Can We Run Off to Travel the World?

Summary

Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode: Can We Run Off to Travel the World?
Date: October 21, 2025
Host: Jill Schlesinger, CFP®
Main Theme:
Jill answers a listener's question about whether she and her partner can financially afford to take an extended break from work to travel Europe for four months, potentially leading to a semi-permanent lifestyle change or partial retirement. The discussion centers on financial independence, risk, re-entering the workforce, and how to plan for major life changes without jeopardizing long-term security.

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Key Discussion Points & Insights

1. Introduction and Listener Context ([03:34]-[04:39])

• Guest: Jessica, 51 (soon 52), long tech sales career, calling from Seattle.
• Goal: Take about a year (or shorter/longer) sabbatical to travel Europe with her partner.
• Relationship & Finances: Five years together, maintain separate finances, independent estate planning.

Jill:
"What someone else's desires are, what your next door neighbor's doing...has nothing to do with what you want to do." (01:38)

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2. Personal Finance Snapshot ([04:43]-[10:41])

• Jessica:
  • Income: $350K–$500K/year (tech sales; variable comp)
  • Assets:
    • Primary home: $680–700K (mortgage: $190K @ 2%)
    • 401(k): $35K
    • Rollover IRA: ≈$1M (pre-tax)
    • Brokerage account: $1.5M
    • High-yield savings: $760K (originally earmarked for a home, now potential travel fund)
  • Expenses: ≈$90K/year (~$8,500/month, includes buffer and health insurance)
  • Kid: 24, mostly independent, still on her health and phone plan.
• Partner: 51, small business owner, financially stable, not combining finances for this plan.

Jill:
"I hope one of you has a lot of money saved. Since you said you've had a long career in tech, I'm thinking you might be the one who has the lots of money socked away. Is that the case?" (04:04)

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3. Logistics of the Travel Plan ([06:59]-[11:33])

• Plan: Four months travel, Europe (maybe longer), house will remain unoccupied (not rented).
• Work: Would need to quit the job (can't take a leave of absence).
• Travel Budget: $7,600–8,000/month in Europe, estimates $25K–60K for the whole trip, including U.S. living expenses.

Jill:
"The high yield savings of 760...you're going to burn up 60 grand. Like, that's my European adventure, is 60 grand." (11:00)

Jessica:
"That is actually more exciting than a cool house." (08:34)

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4. Can She Afford to "Run Away"? ([11:33]-[17:27])

• Can Jessica's Savings Support a Permanent Life Change?
  • Jill and Producer run the numbers:
    • $8,500/month needs for life (U.S. or elsewhere), with the current assets, looks possible but with slim margin for error.
    • Success depends on markets, expenses, longevity, and no large unexpected costs.
  • Withdrawal Strategy: Likely involves drawing from savings and brokerage, then IRA after age 59½, with social security later.
  • Work After Sabbatical:
    • Best option: Return and work part time, or at a lower income (e.g., $100K–$175K/year instead of $350K+).
    • This de-risks the plan and builds in cushion.

Jill:
"Can we generate $8,500 a month for Jessica for the rest of her life? In other words, when she comes back from her European adventure, does she have to get a job? It's very, very close. I mean, can it happen? Probably. But every single thing has to go right...there's really no wiggle room." (12:33)

Jill:
"What would be more likely is you go take your romp, have an amazing time, you return, you get a job that maybe where you don't have to make as much money...that, to me, seems like a more realistic way to approach this." (13:52)

• Alternative Scenarios:
  • Can she live in Europe for same/lower cost and never work again? Not safely, unless she drastically reduces expenses.
  • Can she take on work that she loves, outside of tech, at a lower salary (even $50K/year)? Yes, with caution.

Jessica:
"Absolutely...the question is, is it something I really love to do that's outside of tech...do I need to sort of earn more in the 175? Because that's very possible as well." (14:39)

• Unique Value of Sales Skills:
  • Jill strongly advises not to undervalue sales experience:
    "It is a magic skill, Jessica. It is magic. People don't know how to do it. And if you are good at it, it may mean that you take that skill to something else." (16:34)

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5. Tactical Recommendations & Next Steps ([17:14]-[19:40])

• Before Leaving:
  • Button up estate planning
  • Set up health insurance for travel period and after
  • Make post-trip plans for deploying the $700K idle in savings into investments

Jill:
"By the end of 2026, maybe it's a half a million of the 760 has to be invested. Has to go into that brokerage account to get it working." (19:21)

• Networking While Abroad:

  • Use time before/during travel to network and line up future, less demanding or more enjoyable work.

• Travel Itinerary:

  • First Japan, then Portugal, Spain, France, Italy, ending with Ireland and Scotland. (18:41)

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Notable Quotes & Moments

• Jill on Lifestyle Choices:
  "If you are thinking about doing something, some goal that you have and you want to run it past two people who are certified financial planners…then this is the show for you." (02:12)

• On Reality of Early Retirement:
  "You're really young and…I hope you have lots of longevity in your genes…if your expenses…are $8,500 a month…we're going to have to be willing to spend down some money. I don't know how you feel about that..." (11:54)

• Jessica on Priorities:
  "It would mean working not at all or working less. And that is actually more exciting than a cool house." (08:34)

• Jill on Sales Skills:
  "I would be careful not to throw away just how important that skill is of selling, because I think that is quite valuable no matter where you go." (16:56)

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Important Timestamps

• Listener Introduction & Context: [03:34]–[04:39]
• Current Financial Position: [04:43]–[10:41]
• Travel Plans and Budgeting: [06:59]–[11:00]
• Sustainability Analysis: [11:33]–[17:27]
• Career Pivots & Sales Skills: [13:52]–[17:14]
• Planning Before Traveling: [17:14]–[19:40]
• Travel Itinerary Reveal: [18:41]

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Overall Tone

Warm, direct, and practical—with Jill offering “tough love” and realistic financial planning wisdom while rooting for Jessica’s dreams and encouraging listeners to take informed, personalized leaps.

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Actionable Takeaways

• Take time to run your own numbers if you’re considering a major life change.
• Don’t undervalue your transferable skills when considering a post-corporate career pivot.
• Leaving a high-paying job for adventure is possible, but build in margin for error and future security.
• Major shifts are best supported with proper insurance, estate planning, and thoughtful investment of idle cash.
• Use sabbatical periods to network and prepare for future, fulfilling work.

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For listeners considering similar adventures:
"Can you run away? Whether it's four months, six months, can you do something different in your life? Let us help you work through it." —Jill [19:40]

Transcript

[A]

Introducing Fidelity Trader plus. With customizable tools and charts you can access across all your devices. Try our most powerful trading platform [e-mail] trader+ investing involves risk, including risk of loss. Fidelity Brokerage Services, LLC. Member NYSE SIPC you know what I love most about fall? It's that shift into cozy mode. You know, when I'm cooking at home, it just feels a little bit more special. And Whole Foods makes it so easy to lean into the season without blowing your budget. Just, just the other night I pulled together a weeknight dinner that felt way fancier than the effort I put in. I grabbed some 365 by Whole Foods Market organic pasta and their robust marinara sauce. And then I paired it with no antibiotics ever. Chicken thighs. Simple, hearty. It tasted like I actually had time to cook. And here's something I've noticed lately. Those little yellow low price signs all over the store. They're a reminder that you can save without compromising on ingredients because Whole Foods Market still holds to their high standards. No synthetic dyes, no preservatives I can't pronounce. Just quality stuff. I feel good serving. Whether it's an easy dinner at home or stocking up for a sweater weather gathering, I know I can count on Whole Foods Market for great prices and great foods. Enjoy. So many ways to save on cozy fall meals at Whole Foods Market. Welcome to the Jill on Money show. It's Tuesday, October 21st and we are here trying to help you get wherever it is you want to go. And I just want to underscore that about 3,000 times because what someone else's desires are, what your next door neighbor's doing, what your boss is doing, what your friends are doing has nothing to do with what you want to do. So if you are thinking about doing something, some goal that you have and you want to run it past two people who are certified financial planners. But we don't do it for a living. We talk to you guys, guys for a living, talking heads kind of. And you just want to get a little bit of advice, mentoring, coaching. Then this is the show for you. If that's you, you just go to our website, jillonmoney.com in the upper right hand corner there is a contact us button. You click the button, write us a note and at the bottom it says would you be willing to come on the show live with us? If you check the box, Mark d', Alercio, the very best executive producer in the whole wide world. He, he will take it from there. So all you have to do is jillonmoney.com, contact us while you're on the website. Don't forget to check out the free content that lives there. The free weekly newsletter. There is a blog, there are resources, there are videos. All right there for free. You want to spend a few bucks? You can buy my book, the Great Money Reset. You can subscribe to Jill on Money Live. 45 bucks for the next 12 months. We've got an upcoming webinar. It's coming up in a month and it is going to be awesome. We are going to do year end tax and financial Planning. On Wednesday, November 19th. You must be a subscriber to Jill on Money Live. Again, 45 bucks is all it costs for the next 12 months. You get access to that webinar and then three more and the back catalog of the webinars bonus audio and video content. 45 bucks for the next 12 months. Check it out. Okay. Right now let us get to the matter at hand. We've got Jessica who who joins us from Seattle. Hello, Jessica. How are you?

[B]

I'm great. Thanks for having me.

[A]

Of course. What's happening? What's going on?

[B]

Well, I've had a long career in technology and as of late, my partner and I have thought about running off to Europe. Yes. And that may be temporary. It could be part time. It could be permanent. And what I would love to do is take about a year and have us go explore that opportunity.

[A]

I hope one of you has a lot of money saved. Since you said you've had a long career in tech, I'm thinking you might be the one who has the lots of money socked away. Is that the case?

[B]

We sort of are diversified with real estate and cash and yes, I have saved quite a bit of it.

[A]

Great. Jessica, how old are you?

[B]

I will be 52 in January.

[A]

Do you have any kids that we have to worry about?

[B]

I do. He's 24 years old and so the worrying is subsiding but still a factor.

[A]

Are you supporting the 24 year old or is the 24 year old really launched?

[B]

He's on my phone plan and health insurance, but I am not paying any day to day living expenses.

[A]

You're not paying $1,000 a month in rent?

[B]

No.

[A]

Okay. All right. How old is your partner?

[B]

He is. He'll be 51 in October. Just, just coming up on a birthday.

[A]

Okay, great. Have you guys combined your financial lives?

[B]

No, we have remained fairly independent. So he is. We met about five years ago and have put our lives together. So we have estate planning and all of that taken care of. But we really do stay fairly independent in terms of our, our finances.

[A]

Okay, fair enough. Okay, so right now are you working full time?

[B]

I am.

[A]

How much do you earn?

[B]

I'm in sales, so it's a variable comp. But if I look at my averages, it's, you know, somewhere between 350 and 500.

[A]

Wow. Okay. And is he working right now?

[B]

He is a small business owner and he is working.

[A]

When we're talking about can we run away, are we going to combine all of your resources or are you just looking at your own resources in this, in this conversation?

[B]

So I am looking at my own resources now. He's super generous about like, I stopped working, income stops coming. He's a lot more flexible. So he offers me, I guess, you know, in the case of an emergency. I like, I'm not going to fall on my face, but I really am interested in independently with what I've saved and what I have. Like, you know, where am I on the spectrum of full retirement, partial retirement, you know, can we do this?

[A]

Okay, I got it. And you said you live together, do you own real estate together?

[B]

No, we both own real estate, but not together.

[A]

Okay, so we're going to just talk about your real estate for right now. Okay, so the 24 year old is on. They're on their own in terms of like they're not living with you?

[B]

Correct.

[A]

Okay, so let's talk about your house. What is that house worth?

[B]

My home is worth about 680 to 700,000.

[A]

Okay. Is there a mortgage that still remains?

[B]

Yes, at 190k and the rate is 2%.

[A]

Oh my gosh. Okay, so we're not selling that.

[B]

No.

[A]

Now if you were to run away for a year, would you just, would someone rent it? Would someone stay there? How would you manage that asset?

[B]

So we're planning to go for about four months and then come back to the US So the plan now is to just let it be.

[A]

Got it.

[B]

Perfect.

[A]

Okay. With your current position, would you be able to say, take some sort of leave of absence or would you have.

[B]

To just quit for various reasons? I would just quit.

[A]

Okay, got it. So let's talk about the money that you've squirreled away. You've got money in a retirement plan through work, right?

[B]

Correct.

[A]

How much is in there?

[B]

So the current 401k is at 35,000.

[A]

Okay.

[B]

I have an IRA.

[A]

Okay. What's in there?

[B]

That is just about a million.

[A]

Okay. And that's from old jobs. That you've rolled over, Right?

[B]

Correct.

[A]

And that has not been taxed yet. This is all pre tax traditional retirement money, right?

[B]

Correct.

[A]

Okay, keep going. What else you got?

[B]

I've got a brokerage account that is about 1.5.

[A]

All right, you go, girl. Okay.

[B]

And then I've got about 760k in high yield savings accounts.

[A]

Is that in anticipation of our, of our runaway, Is that our runaway fund?

[B]

I wish I could say I was that well calculated. It was commission checks that had come in. We had intended to buy a home and thought, you know, life has just sort of shifted and we were like, gosh, what if we just, you know.

[A]

What if we just ran away?

[B]

Yeah. And then it would mean working not at all or working less. And that is actually more exciting than a cool house.

[A]

Okay, I'm with you. Okay, so if you look at your spending right now in your fancy career, making you 350 to 500 grand with your house, which actually is fairly affordable for Seattle, to be honest with you. What are you looking at in terms of expenses right now?

[B]

Yeah, I put together a plan for this, this year, basically for the year my total expenses came, you know, to like 90,000.

[A]

Okay. That's not bad.

[B]

And on a regular, you know, month in the, in the US it's, you know, like really I put a lot in there and it's like 8, 500amonth. And so, you know, somewhere in that neighborhood, I'd be quite comfortable.

[A]

Okay. Any other real estate besides your primary residence?

[B]

None.

[A]

Okay, so this is what we got. We got the kid, you know, whatever expenses with your kid don't seem like it's that big a deal in terms of, you know, for a couple more years keeping someone on your insurance. Although if you leave this job, then we have to get you health insurance. Right, Right. So that's going to add. And your kid. Is your kid employed?

[B]

Somewhat.

[A]

Somewhat enough to get health insurance or not?

[B]

He does have health insurance through his dad, so he is covered. I don't have to worry about him. I have budgeted, you know, 500 to $750 a month for health insurance going forward, assuming I don't have a job.

[A]

The 8,500amonth, does that include the health insurance or not?

[B]

It does.

[A]

Okay, great. Perfect. Have you done any exploration of what it would cost you to run around for four months, you know, playing. Would you look at one home base? Would you, you know, say, I'm going to get a long term rental or like, how do you, how do you want to think about the next four months.

[B]

I've done a bit of budgeting on that, and I think it's going to cost me, you know, about 7,600, 8,000amonth in Europe.

[A]

Okay.

[B]

Yeah. So I'm thinking, you know, the whole trip, if I. If I budgeted $25,000, I probably have a really nice time.

[A]

You know, what I was doing in my mind, just because I do these kinds of things, I am conservative. You listen to the program. So I'm thinking that the high yield savings of 760. I just think you're going to burn up 60 grand. Like, that's my European adventure, is 60 grand. Okay. And then the question is, I guess, that we would have to also pay certain amount of expenses. We have to pay for your house and taxes and all that kind of stuff. Right. So even if you said 25 grand, I still have all these other expenses. Right.

[B]

When I did this budget, I have included my US Expense.

[A]

I don't believe it. All right, I'm going to. I know. I'm only kidding. I'm just still going to say 60. We're going to spend 60. Okay, now it's four months, six months later, and you want to know what happens when I come back, right?

[B]

Yes.

[A]

And the question is, can your Money generate your 8,500amonth or 9,000amonth, whatever it is ends up that you would need for the rest of your life? And, you know, look, I'd like to say no sweat, but you're really young and, you know, I hope you have lots of longevity in your genes, but not knowing what your partner's part of this. But if your expenses, you know, Jessica's expenses are 8,500amonth, you know, we're going to have to be willing to spend down some money. I don't know how you feel about that in terms of, you know, could you just start, you know, from 52 to 59, spend some money from your high yield savings account in your brokerage, and then pull money out of your ira, and then do that for a number of years, and then, you know, wait until Social Security. I don't know if you're Gonna make it 100%, Mark. I bet you're running some numbers for me as I yak about this. Can we generate $8,500 a month for Jessica for the rest of her life? In other words, when she comes back from her European adventure, does she have to get a job? It's very, very close. I mean, can it happen? Probably. But every single thing has to Go right? There's, like, really no wiggle room. And, you know, a lot of that money's sitting in cash. You got to get it to work, right? So if you're saying to us, hey, can I, like, what happens if I come back in four to six months, you come back, you've spent 60 grand, everything's cool, and you're like, that was fun. I want to move there. The answer is, then you're going to have to make some different decisions, right? Because then you would have to basically decide, you know, can I live in Europe for a lower cost than the US and never work again? I think what would be more likely is you go take your romp, you have an amazing time, you return, you get a job that maybe where you don't have to make as much money because you are making a ton of money, right. 350, can you make. Can you work less and make a buck 75 and let all of your money just work for you and spend the money for your expenses and, you know, make sure the kid's okay and, like, you're living your life, that, to me, seems like a more realistic way to approach this, or at least thinking about it that way, because that way we don't have to basically hope that every single thing goes correct and right. And that. That you have a little bit of. You build in some fluff in the plan. Do you think that that could be. You could be amenable to doing something like that?

[B]

Absolutely. You know, and the question is, is it, you know, something I really love to do that's outside of tech completely? And if it's. If it's, you know, 50,000, does that solve it? But. Or do I need to sort of earn more in the 175? Because that's. That's very possible as well. It's just that spectrum of can I really go do something I love? Like, I'm, you know, just totally outside of tech, or do I need to kind of bite the bullet and say, yeah, you're going to have to do a job.

[A]

Well, I mean, 50, if you had some other benefits, could be great. So think of it this way. Like, I would have. We would have to see what's. What you got. I'll give you an example. A guy came on the program, and he's like, I work in tech, but he worked at a university, and in his case, he worked in tech in a university, and they put away a ton of money in his retirement account. So he made closer to like 100 grand a year. But they were putting away 15% regardless, into retirement for him, and it took a lot of the burden off him. Then he could just spend his money. Right. And so I think it depends on what we're comparing it to. If you're telling me, you know, it's 50 grand a year and I'm a docent at the museum and I'm still spending exactly the same amount of money, know, I'm not sure about that. I'm more comfortable in the hundred range. I don't. You don't have to kill it. But if you can go, even if you said, look, I know how to do this is the thing that I think about for myself. I'm just going to put myself in your shoes. I am a salesperson by training. I really am. You know, I was a trader, but I was really in sales. When you're a financial planner and someone who is an investment manager, you are selling people on your services. And so I've always thought this is a skill that nobody likes to think is a skill. They're like, no, you're just in sales. I'm like, actually, it's a skill. And you have that skill. And it is a magic skill, Jessica. It is magic. People don't know how to do it. And if you are good at it, it may mean that you take that skill to something else. And it may be that you say, maybe it's just a different kind of a company. Maybe you're in a big, huge company now, you don't want to be in that anymore and you want to be in a smaller company. Maybe you want to sort of work in startup land where you're like, you know what? I want to have fun again. I want to feel like I'm part of whatever it is. But if you want to go outside of what your industry is, I would be careful not to throw away just how important that skill is of selling, because I think that is quite valuable no matter where you go.

[B]

That makes sense. And, and this, this aligns pretty well with, with what I've been thinking as well, to do something. And the question is what? And what are the requirements of that? And I think I have a much better idea now. So.

[A]

Well, and I think that you can do what's cool is if you're really going to give your notice. I don't know when you get bonuses and all that kind of stuff, but you can use your time now to start, like, working that network, firing it up, talking to people, seeing what's out there. It's funny, I have A friend of mine who has worked in like, health tech his whole life. And every time the whatever business he's working in gets like almost medium size, he loses interest, like so fast. And I know for him it's like, I like, I love the jazz of just like I'm part of the beginning and it's exciting. And then there's other people I know who are like the exact opposite. Like, all I want is like the comfort of a big, warm corporation that has really good benefits, that has real. So you can look around and see what's out there. But taking this break is not going to be terrible. I certainly don't feel like there are some people who I'm like, do not give up your job because it's hard to get a new one. But if you are in sales and you are in tech, you know, you're always employable. Right, Right. So I think it's. It sounds great. Where do you want to go first? When we talk about, like, I want to go run away. Where are we? Where's our first destination?

[B]

We're actually going to do a trip to Japan and then we're really heading to Portugal and we're going to kind of move Portugal, Spain, France, Italy, and then hit the Ireland, Scotland on our way out.

[A]

So listen, before you go, of course, you're just making sure, buttoning up estate documents, making sure you have your own health care taken care of, like all of these things, making sure the kids set up. And just in your head just say, okay, 700 grand in that high yield savings account when you get back, when we know what your next step is. I think part of the plan will have to be getting that 700 grand to work.

[B]

Yes, I. Okay, that makes sense, right?

[A]

Like you can dollar cost average, you could start doing it now, but I don't know if you're going to have like, the stomach to do that. But I'm just saying I'd like by the end of 2026, whatever you, you know, maybe it's a half a million of the 760 has to be invested. Has to go into that brokerage account to get it working.

[B]

Yep, that makes perfect sense.

[A]

Jessica from Seattle. I really, I'm excited. Can't wait to get the Travelog photos. We're right here. We're rooting for you. I like this. Thank you. Hey, can you run away? Whether it's four months, six months, can you do something different in your life? Let us help you work through it. Go to jillonmoney.com, click the contact us button. Write us a note. And if you want to join us on the air live like Jessica, check the box. Mark will do everything else. Don't forget, put your hands, metaphorically on someone's back. Someone needs a little push, a little pull in. Just give somebody something of yourself. Change your work. Change your wealth. Change your life. Thank you for listening. We'll talk to you tomorrow. Hey gang, here's the thing about wine. Some of the best bottles are not sitting on a store shelf. They're being crafted at small, independent wineries. But those wines can be so hard to find Sometimes I wish I had a personal sommelier to guide me to find the best wines I normally wouldn't be able to access. Where's that handcrafted pinot that I've been craving? Well, Psalmsation's expert team seeks out incredible wines from top independent producers. These are bottles that you will not find in stores and on shelves. And they aren't mass produced wines. They're handcrafted with care, using pure ingredients and meticulous winemaking. Whether you want a single bottle, a guided tasting experience, or an entire wine club membership, Psalmsation makes it easy to elevate your wine experience. Shop their [e-mail] jillonmoney that's psalmsation.com jillonmoney hi, I'm Nancy Cartwright. You may know me better. As the voice of Bart Simpson on Simpsons Declassified. We're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers, the celebrity guests? Be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.