If I Retire, Does Our Plan Work?

Summary

Jill on Money with Jill Schlesinger

Episode: If I Retire, Does Our Plan Work?
Date: December 18, 2025
Guest: Joy (Listener, Pacific Northwest)

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Overview

In this episode, host Jill Schlesinger takes a call from Joy, a long-term state government employee, to evaluate whether she and her husband can safely retire and maintain their desired lifestyle. Joy seeks reassurance and practical guidance on retiring early, blending pensions, Social Security, personal savings, and rental income to fund the years until both pensions and Social Security fully kick in.

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Key Discussion Points & Insights

Joy’s Big Question: Can She Retire Early and Still Afford Her Plans?

• Joy is contemplating retiring after 25 years with the state government, at approximately 54 years old.
• Her husband (65) is already retired, collecting a healthy pension.

Quote (Jill, 08:10):
"Why are you even hesitating about retirement? I don't get it... Are you worried that you can't, or do you actually know that you can and you just need us to give you permission?"

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The Financial Snapshot

Income and Spending

• Husband’s Pension: $7,000/month (already started)
• Joy’s Future Pension: ~$5,000/month (available at 65; begins in 10 years)
• Husband’s Social Security: ~$700/month (already started, began early)
• Joy’s Social Security:
  • ~$3,500/month at 65
  • ~$4,000/month at 67
  • ~$5,000/month at 70
• Retirement Savings:
  • Joy: ~$350,000 in 401(a), $200,000 in 457(b), $3,000 in Roth
  • Husband: ~$150,000 in 401(k)
• Health Savings Account (HSA): ~$50,000
• Brokerage (Non-Retirement): ~$100,000
• Cash (Checking + Savings): ~$80,000
• Monthly Spending Estimate: $10,000–$12,000 (includes projected healthcare costs)

Real Estate

• Primary Home: Worth ~$1.2M, $500,000 mortgage at 3%
• Rental Properties:
  • Pacific Northwest: $450-475K value, $260K mortgage (3%), $600/mo net income
  • Two in the South (both paid off):
    • One nets $1,200/mo
    • VRBO nets ~$5,000/year

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Assets vs. Anxiety: “I Probably Need More Permission”

Joy felt some unease comparing her non-millionaire portfolio to others' larger retirement balances.

Quote (Joy, 08:10):
"I probably need more permission, even though in my mind, when I think about what people my age have, it's more in the millions rather than hundreds of thousands."

Jill’s Response (08:22):
"Those people don't have two pension checks. You have millions. It's just in the form of pensions... Think of it this way: $12,000 a month coming in from our pensions? That's $144,000 a year. You'd have to have three and a half, four million already saved to generate that."

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Filling the 10-Year Income Gap Before Joy’s Pension

• Joy’s pension doesn’t start for 10 years (her at age 65).
• Plan:
  • Rely first on husband's accounts for withdrawals (~$30,000+ per year)
  • Use rental income to supplement pension/withdrawal gaps
  • Once husband’s account is depleted, shift to Joy’s pre-tax accounts, maintaining cash flow until pensions and Social Security kick in.
  • Possible sale of one rental property in the coming years to boost cash if needed.
  • Keeping the primary home is feasible; selling not required.

Jill’s Calculations (14:23):
"I don't think you're going to even need the brokerage... If we did $30 grand a year out of [your husband’s account], and then use that to cover needs... you can wait... and do the same with your accounts between age 60 and 65. When you claim Social Security, you’re basically set!"

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Real Estate: Keep, Sell, or Simplify?

• Joy wants to keep the primary home and at least one rental for personal use.
• Jill notes that rental management could become more burdensome with age—eventually selling one makes sense for both cash flow and simplicity.

Quote (Jill, 16:50):
"One of these is probably going to go... and you’re going to have plenty of money. But you don’t need to sell them right now."

Quote (Jill, 20:25):
"To make your life less stressful... one of those properties you’re going to need for cash flow. Unless something weird falls in your lap... But you have it, it’s an asset, so use it."

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Health Insurance & Spending

• No retiree health coverage from state, but the $12,000/month spending estimate includes health insurance costs for both Joy and her husband.

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Estate Planning

• Wills, trusts, and other estate documents are in place and currently being refreshed due to changing circumstances.

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Kids & Other Family Considerations

• Children are grown, self-sufficient; one wrapping up college (fully funded).

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Mindset Check: Retiring “For the Money”

• Jill and producer Mark emphasize: Joy shouldn’t stay working out of financial fear, as their plan holds together well.
• Jill gives the green light for retiring on Joy’s target timeline (8-10 months).

Quote (Jill, 20:25):
"Don’t stay for the money, okay? Don’t stay. You have plenty of money."

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Notable Quotes & Memorable Moments

• On pension envy:
  Jill (21:24): "Mark, why did we not get pension jobs? What happened to us?"

• On giving permission:
  Jill (08:10): "Are you worried that you can't, or do you actually know that you can and you just need us to give you permission?"

• On comparing assets:
  Jill (08:22): “You have millions. You have a guarantee, and your guarantee comes with an extra benefit… you don’t have to sweat the risk.”

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Timestamps for Key Segments

• Meet Joy & Outline of Situation – 03:26–05:20
• Pension, Social Security, and Savings Breakdown – 05:20–07:24
• Asset Comparison & Reassurance – 08:10–09:56
• Primary Home and Mortgage Discussion – 09:56–10:45
• Rental Property Portfolio – 10:47–12:49
• Income Gap, Withdrawal Strategy & Future Planning – 13:36–19:37
• Health Insurance & All-in Spending – 12:49–13:09
• Estate Planning & Family – 17:55–18:09, 19:59–20:09
• Timeline for Retirement & Next Steps – 20:09–20:25

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Conclusion & Takeaways

• Joy and her husband have “done everything right” financially.
• Their combined pensions, Social Security, retirement savings, and rental income create a robust, sustainable retirement plan, even if Joy retires well before her pension starts.
• Downsizing rental properties for simplicity and liquidity makes sense, but there’s no urgency to sell.
• Keeping the primary home is sustainable; selling is not required.
• Jill emphatically grants “permission” to retire—reminding listeners that comparing themselves to others without context can be misleading, especially when defined benefit pensions are in play.
• Final takeaway: Joy has plenty of financial security and should feel empowered to transition into retirement on her preferred timeline.

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Host: Jill Schlesinger
Guest: Joy (Listener, Pacific Northwest)
Producer: Mark
Podcast: Jill on Money, Audacy

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Transcript

[Jill]

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[Joy]

Yeah, it's just dark and dreary part of the country.

[Jill]

But you know what, you're bringing joy to us and that is so wonderful. What can we do for you?

[Joy]

Well, I'm trying to figure out if I can leave my job early after 25 years working for the state government.

[Jill]

That's a long time for one job. Was it one job or did you move around and stay in the state government?

[Joy]

I've mostly worked in the state government, did different things, but same agency for the last 25 years.

[Jill]

And you must have an unbelievable pension. So I'm excited by that. So let's go through what's going on. Are you single or married or partnered?

[Joy]

I am married.

[Jill]

Okay. And spouse working.

[Joy]

And how old he is actually retired. He's a little bit older than I am. And he currently has a pension as well of 7,000.

[Jill]

Wait a minute, how old is he?

[Joy]

He is 65.

[Jill]

And how old are you?

[Joy]

I am about 10 years younger.

[Jill]

55. Nice for you. Okay, so he's got his $7,000 a month pension right now, right?

[Joy]

Yeah.

[Jill]

Okay. And if you were to leave your job, like if you literally gave notice today and your pension started, you know, January 2nd of 2026, how much would you receive?

[Joy]

I would receive just a little over 5,000.

[Jill]

Okay, that's great. So two pension checks.

[Joy]

Yeah.

[Jill]

Okay, that sounds really good. How much do you guys spend?

[Joy]

So we currently spend around 12,000amonth. Between 10 and 12,000 and looking, I think, into retirement. We were looking up about 12, maybe the first couple years.

[Jill]

Yeah. Why not? While you're young and healthy. Why not? Right?

[Joy]

Yeah.

[Jill]

Okay, so you're almost covered. I mean, I know your pensions are taxable, so, you know, you won't net your $12,000 a month, but you're pretty close. What else is going on? How about saving in. Did you save in a 403 B or a 457 plan? Any. Any retirement assets that you've socked away in addition to those pensions?

[Joy]

Yeah. So we both qualify for Social Security. His is pretty minimal. He's actually current. He started taking it early, so he's getting only about 700. And I would be getting at 65, around 3,500. And at 60, 67, about 4,000.

[Jill]

Okay.

[Joy]

And closer to 5,000 at 70.

[Jill]

Okay, that's great.

[Joy]

So those are those pieces in terms of what we've saved. I have about 550 in my 401 something.

[Jill]

401A, maybe.

[Joy]

I think it is a.

[Jill]

Okay. Okay.

[Joy]

Actually, 350 in there and 457 is about 200,000 and he has about 150 in his. I think it's a 401K, but I'm not certain.

[Jill]

And just so I'm sure clear about this, both of the, all three of these accounts, the retirement accounts, right, Those are pre tax. They're not Roth accounts.

[Joy]

Right there? Yes, they are all pre tax. I have about $3,000 in a Roth account, but that's very minimal.

[Jill]

What else do you have? You have your tiny Roth of a. Of $3,000. What about safe money?

[Joy]

I have a health savings that has about 50,000.

[Jill]

That's good.

[Joy]

Have a brokerage between the two of us of around 100,000. We have savings are around. Let me see, our checking is around 30, but we have an additional about 50,000 in savings.

[Jill]

Okay, can I just ask you a dumb question? You ready for my dumb question? You have a whole bunch of money. Why are you even hesitating about retirement? I don't get it. Like, you know, you have all this money. I haven't even gotten through all these questions, but just from what you've told me, okay, $7,000 a month for your husband, plus his $700 a month of Social Security. Your pension will be 5,000. You know, 3,500 or 4 grand a month will be coming in in the future. I get it. For Social Security, you only spend 12 grand. A month. You've got a whole bunch of money that is in savings, in retirement savings. You got a whole bunch of money that you've saved in your brokerage account. Are you worried that you can't, or do you actually know that you can and you just need us to give you permission?

[Joy]

I probably need more permission, even though in my mind, when I think about what people my age have is more in the millions rather than hundreds of thousands.

[Jill]

Yes. However, those people don't have two pension checks. Yeah, you have millions. It's just in the form of pensions. You have millions. You hearing that? Just wait. Take a breath for a second, Joy. Take a breath, because those two pensions, like, just think of it this way. We have. I'm going to give you approximate $12,000 a month coming in in our pensions. Okay? And when you think about that and you say, oh, that's like real money. Right? That's $144,000 a year. You would have to have, I don't know how much, Mark, $4 million already saved in retirement. That would generate three and a half, four million. Three and a half, four million. That would generate that. So to compare yourself right now to someone else who doesn't have a pension, who has millions. You have millions. You have a guarantee, and your guarantee comes with an extra benefit, which is you don't have to sweat the risk. The risk is taken is borne by your state of employ, like the state pension bears the risk. You don't have to worry about if the stock market goes down or up. And how to manage that? You're getting these checks no matter what, which is incredible. Okay, so now I'm just saying you're in great shape. You can keep talking now, but I want you to hear that. So let's go to the next step here, which is you have a home that you own. How much is that house worth? Wow.

[Joy]

Okay, first off, thank you. The home we live in is about a million or a little more between 11 and 1 3.

[Jill]

I'll say 1 2. Is there a mortgage outstanding on it?

[Joy]

There is about 500,000.

[Jill]

What's the interest rate?

[Joy]

Oh, it's just around 3%.

[Jill]

And you're going to stay there? Like when you guys retire, you're going to stay there?

[Joy]

Well, we were thinking of possibly selling that home and bridging the gap with the profits of the sale of the home if we needed to.

[Jill]

Oh, my God. You're not going to need to. But do you want to stay there?

[Joy]

Yeah. Well, yes, I'd like to, but yeah.

[Jill]

So if I took a. I just wrote down may sell, but would like to stay ideally. Right?

[Joy]

Yeah, that's fair.

[Jill]

Okay. You have some rental property, I see because I'm looking at your email, so I just scanned that quickly. So tell me about the rental property you have.

[Joy]

Well, we have a, have a rental property here in Northwest that is worth about 450, 475, 260 mortgage, also at about 3%.

[Jill]

Does it work well for you? Like, is it a pain in the neck or is it an easy property to maintain for you?

[Joy]

It's relatively easy to maintain. It's. I'd like to maybe get rid of it eventually, but right now is probably not the best time. It's covering itself so it cash flows.

[Jill]

And covers the cost of the mortgage and the taxes and all that, but there's no additional money that comes in for you?

[Joy]

Yeah, there is about 600 additional above mortgage.

[Jill]

Okay, so plus $600 a month. Got it.

[Joy]

And then we have a couple of rentals down south that are both paid for. And one is a full time rental. I think we're getting 1200 for it. And the other one is a VRBO and it profits about 5000 a year after all the expenses. So it's really not a lot of money. More to kind of take care of itself.

[Jill]

And the second one, that's cash flowing, 1,200 bucks a month. How much is it worth?

[Joy]

That one is about 475 right now.

[Jill]

And the VRBO one, how much is that worth?

[Joy]

That one is about 350.

[Jill]

You would like to keep both of these properties? Is that something that's important to you? Is that, you know, what do you think?

[Joy]

Well, I would like to keep one because we do like to go down there. I think my husband would prefer to keep both for some reason. I think they're.

[Jill]

You can only stay in one at a time. Doesn't he realize that? I agree.

[Joy]

Yes, yes.

[Jill]

Oh, you know what, I forgot to ask you, Joy, when you retire because you worked for state government, will you be entitled to get health insurance?

[Joy]

No, I will not have health insurance.

[Jill]

So when you said 12,000amonth, did that include health insurance?

[Joy]

Yeah, it did for both of us.

[Jill]

Okay.

[Joy]

Yeah.

[Jill]

So I guess what, I mean, I think that what it sounds like is as soon as you guys pull the trigger and you decide that you, Joy, are going to retire, you are going to continue to be in a pretty high tax bracket just because of those two pension checks and because of the income from the rental property. Right. So what are you earning right now, Joy?

[Joy]

I. Right now I'm at just around 200,000.

[Jill]

So your income, plus your husband's pension and the Social Security and the rental income, that it basically puts you in the 24% tax bracket. That's about where you guys are, right? Yeah. So you. I guess when what I'm hearing and you say is like, hey, you know, we'll sell the house if we have to, but you really would like to stay. So I just need a priority check here. You know, ideally, if you keep your house, keep both rental properties, and then we maybe use some of your husband's retirement account to help bridge the gap of money that you might need until you claim Social Security, would you be okay with that? Can we spend some assets down?

[Joy]

Yeah, his account, which has about 150. And then I think, yeah, the brokerage, of course. And I think.

[Jill]

I don't think you're going to even need the brokerage, to be honest with you. Because if you think about it, let's just like, work this through a second. You're going to have your pension, his pension. So that's 12 grand a month. I know it's pre tax, right? You're going to have that, plus you have this $1,200 a month from your rental property. Right. Beyond that, this is before you're not claiming your Social Security. And so I'm looking at this 12, 7, so 13. So you'll have 14 grand pre tax. Okay. So if you think about it, what you need to fund, the difference is just like, what is the net right. You could take probably, I don't know, let's say it's 30 grand a year out of your husband's 150,000. I think this is going to do it. If we did 30 grand a year out of that. Okay. And we then use that to cover whatever your needs are. I think that post tax, that will do the job for you. I think you'll get your 12 grand. Okay. And also it's like an extra benefit, which is we're getting this money out of your husband's account while he's still, you know, before minimum required distribution. We don't have to touch your account. We just don't have to. That 530. We don't have to touch it. We do this for five years. Now all of a sudden, you're 60 years old. You. You'll be able to tap your money for the next group of years before you claim Social Security. Okay. So you'll be able to use your Money and do the same thing. Like, Instead of the 30 grand, I know we're not inflating it. We're not putting, you know, we're not applying an inflation rate, but just let's do simple math. So from there, you got your husband's account. Hopefully we get rid of it. It's done. You spent it down. Then your accounts, the 330 and the 200. From that combination, we do another 30 grand a year or so. Or maybe it's 35 at the time or 40. Take the money out. Then from, you know, your age, say 60 to your age, 65 or 67, you pull that money out, okay? And then the cool thing is that you claim Social Security and kind of, you're done. You're all good. Like, your numbers should look really good. And you can continue to take money out of your retirement accounts. You can let your brokerage account grow. You can, you know, not sell the rental properties if you don't want to. You don't have to sell your house. I think this works for you. I do think, though, that it seems that the two rentals. I don't know if he wants to keep one. You should see which one is, like, less of a pain in the neck because I just think it's going to become more and more annoying to have to, you know, manage these things. So you should figure out, like, whether it's the. The. The one of the, you know, the rental in the Pacific Northwest, whether it's the two southern ones. One of these is probably going to go, and you're going to have plenty of money. But you don't need to sell them right now. You can wait. You can just bide your time. So if you say that I want to actually be done, Joy, you can be done. Mark, do you agree with us? 100%. Don't get hung up on what other people have. I mean, you have the pensions. You have all this real estate which can one day be sold. I mean, you guys are, you know, you're pretty golden. You are totally golden. Not even pretty golden. You're totally golden. Hey, I forgot to ask you, Joy, do you have kids?

[Joy]

We. We do have kids. They're all launched.

[Jill]

Okay.

[Joy]

And on their own. There's. There's one that wrapping up college, but she has a fully funded account.

[Jill]

Great job, right? That's great. That's awesome.

[Joy]

I just want to make sure. I understand. So my pension doesn't kick in for 10 years.

[Jill]

Okay, I got it. Okay. I got it. I got it. So don't worry about it. That's still fine. So your pension doesn't kick in until age 65.

[Joy]

Right.

[Jill]

Okay, so for 10 years. I get it now, now that it was a missing piece of information. So that's okay. We can just take out four for the first few years. Are. Are you. Did you say you're 55 or mid-50s? What? I need the actual year. Like, how old are you?

[Joy]

Actually, I am 54.

[Jill]

You're 54. So we need. So we need six years. Five years in five and a half years. But let's say you're. Let's say six years. Where we need to get money out of. We have to cover your needs. You're going to first tap his retirement account. So that's going to need. You know, you're going to need 50 grand a year for that. Okay. And then I see why. Maybe selling one of the rentals would work. You know, honestly, pick one, tell me which one. You just think you have to. I think you're gonna need to sell one of those then. If we don't have. If we don't have that income for 10 years, we are gonna need some extra cash. We definitely need some money. Which of the properties? The northwest rental, the two southern ones. You pick. But one of those is going to have to go.

[Joy]

Okay, that sounds.

[Jill]

Yeah, that's right. Okay, I got you now. I misunderstood that. So that's good.

[Joy]

Oh, no, that's. That's great because still, I think it all works as I had hoped.

[Jill]

It definitely does.

[Joy]

And this wouldn't require then selling our primary home?

[Jill]

No, don't sell your primary. You want to stay there?

[Joy]

Yeah.

[Jill]

I don't think you need that. Do you guys have your estate documents done?

[Joy]

Yeah, we do. However, we're just going through it again because things are changing. So we have an appointment with our attorney. Two weeks.

[Jill]

Okay, good. That's good. So when do you really want to be done? What do you think?

[Joy]

I think about eight to 10 months is when most of my projects are ramping down. So that would be a good transition time.

[Jill]

Okay, Joy, Then get ready to give your notice and keep in touch with us and let us know how it goes. But don't stay for the money, okay? Don't stay. You have plenty of money. You have assets. Talk to your husband, Say, you know, the plan really does work. We did do a great job. You did do a great job. I don't know why he wants to keep the property, but one of those properties you're going to need for cash flow. Unless there's like something weird that, like, falls in your lap, who knows? But I think that you really. To make your life a little bit less stressful. I mean, because you probably could figure. I could probably figure out how to do it without doing the actual sale of the rental property. Don't do that. You have it. It's an asset, so use it. And by the way, it's an asset that's not working so great. You know, neither of those two in the south is so great. Seems like the one in. In. It seems like the one that's nearby you is doing better in terms of generating cash flow.

[Joy]

Yeah, yeah, yeah. No, this is great to hear. Thank you so much.

[Jill]

It is our pleasure. Mark, why did we not get pension jobs? What happened to us? You had a shot. You had a shot. What happened to your pension? Did you get. What happened to that old CBS pension? I think when I turned the age of 65, I looked at it, I think it'll be about 300 and something dollars. So it's like your coffee budget, which is great. You won't have to worry about your expensive coffee habit. All right. If you are worried about your own financial situation, even though you know you're okay, but you need us to help you, give you a little permission, structure, or run through it with you. We have nothing in this except to try to make your dreams come true or to crush them alternatively. But it doesn't really require much more than us listening to what you say you want to do and then coming up with a game plan. So why don't you get in touch with us? Go to jillonmoney.com, jillonmoney.com, click the contact us button. Write us a note, check the box if you would like to join us live, which is oh, so much fun, and we would love to have you on. And of course, don't worry if you're shy. It's very easy to talk to us. Just listen to Joy. She was very nervous before we came on the air and she was great. So don't forget that you can subscribe. Subscribe to this program, Jill on Money on the Odyssey app, or wherever you find your favorite podcast. By the way, you can get our other podcast, Money Watch, on that same Odyssey app. So check that out. And of course, lift someone up. We love that you do that. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. Christmas is next week, and if you haven't yet, go see Stephen Singer, the I hate Stephen Singer. Guy. He has the number one gift for Christmas. Real natural diamond stud earrings. I'm sure you know that gold and diamond prices are at their highest level in history. Luckily for you, Stephen Singer has locked in his diamond studs at the old prices. His Anita diamond studs still start at just $298, all at the same perfect price as last year. There's no better time to get a pair of diamond studs from Stephen Sing Jewelers. Each pair is eye flawless and near colorless. Plus with Stephen's full value lifetime trade in, you can trade in your studs anytime and get exactly what you paid towards a larger pair. Go to ihatestevensinger.com order right now with fast and free shipping to arrive in time for Christmas. Experience. The difference at Steven Singer Jewelers Online at I hate stevensinger.com I hate stephensinger.com what's up world?

[Joy]

It's Vaughn Miller, Super Bowl MVP, chicken farmer and now host of Free Range. This is a show where I go off the field and off the script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet deep dives, the conversation, this is your podcast. Join me every Wednesday. Follow and listen to Free Range with me, Vaughn Miller everywhere. You get your podcast.