Can I Retire in 18 Months?

Summary

Jill on Money – "Can I Retire in 18 Months?"

Date: March 19, 2026
Host: Jill Schlesinger, CFP® with producer Mark
Guest Caller: CJ from Wisconsin

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Episode Overview

In this episode, Jill Schlesinger takes a call from CJ, a long-time professional contemplating a major life and career transition. With nearly 30 years in the workforce and significant financial assets, CJ wonders if it’s feasible to downshift to part-time work within the next 18 months. Jill and Mark walk through CJ’s financial landscape and explore the viability of his early semi-retirement plan, providing actionable insights and clear-eyed advice without financial jargon.

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Key Discussion Points & Insights

1. Understanding CJ’s Motivation for Change (03:23)

• CJ’s career status:
  • Worked nearly 30 years, 22 at the same company.
  • Main reason for change: boredom, seeking a reset and more time flexibility, potentially in another field or reduced hours.
• Jill’s take:
  • “Once you go to part time, I doubt you’re going back to full time. Come on. Are we? Let’s be honest with each other.” (04:27)

2. The Family & Financial Snapshot (04:43–07:59)

• Demographics:
  • CJ: Age 50, married, three kids (one employed, one in college, one in high school).
  • Spouse: Age 49, self-employed in healthcare.
• Income:
  • CJ: $175,000/year (full-time).
  • Spouse: $100,000/year (gross).
  • Health insurance is only available through CJ’s work.
• Assets:
  • $1.4M in pre-tax retirement (403b/457 plans)
  • $700k in Roth/HSA
  • $200k in brokerage
  • Home fully owned ($500k), building new home ($700k value goal), construction loan in progress.
  • Medical office building (producing $10k/year in rental income).
  • $600k in vacant/recreational land.
• Expenses:
  • Around $5,000–$6,000/month (not including taxes or health insurance).
• Upcoming Changes:
  • New house will be ready by the summer, plan to use sale of current home to minimize new mortgage.

3. College Costs & Kids’ Status (05:33–05:56)

• Two kids still in school, using 529 savings accounts (roughly 75% funded for the sophomore; junior will have enough as well).
• College funding seen as manageable.

4. Retirement and Income Bridge Planning (10:53–17:18)

• Pension:
  • CJ eligible for a $55k/year pension at age 55 (joint and survivor, inflation-indexed).
• Gap Plan:
  • CJ is considering the transition to part-time at age 52, so needs to bridge income for ~3 years until pension starts.
• Cash Flow Strategy:
  • Jill’s suggestion: “You use that 457 as your main source of income from 52 to 55. Then, reduce the draw when the pension kicks in, and let the Roth accounts and brokerage grow.” (13:35)
  • Max out contributions to the 457 (better options, accessible at any age after separation); reduce 403b contributions to increase liquidity for the transition period.
• Social Security Potential (at 67):
  • CJ: $4,200/month
  • Spouse: $2,300/month

5. Real Estate Assets – To Sell or Not? (08:31–10:25, 12:10–12:33)

• Commercial property (medical building): Will be paid off soon. Could be a substantial additional asset (~$700k–$800k value).
• Vacant land ($600k value): Not income-generating. Jill leans toward eventually liquidating some or all if needed:
  • “That’s a lot of money to be tied up in something that we’re not using and not generating any money... I’m on your wife’s side right now. I’m team wife on this.” (10:34)
• CJ reluctant; his wife would like to sell.

6. Feasibility of CJ’s Plan (17:01–18:22)

• Mark sees the plan as “kind of a layup,” primarily because of the strong pension and continued spouse income:
  • “For me, the big thing is that pension. That’s a big pension. And they don’t spend a lot of money.” (17:14)
• Jill’s note of caution:
  • “You need a pinky swear with your wife that if this gets tight… you’ll sell some of these lots off... You have to be willing to do that if things get tight or circumstances change.” (17:16)
• Risks and variables include:
  • Kids needing more help
  • Wife ceasing to work earlier than planned
  • Rising living expenses (possible drift from $6,000 to $8,000/month)

7. CJ’s Future Work & Well-being (18:22–18:37)

• CJ unsure what part-time work he’ll pursue, open to anything, doesn’t mind if it’s not stimulating.

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Notable Quotes & Moments

• On career change and honesty:
  “Once you go to part time, I doubt you’re going to full time. Come on. Are we? Let’s be honest with each other.” – Jill (04:27)
• On liquidity and tough decisions:
  “That’s a lot of money not to be doing anything with... I’m on your wife’s side right now. I’m team wife on this.” – Jill (10:34)
• On risk management:
  “You need a pinky swear... If we can’t do it, we’ll sell some of these lots off.” – Jill (17:16)
• On the financial plan’s strength:
  “Unless I’m missing something, this is one of those kind of layups for me because the wife’s going to keep working. He’s going to be working part time. They have a little bit of rental income. But for me, the big thing is that pension.” – Mark (17:01)

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Timestamps for Major Segments

• 03:23 – CJ introduces himself and his desire for a career reset.
• 04:43 – Personal and family demographics, household income.
• 05:33 – Children status and college funding.
• 06:08 – Breakdown of retirement savings and assets.
• 07:00 – Real estate transition and home financing.
• 08:11 – Family spending, projected expenses, and health insurance needs.
• 09:05 – CJ’s anticipated part-time earnings.
• 10:25 – Real estate holdings: commercial and recreational.
• 10:53 – Details about CJ’s pension.
• 13:35 – Jill explains bridging income with the 457 plan.
• 17:01 – Mark declares the plan a “layup,” highlighting pension and frugality.
• 17:16 – Jill’s key risk-management advice.
• 18:22 – CJ’s thoughts on potential part-time work.

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Final Guidance

Jill’s summary for CJ:

• The early semi-retirement plan can work, thanks to a strong pension, spousal earnings, and substantial assets.
• Maintain flexibility with real estate assets (“pinky swear” to sell some land if cash flow is tight).
• Be prepared for the possibility of expenses rising, spousal retirement timing changes, or kids needing more support.
• Build more liquidity in the short term, favoring the 457 plan over the 403b.

Listener Takeaway

If you’re contemplating a major career reset like CJ, do the homework on your future cash flows, keep your options open, and consider your family’s full asset picture—including illiquid real estate. And, as always, enlist a “team” for an outside perspective, whether that’s a spouse, financial expert, or the Jill on Money community.

Transcript

[A]

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[B]

Welcome to the Jill on Money show. It's Thursday, March 19, and we are here answering your financial questions. Now, sometimes we interrupt these questions with a little bit of breaking news. Sometimes I think just the events warrant us making sure that you feel comfortable with what's going on. But if there's anything going on in your life that requires another set of ears and eyes on the situation.

[A]

We encourage you to get in touch with us.

[B]

All you need to do is go to jillonmoney.com. that's jillonmoney.com. click the contact us button. It is in the upper right hand corner of the website. Wherever you happen to travel on the website, write us a note if you'd like to join us live. Check the box. Mark will do everything else. Now, while you're on the website, don't forget to sign up for the free weekly newsletter, which will also entitle you to the blog. And just generally speaking, whatever it is that's going on, just get in touch with us. You don't have to do this alone. We are your people. We are a community, and we want to make sure we serve you appropriately. Today we are talking to cj, who joins us from Wisconsin. Cj, welcome to the program. What's up?

[C]

Hi, Joe. Mark. Thanks for having me. Yeah, I'm. I'm just looking at potentially exiting my current career and wanting your advice on whether that's possible.

[B]

How come so many people just want to call it quits? Is this because you're miserable? Or conversely, are you just tired or do you want to do something else, like what's going on in your real life?

[C]

I would say the best word probably is just kind of bored, looking to do something else. I've been in this same job for close to 30 years. Current.

[B]

Holy moly. 30 years in the same job. Same company also.

[C]

No. About 22 at the same company.

[B]

That's a lot. That's a. I mean, that's surprising in this day and age to have such a long tenure at one company. So congratulations. I'm sorry it's not so scintillating, but. So what you're seeking is kind of

[A]

a reset to a new career or

[B]

a downshift from what? The amount of time you're spending doing what you're doing.

[C]

Both. Yep. I'd like to just go to part time if that's potent. Possible and maybe go back to full time in the future, but just not have that be a requirement.

[B]

Dude, come on. Once you go to part time, I doubt you're going to full time. Come on. Are we? Let's be honest with each other. I think that's a. That.

[A]

Let's just see if you can do

[B]

part time forever because I think that's a much more. I think that's a more likely scenario. So how old are you, CJ?

[C]

I'm 50.

[B]

You're young are you married? Single? Partnered?

[C]

Married.

[B]

How old is your spouse?

[C]

49.

[B]

Works or doesn't work?

[C]

She works. Yes.

[B]

Oh. So you can just, you know, leech

[C]

off her for a while.

[B]

Right. Which is great. Okay. How much are you earning right now as a full time employee?

[C]

About 175.

[B]

And what about your wife, how much is she?

[C]

About 100.

[B]

So just so we're clear, if you say I'm going to part time and you do something completely different, she can give you your health benefits, right?

[C]

She can't? Nope.

[B]

Oh, okay. So she gets benefits from you.

[C]

Correct.

[B]

Oh. Hmm. Okay, so we just have to make sure you make enough money or have enough money to pay for that.

[C]

Right.

[B]

So let's talk a little bit about what you guys have in like your generalized retirement savings. Oh. Before I start. Kids or no kids?

[C]

Kids. Three kids. One is launched, has a great career, one is a sophomore in college and one is a junior in high school.

[B]

Oh, brother. I mean, you're making a change at quite a time. How are you paying for the sophomore's college?

[C]

We have a 529. It's not quite probably funded, but probably 3/4 funded.

[B]

And what about the Junior? Screw the Junior. It'd be fine. I'm just kidding.

[C]

We should be okay with the junior.

[B]

Okay, so also a 529.

[C]

Yes.

[B]

Okay, now let us get back to you guys. So let's start with retirement assets. What have you guys accumulated so far?

[C]

We have about 1.4 in pre tax.

[B]

Great. That's a huge number in your. You're so young. So that's amazing.

[C]

About 700 between tax free, between Roth accounts and HSA and then about 200 in a brokerage.

[B]

What about just boring savings, checking, that kind of stuff that's all kind of

[C]

rolled into that brokerage number.

[B]

Do you guys have just a home that you own or do you have a mortgage? What's the dwelling situation?

[C]

Yeah, that's kind of. The other issue is we, we have a house right now with no mortgage that's worth about a half a million. But we're also building a new house.

[B]

Oh, why don't you add one more complex part of the story? Come on now. All right, so there's no mortgage, but the, the. So you're building a new home and now you own the lot outright.

[C]

Yeah.

[B]

So when will the new home be done?

[C]

This summer.

[B]

Done, done this summer. And how have you been paying for that? Do you have a construction loan or are you paying it out of cash flow?

[C]

We have a construction loan. Yes.

[B]

Okay. So now pretend it's, you know, August 30th, the house is done. What would the house be worth and what mortgage outstanding balance be?

[C]

My, my hope is it's going to be a little tight, that the house will be worth about 700,000. And between our savings and what we earn until then and what we sell our current house for, that little to

[B]

no mortgage, really, I mean I might need some of that money from the house, but. Okay, so we'll just, I'm going to presume that's something that's important to you. So this, there'll be some small mortgage amount that's outstanding, but the house will have been sold. And now you'll have this $700,000 new home that you love that you can enjoy with your sophomore in college and your junior in high school and stay there for a while, right?

[C]

Yes. Yeah. That'll be our forever home. Yep.

[B]

Everyone says, I always feel like it's a jinx if you say forever home. Just say we plan to stay there for a while. Let's make it nice and fuzzy. All right.

[A]

All right.

[B]

So okay, let's talk a little bit about your expenses. So not including, I'm not talking about saving, I'm talking about the actual out of pocket expenses that you have to live your day to day life. And I presume, you know, I know that the house is costing money along the way, but I kind of want to pretend the house is built already. What do we think the expenses are overall for you and your wife and

[C]

the family all in, not including taxes? Probably 5 to 6,000amonth.

[B]

That's it?

[C]

Yep.

[B]

And does that, that if I say 6,000amonth, does that include health insurance or.

[C]

No, no, no. Not including taxes or health insurance. Right.

[B]

All right, so let's say seven taxes, I'm not so worried about on this. Okay, next. So if we say 7,000amonth. Now here's another question. If you say you go part time, what can I count on you earning in that part time income?

[C]

I think to be conservative, say maybe 20. I would think it'd be more than that.

[B]

Okay, so that your wife is self employed makes 100. And is that 100 gross or is that 100 like she takes home?

[C]

That's 100 gross. But we also another factor is. So she's self employed in health care. We own the building.

[B]

Oh, and wait a minute, hold on a second, hold on. That's the only other property you own.

[C]

We do own some vacant land too.

[B]

All right, let's do the stuff that you're making money on. So you own the medical building. And besides that fact that your wife has access to that, does it throw off rental income a little bit?

[C]

It probably only throws out about 10 grand a year, but we purposely done that to keep her rent low.

[B]

Sure. Okay. But that's just an extra. 10 is good. And what kind of retirement plan does she have for herself?

[C]

She doesn't. That. The numbers I threw out earlier are.

[B]

Oh, those are all you. She doesn't even put money into a Roth.

[C]

No, it's our. It was combined those numbers.

[B]

Okay. Okay, got you. Okay. Expenses of seven grand, the medical building and then all these empty lots. Would you sell these lots or are they available, in other words? I can show them on a balance sheet, but would you actually sell them to do anything with?

[C]

No, it's kind of recreational property that we can keep.

[B]

All right. How much of those lots worth?

[C]

Probably 600,000.

[B]

What?

[A]

600,000.

[B]

That's a lot of money to be tied up in something that we're not using and not generating any money.

[C]

Right.

[B]

You sure you don't want to sell them?

[C]

I don't. My wife would love it, but I don't.

[B]

I'm on your wife's side right now. I'm team wife on this. That's a lot. Are either of you. Well, she won't be entitled to a pension. Do you have any pension benefit in the future?

[C]

Yeah.

[B]

What's that?

[C]

At 55, it'll probably be about 55,000 a year.

[B]

Oh, well, that's a big change. Okay, do I have to make this move from 175 to 20 this year or is there a Runway that we have?

[C]

Yeah, I'm thinking like in 18 months.

[B]

In 18 months. So you'll be 52, right?

[C]

Yep.

[B]

So if you're 52, then I have three years where you work part time so that you guys make 120. But we need some money. You'll be in your house, but you'll need some money set aside. You'll need to live on some extra money to get you to that 55 grand a year that you'll have. So in at age 55, you'll have the 55 in pension, 20 in part time income. And she'll keep earning 100,000, right?

[C]

Correct.

[B]

Okay, so we're right there at 175, which is not terrible, but it's not 270. Is there anything else I should know about in your financial life? Do you have parents you need to take care of?

[C]

No, they're. They're well off. They're good.

[B]

Are you going to inherit money? Is there, is there some argument that I should be not worrying about your $600,000 in land because you have $6 million coming?

[C]

Not that much, I'm sure.

[B]

Darn it.

[C]

Yeah, there's probably some inheritance, but I don't want to count on that.

[B]

What else do I need to know about you guys?

[C]

I think the only other thing is just the commercial property that was. That'll be paid off in a couple years. So that, I mean, at some point we'll be able to cash out on that as well when she, when she retires or exits.

[B]

How much do you guess that the medical building is?

[C]

I'm guessing it's 7 to 800,000.

[A]

But you have this, like, you have

[B]

this, you know, chunk of money. 1.3, 1.4 million. Let's say it's a million dollars after you pay tax on it. Right. You got a million dollars that's sitting on your balance sheet. That's not helping you right now. That's a lot of money not to be doing anything with. So we. Let's say you retire in a couple years, 18 months. You then are you. What are you putting into retirement right now in terms of contribution level?

[C]

I'm. So right now I work at a public institution, so I max out the 403 and the 457.

[B]

And they're both traditional.

[C]

Yes.

[B]

I think. Think you need more cash on hand. I don't think you should max both of those out. Which one has a better platform, the 403B or the 457?

[C]

The 457i like a lot better. The investment choices are a lot better. And I, I like that because it's a deferred comp plan that I can pull money out of before 59 and a half.

[B]

Right. So that one you can get at age 55, is that right?

[C]

As separation from employment, you can start.

[B]

Okay, so even at 52, we couldn't tap into that 457. Right. Okay. How much money is in that 457 right now?

[C]

A little over 800.

[B]

So what I would think is, number one, I would basically, there's no match on your 403B, right?

[C]

Correct.

[B]

So I'd stop doing that. I'd build up more of your cash. I'd put everything else in the 457. So let's say that we have 18 months, presuming we don't have some massive market meltdown. But let's just say let's just say we're, it's, we'll push the clock forward. We've got 800,000 in there. At age 52, you can start using that money to supplement your income. And it's a kind of a dual strategy here. Not only do you get to live on this money, but you also get to start getting some of the money out of traditional assets that are going to keep growing and let the Roth monies continue to crank as long as you can. So presumably if you were able to do that from, you know, 52 to 55, then you reduce the amount that comes out to account for the fact you will get a pension. But you keep using that457 as like your main source of income. Now we go like, push ahead to Social Security. Tell me what the Social Security benefit looks like for you at age 67.

[C]

For me it's about 4,200 and for my wife it's about 2,300.

[B]

Is your wife employed in such a way that if she were to call it quits that she could keep doing because she's self employed? This is the only reason I'm asking. Does she, does she have a date in time or a time that she too would like? A little bit of an off ramp, like all nice for you, cj, but how about me? When do I get my time?

[C]

She, I mean right now, she loves what she does.

[B]

Oh, that's cool.

[C]

She plans to keep working, but she, it's a, it's the type of profession where she could cut back. She works four days a week, she could work three days a week. She worked. Yeah.

[B]

Okay. When you were first talking and walking us through this, I was thinking there's no way you have to sell the lots. Now I'm less sure about that. Although I'm not sure why you're keeping a $600,000 asset that doesn't work. I oddly think this can work. Even though you're really young. Mark, what do you think about this game plan? Remember everybody, here's where we are. CJ's 50. He's very young. He's kind of wiped. And so from age 52 to 55, he's going to pull money out of his pre tax, hasn't been taxed yet, 457 plan, which is now worth about 800 grand. He's going to use that to help fill the gap because they need seven or who knows, maybe it'll be eight. We'll see what the insurance costs are. You use that money up from 52 to 55. You reduce the amount of money from, let's say, 55 on, you're basically going to want to use. We want you to, like, deplete that account eventually, Right. Use that up, and then maybe for 10, 12 years, you start pulling on the 457 plan, the 403B, and you use those funds up, and then you have your Roth assets. Maybe we'll get this medical building sold at some point. Maybe not. Or maybe the lots will be. I'm going to assume that at some point you're going to have, like, another half a million dollars of some assets that flow into your lap from either the medical building or those lots. And then you collect Social Security. Social Security plus your pension gets you pretty close to what your needs are. I think it works. Mark, do you see something bad out in the horizon here?

[D]

No. Unless I'm missing something, this is one of those kind of layups for me because the wife's going to keep working. He's going to be working part time. They have a little bit of rental income. But for me, the big thing is that pension. That's a big pension.

[A]

Yes.

[D]

And they don't spend a lot of money.

[B]

Yeah, I know. There's the only thing, C.J. that I will point out, which is, you know, we're saying five to six a month. Maybe it's six to seven. Maybe it ends up being eight. I think it kind of works. Here's what I think you need to do with your wife. You can do this, but I think you guys need a pinky swear to say. You say to her, if this gets tight, if we can't do it, we'll sell some of these lots off. We'll get some money in the door. You have to be willing to do that if things get tight or if. If your circumstances change. Okay. But if you're not, because if you're. If you're like, oh, no, I want to die with those, I'm going to. You know, like, it's a. It could get a little rough if something changes. For example, what could change? Your wife's 55, and she's like, I totally don't want to work anymore. So now we don't have that hundred grand coming in, and that becomes something big. Or your kids really need your youngest kid, your second kid needs a lot of help. That's something. But if circumstances change, you have the assets to do this. It's just that they're not liquid yet. So I think it works. What are you going to do? Working $20,000 a year, part time. That's what I want to know.

[C]

I'm not even sure. Maybe it could be. You don't know, it could be just retail. I don't know.

[B]

I think you're going to be bored with that. I don't know you at all, but I'm just going to say I think that could be boring. Or maybe you're just fine with that, but maybe you're okay to be bored for a little bit. Right?

[C]

Right.

[B]

There's that too. Cj, do you guys have your estate documents Done? We do life insurance out there.

[C]

Not a lot. We used to have a lot and we ended up cutting back on that.

[B]

I mean, the only thing I want to ask about with the pension is that pension, 55 grand. Is that a joint and survivor or is that for your life only?

[C]

It'll be joint survivorship and it does have an inflation index on it.

[B]

Okay, great. Okay. All right. That's fine. Anything else that we need to know that you have a question about? Are you managing all this okay? You feel okay?

[C]

I feel great. Yeah. This, this helps a lot.

[B]

Amazing. All right. C.J. from Wisconsin is ready to downshift. He is resetting to part time. And if you like, CJ want a little bit of a reality check. You're only 50 years old, but you still want a reality. It's funny when people, people who are 50, it's like, yeah, you've been working for 30 years, so I get it. If you need some assistance, get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note. If you want to come on the air, check the box. And if you are considering a reset, perhaps you would consider buying my book, the Great Money Reset, because it is based on stories just like CJ's. So I encourage you to check that out. We've got links right on the website. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. We always ask that you lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[A]

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[E]

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