Trying to Figure Out Our Next Steps

Summary

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Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode Title: Trying to Figure Out Our Next Steps
Air Date: August 20, 2025

In this episode, host Jill Schlesinger takes a listener call from Gina in Connecticut. Gina and her husband are contemplating early retirement within five years and want guidance on whether they’re financially on track. The conversation blends detailed financial planning with candid emotions, providing actionable insights for listeners grappling with similar life transitions.

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Key Discussion Points and Insights

1. Gina and Her Family’s Situation (02:56–03:56)

• Ages: Gina (56), Husband (60)
• Family: Two children; one financially independent, one finishing undergrad and may pursue a master's (anticipated to self-fund grad school)
• Both Gina and her husband are working full-time
• Current annual household income: Gina ($225K), husband ($140K)

"We're probably a little bit younger than you want us to be to retire, but we're feeling... we're feeling a little burnt."
— Gina [03:02]

2. Current Finances and Assets (04:07–05:37)

• Monthly Expenses: ~$10,000, possibly less in retirement
• Retirement Savings:
  • Gina: $650K in traditional 401k, $118K in Roth 401k, $17K in traditional IRA, $33K in Roth IRA
  • Husband: $910K in traditional 401k, $56K in Roth 401k
• Brokerage/Savings: $20K + $56K in brokerage; $200K in savings
• Real Estate:
  • Primary home: worth $650K, mortgage $162K at 2.35%
  • Condo: worth $350K, $100K mortgage at 3.125%
• Plan: Likely to sell primary residence post-retirement and potentially live in the condo temporarily

3. Retirement Timeline and Flexibility (06:58–09:14)

• Both contemplating retiring in five years; husband more comfortable with continuing work, Gina feels "burnt" and needs a defined plan.
• Open to post-retirement part-time work, potentially in a lower-stress or non-corporate environment—expecting $20K–$50K annual income from this.

"I can't have a plan that's just like, oh, work until you're 65 and just doing this same thing and grinding it out for another ten years."
— Gina [07:33]

4. Modeling Retirement Cash Flow (09:25–12:47)

• Jill creates a provisional retirement plan based on projected savings and income:
  • Pension: Husband will receive about $1,000/month
  • Safe withdrawal from retirement accounts: Approximately $5,000/month
  • Expected part-time income: $2,000/month (for Gina)
  • This covers most but not all estimated expenses ($10,000/month), suggesting the need to reduce spending or liquidate assets (like selling primary home or condo) for full comfort.
• Flexibility & Risks: If Gina retires sooner or their spending increases, the plan becomes tighter and could require additional adjustments.

"If I had that money, even though your house mortgage is so low and it kills me to even think about it. But if you're not like married to this place, you do your part time stuff but then you're like, you know what, I'll sell that house and we'll figure out what happens next. Then I think I feel very comfortable with the game plan."
— Jill [10:40]

• Producer Mark agrees with the overall assessment, advising they could likely keep both properties if they pace their transition and conditions remain steady.

5. Roth vs. Traditional Contributions Discussion (12:49–13:55)

• Gina asks if her husband should shift more 401k contributions to Roth.
• Mark leans toward increasing Roth contributions but suggests gradually adjusting to observe cash flow impact.
• Jill recommends maintaining current allocations until year’s end to benefit from improved cash flow as expenses lighten, then revisiting the Roth decision.

"Before you do that, can we just enjoy your better cash flow for a few months just to see how it feels... then you can shift it around."
— Jill [13:23]

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Notable Quotes and Memorable Moments

• On Emotional Planning:
  "This conversation that we're having with ourselves... Can I really do this for this many, many more years without a game plan? Having the game plan is very helpful in allowing yourself, like the emotional ability to actually get used to this idea. And then we try to marry the emotions with the finances."
  — Jill [14:04]

• On Listener Self-Reflection:
  "It's almost like any financial question. Half emotional, half financial, just only half math."
  — Jill [14:12]

• Pod-Classic Humor:
  "Why did they stay on that plan for so long?"
  — Jill, about adult children on the cell phone plan [03:31]

• On the Power of Part-Time Work in Retirement:
  "I'm really thinking like maybe even working at Starbucks, you know..."
  — Gina [09:25]

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Timestamps for Key Segments

• [02:56] Introduction to Gina & her situation
• [04:07] Spending, savings, and family dynamics
• [05:37] Real estate, home values, and future plans
• [07:18] Burnout, timelines, and psychological aspects of retirement
• [09:02] Part-time work prospects and expected income
• [10:20–12:47] Jill and Mark model possible cash flows and scenarios, discuss risk factors and flexibility
• [12:49] Roth versus traditional contributions—strategic planning
• [14:04] Emotional vs. financial aspects of planning; Jill wraps up with encouragement

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Summary: Practical Takeaways

• Retirement readiness is deeply personal: Beyond the numbers, Gina’s call underscores how psychological exhaustion can drive the retirement conversation—even before reaching a traditional retirement age.
• Flexibility is key: Willingness to work part-time or relocate and to possibly liquidate real estate assets can smooth a challenging financial transition.
• Cash-flow testing is wise: Shifting contributions or expenses gradually—and reassessing after major family milestones (like finishing paying for college)—can ensure decisions feel right both emotionally and financially.
• Blending emotional and financial planning: Jill urges listeners to recognize that any big financial shift is half math, half emotional preparation—emphasizing the value of having a real, actionable plan.

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For more episodes, resources, and Jill’s advice, visit jillonmoney.com.

Transcript

[Jill]

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[Gina]

Hi, Jill. Great to talk to you. I'm great, thank you.

[Jill]

What's going on? What can we help you out with?

[Gina]

Well, I really. I wanted to kind of figure out whether I'm on track to retire my husband and I in the next five years. We're probably a little bit younger than you want us to be to retire, but we're feeling. We're feeling a little burnt. So. I'm 56 and he is 60.

[Jill]

Do you guys have kids?

[Gina]

We have two kids. One is pretty much fully launched, except for the cell phone plan. And the other.

[Jill]

Why did they stay on that plan for so long?

[Gina]

It is just what we do. And the other is finishing college while finishing undergrad this year and then likely going on for a master's. But he thinks his master's can be paid for, so we're kind of setting the expectation that that's on him. We've.

[Jill]

Right. Good luck on that. Yeah, sonny boy. Good luck. And you guys are both working full time right now, right?

[Gina]

Yes, we are.

[Jill]

Do you have sort of a general sense of how much money you spend right now? Don't put the kids stuff in there, but like, just your month to month. Do you have a sense of that?

[Gina]

Yeah, about 10,000amonth. But I feel like we could, you know, over time, we can pull back on that. I don't know that we'll still be spending that much after we. We retire.

[Jill]

Why don't we see if he can.

[Gina]

Okay.

[Jill]

Isn't that more fun?

[Gina]

Yeah, for sure.

[Jill]

How much do you guys earn today?

[Gina]

So I'm at 225 and he's at 140,000.

[Jill]

Okay, that's great. And you are both using retirement plans right now?

[Gina]

Yes, we both have 401 plans through our work. So in my 401k, I have about 650 in traditional and 118 in Roth.

[Jill]

Great. Good on you on the Roth.

[Gina]

Yes, we're trying to really pump the Roth at this point. And he has 910 in traditional and 56 in Roth.

[Jill]

Okay, 910,000. So that you've saved a chunk of money. That's great. Do you save money in addition to that?

[Gina]

So I have another IRA traditional of about 17,000. Then I have another Roth of 33,000. That's it. In the retirement so we do have some brokerage accounts. 20. I have a brokerage account for 20,000. It's basically mutual funds and maybe like one little stock or two. And then there is another brokerage account. I think that's about 56,000. And that also is mutual funds, index funds mostly.

[Jill]

All right.

[Gina]

And then we also have savings of about 200,000.

[Jill]

Okay, great. Do you guys own your home?

[Gina]

We own our own home. We have a mortgage. Our interest rate is 2.35 on the main home.

[Jill]

Okay.

[Gina]

And we owe about 162,000.

[Jill]

How much would you guess it's worth?

[Gina]

About $650,000. Okay.

[Jill]

And you're going to stay there, like, in five years. If I said you're done, we got it. Are you selling this house, or is this house the house you want to keep?

[Gina]

I think we'll probably sell it. We don't really need to be where we are once we're done working. So we'd rather move someplace. I don't know, either north or south. I don't know. We don't. We don't know. Someplace else.

[Jill]

All right, let me just put it this. Maybe we'd sell. We go north, we'd go south. Maybe we'd go east. Well, wait, you can't go that far east.

[Gina]

Or go west.

[Jill]

Yeah. So do you own any other real estate?

[Gina]

Yes, we have a condo near the beach, and it is worth probably about 350. And we own one. 100 on it. 100,000 on it. And the interest rate on that is 3.125.

[Jill]

Is this a house that you want to keep? I mean, the condo you want to keep, just. Or could you live there full time or not really.

[Gina]

We could live there for a short time. Full time, like, couple years. I don't think it's full time forever. And I think it's something I would be willing to sell in a few years, but I don't know that he would want to sell it.

[Jill]

Oh, good. What's his name? That guy? Huh?

[Gina]

Yeah.

[Jill]

When you're married to him, I see when you look ahead, five years is the real number. Like, you feel like that's for real. Like, oh, yes, we can do that. Or if we figured out that you could do it sooner. Are you so fried? Like, I'm trying to gauge, like, how fried are both of you?

[Gina]

I think I. I think he's good to go. He could do another five years. He's fine. Like, he likes his job. I like my job, too, but I'm. I'm kind of getting burnt And I need a plan. Uh, yeah, I, I can't have a plan that's just like, oh, work until you're 65 and just doing this same thing and grinding it out for another 10 years.

[Jill]

Yeah, I get you. Do you have parents who are still alive?

[Gina]

We have one parent who's still alive, completely self sufficient, not likely to run out of money, but also not likely to leave much of an inheritance.

[Jill]

Okay. And you guys are putting money into your retirement plans. You're maxing them out with the catch up and all of that as well.

[Gina]

We're doing the best we can. So he's putting in 20% total, 10% traditional, 10% Roth, and I'm putting in 6% right now, all Roth.

[Jill]

Because you got the kids and you're doing.

[Gina]

I feel like we need money. Yes, we need, like, I need some of that paycheck, you know?

[Jill]

Yeah, I got you. Do you guys. You're not entitled to any pensions or anything, right?

[Gina]

He, after the next five years, will have a small pension, about $1,000 a month.

[Jill]

Okay.

[Gina]

Um, I'm thinking maybe that could help pay for healthcare, you know?

[Jill]

Sure.

[Gina]

So it's something. Yeah.

[Jill]

So if you said, okay, in five years, he's good, you're like five years. But I better know that like I got a game plan for five years. Right? Like that, at that moment. And then, you know, you're 61, he's 65, you're not working at all. In other words, you're like, I need to know, I can hang him up. Or do you feel like, you know what? No, I could work part time or my. I have a company that would allow me to do something a little bit, you know, curtailed schedule. Would you be able to.

[Gina]

I feel like I would want to work part time, not necessarily for my same company or in the same thing that I do, but I feel like I would want to still do some kind of part time work for sure.

[Jill]

Now you make a lot of money, right? 225 grand a year. If I were going to pencil in a part time income amount, are we talking about like 20 grand or are we talking some other number?

[Gina]

I'm thinking pretty low, like somewhere between 20 and 50, depending on what I could find. Like, I'm really thinking like maybe even working at Starbucks, you know, let's say.

[Jill]

Like two grand a month. Yeah, like max. Okay, so then you know that in five years we have his small pension and your two grand a month. So that eats in. Yeah, I know this sounds stupid. Like it's teeny amounts, you think? But it's not. Because if you have 10 grand a month now that leaves me with the 7 grand that you guys need. So then the question is you've got about $1.6 million of traditional money, right? So that in five years, what would that $1.6 million produce for you? Could it really get you where you want to go? And you know, I think that you could probably count on something like I'll make. Let me do round numbers for a second. Let's just say you could get about five grand a month. That's from that retirement account safely, not a problem, easy peasy. So that leaves me a little short, right? So I've got your 1,000 from his pension. You're going to work part time, 61 to 64. Then you get this five grand a month from your traditional account. Then it's an interesting situation because in some respects, like if I had that money, even though your house mortgage is so low and it kills me to even think about it. But if you're not like married to this place, you do your part time stuff but then you're like, you know what, I'll sell that house and we'll figure out what happens next. Then I think I feel very comfortable with the game plan. Cause then you're gonna have a little extra money, you can supplement what you have and then you'll have your Social Security just a few years from later. And then I think it's good if you really want to keep both the condo and the house. Right? I don't know. It doesn't work quite as well. I think you could do it. Mark, don't you think they can do, I mean, I think they can do it. I don't think it's like the slam dunk, but I'm pretty sure they can get there. What do you think?

[Mark]

I think they can get there. I don't, I don't see them having to sell a piece of real estate to make it work because you know, husband's going to keep working. There's still going to be some part time income down the road. There's money that they have, they already have a nice chunk save. It's going to continue to grow and they're still contributing for a while.

[Jill]

The only thing that would change this in my mind is if you said five years is way too long. Like it's, you call me in two years and you're like, remember I said five. There's no way I'm doing five. That changes things because we're counting on you guys doing the saving that you're doing right now. And without that, what starts. If you said in two years, you're done and he keeps working, it might be okay. But you know, we really do lose the ability for you to get more money socked away. Yeah, but I think it's, it is doable. And I listen, it's a slam dunk. If you're like, I'm selling the main house in Connecticut, we're moving to the condo till we figure out what we want to do next. And we're going to save even more money because our expenses will go down even more. And then, you know, wherever we move next, we're not going to spend, you know, we're not going to have a million dollars in real estate value by the time we go to our next. Wherever we go next, then it's totally a slam dunk. But I mean, I think, I agree. I think that you can do it. I just don't want you. If 10 turns into 12 grand a month or, or if you do this, if it's not five years and it's two years, then there's a little more pressure on you guys.

[Gina]

Yeah. Um, can I ask you one other question?

[Jill]

Why not?

[Gina]

About the Roth. So with the 10% that he's putting in traditional, should he switch all of that to Roth or do. Or do like 15% Roth instead of 10?

[Jill]

Mark. Mr. Roth. They do make a lot of money, by the way. You know, they're in, let's see, 360, so they're in 24% as their top bracket right now. You want him to do all Roth? You want them to just keep doing.

[Mark]

No, no. Yeah, no, I would. I think ultimately the goal should be all Roth. But you know, play with it. See how it feels. Maybe go instead of $10, $10, $15 and 5 and see how the paycheck feels.

[Jill]

Here's what I would. But wait a second. Before you do that, can we just enjoy your better cash flow for a few months just to see how it feels there? That like, if you're not paying for college and you don't have this. You know what I mean? Like, why don't we just status quo right now, end of the year, why don't you reassess, then you can shift it around.

[Mark]

They do have a lot of pre tax money.

[Jill]

I know, but I don't want to be. Can't we just have them enjoy good cash flow for a second?

[Mark]

Yeah. Start January 1st, 2026.

[Jill]

January 1st.

[Gina]

Okay. That's fair. Yeah, we'll see how it goes.

[Jill]

Beautiful negotiation that we just had. It's fantastic. I love it. Gina, any other questions?

[Gina]

No, that's it. Thank you so much, Jill and Mark, it was great to talk to you.

[Jill]

It was great to talk to you. I would say on track in a for the five year plan that, that looks good to me. If you are thinking about a five year plan and it doesn't have to be for retirement, like Gina said, like, I want to do something different. This is a really about this conversation that we're having with ourselves where you are saying to yourself, like, can I really do this for this many, many more years without a game plan? Having the game plan is very helpful in allowing yourself, like the emotional ability to actually get used to this idea. And then we try to marry the emotions with the finances. Okay, so if that's you and you need some help doing that, it's almost like any financial question. Half emotional, half financial, just only half math. That's all you have to worry about. You just go to jillonmoney.com, click the contact us button, write us a note if you'd like to join us live. Check the box. Mark will do everything else. Don't forget to check out all the content that lives there, including my book, the Great Money Reset, which is based on all my conversations with you guys. So you can still buy that book? Yes, it is still available and I'm not writing another book, at least for the foreseeable future, that's for sure. All right, you can subscribe to us on the Odysee app or wherever you find your favorite podcast. Would you mind leaving us a rating and review? Wherever you listen, don't forget to do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[Gina]

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[Jill]

Sea Every week on the Moth podcast, we hear from incredible people who have found their own voice.

[Gina]

There's this little bit of wisdom people say all the time, you know, that you should live in the moment. Let me tell you something. There is nothing worse than being forced to live in the moment. The Moth podcast features real people telling their stories live on stage to connect.

[Jill]

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[Gina]

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