To Pay Off My House or Not? - Jill on Money with Jill Schlesinger

Podcast Summary: Jill on Money with Jill Schlesinger
Episode: To Pay Off My House or Not?
Date: January 29, 2026

Overview

In this episode, host Jill Schlesinger, CFP®, tackles a range of listener financial questions, from maximizing safe returns in retirement to whether or not to pay off a mortgage early. She and producer Mark offer clear, jargon-free advice on investing, financial planning fees, cash flow in retirement, and college funding, always weighing the emotional side of money against the mathematics. The recurring theme: understanding personal context is crucial to sound financial decisions.

Key Discussion Points & Insights

1. Retirement Cash Management & Safe Returns ([02:00])

Listener Susan’s Dilemma: Sold her home, retired, and has house proceeds in a high-yield savings account at 3.5%. She and her husband don’t want to risk these savings in the market but want more income.
Jill’s Take:
- 3.5% isn’t bad—at least it beats inflation.
- If this money is truly "extra," consider boosting returns with a CD ladder or a short-term bond fund.
- Safe, high-return options are scarce—especially as rates fall.
- Quote:
  
  “I want to earn a bunch of money, but I don’t want to take any risk. It’s tough, I know.” – Jill ([03:43])
Actionable Advice: Consider a blend—some in cash, some in CDs, and a little in short-term bonds. But expectations must stay grounded.

2. Advisor Fees and Value ([04:46])

Anonymous’ Situation: Mid-40s to early 50s couple spend $12,000/year (1.25% AUM) on a financial advisor but wonder if they get their money’s worth, since most planning tasks are done, and upcoming expenses (like a vacation home) leave little extra cash to manage.
Jill’s View:
- The advisor did the job, but lack of depth and withdrawal strategies is a concern.
- If you can manage things for five years until retirement, the savings ($50-60k) are significant.
- Keep the door open to return to the advisor later, but maybe ask for a more detailed plan now.
- Quote:
  
  “It sounds like they actually did the job...but I also get that they didn’t kind of go into more depth.” – Jill ([06:10])
Mark’s Perspective: Five years isn’t that long, but $50-60k is a lot to save. ([07:04])
Bottom Line: Consider DIY for now but communicate your expectations with your advisor first.

3. Should I Pay Off My Mortgage? ([08:15])

Josh’s Scenario:
- Age 37, wife 35, two small kids, twins on the way.
- Owes $187k at 5.4% interest; has liquid assets in a trust earning 5.2%, savings, brokerage, and retirement accounts.
- Considering using his trust to pay off the mortgage for “peace of mind.”
Jill & Mark’s Advice:
- Strongly advise against paying off: Family is growing, so keeping liquidity is essential.
- The difference in interest rates is negligible; better to keep cash handy for the upcoming large and unpredictable expenses.
- Quote:
  
  “We need you to hold onto your liquid assets. You are about to have a massive change in your household.” – Jill ([09:22]) “There’s no way I would pay off this mortgage, not even if the interest rate were higher.” – Mark ([09:21])
Rule of Thumb: Only pay off early for peace of mind if you are truly flush with assets—e.g., “$4 million in a trust, sure, no big deal.”

4. Creating a ‘Bridge Account’ for Retirement ([10:40])

Andrew’s Situation:
- Close to retirement, wants clarity on the “bridge account” concept (using cash reserves to cover expenses as a market buffer).
- Asks how much to set aside and in what type of account.
Jill’s Recommendation:
- Two to three years of expenses is sufficient; five is overkill except for the extremely risk-averse.
- Keep most in money markets, CDs, or other low-risk cash equivalents for near-term funds.
- Gradually reduce risk as retirement nears.
- Quote:
  
  “It would be very odd if we went into a three-year downward market.” – Jill ([10:59])

5. Can I Afford to Retire Early? ([12:55])

Tim’s Outline:
- Plans to retire at 57; $1.1M in a 401(k), $100k Roth, $300k in investments, rental properties netting $7k/month, $1.4M house (no mortgage), and substantial college and healthcare expenses looming.
- Wonders if he can afford to retire next year.
Jill & Mark’s Assessment:
- Rental income strengthens case for early retirement, but his asset drawdown will be significant.
- Advises earmarking investment funds specifically for college expenses, not cash flow.
- Health care costs are a question mark – must be planned.
- Working a few more years, at least until college is paid, is preferable.
- Quote:
  
  “I think you can probably do it based on what you wrote, but I am not sure it makes sense. How about that?” – Jill ([14:55]) “He’s definitely going to spend down his assets if he does it.” – Mark ([15:05])
Guiding Principle: Early retirement is possible—but may not be prudent. Matching big, predictable expenses with set-aside funds gives more security.

Notable Quotes & Memorable Moments

Jill’s Empathy for Advisors:

“I feel bad because I feel like these folks have done right by them...I’ve been on the other end of that phone call.” ([07:15])
On Mortgage Payoff Temptation:

“If you said to me...‘I have $4 million in a trust, should I pay it off?’ Yeah, sure, no big deal. But you need your money and access to it. So no.” ([09:41])
Retirement Bridge Account Logic:

“Two to three years is fine. And yeah, I like it in boring bank, money market, CD.” ([11:24])
On Retiring While Paying College for Kids:

“I would work four more years, get my kid through college. Suck it up. Easy for me to say. I don’t have the kid I have to pay for college.” ([15:20])

Timestamps for Key Segments

Retirement cash and safe income options: [02:00] – [04:46]
Financial advisor fees and the value proposition: [04:46] – [07:15]
Should I pay off my mortgage early? [08:15] – [10:15]
Bridge account strategy for retirees: [10:40] – [12:55]
Early retirement with big expenses ahead: [12:55] – [15:20]

Tone & Takeaways

Jill’s style is direct, empathetic, and focused on the emotional realities behind money decisions—recognizing when the peace of mind does or doesn’t outweigh financial math. She consistently urges listeners to protect liquidity and plan for the unknown, especially when life is about to get a lot more complicated.

Listeners are reminded to:

Weigh financial math vs. emotional comfort.
Keep options open for future planning help.
Maintain buffers and liquidity, especially amid life transitions.
Think long-term, even when tempted by short-term “peace of mind.”

For more advice or to submit your own question, visit jillonmoney.com

Transcript

A (0:00)

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And make this the year where no opportunity and no customer slips away. Try quo for free. Plus get 20% off your first six months when you go to quo.com jillonmoney that's q-u.com jillonmoney quo no missed calls, no missed customers. Ugh. Could this vintage store be any cuter? Right. And the best part? They accept Discover. Accept discovery in a little place like this? I don't think so, Jennifer. Oh, yeah, huh? Discover's accepted where I like to shop. Come on, baby, get with the times. Right. So we shouldn't get the parachute pants. These are making a comeback, I think. Discover is accepted at 99% of places that take credit cards nationwide, based on the February 2025 Nielsen report. Welcome to the Jill on Money show. It's Thursday, January 29th, and we're here answ your financial questions. If you have one, just go to our website, Jill. On money.com click the contact us button, write us a note. And if you would like to join us live, check the box. Mark will do everything else. While you're on the website, check out all the free content that lives there. We've got a weekly newsletter, comes out on Fridays. We've got another podcast. It's called Money Watch. We've got a blog, we've got a radio show. There are videos, there are resources, all there@jillonmoney.com just bookmark the website so that in case you have a brainchild of an idea and you want to maybe pass it by us, it'll be there. Jillandmoney.com okay, today we are going to be answering some emails. We need to do email shows to help the shy people? This question comes from Substack. Susan writes, my question is I sold my home and started retirement at age 63. My husband is 67. He's still working at and we are both collecting Social Security. We put our proceeds from the sale of our house in a high yield savings account, but now the rate has dropped to 3.5%. We don't want to risk losing any of the money by putting it in the market and we would love to put it in a place that will earn us monthly or yearly income that we can spend without jeopardizing the they say initial money. I think they mean that that big chunk of money, the corpus of the money and in the account. What are your thoughts, Susan? I'm so sorry to say it's very hard. I mean 3.5% is not bad. I mean at least it's ahead of the inflation rate. But I don't know enough about you. It sounds to me like with everything going on that this account, the proceeds of your house in the High yield savings account is maybe extra money beyond other money. So let's presume that's the case. One way to drive a little bit more income is to take that money and just juice it up a little bit by creating a cd, a certificate of deposit ladder, or maybe even put some of the money in a short term bond fund, some of the money in CDs, some of the money in cash. The thing is, if you really don't wanna put the money at risk, there aren't so many great options. And as you're finding as interest rates go down, the whole idea of having this extra cash and having a nice big chunk of money that's generating income is. It becomes a little less appealing. The interest rates go down, the money, the interest you pay is taxable. So all that being said, I'd love to know a little bit more about you and unfortunately what you're asking is something that's sort of elusive for investors. I want to earn a bunch of money, but I don't want to take any risk. It's tough, I know, but get back in touch with us because maybe if there are other things going on in your life, we could come up with some different ideas for you. This message is from Anonymous. Anonymous Rights My wife and I are age 45 and 51. We engaged a financial advisor last year and we're not sure we're getting value for the cost. Okay, so they are paying an asset under management fee and it is 1.25% and that is up to a million dollars. They Happen to have $985,000. They pay about $12,000 a year. Now the asset under management fee drops to 1%. For the next 2 million it goes down. Okay, so they purchased a vacation home which takes a lot of our extra cash flow. So there isn't the question of what to do with too much extra cash flow, at least not for the near future. The financial plan they presented us with did not go into the level of detail that we would have liked I. E. They didn't offer different withdrawal strategies. They do offer tax planning. They are responsive and I trust them. But is it worth it? My thinking is that it may be best to engage someone five years from now when we are closer to retiring and moving towards lower paying jobs. Then they can help us with the tax planning and withdrawal strategies. We have estate planning done, we are insured so there is no value they can offer there. They also set up nicely as far as investment options for 401ks IRAs. So I think we could continue along as they set us up for, for the next five years and that would save us 50 to 60 thousand dollars. What do you think? Well, you know, Anonymous, it kind of stinks for the advisor. It sounds like they actually did the job that. But I also get that they didn't kind of go into more depth. I mean it is possible that you can say to them that you're going to try to manage your own money for the next five years and do it yourself and you want to keep the door open to come back to them and maybe there'll be game for that. You know, I guess it's a real question of, you know, that is a lot of money, 50 or 60 grand. But I also feel a little bit like oh they did set you up and is it nice to have somebody in your back pocket who has helped you thus far. So I don't know, I don't feel strongly on this one. I'm going to say maybe, but I don't know. One market downturn, we'll see what happens.