Making Our Next Move

Summary

Podcast Summary: "Making Our Next Move"

Podcast: Jill on Money with Jill Schlesinger
Episode Date: October 6, 2025
Host: Jill Schlesinger, CFP®
Guest: Bella, caller from Reno, Nevada

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Episode Overview

In this episode, Jill Schlesinger answers listener Bella’s call, diving into the financial considerations for a major life pivot. Bella, a successful entrepreneur and real estate investor in her 40s, is contemplating a significant lifestyle change in six years: traveling the world with her partner and daughter after her child finishes high school. Jill, along with regular contributor Mark, breaks down Bella’s assets, income strategy, and retirement planning—offering tailored, honest advice (and a dose of dream reality-checking) to help Bella (and listeners) understand what it takes, financially and logistically, to make such a big move.

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Main Discussion Points and Insights

1. Life Transitions and Financial Planning

• [01:06] Jill emphasizes that big life transitions—like moving, changing careers, retirement, or funding college—are common sources of financial anxiety.
  • “Usually that's when you start kind of freaking out about your money or thinking about your money, maybe not freaking out.” — Jill
• Jill encourages listeners to reach out for guidance during these periods.

2. Bella's Situation: Goals and Assets

• Bella's Background:

  • In her 40s, has a partner and an 11-year-old daughter
  • Self-employed with a business of 13 years
  • Owns primary residence and two rental properties (no mortgage on primary)
  • Desires a lifestyle change in about six years—world travel, making Reno a home base
  • Partner stays at home but has a side hustle and is on company payroll

• Assets & Income Breakdown ([04:01]–[08:25]):

  • Households earnings from work: ~$150,000/year (excludes rental income)
  • Rental Properties:
    • Rental 1: Worth ~$550k, mortgage $154k @ 3.99%
    • Rental 2: Worth ~$400k, mortgage $174k @ 4.5%
    • Combined net rental cash flow: ~$1,500/month after expenses
  • Savings & Investments:
    • Primary residence: $550k, mortgage-free
    • Roth IRAs: $165k (Bella), $93k (partner)
    • SIMPLE IRA: $16k (recently started)
    • Brokerage accounts: $400k managed + $84k “fun money” (stocks)
    • College savings: $18k in 529, $43k in UTMA for daughter

3. Planning the Next Move: Retirement & Income

• Desired lifestyle: Travel for at least a couple years, possibly work abroad; keep Reno as base
• Planned expenses while traveling: ~$6,000/month ([09:09])
• No pension or significant passive income aside from rentals ([09:13])
• Jill’s Core Advice:
  • Stop paying down low-rate mortgages on rental properties.
    • “Do not pay that down. Please stop the insanity.” — Jill, [06:01]
    • Liquidity and flexibility are more important than being debt-free on low-rate rental mortgages
  • Continue maximizing retirement and brokerage contributions.
    • Currently saving ~$50,000/year (max IRAs, SIMPLE, brokerage)
    • With compound growth, could reach $1.3–$1.5 million in six years
  • Rent out the primary residence while traveling for potentially $2,500/month ([13:11]).
    • Combined with rental income, could reach ~$4,000/month passive income toward the $6,000 target
  • Consider income-generating “side gigs” while traveling.
    • Even $1,000–$2,000/mo reduces stress on investment withdrawals

4. “Can We Make the Numbers Work?” ([12:00]–[16:00])

• Mark and Jill run rough numbers:
  • If Bella keeps saving $50k/year, with rental and primary residence income, and supplements with side income while traveling, the plan is feasible but tight (“priced to perfection”).
  • Contingencies: If Bella can sell her business (even with a payout over several years) or finds part-time work abroad, risk drops significantly.
  • Jill recommends: “If between the two of you, you could figure out how to generate one or two grand a month in income, I like the plan a lot better.” ([15:10])

5. Emotional and Practical Considerations

• Bella is not “burned out” but “bored” ([09:55]) and wants purpose along with adventure.
• Jill urges her not to get swept away emotionally—have financial flexibility and a backup plan.
• Jill repeatedly stresses: Don’t kill liquidity by paying off low-rate rental mortgages early.

6. Other Logistics

• Health Insurance: Must be part of their plan while abroad ([16:51])
  • “You need insurance, so you're going to have to investigate that.” — Jill
• Estate Planning: Check wills, POAs, especially for a mobile lifestyle.
• Timeline Cautions: Consider delaying the transition by a year or two for greater security ([17:01])

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Notable Quotes & Memorable Moments

• Jill’s Mortgage Advice ([06:01]):
  • “Do not pay that down. Please stop the insanity.”
• On liquidity and planning for the huge pivot ([13:45]):
  • “For you guys to pull this off, let me tell you what's critical. Don't worry about making sure that the mortgages are paid off. It is making sure you have a good handle on the expenses that you're going to incur.” — Jill
• On side income and plan flexibility ([15:10]):
  • “If between the two of you, you could figure out how to generate one or two grand a month in income, I like the plan a lot better. I really do.” — Jill
• On emotional drivers ([09:55]):
  • “I'm just bored. I just want to do something different.” — Bella
• On the dream of working abroad ([10:44]):
  • “If I found some work in a different country, that would be amazing.” — Bella
  • “Yes, it would be. And highly unlikely, but okay, let's see. Let's see if you could.” — Jill
  • Mark: “The dream crusher is here today.” ([10:53])
• On keeping future options open ([16:00]):
  • “Give yourself a little bit of grace and maybe push out a couple of years, the game plan, and still be able to do it, but with a little more security.” — Jill
• Jill’s closing encouragement ([16:59]):
  • “Bella, I feel like Europe awaits you, the world awaits you. So ciao, Bella, as they say.”

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Key Segment Timestamps

• [01:06] – Jill introduces the theme: life transitions & financial planning
• [02:29] – Bella introduces her situation and dream for post-high-school travel
• [03:55] – Discussion of Bella’s partner, household structure
• [04:12] – Discussion of plans post-daughter’s graduation
• [04:33]–[08:25] – Asset, income, and investment deep dive
• [09:09] – Expected expenses while traveling ($6,000/mo)
• [09:55] – Emotional drivers behind the change (“just bored”)
• [12:00]–[13:45] – Retirement saving projections & plan feasibility discussion
• [13:45]–[14:35] – Advice against paying off low-rate mortgages; importance of liquidity
• [15:34]–[15:56] – The prospect of selling the business for additional financial cushion
• [16:51]–[17:01] – Risks: health insurance, estate planning, and timeline tweaks
• [17:44] – Jill’s final encouragement and call for similar listener stories

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Takeaways for Listeners

• Life transitions require both math and a gut check—plan for financial and emotional flexibility.
• Don’t rush to pay off low-interest debt if it reduces your financial flexibility (liquidity is king for big pivots).
• Rental income can be a critical piece of post-work life—but understand true cash flow after all expenses.
• Maximize retirement and brokerage contributions while you can, especially before a big income change.
• Health insurance and estate planning are essential for globe-trotting families.
• If your “dream move” is tight on paper, even a small amount of supplemental income or delaying the leap can significantly reduce risk.

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“Let us know if you want to live vicariously through you!” — Jill ([17:44])

For more financial guidance or to ask your own question, visit jillonmoney.com.

Transcript

[Jill]

This message comes from Jill on Money sponsor, Charles Schwab. Independent financial advisors focus on building a relationship with you that goes beyond your portfolio. That's why Schwab is proud to support them. Visit findyourindependentadvisor.com Today's episode is supported by what Should I Do With My Money? An original podcast from Morgan Stanley. And like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries, and dreams, asking questions.

Like, can I retire early?

Like, really early? How do I leave a financial legacy for my special needs child? Menopause is making me feel wacky, and.

It'S shifting how I think about my money.

Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player and feel empowered and supported when it comes to managing your life and finances.

Welcome to the Jill on Money show. It's Monday, October 6th, and we are here talking to you about whatever's on your mind financially. And a lot of the questions that we field have to do with big life transitions. I just noticed that, because usually that's when you start kind of freaking out about your money or thinking about your money, maybe not freaking out. So maybe it's thinking about getting into the housing market. Maybe it's thinking about a new job. Maybe it's thinking about the fact that you're contemplating your future retirement. Maybe you're trying to figure out how to get your kids through college. Whatever it is, these big life events, they can really feel overwhelming. But you don't have to go through this alone. Mark and I are both certified financial planners, and that means that we have studied enough to figure out how to guide you along this journey that you are taking. So if you need some assistance, go to our website, jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the air live, check the box. Mark will do everything else. Right now, we are going to chat with Bella, who joins us from Reno, Nevada. Did I say Nevada? Right? Is it Nevada? Not Nevada?

[Bella]

Yes, that's correct.

[Jill]

Nevada already. I passed the first hurdle.

Okay, Bella, what's up?

How can we help you?

[Bella]

Well, so I'm in my 40s, I have a partner, and we have a daughter who's 11. I have a business I've been running for the last 13 years. And I would like to do something different in about six years when our daughter is done with high school. And so we have a few rental houses in our house.

[Jill]

A few. Hold on a second. Wow. You're like, you're in the. All right. And here's a reference. You won't get the Ethel Mertz category.

[Mark]

Okay.

[Jill]

That's a little I Love Lucy, who is a landlady who's very. I don't know, I don't know. The new version of that. So wait a second. Before we go any further, I just want to make sure I understand this. You're in your 40s, you got a partner, you got a daughter, and you're self employed right now. And when is the time where you want to make some change changes?

[Bella]

Potentially in about six years.

[Jill]

In six years.

[Mark]

Okay, got it.

[Jill]

Only one kid, right?

[Bella]

Yes.

[Jill]

All right, now keep going. Tell me more about what these changes look like for you.

[Bella]

We would like to leave Reno and potentially travel, maybe come back here and there. Keep this as our base because we have a great community here, but also explore different places around the world.

[Jill]

Oh, I love, I love world travelers. Mark is already paying attention. As soon as you said travel the world. He's in. He's all in.

[Bella]

Yeah. That's our passion.

[Jill]

So that's amazing. Does your partner work?

[Bella]

She is on, yes. She stayed at home, Mom. But also does her own side hustle that she loves. And she's also on my company's payroll for now.

[Mark]

Okay.

[Jill]

I mean, it's sort of interesting though. You say six years. That's like when your daughter is launched into college. You don't want to stick around through college potentially.

[Bella]

Not necessarily. I don't really know what her plan is, where she's going to go. I mean, we tried to talk to her, but, you know, it's. She's young, so.

[Jill]

Yes. She's 11 going on 24. I'm ready to buy my first house, Mom. Forget about it. Okay, so let's think about a couple of things. Pieces of this puzzle. So first of all, how much do you guys earn together? Put your salaries and your side hustle and any money that you're actually living on from the business, about 150,000. And that's a good chunk for you. Like you feel good about that amount of money.

[Bella]

Yes.

[Mark]

Okay.

[Jill]

And that does not include the rental income or does it?

[Bella]

Does not.

[Jill]

Okay, so that's your 150 grand. Okay, fantastic. Now your primary residence, how much is that worth?

[Bella]

I would say about $550,000.

[Mark]

Okay.

[Jill]

Great. Is there a mortgage outstanding?

[Bella]

No.

[Mark]

Oh, boy.

[Jill]

Okay, now if you were to make this plan happen, is the plan to sell the rental properties or keep them for income?

[Bella]

Keep them for income.

[Jill]

Okay, so how many rental properties are there?

[Bella]

So we have two.

[Jill]

Let's do a rundown. So two properties, what's the first one? What is that worth?

[Bella]

About the same. $550,000.

[Jill]

Oh, my gosh. For a rental property. Okay, and is there a mortgage on that one?

[Bella]

There is.

[Jill]

How much?

[Bella]

It's $154,000 at 3.99%.

[Jill]

So you're not paying that down early, right?

[Bella]

I am.

[Mark]

Don't.

[Jill]

No, don't, don't. Stop, stop. Please stop the insanity. Just don't do that. I'll explain in a minute, but that's your first piece of advice. Do not pay that down.

[Bella]

Okay.

[Jill]

Second, rental property, what is it worth?

[Bella]

It's probably about 400,000.

[Mark]

Okay.

[Jill]

And mortgage outstanding.

[Bella]

$174,000 at 4.5.

[Mark]

Okay.

[Jill]

I imagine if you're paying down a 4% note, you're also paying down the 4 1/2% note. Stop doing that.

[Mark]

Okay.

[Jill]

Okay, now how. How do these things. Cash flow, forgetting about the extra money that you're paying down on the mortgage. But if you have the mortgage and you keep paying that and you've got expenses associated with it, what is the rental income that these two properties generate?

[Bella]

It's about double the. Just the plain mortgage. So the cash flow is good. We bought these at a time when rents were much lower than they are now. So the cash flow is good for all repairs and, you know, keeping them going.

[Jill]

Okay, so after you've paid for repairs and all that stuff, how much money comes to you on a monthly or an annual basis from these properties?

[Bella]

I would say for both of them combined, I would probably say about 1500.

[Jill]

Okay, great. What about money you've put away for retirement? We know you've got a big investment in real estate. Three properties. What about retirement?

[Bella]

Okay, so I have a roth, which is 165. My partner has a Roth. There's 93 in there. And then this year we just started a simple through my company, and that one combined, we have about 16,000 in that one.

[Mark]

Okay, great.

[Jill]

Any other retirement assets? An old IRA kicking around an old retirement somewhere?

[Bella]

No, but we do have a brokerage with about 400,000 in it, and that one is managed by a financial advisor, just started this year.

[Mark]

Okay.

[Bella]

And then I have another just fun money that I like to do with about 84,000 in it, a brokerage with just stocks.

[Mark]

Okay.

[Jill]

And you're playing with it, if you will.

[Bella]

Correct?

[Jill]

We don't like to say that word, but we.

[Mark]

Okay.

[Jill]

Are there any. Besides your daughter, are there any other people that you're taking care of? Do you have parents that you have to worry about?

[Bella]

I don't think so, no. My parents are doing pretty well and my partners are. They're okay, too.

[Mark]

Okay.

[Jill]

For the 11 year old, do you have a 529 plan or any other savings for college?

[Bella]

Yes, a 529 with 18,000 and a UTMA with about 43,000.

[Jill]

When you decide to travel the world.

Like by Adios, Reno.

Hello. What will we have to be spending to make this worth your while to do?

[Bella]

Yeah, I think it's about 6,000amonth.

[Mark]

Okay.

[Jill]

And there's no prior pension benefits that you would be enabled to. No tap. Right.

[Mark]

Okay. All right.

[Jill]

It's a long way. You're in your 40s, so we got 20 more years before we're looking at your Social Security, but we. So the only thing we have right now is the fifteen hundred dollars a month of the rental income, right?

[Bella]

Yes.

[Mark]

Okay.

[Jill]

And so is there a world in which you would say, I want to travel and go crazy and do that for a couple of years, come back and then work? Because you're really young.

[Bella]

I'm not opposed to not working. I just want to do something different.

[Jill]

Are you like, exhausted from being an owner?

[Bella]

I'm just bored.

[Jill]

Oh, wow.

Okay, fair enough.

[Bella]

I just want to do something different. And I feel like I'm young enough to be able to, you know, explore and find something that would be. I would be a little bit more passionate about.

[Jill]

Well, you got six years to figure it out, right?

[Bella]

Exactly. Yeah.

[Jill]

So it is possible that after six years, if you found something that was a little bit more interesting, engaging, that you may not take off and be like, I'm done forever. It's that. Yeah, I'm taking like a sabbatical and come back and work. Is that. Can I convince you into that mode?

[Bella]

Yeah, potentially. But I would really like to find something abroad. That's. That's the thing. Okay, don't really. If I found some work in a different country, that would be amazing.

[Mark]

Okay.

[Jill]

Yes, it would be. And highly unlikely, but. Okay, let's see. Let's see if you could. All right. Mark, are you laughing? Do you hear Mark laughing?

[Mark]

The dream crusher. The dream crusher is here today.

[Jill]

She's the dream. And I was in such a good mood when I Spent when I got on the air with you. Well, I am in a good mood. And you're in very good shape.

[Mark]

Do you have citizenship elsewhere?

[Bella]

I don't, but I grew up in Germany, and I do speak German, which is an advantage for Europe, which I know is. You know, that would probably not be our number one place to go, but I do have that.

[Jill]

Berlin's kind of a hopping town. Yeah, kind of a cool place. Okay, so how much money are you putting into your retirement accounts right now? On an annual basis. So how much? I want to try to figure out what we're going to have in six years.

[Bella]

Okay, so we're maxing out our Roth.

[Mark]

Mm.

[Bella]

And then I think I probably put another additional a thousand to my brokerage a month.

[Jill]

Okay, so that's 15 grand.

[Bella]

What about in the simple, about $4,000 a month.

[Mark]

Oh, okay.

[Jill]

Between the two of you?

[Bella]

Yeah, between the two of us.

[Jill]

Okay, so that means that you're putting away 50 grand a year for the next six years at least, you know, while the business can generate that.

[Mark]

Right, right.

[Bella]

That's the point.

[Jill]

Okay, that's good. Mark, Isn't that. Does that make you feel better? You already have 300 grand going in, 300 grand going in of contributions. There is about 265, 270 grand in Roth assets, and there's a brokerage account with, combined with the fund account, $484,000. How are you feeling, Mark? You feeling like you want to take off and be done? They're in their 40s, so they'll be 52. Can they be done forever?

[Mark]

Well, I know what they're trying to do. I mean that, you know, with 50 grand a year for the next six years, they're going to have, you know, between 1.3. One and a half million dollars. And I know the idea here is to, you know, eventually rent out the primary residence and have that plus the rentals generate the income that they need to live on.

[Jill]

Yeah, but you can't rent out the primary if you think you're going to come back for the kid. That's. That's tricky. Unless you're willing to just, like, come back and hang out with friends or go to a hotel.

[Bella]

I guess we do. One of the. One of our rentals has a tiny house that.

[Jill]

Oh, okay.

So if I were to make.

If you're getting fifteen hundred dollars a month in rental right now, how much more could we add to that? If you rent out the primary, about.

[Bella]

2,500, I would say.

[Jill]

Okay, so that helps all Right. So now we're at 4,000amonth in today's dollars.

[Mark]

This is why they want to get rid of the mortgages. So that increases their take home.

[Jill]

Yeah, but I think the problem is.

That we need access to your money. So I don't think that that's the case. So what happens is every dollar that you use to pay down that mortgage is money that's not going into the brokerage account. And I think you need liquidity more than you need to pay down those mortgages. Those mortgages will get paid down. And it's good to have a mortgage associated with a rental property.

It really is.

I know you think you're just going to get better income, but it's just, it's a more inefficient way to do that because you can get more income from, or you can get more out of your brokerage account if you put the money away versus paying down a 3.99 or 4.5% mortgage. Which is why I said, because for you guys to pull this off, let me tell you what's critical. Don't worry about, you know, making sure that the mortgages are paying paid off. It is making sure you have a good handle on the expenses that you're going to incur. Your, you collect your $4,000 and then you have the money available to create that extra two grand a month. Now, if you could say to me, hey, Jill, no matter what, while we're traveling, we'll at least get, let's say we get $1,000 a month of doing something somewhere.

[Mark]

Okay?

[Jill]

Then if you have a million or a million and a half bucks socked away, then if we just took $1,000 a month from that kitty, then we're talking. I just think that that is priced to perfection, as I like to say. Meaning that this presumes that there is nothing that we've really missed in all of this in terms of you being able to do it, making the numbers work, not going blowing your budget out, being able to have a, you know, some stability. I think it's a possibility. I don't think it's a slam dunk.

[Mark]

I.

[Jill]

Let's say in six years that, you know, I don't know how old you're. You say 40. So I'm just going to say in six years, you're 50 or five years old. Okay, maybe you're in your late 40s, 53 years old. If between the two of you, you could figure out how to generate one or two grand a month in income, I Like the plan a lot better. I really do. I really do. Now, also, can you sell your business, or is it a business that completely relies on you?

[Bella]

I would like to sell it.

[Jill]

Yeah.

[Bella]

I would like to offer it to my employees, and I think that would give us a little bit more leeway as well.

[Jill]

Yeah. Because if you could sell it, even if you said you don't have to come up with the money all at once, but we'll sell it to you, and, you know, over three years, you pay us out over that, too, would help, definitely.

[Bella]

And that's kind of my idea that.

[Mark]

That.

[Bella]

That hopefully works out that way.

[Jill]

I mean, it's exciting. Don't pay off those mortgages. I feel like you're going to pay them off anyway. But do you understand the math, like, essentially right, because you're. It feels good emotionally, but it is not necessarily the smartest thing because we do need access to money for you. You're so young. If you found yourself in a place where you're like, I really like this new gig. It's great. Blah, blah, blah, blah, blah. I have a feeling that you could, like, kind of give yourself a little bit of grace and maybe push out a couple of years, the game plan, and still be able to do it, but with a little more security. That's my two cents. But, you know, Bella, I feel like Europe awaits you, the world awaits you. So ciao, Bella, as they say. Mark, anything else that Bella needs to know? What about health insurance? What are you going to do while you're, you know, futzing around abroad?

[Mark]

Not.

[Bella]

I haven't really thought about that. We're in pretty good health, so.

[Jill]

Okay, well, you need insurance, so you're.

Going to have to investigate that. That you're going to have to do.

[Mark]

Okay. For sure.

[Jill]

Maybe. Maybe. If you could also just kind of tighten up any documents, you know, like, if some, you know, traveling. I want to make sure your estate documents look good. Everything like that, you know, all that good stuff. If you can do that and prepare, you got six years, maybe eight or nine if you're me. And then I would love it, love it, love it. If you could, you know, at least consider delaying a year or two just. Just to build things up. But other than that, I think you're in good shape. It's a fun. It's totally fun to consider it. Get back in touch with us. We got six years to pull this off, so let's keep in touch and let us know if we need anything else or you find other information.

[Mark]

Out. Okay, great.

[Bella]

Thank you.

[Jill]

Okay, Pleasure. Hey, if you like Bella thinking about traveling the world and ditching life and maybe want to prepare to do something wild and fun like that, get in touch with us. We we want to live vicariously through you. Go to jillonmoney.com, click the contact Us button, write us a note, and if you'd like to join us on the air live, check the box. Mark will do everything else. Don't forget, sign up for the free weekly newsletter comes out every single Friday. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Please leave a rating and review wherever you listen. Lift someone up. Change your work, change your wealth, change your change your life. Thank you for listening and we'll talk to you tomorrow.

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