question. If not, get back in touch with us Rich. This next one is from Emily, who says, Hi, Jill. I'm 56. I earn about $105,000 a year. My expenses are $4,000 a month, and I have about $200,000 equity in a condo that I bought about a year and a half ago. My mortgage is $146,000. She says, I put a lot of money down, you know, as a down payment, and I've been paying down my mortgage aggressively. I wonder what the rate is. Let's see. Oh, her interest rate on her mortgage is 6.125%. She says, I've only got about $250,000 in retirement assets, mostly Roth, $75,000 in a brokerage and checking. So, okay, remember, 56, $105,000 a year, expenses, 4 grand a month. She's got this high mortgage rate. And she said, does your advice not to pay down my mortgage quickly apply? In my case, since I have so little in retirement, I likely will stay in the condo for at least five, five years, but maybe longer. 15. I'm a new listener. I love your show. I also loved your book the Great Money Reset, which really applied to me after coming back to the US After a decade out of the country, a bunch of family upheaval, and restarting my life. Okay, Emily, it's a funny thing that you ask because on in your head, what you're saying to yourself is, I don't have a lot in retirement assets, so I want to get rid of this mortgage. Because then you don't want to be burdened by having the mortgage. I look at it the opposite way, which is you don't have a lot in assets. Therefore, I don't want to sink those available assets into a mortgage, into paying down your mortgage, because, remember, let's just pretend that you had, you know, let's just pretend you had $150,000 right now that's available. Let's say it's in your brokerage account. You say, look, I'll just pay off the mortgage, and then I don't have that monthly payment. But the problem is you don't have the money either, and the money's not growing. And if something bad happens, you don't have access to the money. So the liquidity is really the part about paying down the mortgage in your case. Now, if you had $5 million and you said, I don't want to have this mortgage. Sure, pay off the mortgage. But I think because you don't have a lot of money that is saved already, making sure that you preserve that money is important. And if you're making $105,000 a year and you keep pay, just pay the mortgage off little by little, it'll be fine. And you work for another 10 or 12 years, you know, then we're going to have different, we'll have different opportunities. I don't know what term of a mortgage you took, but certainly if you saying I'm going to, let's just pretend that you say I'm going to stay in the condo at least five years, but maybe longer, 15. Certainly if you don't even know if you're, if you could be there five or 10 years, then I would certainly not pay that down early. So the reason not to pay it down early in your case, Emily, is about having access to your money. Okay. Anonymous says on a recent episode you empathetically stated never commingle an inheritance. Can you elaborate here? Does your ability to protect an inheritance if you are married depend on state law? I'm trying to protect my children and hopefully grandchildren from the Anna Nicole Smith effect. If I were to die first. Thanks to you and Mark for your support of financial literacy. For those of us who have spent our careers doing other things, asking for a friend. Mark, let me be very blunt in this. If you have an asset and you are passing it on to your kid, the way that you title that asset can have a real impact on their lives. And here, here's what I mean by that. When you look at your kind of nest egg, if it passes to your kid, let's just pretend Mark and I are married, right? And you're my parent and thank you for my kiss. I inherit the money and I put it into an account with my husband Mark. Now Mark and I get divorced five years from now. The state where I live, New York, where we live, would say, you, you commingled the asset there was your intention to make it a joint asset. Your spouse will be able to claim half of that money. Let me paint a different picture. You are out there and you say, oh, you know what I'm going to do? I'm going to just put a little trust together. And what'll happen is the money that flows down to my heirs will be very specifically put into a trust that will then be distributed upon my death. My daughter Jill is the beneficiary of the trust. As long as Jill doesn't take money out of this trust and then pop it into an account with someone else, which I wouldn't, because it's already in a trust, then I've preserved the lineage of the money. I don't think that everybody needs a trust, but I think that if you at least have a conversation with your kids about, hey, when you inherit money, specifically if you live in a state that's a community property state, it is important to keep that money separate. Most states will recognize, hey, you brought that into the marriage. That's your asset. If you get divorced, no big deal. But if you want to lock it down, you really want to protect your kids, and you have a bunch of money, I would absolutely consider a trust.

[Mark Tularcio]

I just blew through that book Strangers. You familiar? No, it's the. It's all over the place right now. It's like the best sellers. This woman, Strangers, Bell, Burden, and the Breakdown of Her.

[Jill Schlesinger]

Oh, yeah, yeah, yeah, yeah. I do know that. Yes. I forgot the name of it because I was just. Somebody I know interviewed her. What?

[Mark Tularcio]

Yeah.

[Jill Schlesinger]

Boy, all.

[Mark Tularcio]

All of this is very relatable to that book.

[Jill Schlesinger]

And, you know, it's. It's very doable to make sure that you don't run into that situation, but you have to know the right documents to have. And you've got to be able to actually have an estate plan. Right. Susan has a variable annuity. It's worth $156,000. What do I do with it? Could it be rolled into an IRA? I'm retiring in 13 months. If I annuitize, it'll be 9,300 bucks a year. Okay, so you have a variable annuity. Thank God it's over. The dark period has ended. The question about what to do next is about what other money you have. Would it be possible for you to follow up with us and tell us what is the other form of income that you have? How do you plan on supporting yourself? What other money do you have in an ira? A traditional or Roth? Give us a little bit more detail, and we can better guide you. I would tend to think you could just roll it directly into an IRA and manage that asset. But if there's some reason you want to get the money out because it's traditional money and you want to annuitize it, you know, maybe it's not that much. You know, it's 9,300 bucks a year, but it might be better just to roll it. But let's hear more about you. Maybe that's a good way to get the money out just so you start paying tax on it. But we need a little more info. All right? Okay. Dan wants to talk about homeownership. He says, I enjoy your work and I look forward to hearing you Monday mornings on WTIC in Hartford, Connecticut with Brian Shakman, Poor me, because that will be ending shortly. Your discussion this morning touched on something I've long pondered. Whether or not it makes sense to buy a house. Okay, this is the funny thing. So I was talking about this recently because I was talking about how we've got to stop putting so much pressure on the younger generation to buy a home when buying a home is not a great deal right now. Okay. So Dan says, I'm fortunate. I've owned a home for close to 40 years. My wife and I were able to refinance a small portion of the home's value for. For less than 3% for a 30 year fixed rate loan. However, previous to that, there was pretty much a decade where the house didn't appreciate in value. Such a roller coaster that you're gambling that whenever you choose to downsize or retire, the house will be sold. There'll be a profit, maybe it'll be a nest egg. Add to that considerable amount of time and resources you spend maintaining the home, I really question whether or not I'd been better off renting all these years, taking a part time job I enjoy and investing that money for the future. We easily spend 10 or 15,000. Listen to this, Mark. We easily spend 10 or 15 hours a week maintaining the outside and inside of our house. Above and beyond cleaning, A part time job on weekends or nights for 10 hours would have produced a pretty good investment over the last 30 or 40 years. No, you know, here's the thing. I cannot convince people that renting is a good alternative. But here is somebody asking a smart question. Not only might it have worked, but the other part is that all the money that you have, not just maintaining the house, but what about the down payment, all that equity? Would that have not grown faster over time, over the last 30 or 40 years, being invested in a balanced portfolio? Maybe, maybe not. Here's the thing, Dan. You are where you are, so I wouldn't worry about it. But yeah, I think about that too. I think about the amount of time and energy that we all, you know, spend on these things called homes. So I'm all in with 10 to

[Mark Tularcio]

15 hours a week. My goodness, that's a lot.

[Jill Schlesinger]

That's a lot. He's got a big house he must

[Mark Tularcio]

have a huge mansion.

[Jill Schlesinger]

Well, you know, if you think about that, if you're do it yourselfer, I could see that. You know, I really do. Okay gang, thank you so much for your questions. We are so delighted that you are able to feel free to send us those questions. Get back in touch with us when we say get back in touch with us because we'd love to feel figure out a way to bring you on the air or at least answer your question. And don't forget on the website jillonmoney.com you can always hit that contact us button. We also have the weekly newsletter which is free, comes out on Fridays. That'll get you our blog. 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. Mark, I was listening to another podcast and they often will read the one star reviews just to like laugh.

[Mark Tularcio]

We can't do that.

[Jill Schlesinger]

I will never have you do that.

[Mark Tularcio]

Yeah right.

[Jill Schlesinger]

Ever. You would lose sleep. Remember Jill Schlesinger? Thin skinned. Maybe the only person who puts herself out there who is as thin skinned as I am is. I don't know who else but I am thin skinned. So say nice things please. What else? You know what? So subscribe to us. Pass us along. Tell people about this podcast Podcast. It's the way we grow our audience. Please try to do something nice for someone else today. Change your work, change your wealth, change your life. Thank you so much for listening. We'll talk to you tomorrow. Nerds.

[Lloyd Lockridge]

Today's episode is sponsored by NerdWallet's Smart Money podcast. Ever google a money question and end up 12 tabs deep with 12 different answers? This podcast is your shortcut back to clarity. NerdWallet's Smart Money podcast breaks down financial decisions with a team of trusted journalists. They explain the why behind decisions like investing home buying and choosing credit cards with clear research backed insights. No jargon, no misinformation. Make your next financial move with confidence. Follow NerdWallet's Smart Money podcast on your favorite podcast app. 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.

[Jill Schlesinger]

I've heard my whole life that she indented the margarita.

[Lloyd Lockridge]

And then we're going to investigate those stories and find out how much of it is true.

[Jill Schlesinger]

He gets a patent one month before the Wright Brothers.

[Lloyd Lockridge]

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.