Buckets in Retirement

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Buckets in Retirement

Date: November 20, 2025

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Main Theme & Purpose

In this episode, host Jill Schlesinger, CFP®, takes a listener call from Stacy in Washington State for a "retirement check-in." The primary focus is on organizing financial "buckets" for retirement—how to allocate and withdraw funds from various accounts, whether Stacy is on track to retire at age 57, and which adjustments might make her retirement finances more secure. It's an in-depth, real-world look at practical retirement strategy with an emphasis on flexibility and risk management, served up with Jill's trademark candor and warmth.

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Key Discussion Points & Insights

1. Stacy's Situation: The Quick Facts

[03:34–06:31]

• Stacy is 53, partnered (they share expenses but keep finances separate), with no children.
• Owns her home (worth ~$800,000), mortgage-free.
• Earns $150,000/year, planning to retire at 57, transitioning to part-time work for three years prior.
• Substantial savings: $1.2M in a traditional IRA, $85K in Roth IRA, $25K in Roth 403(b), $55K HSA, $260K in a brokerage account, plus $15K in liquid cash.

2. Planned Retirement and Withdrawal Strategy

[06:31–10:44]

• Stacy intends to retire at 57 (full stop at 57 after part-time transition), then live off the brokerage account until eligible for retirement account withdrawals at 59½.
• She will have a state pension of $1,300/month starting at 65 (with a COLA), and expects Social Security of ~$3,470/month at 67.
• Annual expenses are modestly estimated at $4,000/month, likely to increase to ~$5,000/month in retirement due to health insurance and travel.

Jill's Analysis of the Plan

• Jill supports drawing down the brokerage for the “gap years” (57–59½) and then tapping into the traditional IRA.
• She's impressed by Stacy's savings and controlled lifestyle.
  “Mark, what is with this? These people, they're $4,000 a month. I'm, like, so jealous.” — Jill, [08:29]

3. Risks and Flexibility in Early Retirement

[11:31–16:12]

• Jill highlights the risk of a severe market downturn in the years leading up to and just after retirement:

  “Is it possible between now and the next four years that we have a big market sell-off and that all of a sudden your, you know, $1.3 million…gets lopped into 900 grand?... I personally would never want to retire into a bear market. If I had the choice, I would just keep working.”
  — Jill, [13:02 & 15:13]

• Jill recommends flexibility: either staying full-time longer or working part-time for more years, depending on how the markets and Stacy's assets fare.
• The idea is to "retest" the plan in a few years to ensure security, especially if the market tanks before or in early retirement.

4. Roth Conversions, Health Care, and Expense Planning

[11:31–13:50, 12:05–12:31]

• Stacy inquires about small Roth conversions in the early retirement years. Jill advises prioritizing liquidity:
  “I need your money. Okay, we need that money for sure.” — Jill, [11:45]
• Health care coverage post-retirement is available via Stacy's state employment, but will cost about $1,000/month—not yet included in current expense estimates.
• Jill urges caution about underestimating expenses and the impact of inflation and health care costs.

5. Asset Allocation Before Retirement

[16:46–17:19]

• Stacy asks if saving money in a high-yield account versus the brokerage makes sense for greater liquidity as retirement nears.
• Jill suggests splitting savings between the brokerage and high-yield accounts:

  “I would really look at brokerage and high yield savings. Those two. That's what I would do for sure. Just to preserve that early retirement optionality.”
  — Jill, [17:15]

6. Estate Planning & Final Advice

[16:40–16:42]

• Stacy confirms she’s set up her estate plan.
• Jill concludes that success in Stacy’s plan depends on being flexible and revisiting the plan as markets and personal situations change.
• The “dream” is alive, but the real key is adaptability as circumstances evolve, not a rigid commitment to a date or drawdown schedule.

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Notable Quotes & Memorable Moments

• Jill’s humor about modest lifestyle:

  “Mark, what is with this? These people, they're $4,000 a month. I'm, like, so jealous.”
  [08:29]

• On the “bear market retirement” dilemma:

  “I personally would never want to retire into a bear market. If I had the choice, I would just keep working.”
  [15:13]

• Jill urging practical caution:

  “53 is really young. You could live for 40 years… once we get into your 60s, you're good, but it's a long time to get there. So 10 to 13 years of just pulling money out of your retirement account is something that can be a little edgy.”
  [14:08]

• On partnering with someone less wealthy:

  “Is your partner, like, much richer than you?”
  “No, much less rich than me.”
  “That's terrible. What were you thinking? What on earth were you thinking, for God's sakes?”
  [13:50]

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Important Timestamps

• [03:34] — Introduction of Stacy and overview of her finances
• [06:31] — Retirement accounts and withdrawal timing
• [08:29] — Discussion about expenses and lifestyle
• [10:43] — Tax considerations in Washington State
• [11:31] — Withdrawal strategy and Roth conversion question
• [12:05] — Health care costs in retirement
• [13:02] — Jill's concern about market risk and flexibility
• [15:13] — Advice about retiring in a bear market
• [16:40] — Estate planning confirmation
• [16:46] — Liquidity versus brokerage for pre-retirement funds
• [17:15] — Jill's summary on where to save next

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Conclusion

Flow & Takeaway:
This episode delivers a realistic, reassurance-laden approach to retirement planning. Jill’s guidance embodies both empathy and professional caution, emphasizing that even well-prepared savers like Stacy need to stay nimble and be ready to change course in the face of market volatility. The tone remains light, encouraging, and sensible throughout.

Listeners left with two main lessons:

• Plan meticulously, but be ready to adapt if the investing landscape shifts.
• Prioritize liquidity approaching retirement, and err on the side of caution with early drawdowns.

Jill’s invitation: If you’re tackling similar questions and want a tailored conversation, reach out to the show!

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Transcript

[A]

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[B]

Welcome to the Jill on Money Show. It's the Thursday, November 20th and we are here trying to help you along that financial journey. So wherever you are at the very.

[A]

Beginning, maybe you're just starting your career.

[B]

Your family, your household.

[A]

Maybe you are actually mid career.

[B]

Maybe you're towards the end, you're looking at retirement. Maybe you're beyond retirement and you're thinking about how do I manage what's going on in my life? How do I help my kids without enabling them? Whatever it is that's going on for you, Mark and I want to help you out. We are both certified financial planners.

[A]

More importantly, we are both voyeurs. We love hearing your stories.

[B]

We love to understand how we can help you out. We have nothing to sell except whatever advertising is done on this podcast and of course my subscription service or a book here and there. But you know, no product, no service, no nothing. Mark, somebody called me recently who used to work at CBS News, now works at ABC and said, I would pay.

[A]

You if you wouldn't mind helping me.

[B]

With my financial situation. I said, I am not registered. I don't do that. But I'm happy to help you. So it was very funny from years ago that she was at cbs. Now she's at abc and everyone's just kind of freaked out. So we get that a lot of workers on edge, certainly those of us in the media, but in other areas as well, you just don't know. So we're here for you. Go to our website, jillonmoney.com click the contact us button. Let us know if you want to come on the air by checking the box. And you know who did that? Stacy from Washington state and she joins us today. So hello, Stacy. How are you?

[C]

Jill? I'm great. How are you?

[B]

Great. What's up? What can we do for you?

[C]

Well, I'm kind of coming on for sort of the same reason a lot of folks do, just sort of for a little retirement check in. Can I retire on my plan? Do I need to work a little longer, but more so to kind to look at my buckets. I have money in all these different pools and sort of when to use these once I get into retirement, when to put money in them in the next few years before I retire.

[B]

This all makes sense to me. Okay, so let's go into like just who you are and what is going on. So right now, how old are you?

[C]

I am 53.

[B]

Okay. Married?

[A]

Single?

[B]

Partnered?

[C]

I am partnered.

[B]

Okay. And do you combine financial stuff with your partner?

[C]

We share expenses, but we don't combine finances.

[B]

Okay, so we're on our own.

[C]

Yes.

[B]

Got it. Do you have children? No. Wow. Hear that, Mark? No. With a little H in there, like. No. No. Thank you. You remember when you were like that, Mark? Did you, Mark, did you think you were going to have kids or not? Yeah, one. One only. I kept thinking for two, but that was me. Okay, Stacy, let's find out a little bit more. You're working full time. How much do you earn?

[C]

About 150.

[B]

And are you and your partner living together?

[C]

Yes.

[B]

Okay, does one of you own and not. But not jointly? Like who's the dwelling situation? Is it someone own a home?

[C]

Yeah, I own the home.

[B]

Okay, what's the house worth?

[C]

About 800.

[B]

Mortgage or no mortgage?

[C]

No mortgage.

[B]

See, that was the same thing as a kid. No mortgage. Okay. On your $150,000 income, are you putting money into a retirement account?

[C]

Yes.

[B]

How much?

[C]

So this year I've put about 60,000 away.

[B]

Wow. Tell me more. That's a lot.

[C]

I'm hoping to retire in four years, so I'm hoarding.

[B]

Okay. I like hoarding. So. So here's our goal. Mark, write this down. We got retirement at age 57. How much money is in the retirement account? How much, like, have we saved so far? Let's just do this methodically. So let's do retirement accounts first.

[C]

So I have a traditional IRA with $1,200,000.

[B]

Okay.

[C]

And then I have a Roth IRA with about 85.

[B]

Okay.

[C]

I have a small Roth 403B with my current employer with 25,000. An HSA with 55.

[B]

Great love.

[C]

And then I have a brokerage account with 260.

[B]

Will you, since you mentioned 403B, will you be entitled to a pension?

[C]

Yes.

[B]

Yes, baby. How much will the pension be?

[C]

So it should be about 1300amonth pension.

[B]

Of $1300 a month. Will that start at age 57?

[C]

I can defer it until 65, which is my plan.

[B]

Okay. And so that would be 1300amonth at 65. Correct. Okay, got it. What else do we need to know about you and, you know, kind of the game plan? Four years, never work again. Four years part time. Like what happens in four years?

[C]

Yeah. So my hopes is next year to stay full time, to go part time for the remaining three years, and then hopefully not work anymore. But I. I have the ability to do part time or per diem work at my job, so I could.

[B]

Oh, that's good. Oh, I forgot to ask you. Savings, just like boring money that's floating around in addition to that brokerage account.

[C]

Yeah. So I just opened a high yield savings, thinking I could put money in there over the next couple of years. So that's only got about 5, $6,000 in it, and then maybe about 10,000 between checking and saving.

[B]

Okay. And that's it. No rental property, no vacation home? No. Anything else crazy out there?

[C]

No. Pretty low maintenance, simple life parents that.

[B]

You need to worry about? No.

[C]

Both still living, but healthy and financially stable.

[B]

How financially stable? Can I count on an inheritance?

[C]

Not from dad, Possibly from mom, but not counting on it.

[B]

Got it. Okay. So you share your expenses with a partner. What's your share of expenses? What do we need to do at age 57? What is it that we're trying to produce from your various assets?

[C]

So I'm very much overestimating because we do not Live a very expensive life. And so overestimating. I think about 4,000amonth, which I know doesn't sound like a lot.

[B]

Mark, what is with this? These people, they're $4,000 a month. I'm, like, so jealous. I overestimated.

[A]

Over.

[B]

Are you going to. You guys going to stay in the house?

[C]

I think so, yeah.

[B]

Do you happen to have your Social Security benefit in front of you? Do you know what that would be?

[C]

I do, yeah. So 67, it would be about 3470, which is what I'm going for. About 4200.

[B]

Okay. And you're healthy and you've got longevity because your parents are alive, so. Okay. And when you are talking to your partner about this, are we looking at both of you kind of chilling out at the same time? Are you, you know, is something. Could something change in this?

[C]

Yeah, we both want to retire about the same time. He's already cut hours a little bit. And so, yeah, we want to travel and just enjoy life while we.

[B]

Okay, all right. The 60 grand a month that you. I'm sorry, month. Ha. 60 grand a year. Wait, I mean, that's pretty amazing. So the $60,000 a year right now is only going into retirement accounts, Is that what you're telling me?

[C]

Yeah. So the last couple years, I've just been lobbing it all into the brokerage so I have a little bit of money to live off of until I can chip into the retirement accounts.

[B]

Okay, great. So the game plan would be this is what I just make sure everybody gets this. Stacy keeps pounding it out. One more year, three more years of part time. When you go part time, what will that amount be?

[C]

So it'll be about 100,000 a year.

[B]

Okay. And then at age 57, you say, see ya, sayonara, goodbye. And then at that point, living off the brokerage account for a couple of years, is that your game plan?

[C]

Yep.

[B]

Okay, so we make sure you have the money out of there, which you will, because you're saving so much Money now you're 59 and a half. And that is when you're going to start tapping into your traditional retirement account. Right, Right. From there, you will pull, I don't know, six grand a month. Is that probably right? Yeah, I guess so. I think that's about right. Because you have to. You don't have state income tax in Washington state, is that right?

[C]

Correct.

[B]

So you just have to. We just have to worry about paying your federal tax. That's not so bad.

[A]

Right.

[B]

So if you did that I think you should be okay. So you start pulling that money out, let's say for 10, 12 years or 10 or 13 years, you'll, you know, it'll, the pension will kick in. So I'm not even looking at that making a meaningful difference. That pension will kick in, but you'll suck that money out. That traditional account is going to go from being over a million something dollars, and you, you're okay, you're going to spend it down because that's what our goal is, that you're going to start pulling money out of that, you're going to let your Roth continue to go up in value, and then by the time you are 67 or 70, we got Social Security and your pension covers your need. Is that your game plan?

[C]

Yeah, that's pretty close. My only other thought was between those first two years of retirement, before I get into my retirement accounts, would it be worthwhile to just do some small Roth conversions when I have no, I need your money.

[B]

I need your money. Okay, we need that money for sure. Here's what I was thinking. What are you going to do for health care? Do you get health care at fit? You know, like, what's going to happen?

[C]

So I'm a state employee, so I can stay on their health care, but it still costs about a thousand dollars a month for medical, dental, vision, but I can stay on it.

[B]

When you say $4,000 a month, you're not including that thousand dollars or are you?

[C]

I am including that. Well, not currently. So What? I'm. My 4,000amonth now doesn't include health insurance because I'm still employed and it's really cheap.

[B]

Yeah.

[C]

When I retire, I'll be paying $1,000 a month. So I figure my retirement expenses will jump quite a bit with health insurance. Plus I want to travel a lot, so.

[B]

Okay, if I, if I told you I'm a little bit anxious about like five grand a month starting at age 57, do you think you could make do the hundred grand for another year or two after 57 to get you to 59 and a half? Did you hear that pause, Mark? Let me just tell you what she was thinking. No.

[C]

I mean, if I need to, but do you think I need to?

[B]

Here's why I think there's a possibility that you could need to. All right. I don't know what the market's gonna do, but is it possible between now and the next four years that we have a big market sell off and that all of a sudden your, you know, $1.3 million in retirement assets, traditional. And Roth gets lopped into 900 grand. Yeah, I think that could happen. I think that's a good possibility. And if that were to happen and you're no longer working and you're pulling out six grand a month to cover that, or 6,500amonth to get to your expense level that you'll need, I don't know. That could be close. So what I think may be a plan to explore with you and your partner. By the way, is your partner, like, much richer than you?

[C]

No, much less rich than me.

[B]

That's terrible. What were you thinking? What on earth were you thinking, for God's sakes? Okay, so what I would say is this 53 is really young. You could live for 40 years. And is that pension that you have, does that have a cost of living adjustment?

[C]

Yes.

[B]

Okay. So I think obviously once we get into your 60s, you're good, but it's a long time to get there. So 10 to 13 years of just pulling money out of your retirement account is something that can be a little edgy. The way to protect yourself would be to say one of a couple of different things. Do you hate your job or not?

[C]

No.

[B]

Okay, so is it like, I just want to, like, chill out and have less time or. So there's two ways to think about it. One is to like, why am I going part time? I might as well keep making the 150 grand, put as much money away as I can, see where I am. Instead of in four years, think about six years and see what happens. Or you could take the view, I'll work hard for another year and then my part time income. Let's just do that for a longer period. So one of those two things is what I think is going to be the pathway forward for you. That's my guess.

[C]

Okay, so you think if I just stayed full time until 57, that would do it as opposed to going part time?

[B]

I think we have to see. Here's what I'm going to guarantee you.

[C]

Yeah.

[B]

If you do that, you have a better shot of making this work. And you're gonna feel a lot better if in the next four or five years the market collapses and you're making money.

[C]

Sure.

[B]

I think you're just gonna have to retest this. I really do. I think you're gonna have to really see where you are in a few years where you know, what you're making a better sense of, like what the future holds. And, you know, maybe you're gonna say to yourself, eh, I'M gonna go to 100 grand. Maybe you do it, you know, four years. Maybe you work full time for a few years and then you go to 100 grand for a few years, but you get to another place where you are a little bit more comfortable. But I think it has a lot to do with that traditional account. It's going to grow, but it's also going to go down in value at some point. And I don't know how you're going to feel about that. I personally would never want to retire into a bear market. If I had the choice, I would just keep working.

[C]

Okay. Makes sense.

[B]

Right, so. But I think you've done a great job. I think that there's a lot to be said here, and presumably your house is a great asset. So amazing there, you know. This is not a dream crusher situation, is it, Mark? This is more of like a negotiation. Just. Just have a little flexibility, that's all. Yeah, flexibility. Thank you. That's exactly what we need. Mark, I appreciate that you are not married, which makes me want to also ask you whether you've done your estate planning yet.

[C]

Yes. Yeah.

[A]

Great.

[B]

And so is there anything else that's on your mind that we can help you out with?

[C]

I think the only other thing would be for the next four years. You know, I put so much in the brokerage the last few years, I opened the high yield, thinking I would start putting money in there to have some liquidity.

[B]

Yep.

[C]

Would that be the best place to put money over the next four years? Should I put more in the brokerage?

[B]

Well, I mean, I like having liquidity. I like having savings. So I would say, you know, if you go. If you put money up to the match for your current 403B. Right.

[C]

They don't have a match, unfortunately.

[B]

All right, so if you. I would. I would really look at brokerage and high yield savings.

[C]

Okay.

[B]

Those two. That's what I would do for sure. Just to preserve that early retirement optionality. Okay, okay. Okay. If you're like Stacy and me, you want to stop working. No, I'm just kidding. I'm not me. But if you're like Stacy, you want to stop working and you want to see whether the assets that you've built up can suffice, or if you need to think of a couple of different ways forward, get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note, give us lots of detail if you're not going to come on the air, and if you want to Join us. Check the box, Mark. We'll do everything else. Check out all the content that lives on our website because it's there for you. So we have another podcast. It's called Money Watch. We have a radio show, there's a blog, there are videos, there's resources. Everything is on jillonmoney.com you can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. And we always ask that you do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you to tomorrow.

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[D]

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.