Do We Have Enough to Retire and Live Large?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Do We Have Enough to Retire and Live Large?
Date: June 1, 2026
Host: Jill Schlesinger
Guests: Mark (Producer), Eli (Listener, South Carolina)

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Overview

In this candid and insightful episode, Jill Schlesinger responds to a listener, Eli, who wants to know if he and his wife can “really retire and live large” at 55 given their assets — and still sleep at night. The conversation dives deep into the numbers, examines the psychological dimensions of retiring early with wealth, and demystifies the sometimes intimidating “Monte Carlo” simulations used by financial advisors. The episode also showcases the practical and emotional aspects of retirement planning, especially for high savers unsure how (or if) to shift gears and enjoy their money.

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Key Discussion Points & Insights

Jill’s New Video Podcast for Younger Listeners

• Jill promotes her new video podcast, Money Moves, aimed at listeners under 45 to help them get proactive with their finances early on ([03:15]).
• Mark jokes he’ll wear the same shirt each episode; Jill enthuses about the show’s new approach ([04:10], [04:25]).
• Jill gently pokes fun at the generational differences in financial advice and warns against offering outdated wisdom ([05:08]).

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Eli’s Situation: The Numbers

Basic Demographics and Income

• Eli and his wife are both 55, living in South Carolina ([07:44]).
• Eli: Full-time employee, earning ~$400k/year (base + variable pay); Wife: Consultant, earning ~$200k/year ([08:05], [08:29]).
• No children, “no plants, no pets” ([08:38]).

Real Estate

• Primary residence: Worth $1.6M–$1.8M, $400k outstanding on a 2.25% 15-year mortgage (10 years left) ([08:47]-[09:10]).
• Beach condo: Paid for, worth ~$460K ([10:18]).

Assets

• 401(k): $268K (mix of traditional and Roth) ([10:34]).
• IRAs: $4.2M (combination of rollover and SEP IRAs) ([11:34]-[11:55]).
• Taxable brokerage: $5.8M ([11:00]).
• Cash: ~$125K ([12:42]).

Debt and Ongoing Expenses

• Mortgage: Around $5,000/month with taxes and insurance ([13:19]).
• Monthly spending: $14–18K/month; Jill pegs it at $18K for planning ([12:57], [13:05]).
• No pensions; all retirement savings are self-funded ([09:38]).

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Jill’s Assessment & “Gut Check” on Retiring Early

Monte Carlo Simulation: Helpful or Anxiety-Inducing?

• Jill explains the “Monte Carlo” simulation — a tool financial advisors use to predict the probability of financial success in retirement ([06:06]):

  “Financial advisors love this crap… but I think giving it to a client is really jarring sometimes. And also it doesn’t really reflect what happens in life.”
  — Jill Schlesinger ([06:06])

• Eli seeks actionable advice to reconcile simulation results with his gut feelings ([07:36]).

Breaking Down the Numbers

• Jill “haircuts” the pre-tax retirement accounts to account for taxes, estimating ~$3M net from IRAs ([14:38]).
• With taxable brokerage and after-tax retirement funds, Eli’s “spendable” nest egg is roughly $8.8M ([15:36]).
• At a conservative withdrawal rate (3.5%), this could generate ~$310K/year before Social Security ([15:36]).
• Social Security benefits likely to be $80–100K/year combined for Eli and his wife ([16:34]).
• Conclusion: Their spending ($220K/year) is well within their safe withdrawal rate, and even with conservative estimates, they “have no problems, none.” ([16:53])

The “Living Large” Question: How Much Spending is Too Much?

• Eli admits to saying, “I think we spend too much”; Jill laughs and reassures:

  “Oh, stop it. You got $10 million. Stop it.”
  — Jill Schlesinger ([12:54])

• Eli worries outdated habits from decades of saving might keep him from enjoying what he’s built, and admits to the “mental barrier” ([13:45]-[17:06]).

Eli's Real Fear: Is It Okay to Spend More — or a Lot More?

• Eli contemplates spending $30K/month early in retirement for “living large” but frets over its sustainability ([17:12]-[17:55]).

• Jill challenges this, suggesting occasional year “splurges” are fine, but consistently doubling spending isn’t realistic for a 40-year retirement ([17:56]-[18:42]).

  “If you want to spend 30 in a year, you’re having a great year, fine. Can you go back to 15 then? … Because you’re young. You can live for 40 years.”
  — Jill Schlesinger ([17:56])

• Mark calculates that Eli’s wife’s consulting income could help fund near-term splurging ([19:33]).

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Emotional Side of Retiring Early

• Eli admits his mindset is “Depression-era mentality,” making it hard to step off the treadmill ([20:22]-[20:36]).

• Jill diagnoses the anxiety:

  “I think you should have a game plan to say… I want to scale back a little bit... and during that time when you’re scaling back, you’ve got to figure out what the hell you’re going to do with yourself, because it sounds to me like there’s a little anxiety around that too.”
  — Jill Schlesinger ([22:27])

• Eli admits, “I just don’t want to be bored” ([23:23]).

Advice for the Transition

• Jill suggests an incremental approach: gradual scaling back rather than a cold-turkey retirement ([22:24]-[23:23]).
• Keep the house only if they love it; selling could reduce monthly expenses and free up capital ([23:34]-[24:22]).
• Update estate documents ([23:34]).

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Listener and Societal Reactions

• Mark predicts listener jealousy or accusations of bragging, which Jill firmly rejects:

  “We don’t have braggarts. We have people who are like, as I say, no judgment…”
  — Jill Schlesinger ([24:56])

• Both urge listeners to “worry about yourself” and measure success on individual terms ([25:12]).

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Notable Quotes & Moments

• On Obsessive Saving:

  “You’re so used to saving… In your head, man. Did you come from meager beginnings? Yes. Why are you such a good saver, like? And why are you driving yourself crazy?”
  — Jill Schlesinger ([20:22])

• On Enjoying Wealth:

  “You should take nice vacations while – I mean, why can’t you take a nice fancy vacation while you are working?”
  — Jill Schlesinger ([21:27])

• On Risk and Reality:

  “Your dashboard is misleading in some respects, but you have control over this. That’s really the most important thing.”
  — Jill Schlesinger ([20:43])

• On Comparison:

  “People get so bent out of shape when other people have large sums of money. …Just worry about yourself.”
  — Mark ([25:12])

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Timestamps for Key Segments

• 03:15 – Jill promotes Money Moves, her new video podcast for people under 45.
• 05:27 – Introduction of Eli and initial description of financial situation.
• 08:44 – Real estate deep dive and mortgage details.
• 11:00 – Asset rundown: IRAs, 401(k)s, brokerage, cash.
• 12:54 – Spending discussion and what "living large" means post-retirement.
• 14:38 – 16:27 – Jill’s “haircut” calculations: taxes, withdrawal rate, realistic income/safety.
• 17:06 – 18:42 – Eli voices fear of overspending; Jill challenges assumptions on “living large.”
• 22:24 – 23:23 – Jill outlines a gradual exit strategy and addresses emotional anxieties.
• 24:50 – Addressing potential listener responses; no-judgment approach.

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Tone & Final Takeaways

• Tone: Warm, humorous, straight-talking, and empathetic. Jill blends technical expertise with “tough love,” cutting through anxieties and emphasizing practical, actionable steps.
• Main Takeaway: Even with massive assets, the transition into retirement is as much emotional as financial. Planning is essential, but so is acknowledging the psychological hurdles of enjoying what you've earned.
• Action Steps: Know your true living expenses, factor for taxes, have an exit strategy, update legal documents, and gradually ease into the next stage of life — all while remembering to focus on your own goals, not on comparisons with others.

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For those considering a major life transition, this episode offers not only rock-solid financial guidance but also reassurance that it’s okay (and possible) to truly enjoy the fruits of lifelong saving.

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Transcript

[Jill Schlesinger]

Hey gang.

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You know, I always say to make smart financial decisions. So let me ask you this. What exactly is that old car in your driveway doing for you right now? Seriously, is it an extra car? Nobody drives anymore. Maybe it doesn't run. Do you keep saying you'll sell it one weekend and suddenly it's been two years? No. Meanwhile, it's taking up space, costing you money, and slowly becoming part of the landscape. Here's the easy solution. Donate it to Cars for Kids. And yes, it's that Cars for Kids, the one with the jingle you absolutely know already. 1877 cars for kids. Here's why people love to donate to Cars for Kids. It's ridiculously simple. You go to carsforkids.org Jill that's cars with a K. Answer a few simple questions and you're done. The they'll come pick up the vehicle for free, tow it away, handle the paperwork, and you'll receive a tax deductible receipt.

Done.

Cars4Kids has been doing this for over 30 years and has accepted more than a million vehicle donations. So if you've got a car you're not using, turn it into something meaningful. Go to carsforkids.org Jill that's cars with a K. And fair warning. Now that jingle's going to be stuck in your head for the rest of the day. Welcome to the Jill on Money Show. It is Monday, June 1, and we are here Answering your financial questions. If you have one, all you need to do is go to our website, jillonmoney.com in the upper right hand corner, there is a contact us button. When you click that button, a form will pop up. That form will basically give you an opportunity to tell us everything that's on your mind and also let us know what are the questions that we can try to help you out with. Now, if you'd like to join us on the program live, check the box and you're going to see. Are there two boxes there now, Mark, or just one? There's two. One says audio and one says video. Right. Okay. So if you want to join us via audio. Fantastic. Check the box. If you are un. This is very mean and ageist. But if you're under the age of 45, check the video box. Why? Because we have a new show. It is launching and it is really geared towards younger listeners, viewers. And the show is called Money Moves. And I am so psyched for this because even though I said I would never do a video podcast, this one's kind of cool. So the premise of the program is that sort of like what we do here, but for people who are just starting out their financial journeys. So, you know, basically a show that helps you take control of your financial life earlier on when you can make a huge difference. So if you're listening right now to this program, you've got anyone in your life under the age of 45 or you just want to hear what the under 45 people are up to, then subscribe to us. Follow us. We have [e-mail] this is also going to be a YouTube show. Aunt Jill will be there and Mark also on camera, much to his chagrin. So are you thinking that you have to, like, jazz up your wardrobe a little bit, Mark?

[Mark]

No, I will. In fact, for every. Every single episode that we do, you will see, soon enough I will be wearing the same shirt.

[Jill Schlesinger]

What are you talking about? It's gonna be like your lucky shirt.

[Mark]

You'll see.

[Jill Schlesinger]

Okay. Is it the Jill on money pullover?

[Mark]

No, it's not.

[Eli]

Okay.

[Jill Schlesinger]

Is it like. Oh, okay. I'm excited to see what this is all about. I like it. And it's an exciting thing to imagine that you will wear the same shirt every time. Anyway, everything is on the website. Thank you so much for supporting us. This show means a lot to us and we're gonna really try to make a go of it doing what we do here. But really, again, gearing this towards a video show, but also to people who can really get frustrated with the advice that you and I, like any older person, gives. I was just writing an article, Mark, which I think you're going to love. It's going to be for the next blog post. It's called Stop giving Bad Financial Advice. Is that good for. For the people of my age? Ish.

[Mark]

Yeah, we don't get bad advice.

[Jill Schlesinger]

No, but you know what I mean. Like the people that we hear about, like when we hear about from one of you guys and you're like, I'm going to give my. I want my kid to buy a house. And we're like, really? Does the kid want that? That's what we're talking about. Okay, so let's get this show started. We are talking to Eli, who joins us from South Carolina. Hello, Eli.

[Eli]

Good morning, good afternoon. Hello, Jill.

[Jill Schlesinger]

What's happening? What can we do for you?

[Eli]

Well, my wife and I have been savers for a very long time, and we have had a financial plan that said we can retire at 55. And when I look at our dashboards, we like to be in blue. Our dashboards have red, yellow, green, and blue.

[Jill Schlesinger]

Well, tell me where. Where does the. Where does the other color scenario come in? What's going on?

[Eli]

Well, the blue means whenever you do that Monte Carlo sort of shaking the dice, it ends up better than green.

[Jill Schlesinger]

Okay. I want to just say that we should rebrand Monte Carlo because we had a caller many years ago who asked about the Monte Cristo, and I thought it was a much better. It's a better sandwich and a name for this. Okay, so everyone who's listening, the Monte Carlo simulation is something that nerdy math people like to put together that essentially gives you the probability that all goes well in the future based on your financial goals and given the. The money that you have accumulated. Financial advisors love this crap. It's nice. And I think they should do it themselves. But I think giving it to a client is really jarring sometimes. And also it doesn't really reflect what happens in life. But. Okay, so your dashboards are a little bit all over the place that, yeah, there's a probability that you'll be fine. And maybe if we have bad markets and a bad string of luck, you won't be. Is that basically how it turns out?

[Eli]

That is 100%, Jill. And. And now approaching my 55, my 55th year, and, you know, according to the dashboard, I can retire. There's that difference between what the dashboard said and what I'm feeling and what is actually True life. And so I'd like to put those two pieces together a little bit to get either one be more actionable about how our financial picture looks and what the practicality of it is versus what looks really great when we talk to our financial advisors.

[Jill Schlesinger]

Okay, so let's take one step back. Let's kind of. Let's flesh out the details. So you're 55. Is your wife also 55?

[Eli]

Yes, we're both turning 55 this year.

[Jill Schlesinger]

Okay, and you, Are you both working full time?

[Eli]

I am working full time, and my wife has her own consultancies.

[Jill Schlesinger]

Okay, let's start. For what? Let me go to you first. So how much do you earn?

[Eli]

I make 215 base and another 175. 200 in variable.

[Jill Schlesinger]

And has it been 175? Have you been able to generate that money or. Yes. Okay, so it's fair to say that we could even. Just 400 is about what you're making. Is that about right?

[Eli]

Yes. In the zone between 375 and 400.

[Jill Schlesinger]

Okay, I'm just going to say that then. All right, let's do that. Okay. Now your wife, she is a consultant. And how much does she earn?

[Eli]

She has one client, and she brings in about 200. 215.

[Jill Schlesinger]

Let's say 200.

[Eli]

Okay.

[Jill Schlesinger]

Do you guys have kids?

[Eli]

Nope. No kids, no plants, no pets.

[Jill Schlesinger]

Okay. Now you are in South Carolina. Do you own your home?

[Eli]

We do.

[Jill Schlesinger]

What's it worth?

[Eli]

It's worth between $1,600,000 and $1,800,000.

[Jill Schlesinger]

Oh, look at you. Hmm. Look at you. Is there an outstanding mortgage?

[Eli]

There is. There's about $400,000 outstanding mortgage.

[Jill Schlesinger]

What's the interest rate?

[Eli]

2.25.

[Jill Schlesinger]

Oh, my God. 30 year.

[Eli]

No, 15 year.

[Jill Schlesinger]

Okay. And when did you get that? When did you assume.

[Eli]

We. We got 10. We got 10 more years left.

[Jill Schlesinger]

10 to go. Got it.

[Eli]

Yeah.

[Jill Schlesinger]

Do you intend to stay there? I really.

[Eli]

Not really, but I feel like I, you know, I love this house because I love this mortgage.

[Jill Schlesinger]

I could be that person. Yeah, totally fall.

[Mark]

Terrible reason to stay someplace.

[Jill Schlesinger]

Stop it. It may not be. It may be the third worst, but it's not the. The terr. All right, Eli, do either. I presume neither of you have pensions that are floating around, is that right?

[Eli]

No, it's all 401k stuff.

[Jill Schlesinger]

So let's talk about what you guys have accumulated. So let's start with retirement assets. And you have a current 401k.

[Eli]

I do. So the only other thing I'm going to add to property. We also do have a place at the beach that's paid for.

[Jill Schlesinger]

Isn't South Carolina like a whole beach?

[Eli]

Okay, it is, but you know, when you live in, when you live in the city, you like to go see the trees and you know, it looks like the notebook or you know, you know, all that it looks, it's just different.

[Jill Schlesinger]

Or the help, if I may. Yeah. Invoke the. The South. Okay. What is worth.

[Eli]

It's about 460.

[Jill Schlesinger]

And that, that is something you want to keep?

[Eli]

I think so. Because if we don't, if we don't use it every weekend, it could go on the rental market.

[Jill Schlesinger]

Okay. Now let's get back to retirement assets. You've got a 401k. Is it traditional or Roth?

[Eli]

You know what, it was all traditional until this year. What I typically do is I do 100% to the 401k at the beginning of the year until it's done. So I don't pay myself until I pay my 401k. So I've got 260,000 in traditional and 8,000 in Roth.

[Jill Schlesinger]

268. Okay, and what else do you have?

[Eli]

We have a brokerage account of 5.8.

[Jill Schlesinger]

Oh, see that mark? See where he went? 5.8 million.

[Mark]

Here comes the hate mail.

[Jill Schlesinger]

Here comes the hate mail. But it's in a brokerage account, which is interesting.

[Eli]

Well, because we were trying to be good savers for our entire life. We were, we were, we were like living off of one paycheck. And, you know, before COVID we were making double.

[Jill Schlesinger]

Oh, wow. Okay. So the brokerage account. Double joint account. And are you telling me the only retirement asset in your name is. Is this the 401k? Do you have also have an IRA floating around?

[Eli]

I do. Between the two of us, we've got 1.3 in one rollover and 2.7 in another rollover.

[Jill Schlesinger]

So 4 million in IRAs. Yeah.

[Eli]

And then, and then we also, for my wife's consultancy, she has a self employed IRA.

[Jill Schlesinger]

And what's in there?

[Eli]

A little bit over 200.

[Jill Schlesinger]

So you have 4.2 million in traditional IRAs, right. Okay, just checking it. All right.

[Mark]

This is the most we've had in a while.

[Jill Schlesinger]

I love it.

[Mark]

In terms of is everyone.

[Jill Schlesinger]

Where are the advertisers from Schwab and Fidelity? Like, what are you guys doing? You're dropping the ball. Because I'm about to get Eli to go move his money to you. Okay, wait a second.

[Eli]

All my money is infidelity?

[Jill Schlesinger]

There you go, managing it yourself.

[Eli]

No, I got a financial advisor.

[Jill Schlesinger]

Oh, okay. All right. I forgot Monte Carlo, Monte Cristo, I

[Eli]

mean, because I can't do that myself.

[Jill Schlesinger]

You don't need to. Don't worry. All right, besides the traditional, the Roth, the 4.2 million in IRAs, the 5.8 in brokerage, what about anything else? Do you have crypto? Do you have high yield savings? Like, what else is going on?

[Eli]

We have buck 25 in. In flourish in our checking account.

[Jill Schlesinger]

Now, ready for the hardest question I'm about to ask. How much? How much do you spend?

[Eli]

I think we spend too much.

[Jill Schlesinger]

Oh, stop it. You got $10 million. Stop it. Come on.

[Eli]

No, no. We are spending probably between 14 and 18,000amonth.

[Jill Schlesinger]

Let's say 18. Let's just 18 as your number. That's your boat.

[Mark]

I'm curious what they're spending on, though.

[Jill Schlesinger]

Well, they have a big life. They have no kids, right?

[Mark]

No kids.

[Jill Schlesinger]

You got. What do you. You got some clubs? You play golf or something or.

[Eli]

So, like, you know, overhead is kooky because, like, our mortgage is, with taxes and insurance, it's more than five grand a month.

[Jill Schlesinger]

I mean, I. Can we just, like, calm down for a second? If you spend. I'm even going to guess, like, let's say you said you're telling me 18. I mean, let's just say I'm going to round it up. You spend 220 grand a year and making six. Who cares?

[Eli]

I know, but. But normally, like, my whole. Our whole, like, last 30 years has been saving 50% of our money.

[Jill Schlesinger]

So what? Like, why we pass is not present right now. Remember, like, past performance is no indication of future.

[Eli]

I know. That's a History Channel.

[Jill Schlesinger]

I mean, come on. All right, so let's just do something fun for a second. You got IRAs, and that's 4.2 million, right? And then we have this other money, this traditional. So that's another 260. Okay, hold on a second. I'm just going to do something fun. So, Mark, there's. In traditional assets, there is 4.46 million. Let's give that a haircut, because that's as. As Ed Slott likes to say, that ain't all your money. You have a joint owner, and that joint owner is Mr. Uncle Sam to you. Okay.

[Eli]

Yeah.

[Jill Schlesinger]

So let's take that down. Let's say that you have to give 30% up for taxes. Okay? So let's even. I'll even. Let's say you got 3 million after. That's really yours of your 4.63 is yours. Okay. Yeah. All right. Now, so what we have is 5.8 in that brokerage. I know there's probably some. There's probably some deep cost basis issues, but let's just use this 5.8. Like if you were to say what if you looked at the statement right now and it said cost basis, what do you think the cost basis is on the 5.8? 3, 2, 1.

[Eli]

Yeah, I don't know the answer to that. I'm embarrassed.

[Jill Schlesinger]

Why? Don't be embarrassed. That's more important than your Monte Cristo is to understand of that $5.8 million, what's going to be taxable? In other words, when you sell it, what's going to be a what? Where are you going to take a tax hit? $8.8m is basically what I'm thinking about. You got. I'm just. I'm just doing like fun quick back of the envelope. Okay.

[Eli]

Yeah.

[Jill Schlesinger]

So let's say that you have $8.8 million. Some of it is taxable. But let's just for fun, just see, like, what it would be, what that could generate of. On a 4% withdrawal rate. I'll even use three and a half. Okay, just to be clear, three and a half percent withdrawal rate, which you'll hear our interview when we have Ben Carlson on the air, which he thinks is, like, really silly. He thinks four is like so safe and it's dumb not to. But three and a half for you gives you $310,000 a year. You spend 220. Even if I'm wrong, let's say I've screwed you up because tax wise, the brokerage account has a larger tax liability. Let's say that you generate 250 grand a year from your portfolio to float your life. Guess what? That doesn't include Social Security. So tell me your Social Security numbers, Jill.

[Eli]

I'm embarrassed. I don't have them, Mark.

[Jill Schlesinger]

They make a lot of money. What's the pat. What's the top Social Security payment right now? Both of them have.

[Mark]

I would say they're both probably together. They're probably going to get like, you know, 80 grand a year.

[Jill Schlesinger]

Yeah, at least.

[Mark]

At least.

[Jill Schlesinger]

Yeah. So I'm going to guess it's probably closer to 100, but let's say 80. All right, so by the way, you have no problems, so everyone take a deep breath. Seriously. No problems. None.

[Mark]

It's mental for him.

[Jill Schlesinger]

It's so mental. First of all, why would you. Who cares? If you're not saving money, you're Spending money because you've already saved the money. You've already done the work. Do you want to quit or not?

[Eli]

Oh, my God, I do. But I'm like, here's your notice right now.

[Jill Schlesinger]

Come on, conference us in. Yeah.

[Eli]

Here's what my deepest fear is. Like, at the age of 55, I want to spend, like, $30,000 a month, and then I'd like to do, like, a decreasing balance because, like, I'm 55.

[Jill Schlesinger]

But wait a minute.

[Child]

You.

[Jill Schlesinger]

You just tell me at 18, you're like, oh, that's a lot. What do you. You want to spend 30 on what?

[Eli]

Well, but the thing is, is if I'm not working, I'm gonna have more leisure time.

[Jill Schlesinger]

Oh, how about you get a little philanthropic here? Wait a second.

[Eli]

We're. We are. We're philanthropic, Jill. I swear we are.

[Jill Schlesinger]

Okay? If you want to spend 30 in a year, you're having a great year, fine. Can you go back to 15 then? Because I don't think you can spend 30 straight line every year. No, I just don't think you can do that because you're young. You can live for 40 years. Right?

[Eli]

Right.

[Jill Schlesinger]

So if you're telling me I want to spend 30 for the first couple of years, but then we're going to kind of go back into, like, 18 land in today's dollars, right. Then I think it's fine. That's really what the Monte Carlo's trying to do. It's trying to smooth out those years. But let's just talk about it in reality, like, 30 grand's a lot of money. You're going to spend twice as much money as you spend right now, because. Why? Because you're going to take a $12,000 trip every year. I don't think that's happening. I mean, you could do it a couple times, but I don't think doing it every year for the first 15 years of your retirement. And by the way, that 18,000 that you gave me, doesn't that include your current vacations and stuff?

[Eli]

Right now it does.

[Jill Schlesinger]

So you're like, an extra 12 because we have to go to Saudi sands in South Africa and have, you know, marble floors in the desert in the. In the African bush and look at the elephants.

[Mark]

Yeah, 18 to 30. I mean, 18 to 30. It's a big jump.

[Jill Schlesinger]

I mean, also, like, I could spend an extra 12 grand on a vacation, no sweat. Get. But, like, I don't do that. I. I wouldn't necessarily think that that's a good game plan for every year. So if you want to do that? Like, so why don't you. Like what? Like right now you're taking nice trips, right?

[Eli]

Well, we bought this condo.

[Jill Schlesinger]

So then, like, either, either you sell the condo and that's your fun money account and you have 10 years of, like, ex. Like, if you're like, okay, I. I don't need this beach thing.

[Eli]

Right.

[Jill Schlesinger]

Sell it. And now you have a little fluff. You can even keep that. Your, like, extra fun money, huge vacation fund.

[Mark]

What about your wife? Your wife will keep doing the consultant?

[Eli]

Yeah, I think so. I think. I think it's. She really likes the. Just the mental part of it.

[Jill Schlesinger]

Yeah, you're done. But she's all right. I like her better than.

[Mark]

That's a nice. That's a nice chunk of income.

[Jill Schlesinger]

So it is like, she could. She could finance your $30,000 for a couple of years. Yeah, I think you're. I mean, do you really hate work? You have to be honest. You hate it or what?

[Eli]

Yeah, for the most part.

[Jill Schlesinger]

But, you know, can you do something? Like, can you get. Can you give me an off ramp for a year or two?

[Eli]

Oh, 100. Because. Because really, at the end of the day, anything that I want to make an investment in, in, you know, home renovations, special trips and that stuff, I want to do that while there's money coming in the door.

[Jill Schlesinger]

All right.

[Mark]

You know? Yeah, but you're. Yeah, sure. Okay. But you probably don't have to. You're just freaking yourself out a little bit.

[Jill Schlesinger]

Totally.

[Mark]

Because you're so nice.

[Jill Schlesinger]

And 30 grand a year, even though I'm only spending 18 now.

[Mark]

He's so used to saving.

[Jill Schlesinger]

I know. In your head, man. Did you come from meager beginnings? Yes. Why are you such a good saver, like? And why are you driving yourself crazy?

[Eli]

You know, it's that depression, error mentality, I think, that I was kind of brought up with.

[Jill Schlesinger]

Okay, fair enough.

[Eli]

Yeah.

[Jill Schlesinger]

Yeah. Thankfully, I'm not afflicted with that, so I think you're going to be fine. I think your dashboard is misleading in some respects, but you have control over this. That's really the most important thing. You really do. If your wife's going to keep working and if you're like, well, you know what I want to do? I want to have $30,000 vacations right now, at least for as long as she's making 200. Even if he didn't make 375 or 4. Let's say that you went to 200, right? You go to your base, you guys pay your bills on Your base salary. Okay, we do. And that's fine. And that, so you guys have that and then you can tap into this money that you've saved. You should take nice vacations while. I mean, why can't you take a nice fancy vacation while you are working?

[Eli]

Oh, yeah, we could do that for sure.

[Jill Schlesinger]

So why don't you do that for a bit and why don't you keep letting the money grow? But if you hate working, then you can, you can retire when you're 55, that's fine. And you can use some money for. You got to see how your cash flow goes. But if you have a rotten year, you cannot spend 30 grand.

[Eli]

Right?

[Jill Schlesinger]

There's just no way not going to work. I mean, whatever, you'll be fine. But it's not great when you're so young. That's what I would say. When you're, when you've got a 40 year retirement, you will have a retirement that lasts longer than your working life.

[Eli]

Yeah, for sure.

[Jill Schlesinger]

That way. So if you want out at 55, I think it's great to say 18, 20 grand a month, fine. But once you start to say, I want to do 30 and I want to travel, like you're already traveling. So how much nicer travel are you going to have?

[Eli]

No, you're, you're. You, you're on it. I think you, you may be in the wrong profession, Jill.

[Jill Schlesinger]

Why?

[Eli]

Because maybe you should be a psychiatrist or a shrink.

[Jill Schlesinger]

Yeah, that's no fun. Because they have. Then you have to come to the conclusion and I have to guide you there. That is exhausting for me. I've been in therapy my whole life. It's very tiring. I like telling people what to do. You're great. You're fantastic. I think that you guys need to have a real conversation. Eli, you know what I actually think? I also think you need a game plan of, like, how are you scaling out of what you're doing? And I don't think you are the type of person who's going to be good. Just saying, I quit, boom, done. And you go from 400 to zero. I think you should have a game plan to say, okay, here I am, I'm turning 55 this year. I know I could retire, but what's my goal? Well, you know what? I want to scale back. I'm tired. I've been working really hard. I want to scale back a little bit. 56, 57, you know, a couple years where you see like, I just want to scale back. And during that time when you're scaling back, you've got to figure out what the hell you're going to do with yourself, because it sounds to me like there's a little anxiety around that too.

[Eli]

Oh, 100%. I just don't want to be bored.

[Jill Schlesinger]

You're not going to be bored. There's so many things in the world to do. I. I have great. I have great confidence. Do you guys have your estate documents done?

[Eli]

They need to be updated, but we do have one set.

[Jill Schlesinger]

Okay, just make sure that you got that. Yeah, I don't think you need to sell anything. Don't worry about that. I mean, only keep the house if you want the house, obviously. Don't worry about the mortgage. If you sold the house right now, by the way, and you pocketed a bunch of money, you're gonna have to pay some tax, obviously, on capital gains, but whatever. You have that and you say, hey, you know what? I just want a smaller place and an easier place, and I'm gonna buy it for cash, and I'm gonna end up, I don't know, with a $900,000 paid for City Place and a $460,000 beach house. No mortgages. And now instead of the, you know, 18,000, you free up that five grand a month that you're paying out. I don't know. There's a lot of ways to make this work where you can spend more money.

[Eli]

Yep. No, that. That makes a lot of sense because the. In South Carolina, the insurance is crazy on these houses.

[Jill Schlesinger]

Of course. Of course. I know all these. You know all the coastal places.

[Eli]

Yeah.

[Jill Schlesinger]

All right. Mark, don't you think that we're going to. Is Eli going to create a lot of anxiety among people listening? You have $10 million. Why can't you be happy? He is happy. It's just that he doesn't know how to not work. And I think that's what we are. That's what we share.

[Mark]

Oh, he's just calling to brag. That's what they'll say. No, no, no, That's. That's what they'll say.

[Jill Schlesinger]

But. But isn't that a funny reaction? I don't get that ever. Like, I don't feel like that is not our. Our listenership. We don't have braggarts. We have people who are like, as I say, no judgment. There's no judgment here. You have 10 million or you have $10. I don't really care. People, where do you want to go? What's going on?

[Mark]

People get so bent out of shape when other people have large Sums of money. Okay, I don't get it. I really don't. Just worry about yourself.

[Jill Schlesinger]

Exactly. You. You are where you are, and we're meeting you there. All right, gang. If you have 10 million, if you have 2 million, if you have $2, doesn't matter. Go to our website, jillonmoney.com, click the contact us button, write us a note, let us know if you would like to come on the air. And don't forget to subscribe to our Brandy new show. It's called Money Moves. Check it out. It's on our website now. If you don't subscribe to this show, you can do it on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen and of course, lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

[Child]

Are you really buying a car online on autotrader right now?

[Parent]

Really?

[Child]

At a playground?

[Parent]

Yeah, really. Look at these listings from dealers.

[Child]

Wow, your search can really get that specific.

[Parent]

Really?

[Child]

And you just put in your info and boom. Cars in your budget.

[Parent]

Mom needs a second.

[Child]

Honey, you can really have it delivered.

[Parent]

Really? Or I can pick it up at the dealership. One sec, sweetie. Mommy's buying a car.

[Jill Schlesinger]

Mommy, look.

[Child]

I think you kid is walking up the slide.

[Eli]

Kyle. Again?

[Jill Schlesinger]

Really?

[Parent]

Auto trader? Buy your car online. Really?

[Jill Schlesinger]

Hi, this is Jill Schlesinger, CBS News business analyst, certified financial planner, and the host of the Jill on Money podcast. Beginning, middle or end of the year,

it's always a great time to take

control of your financial life. And the Jill on Money podcast is here to help your questions make it possible for me to provide uncommon, conventional and entertaining insights on your money and more importantly, on your life. Follow and listen to Jill on Money wherever you get your podcasts.