Downshift or Double Down?

Summary

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Episode Summary: "Downshift or Double Down?"

Podcast: Jill on Money with Jill Schlesinger
Date: September 15, 2025
Host: Jill Schlesinger, CFP®
Guest/Caller: Elise

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Overview

In this episode of Jill on Money, Jill Schlesinger takes a listener call from Elise, a mid-career professional seeking a “gut check” on her family’s finances. Elise and her husband are considering a major life change: possibly moving out of their city for more space and family support, and maybe even taking their careers in a new direction. The discussion revolves around balancing retirement and college savings, assessing housing decisions, and, most importantly, evaluating how career choices interact with personal well-being and financial security. Jill unpacks the tough reality of high-cost living, steady (but not extraordinary) incomes, and the evolving priorities of a young family.

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Key Discussion Points & Insights

1. Introduction & Caller Background (01:25–04:35)

• Elise (45) and her husband (46) live in the Northeast, both work full-time, and are parents to a 6-year-old and an 18-month-old.
• They juggle expensive childcare and rent, feeling squeezed but "okay."
• Elise describes herself as an "obsessive listener" of the show.

Memorable Moment:
“I think I’m just gonna sleep when I die is really where we’re at.”
— Elise, regarding parenting an 18-month-old (04:13)

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2. Financial Snapshot (04:36–07:52)

• Income: Household earns ~$320k, plus unpredictable bonuses.
• Retirement Savings: Aggressively contributing to retirement. Elise’s 401(k) = $385k, Husband’s 401(k) = $60k. Additional rollovers and Roth accounts.
• Brokerage & Cash: $35k in a brokerage, $250k cash savings (emergency fund and/or possible home down payment).
• 529 College Savings: $83k for the older child, $37k for the younger.
• Rent: $3,000/mo for a space that is “getting tight.”
• No significant debt—only ~$9k in low-rate student loans.

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3. The Crossroads: Relocation & Life Choices (07:52–13:33)

a. Why Move?

Elise feels they will outgrow their current apartment, especially with both working from home, and contemplate moving closer to family.

b. What Would Moving Cost?

• Houses near family cost $800k (possibly $500–900k).
• Mortgage estimate: $700k mortgage at 6.5% → principal & interest ~$4,400/mo.
• Property tax: ~$10k/year.
• Overall housing cost could double (from $3k to ~$6k/month).

Key Quote:

“You’ve got well below market rent in your area... Moving is not like the slam dunk save.”
— Jill (10:51)

c. Lifestyle Triggers

• Question: Can Elise afford to “slow down”—take a lower-paying, less demanding job?
• Jill highlights the need to clarify what a “better life” means for Elise and her family.

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4. Crunching the Numbers & Gameplan (13:34–17:42)

a. Downshift Risk Analysis

• Jill walks through the risks: housing costs may increase, possible reduced retirement contributions, college is on the horizon, and the unique benefit of current low rent is hard to replicate.
• Jill preaches prudence: do not pull back on retirement savings yet.

Notable Exchange:

“I want to point out the obvious... wow, this is not looking so great for my game plan.”
— Jill, on moving’s financial downsides (12:56)

b. Career Reevaluation Homework

• Elise is well-regarded (“recruited regularly”), but her current job offers important parental benefits.
• Jill recommends exploring the job market methodically—see if a job at $200–220k could offer better balance.

Quote:

“You don’t know what’s going to happen next... given that you are feeling kind of fried, I think now is a good time to look.”
— Jill (14:24)

• Consider renting first if relocating, then buy after settling and (preferably) once mortgage rates improve.

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5. Family Protection & Estate Planning (17:43–18:22)

• Insurance: They have life insurance, plan to increase coverage.
• Estate Planning: Documents drafted, just need witnessing and notarization.

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6. Parting Guidance & Action Steps (18:23–18:41)

• Jill tells Elise to only make a major move if it makes life genuinely better.
• Continue funding retirement; pause extra 529 contributions for now.
• Homework: Research the job market, network, and focus on what “better” really means for their family.

Closing Advice:

“You’re only going to do this if your life’s going to get better. If you’re basically replicating the life you have and just making less money—no, thank you.”
— Jill (18:23)

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Timestamps for Important Segments

• 01:25 – Elise introduces her family and situation
• 04:35 – Financial snapshot (income, kids, lifestyle)
• 07:52 – Specifics on housing, relocation, and financial goals
• 10:51 – Jill analyzes housing cost realities
• 12:56 – Acknowledging the challenge of the numbers
• 13:33 – Career introspection: Can Elise downshift, and what would that look like?
• 14:24 – Jill urges strategic career research
• 17:43 – Check-in on insurance and estate planning
• 18:23 – Jill’s parting summary and action steps

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Memorable Quotes

• “I think I’m just gonna sleep when I die...”
  — Elise (04:13)
• “You’ve got well below market rent in your area... Moving is not like the slam dunk save.”
  — Jill (10:51)
• “You don’t know what’s going to happen next... given that you are feeling kind of fried, I think now is a good time to look.”
  — Jill (14:24)
• “You’re only going to do this if your life’s going to get better. If you’re basically replicating the life you have and just making less money—no, thank you.”
  — Jill (18:23)

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Takeaways

• Life transitions require holistic, honest analysis—not just financial calculations but also personal and career reassessment.
• Low rent can be a major hidden financial asset in high-cost areas—don’t give it up without real purpose.
• Job market research and networking are crucial for anyone at a career crossroads; don’t settle for “just less money” if it doesn’t mean a better life.
• Pause before big financial moves, especially with major variables (job, location, mortgage rates) up in the air.

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Anyone grappling with similar mid-career, family, and financial crossroads will find both practical steps and empathy in this lively conversation. As Jill says, sometimes the wisest move is to simply “take a breath,” assess your options, and prioritize what will genuinely lift your family up.

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Transcript

[Jill]

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[Jill]

Welcome to the Jill on Money Show. It is Monday, September 15th and we are here answering your financial questions. If you've got one, just give us a Holler. 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 does everything else while you're on the website you will see that we've got another podcast. It's called Money Watch. We drop that on the weekends, on Saturdays and Sundays, a little bit of a deeper dive into some of the basic building blocks of your financial life. We also have a blog, we've got a free weekly newsletter, we've got videos and resources all [e-mail] of course. Mark this is the last week that you will have my Cycle for the Cause up. This is the week, ladies and gentlemen, I need you to just put some good vibes out for me because on Friday of this week I begin my three day bike for the cause, a 275 mile three day event. Thank you all who have been thinking about me, who have supported me, who have given me song recommendations for my training playlist. It has been very, very important to feel the hands on my back as I do this. Once again, maybe my last time. Mark, I keep saying it's my Last time, but maybe this one do it anyway. Thank you all for that. With that said, let us turn to you. We're talking to Elise, who joins us from the northeast. Hi, Elise, how are you?

[Elise]

Hi, Jill. Hi, Mark. So happy to be here. I've been an obsessive listener for the last year or so, even diving into some older episodes, and I shout your.

[Elise (continued)]

Work from the rooftop. So thank you for everything. It's been awesome.

[Jill]

Well, that is wonderful, by the way, everybody who's listening. I love the obsessive listeners. You get a lot of credit for going to the back catalog. You can tell us how we've done better, worse. Maybe we've made a bad suggestion to somebody. You get to go back and kind of piecemeal it. Elise, what brings you to us today?

[Elise]

Yeah, so I've been wanting to talk as I think me and my family are about to be at a bit of a crossroads. And I just wanted to sort of get a gut check on where we are for retirement and what we might.

[Elise (continued)]

Need to think about in the short.

[Elise]

And medium term as we make some bigger life decisions.

[Jill]

Okay, so family's at a crossroads. So let's talk about the family. That's you and a partner? Yes.

[Elise]

Yeah, me and my husband.

[Mark]

Okay.

[Jill]

How old are you guys?

[Elise]

I'm 45 and he's 46.

[Jill]

You have some kids?

[Elise]

Yeah, we have. We are in the older parent set, I believe we have a 6 year old and an 18 month old.

[Jill]

Tell us about that a little bit. Because, you know, mark has a six year old and no 18 month old. So they were thinking about that 18 month old and then they were like, one's good too. How's that baby this time around?

[Elise]

He is adorable and happy, happy, happy. But, you know, is not interested in sleeping, so I think I'm just gonna sleep when I die is really what we're at.

[Jill]

Oh, God.

[Elise]

We'll get there. We'll get there.

[Jill]

All right. So are you and your husband both working full time or is one at home more? What's going on?

[Elise (continued)]

Yep, we're both working full time.

[Jill]

How are you dealing with childcare? Who's taking care of the kids when you're working?

[Elise]

The younger one is in a daycare full time and the older one is a in a potpourri of care across after school care camps in the summer, day camps when schools closed, et cetera, et cetera.

[Jill]

So where are those parents who are going to bail you out of this now?

[Elise]

They are deeper into the northeast. How about that?

[Jill]

All right. Okay. So how much do you guys earn together?

[Elise]

Together we're around 320. And I do get, I do get bonuses. They've been a little. I've received them, but I never really know if it's going to happen or.

[Elise (continued)]

Just sort of based on company performance.

[Jill]

But how's your cash flow? I mean, I know daycare is really expensive in a place like the Northeast. I happen to know where you live and so not a cheap place to live. So how is the cash flow?

[Elise]

You know, we're, we're okay. I would love a little more. It would be nice to go on a date with my husband every so often and not feel like we're being bad. But no, I mean, between rent and daycare, you know, we're, we're okay. We're okay. It could be better, it could be.

[Elise (continued)]

A lot worse, but we're, we're fine.

[Jill]

Are you guys putting money into retirement plans?

[Elise]

Yes. We've both sort of been like, we've been aggressive. Like I've been aggressively listening. I've been aggressively investing in my 401k.

[Elise (continued)]

For the last several years, maxing out.

[Elise]

And my husband had a career change like in the last three, four years. So he's a little bit still at the bottom of the totem pole over there, but is.

[Elise (continued)]

I've encouraged him to max out as well.

[Jill]

How much money's in your 401k right now?

[Elise]

Yep. My current mine currently has about $385,000.

[Jill]

That's great. And what about your husband?

[Elise]

He's at 60.

[Jill]

Any other money that you have set aside for retirement specifically? We'll talk about the kids in a second.

[Elise]

Yeah, for sure. Some rollovers that we had from past jobs. 376 and 14K and then, and sorry, these, and these are all Pre tax Roth 15k and like 8k.

[Jill]

Okay.

[Elise]

Traditional. I think we're around 10k.

[Elise (continued)]

A traditional IRA.

[Elise]

And then thanks to you guys, I, I recently finished up a CD and threw that into a brokerage account.

[Elise (continued)]

So I've got like 35k in a brokerage that is still, I'm still sort of figuring that piece out.

[Jill]

And what about just cash in the bank?

[Elise]

We have about 250k.

[Jill]

Wow.

[Elise]

Yeah.

[Jill]

That's a lot.

[Elise]

It's. Well, we've, we've kind of been. Are we moving out of the city? Are we not moving out of the city? Kind of thing. And so it's kind of a combination of emergency and down payment.

[Jill]

How much is your rent?

[Elise]

My rent is 3,000amonth.

[Jill]

Are you in space that can accommodate these two little kids as they get to be bigger kids, or do you. Will you have to move at some point, no matter what?

[Elise]

For my sanity, we will have to.

[Elise (continued)]

Move at some point point.

[Elise]

Because I also currently work from home. So it's, it's. It's getting a little tight.

[Jill]

Okay, so you have a bunch of money. You're putting money into retirement. You're doing okay. You're not killing it because, you know, you live in a high cost of living area.

[Elise]

Yeah.

[Jill]

So if you. Okay, let's go back in time for a second. So what's the wish list that you want? What's the problem we're trying to solve?

[Elise]

I'm trying to solve if and when we move out of the city we live in, what kind of salary I need to maintain or we need what kind of household income we need to maintain to stay on track to have, say, $4 million when we retire at, say, let's call it 65.

[Elise (continued)]

Because I don't think either of us can sit still that long before that.

[Elise]

You know, and knowing that our kids will be going to college around the time we're retiring. And, you know, and we have been putting money in the 529 as well.

[Elise (continued)]

So that's, that's there too.

[Elise]

Okay, so really just like, can we slow down a little bit? And if so, what could that look like? I guess.

[Jill]

How much money is in the 529 plans right now?

[Elise]

Yeah, for the older one, we have 83K, and for the baby, we have 37K.

[Jill]

That's great. Okay, let's play a game. We're going to move to where your family is.

[Mark]

Okay.

[Jill]

What do I have to pay for a house to be in that neighborhood?

[Elise]

Sadly, it's not that much less. I would say, you know, anywhere from, like five till to 900. 500.

[Jill]

Oh, can you make it wider? All right, let's say 800,000.

[Elise]

Let's say 800.

[Jill]

Sure. 800,000. You've got 250 grand in cash, Mark, how much you want to put down? 10% on this house. What do you want to put down? I'm not using all their cash up. So tell me what you want to put down from there.

[Mark]

$250,000.

[Mark (Mortgage Calculation)]

I mean, no less than that.

[Jill]

Let's put $100,000 down. Okay, let's put $100,000 down.$100,000 down. And then can I have a mortgage calculation for $700,000, please?

[Mark (Mortgage Calculation)]

What rate do you want to use? Like 6.5%?

[Jill]

Yeah, let's just see what 6.5% looks like.

[Mark (Mortgage Calculation)]

I mean just principal and interest.

[Jill]

4400 significantly more than your rent right now.

[Mark]

Okay.

[Jill]

That said, there are some ways to work around it. Is the place where you would be moving a place where property taxes are high or like what, what, Give us a little bit of the place.

[Elise]

Yeah, I mean I would say that they're, they're probably, let's call it like 10k a year.

[Jill]

All right, so if we look at your housing costs, just, I'm going to just, let's, let's kind of make this simple. Let's say your housing costs now are three grand a month and they probably go to six grand a month. So it would double. Now the question is, you know, I don't know how much you're putting money into your retirement accounts. You would not be able to, certainly not be able to save as much money as you have been saving. So how much money have you been putting into the 529 accounts?

[Elise]

I mean that's been, I've been doing the mice where I live has a tax, is tax friendly with the 529.

[Elise (continued)]

So I'm putting like 10k a year.

[Jill]

For that advantage for each or.

[Elise]

Oh, just in general.

[Mark]

Yeah. Okay.

[Jill]

It's so weird because you're in a high cost of living area, except you've got low ish rent. You've got well below market rent in your area. So moving is not like the slam dunk save. It really isn't. So how do we make your life better?

[Mark]

That's the question.

[Jill]

And is it, you know, we stay in this current place that's so cheap or even if you had to get a bigger place and you say okay, it would go from $3,000 a month to $5,000 a month to make your life better. You know, could you then take a different job where you would make less money and you would maybe not have as much free cash flow to put into the 529 accounts? I mean, I guess that's possible. I don't know how much you hate your job and I don't know what the alternative is. So you make 320 grand together. What's you, what's you as like, I'm thinking that you're the one, it's not your husband who wants to do this, but you. What's your current salary plus bonus about.

[Elise]

Yeah, I'm, I'm 260 and then I didn't count the bonus into that original number. I mean my bonus is somewhere between.

[Elise (continued)]

20 and 30k typically.

[Jill]

What would it mean to have a better life for you? In other words, how much less? You must know, it must be something about the job. Is it, you know, maybe you could downgrade it to something else. But what do you think that you could make? Get a job? Because by the way, the labor market's changing day by day. What is, what's the amount of money you could make?

[Elise]

I mean, that's kind of what I'm trying to figure out, you know, honestly. And it's, it's like, I don't know. You know, the thing that has been on my mind is can we pull. Afford to pull back on retirement a little bit? Not, you know, a ton, to maybe have a more aggressive down payment, for instance, that, that might help offset those monthly payments, you know, stuff like that. So I'm trying to like, think in that way too. You know, I think like, monthly expenses were typically around 11k with everything in.

[Jill]

Look, I mean.

[Mark]

Okay, wait a second.

[Jill]

I want, I want to point out the obvious, which is, I'll just say the thing that you're thinking, which is, wow, this is not looking so great for my game plan. It's not that it doesn't look great, it's just that it's so weird because your rent is so low that we can't get like a real savings by moving out of the high cost of living area. Okay, now can you stay in this job and, you know, exist? I don't know. Only you know that. I'm not going to tell you, like, just suck it up. Like, is there another job in the, in your industry where you'd be willing to make less and have a better life? I think that's a question you should ask yourself. Have you actually looked around for another job?

[Elise]

Not intensely. I'm recruited, you know, on a, you know, it's a. It's humbling. But I'm recruited on a fairly, fairly regular basis, you know, and my job has been really good to me. You know, I've had, I've had several years with this organization and I have some benefits that as a working parent, are really meaningful to me. So it's, it's kind of the. What's, you know, is the money worth it always? Not necessarily so.

[Jill]

Okay, so here's what I, I think I have homework for you before we start, like on this path. First of all you're doing. Take a deep breath. I hear it. I hear the anxiety. I hear that it's scary. You're in very good shape. There's no debt anywhere around here, right?

[Elise]

We have like my husband has like.

[Elise (continued)]

$9,000 left on student loans. That's it.

[Mark]

Okay.

[Elise]

I can't remember what the rate is, but it's low.

[Mark]

Okay.

[Jill]

So what I think would be helpful would be for you to take a breath. I don't want you guys to necessarily pull back on the retirement right this second. I would keep doing the retirement. I would not worry about your 529s right now. They're really young and you've got a good chunk of money in there. I think you should really look at the job market in a more methodical way. I think you should find out what else is going on in your industry. I think you should work the heck out of your network. I think you should do like a whisper campaign. It doesn't, I don't want to make it sound like you're disloyal. Things happen in companies like I'm a very loyal person when it comes to, like when people have been good for me. But I think that it would be naive for us to think that corporate America is as loyal to us anymore. And so you don't know what's going to happen next. And given that you are feeling kind of fried, I think now is a good time to look. And you might be fried just because you're not sleeping, because you have this baby. It may be that you're fried because like I don't really like my job or I'm tired of my job. It may be a lot. This is a very normal mid career question to have, but I don't think you can answer it until we have more of the variables that are spelled out. And specifically I would like to know, you know, could you find a job where instead of making 280, 290 yourself, like could I find a job at 220 where I felt really good or 200 and that we could make the numbers work and it's just a better lifestyle and a lifestyle that works and then we can start working on, okay, if that's a job that I can find, then what are we talking about in terms of buying something? Maybe if you move closer to your family, we say, okay, you know what, you're not going to buy, you're not going to buy right now until we have interest rates come down some more. So you rent for a year or two, you make sure you like it and then we go from there. But I think the real answer to the question of, you know, can you do this? Is about what you could find as an alternative to Your current workplace. And you know, I often, I'll get this question from people. This is like a very big pandemic related question. This is why I wrote my book the Great Money Reset. Because I am very aware of the fact that different times, the ideas around like what you thought your career path was going to be change once you have kids, once you're married, once you're like living life. So it doesn't mean you're disloyal, doesn't mean anything. It's just like, let's look at where you are and let's see what the alternatives are. Maybe. Okay, I'm going to just make this up. Okay, so let's say that you find out you can like find a job for 200 grand a year and you would move to, closer to your family, but not like immediately right there, but like closer and you could find rent that is a much larger space for, you know, instead of three, you'd, maybe it would still be rent, you know, four grand a month and you'd be a happier human being and then you could work longer and like that. This does not seem like a bad idea. But again, I'm going to have to have you do a little bit of work.

[Elise]

Sure, sure.

[Mark]

Okay.

[Jill]

Now let me ask you something. Do you have insurance? Do you have estate documents or have you done all the, the real hardcore planning stuff?

[Elise]

Yes. So we have, we have insurance. I'm actually looking at increasing what we have a little bit. That's, that's other homework I've been, I've.

[Elise (continued)]

Been putting off but need to do.

[Jill]

Okay.

[Elise]

And then we, you'll laugh. But we have, we do have our estate documents completed. We just need to get the witnesses and notoriza. So we're, we're nearly done.

[Jill]

Mark, Mark, go over to Elisa's place. You can get that done. I know, yeah.

[Elise]

Oh yeah, we're good.

[Mark]

Okay.

[Jill]

I think you're good. Get back in touch with us as soon as you get some better, a better feel for what's available to you. You're only going to do this if your life's going to get better. If you, if you're basically replicating the life you have and just making less money. No, thank you.

[Elise (continued)]

Absolutely.

[Jill]

All right.

[Elise (continued)]

Absolutely right.

[Jill]

All right. Take a deep breath. Poor Elise. Six year old and an 18 month old who hasn't sleep. Mark, this woman is at her wit's end. So we're going to, we're going to figure this out with her. Hey, if you're like Elise, you're mid career you got kids, there's a lot going on and you're feeling like a little bit. As they say at sixes and Sevens, you should give us a Holler. Go to jillonmoney.com, click the contact Us button, write us a note, and if you'd like to join us on the live, just check the box. And if you do find yourself in that situation, check out my book, the Great Money Reset. Because this is exactly the kind of a situation that we really did talk a lot about during the pandemic. And you know, we still do. So the book is written for people like that. You can subscribe to us on the Odyssey app or wherever you you find your favorite podcast. And don't forget to try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.

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[Judge Dan Mentzer]

Jill on money three judges, one bench, zero room for nonsense. I'm Judge Dan Mentzer. Joining me are Judge Rachel Juarez and Judge Yodit Towelde. And on Hotbench, we don't just hear cases, we debate. What she's asking for is for the payments that she made on his car.

[Elise]

But there's still payments to be made.

[Judge Dan Mentzer]

Correct and we deliver justice. That is the verdict to the court. Follow and listen to the Hot Bench podcast on the free Odyssey app or wherever you get your podcasts.