Are We Ok to Be Work Optional?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Are We Ok to Be Work Optional?
Date: April 24, 2026
Host: Jill Schlesinger
Guest: Listener Linda from Illinois

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Episode Overview

In this episode, Jill Schlesinger takes a listener call from Linda, who was recently laid off after a 30-year career. Linda seeks candid, practical advice on whether her and her husband’s finances can support an early, “work optional” retirement—or if additional part-time work is necessary. The conversation focuses on the emotional and financial aspects of a sudden, unexpected transition from full-time work, evaluating assets, spending needs, and social security timing. Jill provides her signature mix of empathy and straightforward financial guidance.

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Key Discussion Points & Insights

1. Emotional Impact of Unexpected Retirement

Timestamps: [04:23]–[06:00]

• Linda, 59, was laid off from her job after 30 years. While not entirely shocked, she admits to feeling “gut sucker punched.”
• Currently in “work detox”—focusing on rest, health, and self-care. No immediate desire to return to work but is open to something part-time in the future.
  • Quote [05:25]:
    “I'm in a detox, so work detox. Just trying to get sleep again and kind of chill out. I definitely have no desire to go back to work.” — Linda

2. Financial Picture: Assets, Income, and Spending

Timestamps: [06:00]–[11:09]

• Linda and her husband (62, working part-time) have planned for retirement but were thrown off by the earlier-than-expected timeline.

• Annual spending is $12,000–$14,000/month (buffered for safety, includes $20,000/year for travel).

  • Quote [06:34]: “I've been tracking all of our spending and it's between $12,000–$14,000 a month...I always round up because I want lots of buffers.” — Linda

• Key financial assets:

  • $1.8M in 401(k)
  • $350k in traditional IRAs
  • $10k in Roth IRA
  • $55k in HSA
  • $260k in brokerage account
  • $185k in high-yield savings/CDs
  • $300k severance payout pending (lump sum, expected in June; will face taxes)
  • Pension: option for lump sum ($150k) or annuity (about $1,000/month joint life)
  • Home: valued at $600–$650k, owned outright

3. Health Insurance Transition

Timestamps: [08:23]–[09:15]

• Plan: Use COBRA for the rest of the year, then evaluate ACA or employer retirement benefits.
• Retirement health insurance from former employer is pricey (about $2,000/month for both; drops to $1,000/month after husband turns 65).

4. Kids and Extended Family Financial Obligations

Timestamps: [11:09]–[12:46]

• Two grown daughters, both financially independent (besides still being on family phone plan—a humorous point for Jill).
  • Quote [12:27]: “They're still on our phone [plan].” — Linda
    “That is it, that’s the final cord that must be cut.” — Jill
• Parents are still alive but financially secure; Linda not expecting to support them.

5. Income Streams and Social Security Planning

Timestamps: [12:48]–[14:22]

• Husband’s current part-time income: $20–$25k/year.
• Social Security:
  • Linda plans to claim at 67 ($4,050/month)
  • Husband could claim at 65/67 ($1,600/month), but no set plan. Collectively, about $5,600/month from Social Security at full retirement age.
  • Jill stresses the importance of income planning for the years between now and Social Security eligibility.

6. Assessing "Work Optional" Feasibility

Timestamps: [14:23]–[19:50]

• Jill and producer Mark assess Linda’s situation as “…close, a tiny bit close”—enough assets, but high spending and untaxed retirement accounts mean there’s relatively little margin, especially in the gap years before Social Security.
  • Quote [15:44]: “People are gonna hear, ‘oh, they got millions, they’re fine.’ $14,000 a month is what gives me pause. If you told me it was eight or nine thousand dollars a month, I’d say, no problem.” — Mark
• Advice: Ideally, Linda or her husband work part-time (earning $2k–$3k/month) for a few years to bridge the gap and protect portfolio solidity, especially until Social Security starts.
  • Quote [17:45]: “I would feel better if...not this minute, but in a year from now, if you had an ability to just do a little something, two, three grand a month. Do you think that that sounds horrendous right this second?”
    “No, that’s fine.”
    — Jill and Linda
• Roth conversions aren’t optimal right now; drawing down some traditional assets to meet income shortfall likely makes better sense.

7. Emotional Reassurance and Advice for Listeners

Timestamps: [19:50]–[21:57]

• Jill affirms Linda’s instinct to take a post-job “gap year” to recalibrate.
  • Quote [19:50]: “You have earned the right to take your gap year, as the kids would call it...I think that’s the hard part. When you’ve worked in one company for 30 years, it’s pretty remarkable.” — Jill
• Encourages keeping professional network alive in case part-time or consulting opportunities arise.
• General advice to all listeners: Unexpected career changes are common; planning flexibility (“Plan B”) and emotional adjustment are key.

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Memorable Quotes

• [05:25] Linda: “I’m in a detox, so work detox. Just trying to get sleep again and kind of chill out. I definitely have no desire to go back to work.”
• [06:34] Linda: “I've been tracking all of our spending and it's between $12,000–$14,000 a month...I always round up because I want lots of buffers.”
• [12:27] Linda: “They’re still on our phone [plan].”
  [12:28] Jill: “That is it, that’s the final cord that must be cut.”
• [15:44] Mark: “People are gonna hear, ‘oh, they got millions, they’re fine.’ $14,000 a month is what gives me pause. If you told me it was eight or nine thousand dollars a month, I’d say, no problem.”
• [17:45] Jill: “I would feel better if...not this minute, but in a year from now, if you had an ability to just do a little something, two, three grand a month. Do you think that that sounds horrendous right this second?”
  Linda: “No, that’s fine.”
• [19:50] Jill: “You have earned the right to take your gap year...When you’ve worked in one company for 30 years, it’s pretty remarkable.”

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Important Timestamps

• [04:23] Linda joins, shares news of recent layoff.
• [05:25] Linda’s immediate post-work “detox” stage.
• [06:34] Breakdown of current spending and travel.
• [07:20] Details of severance package and tax implications.
• [08:23] Health insurance plan post-layoff.
• [11:09] House, children, and parents’ circumstances.
• [13:42] Social Security strategy and figures.
• [14:23] Jill and Mark run the numbers, discuss feasibility.
• [19:50] Jill gives emotional support and advice for gap year.

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Episode Tone and Style

• Jill’s tone is empathetic, pragmatic, and a touch humorous (especially about parent/child phone plan dependencies).
• No-nonsense: She doesn’t sugarcoat the slight financial gap, but also validates Linda’s need for recovery time.
• Encourages realistic planning, flexibility, and emotional self-care—crucial in unplanned early retirement scenarios.

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Takeaways

• Even diligent savers with “millions” can feel uncertainty in early/unplanned retirement, especially with high spending and healthcare costs.
• Emotional adjustment is as important as financial calculation in major life transitions.
• A modest amount of part-time or consulting work can make a big difference in retirement sustainability.
• Listeners are urged to cultivate a Plan B for unexpected career developments—and to reach out for practical advice without shame or jargon.

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If you’re facing a similar crossroads, Jill recommends revisiting spending assumptions, considering even small part-time income, and granting yourself time to emotionally process career changes—then re-evaluating with clear eyes in a year.

Transcript

[A]

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[B]

Hi. Thanks for letting me join today. I love your podcast, of course. So I wanted to reach out because I just recently was laid off from my job. It wasn't a total surprise, but I had worked there for 30 years. Wow.

[A]

Oh, my God. Okay, but you know what? Even if it's not a surprise, even like, I gotta tell you something, I'm in an organization right now where there's been multiple rounds of layoffs. And I promise you that if, if my name were on one of those lists in these various times, I would have not been surprised, but I was still would have been like kind of gut sucker punched. So I'm sorry that happened to you. So, yeah. 30 years. Wow. How old are you?

[B]

I'm 59.

[A]

Married?

[B]

Yes. My husband's 62.

[A]

Is he working still?

[B]

He Works just part time, a couple days a week.

[A]

Okay. All right. So are you, are you still in the morning mode or are you in activity mode? What's happening for you?

[B]

I'm in a detox, so work detox. So I love that. Just trying to like get sleep again and kind of chill out. I definitely have no desire to go back to work. Certainly I've read ready to retire my career. Okay, kind of let that be. But you know, down the road, maybe in a year or two, maybe I would consider part time. But for right now, I'm definitely in that mode of time to just focus on me, you know, get my life all strained out from a health and fitness and chilling perspective.

[A]

Good for you. It's a lot I have to say. All of my friends who have retired, whether it's their choice or not, have said that that detox period is vital. That like, just to get your. It's like getting yourself back. And it's fascinating to see. It really is that like, I can't wait to figure that out. Mark won't let me retire, so I. I'm not going to need detox from this. It'll be everything else. So have you guys spent a bunch of money in the past and are you nervous about that? Have you saved money? Like, how are you feeling?

[B]

I feel, I mean, we have good savings. This was, I would say probably a couple years earlier than when we had expected. We expected to retire maybe when I was closer to 60 to 62. So it's a little bit earlier. But we do have money saved. We spend about. I've been tracking all of our spending and it's between 12 to 14,000amonth. That's a little bit. It's generous. I tend to always round up because I want lots of buffers. And it does include some traveling because we do traveling now. And so it does have about 20,000 a year in travel. Okay.

[A]

Now did you get a big package out or was it like, here's the door, good luck.

[B]

I did get a severance. It's a year of salary, so that's three, 300,000.

[A]

Okay, and how is that? Is that doled out monthly or is that a lump sum that you got?

[B]

It'll be a lump sum. So right now I'm still technically on the books. There's like a non working period and then. So I'll get that paid out in June and it'll be one big lump sum. So I'm sure we'll have to owe some taxes on that.

[A]

Right. Did you have a 401 at work.

[B]

I did. So I have about a million eight in the 401k.

[A]

That's great.

[B]

And then between. I also had another IRA and my husband does two. And so that's about 350,000 total for those two.

[A]

Okay, traditional.

[B]

Traditional, yep.

[A]

Got it. What else?

[B]

I have a small Roth of 10,000 and then healthcare savings account about 5,55,000.

[A]

Okay, when you get. So right now, when you are severed, what happens for your health insurance? Will you go on cobra?

[B]

I.

[A]

We.

[B]

We will go on COBRA for sure for the rest of the year because we've had so much paid in already for deductions and stuff. But then after the end of the year, I'll evaluate will we go on like ACA or. I still have the option to use the retirement through my company, so I still have all of my retirement benefits. Okay, so they do have healthcare retirement coverage, but the prices they initially gave me is they're pretty much similar to like what COBRA would be. So they're. It's pretty expensive. It's about 2,000amonth for both of us. And then once my husband turns 65, it'd be about a thousand. Okay.

[A]

Okay, so $1,800,000 in the traditional 401k. Three hundred and fifty thousand dollars in traditional IRAs. Between the two of you, small Roth HSA, are you entitled to a pension or not?

[B]

Yeah, so I do have a pension, and right now the lump sum benefit is $150,000.

[A]

Do you have a bunch of choices about annuitizing the pension or is it only a lump sum? Is it a cash balance plan that's sort of shut down?

[B]

No, it has the whole suite of choices. It's just the payout, when I've looked at it, is only about 1,000amonth, and that's one that has a joint so that it would cover my husband if something happened to me. So just based upon the small amount, I always figured we just take the lump sum.

[A]

Okay, fine. How about other money? How are we generating all this $14,000 a month of travel and excitement and fun and detox?

[B]

We.

[A]

What other money have you guys saved up?

[B]

So we have about 260,000 right now in a brokerage.

[A]

Okay, great.

[B]

We'll be getting that severance money, obviously. And then we have about 185,000 in high yield savings and CDs just socked away.

[A]

I love it. Perfect. That gives you a little peace of mind, right?

[B]

Yeah. Yes. Yeah. I took my bonus this year and put it all into the savings just Anticipate in case something happened.

[A]

So, okay, what about your house? You own your home?

[B]

We do, we own our home and so it's worth about 600 to 650 right now.

[A]

Do you think you'd stick around there? Is that your intention?

[B]

Yeah, until we figure out what our kids are doing, our growth. So we have two grown daughters that are all out on their own. And so like we plan to stay here for say certainly the next five to ten years.

[A]

Okay.

[B]

My father's still alive, my mother in law is still alive, and they're nobody nearby. So we want to be around for them. But who knows, who knows? In seven, ten years, who knows where we'll be?

[A]

Any, any need to take care of them besides, you know, sort of the, the being close by financial obligation to them?

[B]

No, they have money set aside. I expect we may get a little bit, you know, but nothing that we're banking on and stuff, but, but nothing that we have to provide for them.

[A]

So they're okay financially is the most important thing. Okay. And the kids are okay also. They're on their own.

[B]

Yes. Parents are launched and on their own.

[A]

What is the key to that, Ms. Linda? Was that good luck or was that what, what, how did we get them launched when so many before them have come and said to me, oh no, we are not, they're not launched.

[B]

I mean, we supported them through their college, you know, we paid for their college and kind of then said, you know, that's it. You know, there's my, one of my daughters has had, you know, job changes and so we had to help her out a month or two with that. But they're pretty independent, they take care of their money and so far, so good, I will admit. They're still on our phone.

[A]

This is the funniest thing. I cannot tell you the number of people who are like sheepishly tell me friends of mine whose kids are like, have good jobs. Oh, they're still on my phone plan. I'm like, I don't understand. That seems like the last. That is it, that's the final cord that must be cut. Okay. So Linda, you said your husband works part time. How much does he bring in?

[B]

About 20 to 25,000 a year.

[A]

Okay. And you don't want to be held to having to do that. Like, you know, he's, he's doing his thing, whatever. It's like he's working for his health insurance. What is it that you think is going to be the most likely path? Like maybe you will, maybe you won't, but I don't want to have to. So we have to figure out if all the assets you have can generate the money you need this 12 to 14 grand a month. Right. And tell us about the Social Security strategy that you. It sounds like a couple of the parents are older, so you've got some longevity.

[B]

Yeah, I mean both of our parents are. One parent died younger and then there are parents that are still alive now are like 85.

[A]

Okay, so what's your game plan? 67 or 70 for Social Security for you?

[B]

I was thinking 67.

[A]

Okay. What's the amount at 67?

[B]

4050.

[A]

Okay. And your hubby?

[B]

We were just thinking maybe 65. I mean there's no magical thing.

[A]

Give me 67 just for the heck of it.

[B]

Do you know his, his is 1600. Okay.

[A]

All right. So you know, in some group of years, five, seven years, we're going to have $5,600 that's coming in. So that's, you know, some chunk of your Social Security. Do you think it's fair to say that by the time 67 rolls around, your husband's going to be done with the 20 to 25 gr?

[B]

Yeah.

[A]

Okay.

[B]

Yeah, we're thinking yeah, until. Or actually maybe 68. Till I turn 65.

[A]

Okay, fine. And so then what we need to figure out is do you have the money that would allow you to just never worry ever again? Like this happened a few years before you had planned on it, but you know, still you do have a bunch of money that has been saved. You're going to have, let's say that this lump sum, 300 probably turns into, I don't know, let's just call it 200 after you pay your taxes. So you'll have 460 in your brokerage and you've got your emergency reserve and then you've got this like 2.4 ish in traditional assets. Right. Oh, and we'll have, I'm sorry, we'll have the pension, also the lump sum pension. 5. So right, that's. Yeah. Okay. So that is 5. So yeah, 2.3 ish in your pre tax and the kids are on their own and your parents are. Okay, so mark 2.3 million. Let's. What would happen if, you know, let's say this year is fine. Right. This year you're going to have plenty of money. You're going to live through. You're going to live on some of the money you have in brokerage, but you're going to be fine. Right. Because this will come, you'll take 100,000 outside of this and make sure you can live on that. And then there'll be the 300. Then the question is, what do we do from 60 to 67? Right. And from 60 to 67. I know you asked about converting to a Roth. I think you might be better off just pulling money out of your retirement account to live on it and just do that a little bit at a time so that you can support yourselves. Now the question is, will you run out of money or not? Mark, you got your magic calculator going. Yeah, it's. It's tough. It's close. I mean, you know, people are gonna hear, oh, they got millions. They're fine. $14,000 a month is what gives me pause. If you told me it was eight or nine thousand dollars a month, I say, no problem. You guys are good. 14,000, it's. It's a big number. Well, also, because the 2.3 hasn't been taxed yet. Right. Okay. So even if we said, you know, let's say that by the time you get there, you're gonna have 2 million, and then you could kind of pull, you know, meaning, like, you'll have 2 million after tax. I'm looking at. And we're going to, you know, pull money out. I think that there is a case to be made that even if you could, Linda, just, you know, do the sort of a similar thing to your husband, like two grand a month bringing in, I think that would be helpful, because I think from 60 to 67 is where we're mostly concerned, right. That you would have. You have a little bit more income, and if you could have, you know, 50 of your 12 or 14 grand set, that would be really helpful. Right. And then from there, like, we're going to have to, like, kind of spread this out because, you know, you could live for 30 or 40 more years. You really could. So I think what it looks like to me is that it's kind of close. I would feel better if, you know, again, not this minute, but. But in a year from now, if you had an ability to just do a little something, two, three grand a month. Do you think that that sounds horrendous right this second?

[B]

No, that's fine. No, that's.

[A]

Yeah. I mean, like, it's. It could even be, honestly, if you figured out how to say, like, hey, I'm going to work three and a half days a week doing something, and you can do that and get some health insurance. That's. I mean, the health insurance is a bear for you guys, it just is. But I think you're gonna have to, you guys are gonna have to come up with, you know, at least a third of your need. That 12 to 14 grand a month between the two of you in your part time income. You can't afford to convert right now because the conversion will eat into your other money. So it would, I think it would make sense to, yes. Pull a little bit of money out of your traditional assets, especially while you're not making as much money. And you know, I might even think about what would happen if you waited till age 70, depending on how things are going. But we'll have a lot of time to figure that out. And if you land in a place where you're like, oh my God, Jill, I'm making, you know, $55,000 part time and I get health insurance, things are going to look better. It's just a tiny bit close. A tiny bit close. And I see why the three more years would have really made a difference. But we, you know, again, you didn't ask for this. You know, this happened to you. What, what do you, how are you hearing this?

[B]

I think that's what I maybe expected you guys to tell me. Yeah. So I'd love to be one of those. It's like, oh my gosh, you've got it made. But I thought too, it's a little bit close. So there may be a period of time that we both do need to do work. The part time.

[A]

Yeah.

[B]

Especially like you said, like, it's the insurance thing and I haven't done research to see like if there's anything else. I'm just kind of staying very conservative on my assumptions and keeping buffers and stuff. But, but yeah, I thought that. Okay, well, just this right now, it's just like I'm so done with working that I just need to like kind of wait it out a year and stuff and then I think I'll have a different perspective on doing a part time job.

[A]

I agree. And I think it is good. You have earned the right to take your gap year, as the kids would call it, and to just, and to kind of like recoup, like just be like, okay, let me get myself back. I think that that's the hard part. When you've worked in someplace and then you worked in one company for 30 years, it's pretty remarkable. So it would, it seems to me that this is a, a well deserved break. Let's kind of see where you land after. Keep your little network alive. I'm sure you've got one. And, you know, it's funny. We were just talking to a guy. Same exact thing happened. You know, he got. He got laid off a year and a half ago. He started a little consulting practice. He's not going to go back to making the big money he did make, but he's like, hey, you know what? I'm doing okay. I'm making it do. I'm covering my expenses. And he's like, I can do this longer than I could have done my other job. And then maybe that's what might emerge for you. Maybe, you know, and if it's all, like, freaking you out too much, you know, we're here for you. So we're happy to talk to you again.

[B]

Okay, awesome. Thank you so much.

[A]

I'm sorry about that. You had to work for a bad place, and maybe it wasn't so bad. But anyway, I'm sorry for your rotten luck. And, you know, when everyone listening, it's funny when we talk to people like labor economist Teresa Gillard Duchy, and she'll talk about this idea that you have an idea about when you want to retire. You don't know what's going to happen in the future. You know, Linda thought she was going to work at this place till she was 62, and all of a sudden she's 59, and something changes. And all of us have game plans. We think we know what we're going to do, but part of the process is reacting to what has happened to you and trying to lay out different opportunities for you. So if that's you and you're kind of like, have an inkling that things could change in your workplace, and you want some help developing your plan B, get in touch with us. Go to Jill on money dot com, click the contact us button, write us a note. And if you'd like to come on the air live, check the box. Mark will do everything else. And remember that you can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. It is Friday. Let's do some business. Our music is composed by Joel Goodman. Mark Tularisio is our executive producer and king of all things web, and we are distributed by the fine folks at Odyssey. Try to lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you on Monday.

[B]

Nerds.

[C]

Today's episode is sponsored by NerdWallet's Smart Money podcast. Ever Google a money question and end up 12 tabs deep with 12 different answers? This podcast is your shortcut back to clarity. NerdWallet's Smart Money podcast breaks down financial decisions with a team of trusted journalists. They explain the why behind decisions like a investing home, buying and choosing credit cards with clear research backed insights. No jargon, no misinformation. Make your next financial move with confidence. Follow NerdWallet's Smart Money podcast on your favorite podcast app. Hi, my name is Lloyd Lockridge and I'm the host of a new podcast from Odyssey called Family Lore. In this podcast, I'm going to have people on to tell unusual and sometimes far fetched stories about their families.

[A]

I've heard my whole life that she invented the margarita and then we're going

[C]

to investigate those stories and find out how much of it is true. He gets a patent one month before the Wright Brothers. Oh my God. Please follow and listen to Family Lore, an Odyssey Podcast available now on Apple Podcasts, Spotify or wherever you get your shows.