Do I Have Enough to Slow Down?

Summary

Podcast Summary: "Do I Have Enough to Slow Down?"

Podcast: Jill on Money with Jill Schlesinger
Episode Date: December 29, 2025
Host: Jill Schlesinger, CFP®
Episode Theme:
This episode addresses the financial, emotional, and practical considerations of "slowing down" or semi-retiring. Jill takes a listener call from Mary, a 63-year-old realtor, to analyze whether Mary is financially positioned to scale back from full-time work, while still maintaining her lifestyle, funding some travel dreams, and ensuring long-term financial security.

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Main Theme & Purpose

Jill helps listeners wrestle with the common concern: "Do I have enough to slow down or semi-retire?" Working through Mary's numbers and circumstances, Jill illustrates principles about financial independence, spending, retirement tax strategy, and living out your dreams without fear or guilt.

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Key Discussion Points and Insights

1. Introduction to Mary’s Situation (03:03–05:21)

• Who is Mary?
  • 63 years old, realtor, labeled herself a "worrier"
  • Wants to shift from full-time (7 days a week) to part-time, or possibly retire
  • Sold a townhouse, now owns a 2-bedroom, 2-bath condo mortgage-free ($325,000 value)
  • Savings: $1.6M in brokerage (mostly taxable), ~$500k cash, $400k in tax-advantaged accounts, $1,500/month ex-husband’s pension, Social Security eligibility

"I'm looking for some practical advice. I tend to be a worrier... I'm ready to slow down. So the question I have is: do I have enough reserves, savings, etc., to make that happen?" – Mary (03:10)

2. Analyzing the Numbers (05:22–07:39)

• Spending Needs
  • Comfortable on $4,000–$5,000/month; Jill assumes $5,000 for calculation
• Income Sources
  • $1,500/month pension (continues as long as ex-husband is alive)
  • Potential to make ~$1,500/month part-time (uncertain)
  • Social Security at age 70: Expected to be ~$3,700/month
  • Significant cash buffer: $500,000 sitting in a bank (immediate spending cushion)

"Let's just say that even if you do it for four or five...you take $50,000 a year out of that amount and you're covered, your expenses are covered..." – Jill (07:39)

3. Creating a Cash Flow and Withdrawal Plan (07:40–08:21)

• Jill suggests that Mary is financially secure enough to slow down now, drawing from her large cash reserve to fund living expenses during the gap years to age 70.
• Even if she draws $50,000/year for several years, there's sufficient cash and investments to ride out market swings and unforeseen expenses.

"You burn your cash, go through it, leave yourself with a couple hundred thousand dollars at the very end. By the time you're 70 and you are pretty well set..." – Jill (07:39)

4. Social Security and Pension Planning (07:08–08:29)

• Key consideration: Ex-husband’s pension ends upon his passing.
• The goal should be to delay Social Security until age 70 for maximum benefit, using savings to bridge the gap.

5. Roth Conversion & Tax Strategy (08:30–10:50)

• Jill raises the question of Roth conversions as a tax-preferential strategy while Mary is in a lower tax bracket (before RMDs and Social Security).
• Two strategies discussed:
  • Convert enough IRA to Roth each year to stay within the 22% bracket
  • Consider pushing into the 24% bracket because taxes are unlikely to go down

"I would start converting. I really would. You can use some of your cash. You're going to do it slowly over time. And if you do it, you've got like this 7-year horizon before you start taking Social Security..." – Jill (09:41)

6. Living Life: Travel and Enjoyment (10:50–11:47)

• Mary wants to travel more, especially to Italy where her sister has a place.
• Jill encourages spending on these enriching experiences, reassuring Mary that “slow down” includes living dreams, not just covering expenses.

"This sort of feels like there’s like many movies that are made about 60-year-old women who are traveling to Tuscany. So I think that you could just, like, binge all of those movies and figure out where you want to go." – Jill (11:24)

7. Estate Planning & Family Considerations (11:47–12:02)

• Mary confirms her will, health directive, and durable power of attorney are in order and under review.
• Children to be provided for by other family members.

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Notable Quotes & Memorable Moments

• On Retirement Guilt & Freedom
  "Now that’s ridiculous [working 7 days a week]." – Jill (05:55)
  "I think you’re in great shape. Go find that Italian stallion. Exactly." – Jill (12:08)

• On Outliving Savings Anxiety
  "Yes, you could totally do this." – Jill (07:33)

• On Travel and Defying Stereotypes
  "If I could mesh Eat, Pray, Love and Under the Tuscan Sun…" – Mary (12:20)

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Timestamps for Important Segments

• Mary’s introduction and concerns – 03:03
• Assets and spending details – 03:53–05:21
• Retirement income calculation – 05:22–06:50
• Social Security and pension analysis – 07:08–08:21
• Roth conversion discussion – 08:30–10:50
• Travel plans and lifestyle dreams – 11:07–11:47
• Wills and estate preparations – 11:47–12:02
• Final encouragement and wrap-up – 12:08–12:31

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Episode Tone & Takeaways

The conversation is supportive, direct, and gently humorous. Jill’s hallmark style—cutting through worry, jargon, and guilt—shines through as she delivers a verdict: Mary can and should slow down, enjoy her savings, and pursue her travel and lifestyle wishes.

Listeners get a clear look at:

• Practical application of retirement math (spending vs. income and asset drawdown)
• The psychological hurdle of moving from saving to spending
• Timely tax strategy insights for those with significant pre-tax assets
• Importance of legal documents and communicating with family

Bottom line:
Mary is more than ready to slow down—and so might be many listeners in similar shoes, if they run their numbers with candor and care.

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For further information or to submit your own question to Jill on Money:
Visit jillonmoney.com and click "Contact Us".

Transcript

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[Jill]

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[Mary]

So I listened to the podcast, a fairly recent listener, and really just love the way you approach everything without judgment and just like you are where you are. And so. So I'm looking for some practical advice. I tend to be a worrier. I've heard you speak to people like me before. I've done a variety of different things. I'm 63 years old and I'm a realtor. But I'm ready to slow down. So the question I have is, do I have enough reserves, savings, et cetera, to make that happen? What I chose to do a couple years ago, I was living in a townhouse closer to the beach. I elected to sell that because the market was strong and I purchased a two bedroom, two bath condo and I have no mortgage.

[Jill Host]

Oh, that's nice. Well, let's start with that. How much is that worth?

[Mary]

I'm going to say about 325.

[Jill Host]

Okay. No mortgage.

[Jill]

Great.

[Jill Host]

All right, so tell us what else, how else are we going to finance this slowdown? How much money have you accumulated? Do you have your own retirement account because you're self employed?

[Mary]

Mm, I have a, it's a, it's in various categories, but in total in a brokerage account, about 1.6.

[Jill Host]

Great. So that's some, some retirement and some non retirement in that 1.6.

[Mary]

Yes. And there's also, well, I have a quadro allocation, but I think that is also tax restricted. But I have saved. I have about 500,000 in cash.

[Jill Host]

So 1.6 million in assets. Is it fair to say that like half of that is in pre. Is it pre tax money? Is it more than half? I'm just trying to get a sense of your future tax liability.

[Mary]

I would say that that 1.6, and I'm looking at my report here is, is in the tax taxable category. I also have about, I mentioned the 500, which is strictly cash, and then there's about 4 to 500. That is not restricted.

[Jill Host]

Okay, I got it pre tax and then 400 grand in a taxable brokerage. So you got 2 million bucks invested and then a half a million dollars in cash. Yes, Doing a million bucks, as we say up here in nyc. Okay. How much money do you spend?

[Jill]

Big shot?

[Mary]

Not much. I'm a, I'm a pretty conservative person. I think conservatively between 4 and 5,000amonth is, is more than adequate for me.

[Jill Host]

Wow. Let's say Five. When you say slow down. And because you're a realtor, it is possible that you would make some money for the next couple of years or do you just want to quit? Are you done?

[Mary]

No, I think the, the question mark is what the market will do and what I will able. Will be able to do within that market if I do. I mean, I'm working seven days a week now.

[Jill Host]

Now that's ridiculous.

[Mary]

Yeah, so I'm interested in, you know, two. Two days a week. And I feel like. Oh, I forgot to mention I have one other thing. In that ex husband's pension, there's 1,500amonth.

[Jill Host]

Is that already starting to pay out?

[Mary]

Yes.

[Jill Host]

So there's so of their 500 5000amonth that you're needing, you get 1500amonth from through the pension or quadro. Right. And then is it fair to say in two days a week that, you know, you could do a couple, three sales in a year? Like, could you make, say, another $1,500 a month?

[Mary]

That's what I think. If, if the, you know, the business I'm in right now, because it's structured such that we do work seven days a week, if they would consider allowing me to do that, I think I could make that work.

[Jill Host]

Okay, I'm going to just put that as a question mark because maybe we won't get that. Obviously, you know, you've got plenty of cash. So even if we said of your. What is your full retirement age? 67. Is that your Social Security? Okay, what's the Social Security amount that you would be entitled to?

[Mary]

I believe it's about 2800.

[Jill Host]

The ex's pension is that forever? For your whole life.

[Mary]

It terminates upon his passing.

[Jill Host]

Oh, shoot. Then you can't even, you can't even root for him to die. That's too bad. That's such a bummer. Okay, but it'll be there for. I mean, is he in decent health?

[Mary]

Yeah, I think so. I think so. And, and I'm looking at trying to wait until 70 to take the.

[Jill Host]

Yeah, I think that would be great if you could. I mean, listen, here's, here's the game plan. Yes, you could totally do this.

[Jill]

Big deal.

[Jill Host]

You got 500 grand in cash. Let's just say that even if you do it for four or five, let's say four years or even five years, you take 50 grand a year out of that amount and you're covered, your expenses are covered, and you know, 50, it's even a little bit less because of the pension. You're fine. And you could do it probably till age 70. You burn your cash, go through it, leave yourself with a couple hundred thousand dollars at the very end. By your time you're 70 and you are pretty well set because then essentially at, you know, when you're, when you're 70, what's the, what's the amount when you're 70 for your Social Security, I.

[Mary]

Want to say it's 37, 36.

[Jill Host]

Oh my God, Mary, you're in great shape. How much money were you making in like the good times?

[Mary]

200.

[Jill Host]

I mean, you're going to be in a very low tax bracket, right?

[Mary]

That is my question. I listened to you and you talked about the Roth conversion and I actually sent an email to my accountant and he said, it's not a simple answer. Call me. So I was going to do this first and then give him a call and.

[Jill Host]

Yeah, because let's say after this year, let's say next year, your income, even if you, even if you do, let's say you do work part time, you have three grand a month of taxable income, right? Pension, plus the part time, right? Okay. Now worst case scenario is like, oh my God, I made too much money. And now you're in the 22% tax bracket. You could start converting your pre tax accounts and you could start to convert that into a Roth ira. Now, there's two ways to approach this, all right? One is to say I'll just do it up to the 22% tax bracket, which would mean you could convert enough up to $89,000. You're, we'll see how your accountant feels about this. But I would go to the 24% tax bracket because you always say taxes.

[Mary]

Aren'T going to go down.

[Jill Host]

I don't think so. I really don't. You know, right now if you think about it, you've got $1.6 million, right? And if you didn't touch that, it's going to grow even if you're not putting money into it, right? It's going to grow. So when we talk about, well, you're going to be forced to take some money out, y know, you could have 2 million bucks in there, you could have $1.8 million that's in there. So you're going to have to pull out 65 the first year you retired, $66,000. On top of that, you would be getting Social Security. So you are already encroaching on the 24% tax bracket, right? So I would start converting. I really would. You can use some of your cash. You're going to do it slowly over time. And if you do it, you've got like this 7 year horiz before you start taking Social Security where you know, you can live on the money and you can also convert some of the money. And then what I'm hoping is that by the time you're at Social Security age, you can sort of be at. Half of my money has already been taxed. Half of it has not been taxed.

[Mary]

That makes me feel that, that feels right to me because again, of my more conservative nature, I would like to have that and available to me. One other thing that I'd like to consider along the way too is between now and then, you know, taking some of this money as well and doing some traveling.

[Jill]

Where are we going?

[Mary]

Well, I went to it. My sister has a place in Italy, in Sardinia.

[Jill Host]

Come on, how awesome is that?

[Mary]

So I know that that's on the list.

[Jill Host]

Have you never been?

[Mary]

I've been. I've been. But I want to go back and I want to see other parts of Italy that I didn't see the first time.

[Jill Host]

Yes, I would be. This sort of feels like there's like many movies that are made about 60 year old women who are traveling to Tuscany. So I think that you could just like binge all of those movies and figure out where you want to go.

[Mary]

Right? I would love to live that life.

[Jill Host]

I think that would be great. You're in fantastic shape. Have you done. So you do have kids? I didn't even mention I have two children.

[Mary]

They are going to be provided for, most likely through other methods, other family members.

[Jill Host]

Oh, good.

[Mary]

I have my durable power of attorney, my health directive and my will in my office under review.

[Jill Host]

Okay, well, let's get that done. Mary, I think you're in great shape. Go find that Italian stallion. Exactly.

[Mary]

That's nice.

[Jill Host]

That's right. And you're going to have. I feel like there's going to be a lot happening in Mary's life in the next few years. And it's going to be. It's like Eat, Pray, Love. That part of the book where she's in Italy.

[Mary]

You're like, yes, if I could mesh. Eat, Pray, Love and under the Tuscany.

[Jill Host]

I mean. Yeah, you're in. Excellent. Good luck. Thank you so much for getting in touch with us. Go ahead and give your notice and be done with it.

[Jill]

If you need some guidance, if you're looking at your year end finances and say you want to do something different, or maybe you want confirmation that you're on the right track for 2026. Get in touch with us go to jillonmoney.com click the contact us button, write us a note and if you would like to join us live, just check the box. Mark does everything else. You can subscribe to us on the Odysee app or wherever you find your favorite podcasts. We always ask that you lift someone up. Change your work, Change your wealth. Change your life. Thanks for listening. We'll talk to you tomorrow.

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