Taking Advantage of a Unique Year

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Taking Advantage of a Unique Year

Date: December 26, 2025
Host: Jill Schlesinger
Producer/Contributor: Mark
Caller/Guest: Jennifer (Washington, D.C.)

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Overview

Main Theme:
Jill Schlesinger helps caller Jennifer navigate the financial decisions stemming from an unusual year in her life—one with a dramatic drop in income due to a planned career break—by exploring strategies like Roth conversions, donor-advised funds, retirement contributions, and tax planning. The episode is a masterclass in using transitional years for unique tax and investment opportunities, all discussed in Jill's engaging, practical, and approachable style.

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Key Discussion Points and Insights

1. Jennifer’s Unique Year: The Backstory

• Situation: Jennifer, aged 54, is a former high earner who left her job in August 2024 after 17 years, lived entirely off savings in 2025 (only $40K earned via consulting), and only recently re-entered the workforce with a new (lower, but comfortable) salary.
• Quote:

  “I feel like I have an opportunity to do something with the uniqueness of the year, and I wanted to consult some experts before I do anything stupid.” — Jennifer, [03:30]

2. Career, Income, and Mindful Downsizing

• Previous income: $235,000 base + 25% incentive
• Current income: $190,000 base + 5% incentive (approx. $200K total)
• Marital/family status: Single, no kids, no pets; self-sufficient father; sister recently deceased

3. Living Without a Paycheck

• Used planned savings—no financial stress, enjoyed time off (mahjong, volunteering, hiking, travel).
• Emotional and physical recovery emphasized.
• Quote:

  “It really wasn’t until probably 10 months later that I was really in a place where I thought, okay, I’m ready to go back to work.” — Jennifer, [06:28]

4. Current Financial Landscape

• Retirement savings:
  • 401(k): $940,000 (pre-tax)
  • 457(b): $150,000
• Brokerage: $810,000
• Cash/High-yield savings: $150,000
• I Bonds: $23,000
• Loose cash: $50,000
• Home equity:
  • Value: ~$610,000
  • Mortgage: $210,000 @ 2.99%
• Annual spending (incl. travel): ~$8,500/month (was $9,500 with COBRA)

5. Retirement Contributions & Planning

• Plans to prioritize Roth 401(k) contributions at new job to maximize employer match (8%).
• Has 10-year work horizon; open to longer if feasible.
• Quote:

  “I think another decade of work is probably doable. I like to work. There’s no reason that I need to stop early.” — Jennifer, [10:07]

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Strategic Financial Moves: Jill’s & Mark’s Guidance

6. Roth Conversions: Seizing a Low-Income Year

• Jill identifies the gap year as a rare opportunity to move pre-tax dollars into a Roth account at a lower tax rate.
• Suggests converting the entire 457(b) ($150K) in 2025, paying the tax from cash savings.
• Recommends that Jennifer remains in the 24% tax bracket.
• Quote:

  “My inclination is to try to convert a bunch of this... If we could convert you and stay in the 24% bracket would be very interesting to me.” — Jill, [11:06]

7. Practical Steps for Conversions & Rollovers

• Roll the 457(b) to Vanguard (where her brokerage is), then convert to a Roth IRA.
• Emphasizes urgency to complete this before year-end.
• Quote:

  “Like today. So here’s what’s going to happen... Let’s get this done.” — Jill, [13:56]

• Mark clarifies the mechanics:

  “Yeah, she’s got to roll Lincoln into Vanguard. And once it’s in Vanguard, you’ll see the option to convert that traditional IRA into a Roth IRA.” — Mark, [14:01]

8. Donor-Advised Fund (DAF) & Charitable Giving

• For future years (when income is higher), suggests creating a DAF funded with appreciated assets from the brokerage to optimize charitable deductions and allow for incremental Roth conversions.
• Guidance to gift $20,000/year to DAF, matching Jennifer’s past giving patterns.
• Quote:

  “Maybe you just do like 20 grand a year into your donor-advised fund and that’ll give you a little bit of room to convert because you’re going to take that money off the top.” — Jill, [15:47]

9. Estate Planning: The Emotional Dimension

• Jennifer faced the recent loss of her sister (one of her executors); needs to update estate documents to appoint her niece.
• Jill highlights importance of keeping estate documents current.
• Offers empathy for sibling loss, reminding listeners of the often-overlooked emotional toll.

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Notable Quotes & Emotional Highlights

• On the emotional impact of a career break:

  “It took much longer to get my body to agree to that. It really wasn't until probably 10 months later that I was really in a place where I thought, ‘Okay, I’m ready to go back to work.’” — Jennifer, [06:28]

• On financial security:

  “If I hear you correctly, I’m not gonna become a homeless bag lady?” — Jennifer, [18:02]
  “I’m going to say state affirmatively, there’s no freaking way.” — Jill, [18:11]

• On the privilege and cost of taking a break:

  “Listen, it takes longer to recover from these high stress jobs.” — Jill, [18:38]

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Important Timestamps

• Jennifer’s situation and motivations: [03:26]–[04:56]
• Asset and spending overview: [07:07]–[08:41]
• Discussion of Roth vs. pre-tax strategy: [10:16]–[11:32]
• Roth conversion plan explained and confirmed: [13:00]–[14:13]
• Donor-advised fund discussion: [15:35]–[16:51]
• Estate planning and personal reflection: [17:07]–[18:11]
• Affirmation of Jennifer’s secure future: [18:11]–[18:38]

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Tone & Style

The episode is warm, practical, and occasionally humorous. Jill and Mark are empathetic, candid, and jargon-free, always focused on actionable, savvy advice. The rapport with Jennifer is collegial, supportive, and sensitive to both her financial and emotional journey.

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Conclusion & Takeaways

• Use temporary drops in income as opportunities for strategic Roth conversions.
• Keep retirement and charitable contributions optimized for both current and future tax savings.
• Don’t neglect estate planning, especially after significant life changes.
• Emotional well-being is as important as financial health—take time to recover from big changes.
• With strong savings and discipline, career breaks can be both financially and personally rewarding.

Quote to Remember:

“You’re going to be in great shape. Okay.” — Jill, [18:23]

Jennifer departs reassured, with clear next steps and the confidence to act on what Jill calls “a unique year”—a message relevant to anyone experiencing big changes or contemplating a reset.

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For More

Check out jillonmoney.com for related resources, newsletters, and more content.

Transcript

[Jill]

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[Mark]

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[Jill]

Welcome to the Jill on Money show. It's Friday, December 26th and we are here the day after Christmas. Actually really focused on one thing. You, you, your needs, what's going on, your lives, your money, trying to help you get wherever you want to go. So if you have some thoughts, maybe you have got some time off and maybe you're making a little bit of space for yourself and what you are contemplating for next year. Or maybe thinking about a big issue going on and you'd like us to help weigh in, go to our website, it's jillonmoney.com and in the upper right hand corner there is a Contact Us button. You click that button and write us a note. If you would like to join us on the air. Check the box. It's Very easy to do. Mark will chase you down. While you're on the website, you can check out all the free content that lives there. We've got a free weekly newsletter. We've got another podcast that's called Money Watch. We've got a blog, we've got videos, We've got resources and even a radio show. Yes, there's still Radio Gang Swear. Really is. Anyway, check it out. And if you're thinking about some topic that maybe we haven't covered, Mark and I are very interested in hearing what's on your mind. And so if you have a suggestion for maybe a guest or a topic or anything you'd like us to cover next year, please send that along. We'd love to hear from you. Today we are going to talk to Jennifer, who is on the line with us from Washington, D.C. hello, Jennifer, how are you?

[Jennifer]

Hello, Jill and Mark. I'm doing well.

[Jill]

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

[Jennifer]

Well, I've had a bit of a unique year and so I feel like I have an opportunity to do something with the uniqueness of the year. And I wanted to consult some experts before I do anything stupid.

[Jill]

Oh, I love that. Well, let us find you some experts and then we'll get back to you. Okay. Now tell us what, how old are you?

[Jennifer]

I'm 54.

[Jill]

And tell us about the uniqueness of this year. What has happened?

[Jennifer]

So I'm a former high earner. I would say I left my job for very good reasons last August 2024.

[Jill]

Okay.

[Jennifer]

And I really hadn't. Haven't worked at all in 2025, except I did a little bit of consulting. Only made, I want to say, $40,000 this year.

[Jill]

Okay.

[Jennifer]

I've just accepted a job I started last week and I'm back to my high earning, but less, less than I was making before, but still what I would consider a perfectly acceptable salary. So I have.

[Jill]

Wait a second, Jennifer, when you said you, you know, were former high earner, what were you making? And then what's the new salary I was making?

[Jennifer]

My base was about 235 and I had a incentive opportunity that usually was in the 25% range.

[Jill]

Wow. All right, so that's a lot of money. What's the new job?

[Jennifer]

The new job is 190.

[Jill]

Okay.

[Jennifer]

Only like a 5% incentive.

[Jill]

Okay. But like you probably so maybe like 200 grand a year is probably what you end up. Exactly. Right. Okay. And Jennifer, are you married, single, partnered? What's going on?

[Jennifer]

I am single, no children.

[Jill]

Okay. Makes it Planning a lot easier. Pets. Any pets?

[Jennifer]

No pets.

[Jill]

What? Okay. So in the past year, how did you support yourself?

[Jennifer]

Savings. I planned for this for a long time. I was at my former job for 17 years and there was a planned turnover and I knew it was coming, so I just saved. Socked away the money for a couple of years and just lived off of my savings.

[Jill]

Incredible. How did it feel not to work for a while? Like just take us back in time. What did that feel like? I'm kind of excited to hear this. I hope it's a good thing.

[Jennifer]

It is a good thing. It was something I planned for. It was a dream come true. I am a workaholic, so I was a little nervous about what I would do with myself, but I figured it out. I played a lot of mahjong. I did some volunteering, I went on a lot of hikes, I went on a lot of trips and just. I just lived my life and it was great.

[Jill]

What did it feel like? Like, in your body? Like one of the things. A friend of mine retired and she said to me the thing that was most obvious is just how sleep deprived she was and how she just needed to take care of her physical body. Did you find that as well?

[Jennifer]

Absolutely. And the other thing that I thought was interesting is I thought that it would be just, you know, take a couple of months off and I'd be ready to get back out there. But it took much longer to get that my body to agree to that. It really wasn't until probably 10 months later that I was really in a place where I thought, okay, I'm ready to go back to work.

[Jill]

It's like you had to detox.

[Jennifer]

Yes.

[Jill]

Right?

[Jennifer]

Yes.

[Jill]

Incredible. Okay, so let's talk a little bit about, like, for you, what you are thinking about now going ahead. You can live on your 190 or 200rand a year income. Like, no problem there?

[Jennifer]

Yes, I think so. We'll find out.

[Jill]

Okay, very good. How much money have you saved so far in terms of like. What about retirement? Where's the retirement? The old account from the former employer. Where's that money?

[Jennifer]

Yeah, so I have a. It's all pre tax. That's. That's one of the opportunities that I like your advice.

[Jill]

How much is in there?

[Jennifer]

I have. In a 401k, I have 940,000.

[Jill]

Okay.

[Jennifer]

In a 457b, I have about 150,000.

[Jill]

Okay. And nothing's been taxed yet, which is no Roth. No Roth. Okay. Brokerage account.

[Jennifer]

I have a brokerage that currently has about 810,000.

[Jill]

Wow. Okay. And cash?

[Jennifer]

Cash. Right now, I still have from my Socket away live on it fund. I have 150,000 still in my high yield savings account.

[Jill]

Okay.

[Jennifer]

I have 23,000 in I bonds, and I have about 50,000 in just cash.

[Jill]

Okay, got it. You own your home?

[Jennifer]

I do.

[Jill]

How much is it worth?

[Jennifer]

Zillow says it's worth 650, but I would say in this market, 610.

[Jill]

Let's say six. Let's go crazy. And what about the mortgage? Is there one remaining?

[Jennifer]

Yeah, it's 210,000.

[Jill]

What's the interest rate?

[Jennifer]

2.99%.

[Jill]

So you're not moving?

[Jennifer]

Nope.

[Jill]

Any rental property, vacation homes? Nothing else?

[Jennifer]

No.

[Jill]

And do you have anyone you have to take care of? Care of? I know you said you're single with no pets and no kids, but how about parents?

[Jennifer]

I think my. My father's still alive. I think he's. He's gonna. He's gonna make it all on his own.

[Jill]

And when you were living on your own without, like, except for that consulting income of 40 grand, what were your actual expenses? What did. What did you end up spending? Generally.

[Jennifer]

Generally, my expenses. Last year, including all of my travels, I did the math, and it was about 8,500amonth. It was actually 9,500amonth, but 1,000 of that was Cobra.

[Jill]

Okay. And what are you putting into retirement for a contribution?

[Jennifer]

That's what I haven't figured out yet. They do offer a Roth, so I will be doing Roth. I know Mark will encourage that.

[Jill]

Yes, indeed.

[Jennifer]

They'll match up to 8%, so I'll probably start at 8% and see where things go from there.

[Jill]

That seems perfect. That's fine. Just looking ahead, you took this. Let's call it a gap year.

[Jennifer]

Yes.

[Jill]

Do you have an idea about what it is you think you're going to do in terms of longevity? I know you've just started this job, so it's hard to say, but, you know, do you look ahead and say, listen, I want to do this for 10 years, or I want to do this for five years? Like, do you have a number in your head?

[Jennifer]

I think another decade of work is probably doable. I like to work. There's no reason that I need to stop early.

[Jill]

Okay. Okay. And so now is the big question about converting retirement assets, because now you're in a. Well, I mean, you're in a very low tax bracket for 20, 25, so you do have an opportunity here. Right.

[Jennifer]

How do I convert how much should I convert and is there anything else that I should be doing? Donor advised fund. Donor advised fund. Probably next year, right.

[Jill]

When you're making money. Right. Okay, so the pre tax 940, where is that held, is that at?

[Jennifer]

It's at my former employer's 401k.

[Jill]

Okay. And what about your current 401k, is it a good plan?

[Jennifer]

I have no idea.

[Jill]

Okay. And the 457, same thing is that held? Like is that a Fidelity account or a van?

[Jennifer]

It's a Lincoln Financial Group.

[Jill]

My inclination is to try to convert a bunch of this.

[Jennifer]

Yep.

[Jill]

And you know, listen, I know that you are at, you know, you're single, just go get married. I could expand your tax bracket.

[Jennifer]

I tried that once. It wasn't worth it.

[Jill]

I understand. Never is. But I think if we could convert you and stay in the 24% bracket would be very interesting to me.

[Jennifer]

Yeah.

[Jill]

So here's what I'm thinking. You know, you only you had consulting income of 40, but did you have expenses against that?

[Jennifer]

That excludes the expenses. My actual income was about 47.

[Jill]

Okay, so we have 40 and then like a couple thousand from the new job. Right. So I'm thinking, bear with me here. I'm thinking that maybe you blow out of the whole 457 plan and convert it all this year. Oh, here's why. I mean, you have to just play with these numbers. I don't want to mess with your tax brackets, but I think you can convert that whole thing and stay in 24%. And you have money to pay the tax that that's due because you have all that cash that's sitting around waiting to do something with. Okay. I think Lincoln Financial, they tend to be expensive plans because it's a life insurance company. Okay. And so if you were to get rid of that whole thing, convert it right now and you have that 150 grand of income and then we have your 40 and then maybe a few thousand. I think that keeps you in the 24% bracket. Are you a. An itemizer?

[Jennifer]

Yes.

[Jill]

Okay. So I think that you will be. It'll be fine. I think you'll stay in 24%. Now, of course, you have to pull the trigger fast. Right?

[Jennifer]

Yes, I know.

[Jill]

So the only thing is that if you want another set of eyes, do you do your own taxes or do you have someone do them for you?

[Jennifer]

I do everything myself.

[Jill]

Run it through the mill and make sure I'm not popping you into a new tax bracket. But I think that that's Going to be fine. Then you get rid of that. That's done. And you take advantage of it. You're like, okay, I'm in the 24. You'll be in 24 next year also.

[Jennifer]

Yes.

[Jill]

You know, if you make too much money in that brokerage account, you might just from dividends and income, you could pop up a little bit into 32, but I doubt it. I doubt it just in terms of your income. So I think that that's what I would do right now because that's taking advantage. And let's convert that and let's be done. Now you've got a nice Roth account, right? The old 401K. Is that held? That's not held at Lincoln Financial?

[Jennifer]

No, it's not.

[Jill]

Okay. Do you know where it's held? Just curiosity.

[Jennifer]

I wish I did.

[Jill]

But where do you have your brokerage account?

[Jennifer]

Vanguard.

[Jill]

Okay, great. So at Vanguard, you're going to open up, you're going to convert and open this account.

[Mark]

Like today?

[Jill]

Like today. So here's what's going to happen. I think she has. Does she have to roll over Lincoln immediately?

[Mark]

Yeah, she's got to roll Lincoln into Vanguard. And once it's in Vanguard, you. You'll see the option to convert that traditional IRA into a Roth ira.

[Jill]

Yeah. So you got to get on this. So let's get this done.

[Jennifer]

So I have done the first part of this, which is to open the Roth at Vanguard.

[Jill]

Okay.

[Jennifer]

It has $0 in it right now, but you can.

[Jill]

But what we have to do is we definitely have to get Lincoln to give you the rollover paperwork. And hopefully you can do this like a tape to tape transfer. Now I think that's the number one thing, best thing that you can do right now. And so you'll have some assets, you'll put money into the Roth. Now the question is whether you do more conversions after that. I think that there's like, it depends. You sound like you're somewhat charitably inclined.

[Jennifer]

Yes, I am.

[Jill]

I think that there is an opportunity for you to kind of wait and see a little bit. You could convert a little bit. Like if every year you said, well, you know, I'll convert a little bit of that $940,000. Right. And I'll put. Make sure I stay in the 24% bracket. But every year you have a possibility of doing. Even if it's 20, 30, 40 grand a year, I would just keep doing that and you can stay in the 24%. Eventually you'll be able to use your pre tax account to do qualified charitable distributions. But you gotta be seventy and a half to do that. So then the question is, should you open up a donor advised fund with your brokerage account? How much do you usually give on an annual basis? Do you know, like a general.

[Jennifer]

Well, this year less. Just because I was trying not to be a homeless bag lady, but in the past, I would say 5,000 a year to 10,000 a year.

[Jill]

So one thing that you might want to think about is that you could potentially, let's just say that you take your old 401k, you can roll it into Vanguard, by the way. Also, I would like, I would get everything consolidated nice and neat. But what you could do is you could start taking low cost basis assets from your brokerage account. Maybe you just do like 20 grand a year into your donor advised fund and that'll give you a little bit of room to convert because you're going to take that money off the top, right. And then you're going to have a little bit of room to convert. I think that could be a kind of a good game plan. You should definitely, you know, again, you. If you needed to talk to somebody about it or. But you. It's pretty easy to do because you know it's going to say, okay, I'm taking a charitable deduction of a certain amount for this year for 20, 26. And then you'll see what your taxes look like if you kind of run it with that. And then you'll see how much room you have to do your conversions.

[Jennifer]

I like that.

[Jill]

That's a good idea, right?

[Jennifer]

Yep. I knew there was something I was missing here. And you've put the pieces together.

[Jill]

I don't know if there's real. I'm sure I'm missing things. Let me ask you another question. With all this dough, you got your estate documents done?

[Jennifer]

Yes.

[Jill]

That does not sound. Mark. We believe that sound like. Does that sound like she just. L I hope that I have my estate documents done so she won't ask me.

[Jennifer]

I have them done. I have a problem though, because one of the executors has passed away. So I need to. I had two executors and one of them was my sister. She just passed away last year, which is the other reason why I did this gap year. So I need. I need to update them with now her daughter as my executor.

[Jill]

Okay, well, that's an easy update. I'm so sorry for your loss.

[Jennifer]

Thank you.

[Jill]

Terrible. Just terrible. So much loss out there. It's gonna be, you know, I think that thankfully you were able to take some time, take care of her, take care of you, and I think the next part's gonna be pretty easy for you, I'll tell you that much, Jennifer. So any other questions for us?

[Jennifer]

So not to open a can of worms, but if I hear you correctly, I'm not gonna become a homeless bag lady.

[Jill]

I'm going to say state affirmatively, there's no freaking way.

[Mark]

You're $2 million now. You're going to be working for another decade. You're going to have over $3 million. You're only spending, you know, 8,500amonth.

[Jill]

Yeah. And you're going to get 70. Your Social Security is going to be 3,4000 bucks. Then you're going to have all this money that we can use. It's going to be perfect for you. You're going to be in great shape. Okay.

[Jennifer]

Music to my ears.

[Jill]

And I'm glad that you were able to take this time. Good for you. Really. Yes. Thank you everybody. Listen that it takes longer to recover from these, these high stress jobs. Mark. I'm going to take a long time. I'm going to have no time to recover. None. None.

[Mark]

Recover from what? From which one?

[Jill]

Cbs.

[Mark]

Cbs. Okay. I just wanted to make sure I'm.

[Jill]

Not recovering from you. You're like the fun part. Come on. What a great. It's a great story. Except for the sister passing away. That sucks. I always get very. I always get like a little bit of emotion like went around like sibling loss. I don't know why. Because it's like unimaginable.

[Mark]

You're close with your sibling, that's why.

[Jill]

Yeah, but. No, but it's like because when you have a sibling who passes away, it's like the focus is always on the spouse or the kids. It's like the sibling kind of gets short shrift in all the. I don't know, it just seems horrible. Horrible. So I think it's so nice that she got to take some time with her sister. Anyway, don't want to be a downer here. It is the holiday season and you know, I do think that we always miss the people who aren't around for these periods of time. So hope you go out and hug anyone close to you and be grateful for what you have. If you need some financial assistance, we are happy to assist you. Go to jillonmoney.com Click the Contact Us button. Join us on the air by checking the box. Sign up for the free weekly newsletter. Check out everything that is going on on that website. Hey, my book the Great Money Reset. Feels like there's a lot of people resetting their lives. And if you want to learn the 10 Bol Bold steps to turn chaos into opportunity, you can check out that book. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen. Hey, it's Friday and it's the Friday after Christmas, so we're gonna do extra special thanks. First of all, thanks to you guys because this show is only possible with you. Our music is composed by Joel Goodman. Mark Telerso is the best executive producer in the whole wide world. He's also the king of our website. We are distributed by the lovely folks at Odyssey and we very much appreciate them. We ask that you lift someone up. It's in the spirit of the time and every single day we want you to do that. Change your work, change your wealth. Change your life. Thank you for listening and we'll talk to you on Monday.

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