Squinting to See Light at the End of the Tunnel

Summary

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Podcast Summary: Jill on Money with Jill Schlesinger

Episode: "Squinting to See Light at the End of the Tunnel"

Date: October 15, 2025

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Episode Overview

In this episode, host Jill Schlesinger, CFP®, is joined by co-host Mark to assist a listener named Richard from South Carolina on his journey to retirement. Richard, who has spent nearly three decades in a high-stress customer service role, seeks guidance on whether he can afford to slow down or retire early given his current savings and financial commitments. The conversation explores burnout, retirement savings strategies, tradeoffs in financial planning, and prioritizing mental well-being—delivered with Jill's trademark empathy and straightforward advice.

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Key Discussion Points & Insights

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1. Burnout in Customer Service and Societal Frustration

• Richard’s Situation: After 28 years in customer service, Richard feels exhausted and disheartened by the increasing anger he encounters daily.
  • Quote:
    • “I get yelled at in grocery stores if I'm in the wrong line.” — Richard (04:44)
    • “It really is exhausting to be in that place. So, I get it.” — Jill (03:27)
• Societal Observations: Jill and Mark observe a noticeable uptick in general irascibility, even in public settings where “everyone is supposed to be relaxed.”
  • Quote:
    • “Within the last week, I saw... elderly people on the street yelling at each other. I'm like, what is going on?” — Mark (03:57)
    • Jill playfully wonders: “If everybody’s getting high all the time, that essentially people are a little more mellow? Like, you didn’t see fights breaking out at dead concerts, at fish concerts. Why is this happening now?” (04:13)

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2. Richard’s Financial Profile & Retirement Goals

• Current Status:
  • Age: 52 (turning 52 end of the month)
  • 28 years in customer service
  • Single, unmarried, no children; fully independent
  • Salary: ~$85,000–$90,000/year
  • Retirement Savings:
    • Roth 401(k): $870,000 (contributing 24% of salary)
    • Brokerage Account: $26,000
    • Cash Savings: $3,000
    • Treasury Money Market: $5,000
  • Homeowner: Home worth ~$530,000, mortgage of $184,700 at 2.625% (ends 2041)
  • Pension: Will pay $500/month
  • Anticipated Social Security: ~$3,300 @ 67; ~$4,000 @ 70
  • Car Loan: $33,700 @ 4.9%, six-year term, double payments currently
• Monthly Expenses: ~$6,000–$6,500
• Healthcare Uncertainty: Concern over coverage if retiring before 65
• Retirement Aspirations:
  • Ideally slow down at 60, fully retire by 62–65, stop aggressive savings, possibly reduce work hours and income to $70,000, eventually down to $40,000 (08:07–09:08)

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3. Jill and Mark’s Action Plan for Richard

• Short-Term Recommendations:
  • Maintain current savings rate for a few more years; possible to reduce later for more flexibility and improved quality of life (10:13–11:31)
  • Prioritize cash/emergency savings over paying down low-interest debt aggressively
  • Stop making double car loan payments; use that extra to build liquid buffers (12:02–13:29)
  • Use tax refunds for cash savings, not additional debt paydown
    • Quote:
      • “When you get that tax refund… bank it. Do not put it away into that car. Don’t pay off the car loan. Just put it in the bank and give yourself…breathing room.” — Jill (13:34)
• Mid-to-Long-Term Framework:
  • By age 60 (eight years out), with continued savings, Richard could have ~$1.6 million in retirement assets (10:13–10:26)
  • At 60, reduce work to ~$70,000/year, phase out retirement savings contributions, supplement income as needed with modest withdrawals
  • Plan to further downshift work hours or income at 62 or 65, using investment assets and Social Security to cover gaps
    • Mark: “He’s not even going to be withdrawing, you know, say 3%—he’s going to be pulling out less. So… there’s not a lot of problems here.” (11:20)
  • Keep an eye on healthcare options and costs for early retirees

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4. Emotional Wellness & Giving Yourself Grace

• Jill’s Emphasis:
  • Prioritize mental health and self-compassion—reduce unnecessary financial pressure
    • Quote:
      • “It would be far more interesting for you to give yourself a little grace here and to allow yourself to, like, breathe and live, especially if you’re not…feeling bad.” — Jill (12:54)
  • Use vacation to reset and prevent burnout.
  • Don’t get hung up on “work-til-you-drop” thinking if the financial foundation is strong

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5. Notable Quotes & Memorable Moments

• Jill, reassuring Richard:
  • “We cannot let him be miserable for 10 more years. We just can’t!” (09:46)
• Mark’s calculation:
  • “If he is gonna work until he’s 60… he’s going to have conservatively $1.6 million by the time he’s 60.” (10:13)
• Richard’s relief:
  • “Just knowing that I'll be able to... reduce the amount of time that I'm putting in…would make things so much better.” (11:41)
• Jill’s signature encouragement:
  • “Change your work, change your wealth, change your life.” (16:31)

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Timestamps for Major Segments

• Listener Call Introduction — 03:14
• Details of Richard’s Career and Burnout — 03:37–04:55
• Financial Assessment and Retirement Savings Deep Dive — 05:09–07:56
• Discussion of Retirement Timeline and Income Scenarios — 07:56–09:46
• Jill and Mark’s Step-by-Step Planning — 10:13–11:31
• Shifting Focus from Debt Repayment to Building Cash Flexibility — 12:02–13:34
• Emotional Support and Practical Next Steps — 14:05–15:22

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Summary of Advice to Listeners

• Prioritize a balanced approach: save diligently now if you’re able, but don’t sacrifice quality of life for future security you may already be building.
• Know the power of gradual change—transitioning to part-time or reduced hours is a viable off-ramp to full retirement.
• If you’re burned out, take steps—sometimes reducing financial pressure (not overpaying loans, saving your refund) can help your mental well-being.
• Reach out for outside perspective—sometimes clarity comes from talking it out.

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Final Thoughts

Jill’s compassionate, actionable advice cuts through the complexity and emotion of retirement planning. The episode is a reminder that good financial decisions are about more than just numbers—they’re also about building a life you want to live.

“We really have to see what’s available for you in terms of medical coverage between 60 and 65... I want to get you to this place where we can slow you down a little bit.” — Jill (14:33)

If you’re facing similar struggles, Jill encourages you to reach out and workshop your plan directly on the show.

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Transcript

[Sponsor/Announcer]

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[Nancy Cartwright]

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[Jill Schlesinger]

Welcome to the Jill on Money Show. It's Wednesday, October 15th and we are here trying to help you make better, less bad, more considered financial decisions. If something is going on in your life, in your real life and it touches money in any way, shape or.

[Sponsor/Announcer]

Form, then please, please get in touch with us.

[Jill Schlesinger]

All you need to do is go to our website, jillonmoney.com that's jillonmoney.com and there you'll see in the upper right hand corner a little Contact Us button. When you click that button, a form pops up. You write us a note. Very easy to do, right? Give us a lot of detail if you don't think you're gonna be coming onto our program live. But if you do wanna come on Live, which is so much more fun, it really is, then please just make sure you check the box and Mark will do everything else. Now while you're on the website, I very much encourage you to subscribe to Jill on Money Live. That's where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content. It's all for 45 bucks for the next 12 months. Our next live web is on Wednesday, November 19th at 7 Eastern Time. Okay gang, you liked her. We loved her. Jana Davis, she is from Abacus which is a wealth management firm on the west coast. She came on as a guest a couple weeks ago and we just said we got to get her back. People loved her and so do we. So she is going to come back and do year end tax and financial planning. It is going to be a robust conversation and it's going to go fast because we are going to Bang out questions one at a time. But we're going to get there and we're going to get through it. And Wednesday, November 19, that gives you plenty of time to make the changes that we think you ought to consider before the end of the year. Okay. Today we are talking to Richard from South Carolina, who's going to tell us why he wants to get in touch with us right now. Richard, what brings you to the program?

[Richard (Caller)]

Well, I'm at the point where I kind of looking to slow down at work. I'm not really, you know, that happy at work. And one of those customer service type jobs where, you know, you kind of get screamed at all the time.

[Jill Schlesinger]

It's exhausting. It really is exhausting to be in that place. So I get it. Let's find out a little bit about you. So first of all, how long have you been in this customer service role?

[Richard (Caller)]

28 years right now.

[Jill Schlesinger]

Oh, my God, you've had it. Has it gotten worse? Has. Have people lost their minds? Basically, yeah.

[Richard (Caller)]

I mean, people have just turned more like, angry. But it kind of happens everywhere you go now. I mean, I get yelled at a grocery stores if I'm in the wrong line. So.

[Jill Schlesinger]

You do. I don't think that's nice. I don't like that at all. Mark, do you get yelled at in grocery stores?

[Mark (Co-host)]

I don't, but I got to be. I got to say, I completely agree. I noticed that people in general are just angrier. And within the last week, I saw on two separate occasions for. For really no reason at all. And these are like elderly people on the street yelling at each other. I'm like, what is going on?

[Jill Schlesinger]

Okay, I have a question about this just in general. Mark and I live in New York City, a place where there is seem to be a lot of people smoking pot or vaping. Okay. And if everybody is doing that, why are we all so uptight? Wouldn't you think that if everybody's getting high all the time, that essentially people are a little more mellow? Like, you didn't see fights breaking out at dead concerts, at fish concerts. Why is this happening now? Okay, somebody is going to tell me what's going on, but we're going to first figure out whether you, Richard, can call it quits. So tell us about yourself. How old are you in this now that you've put 28 years into this place?

[Richard (Caller)]

I am going to be 52 at the end of the month.

[Jill Schlesinger]

Okay. And do you work in a job that has a pension plan?

[Richard (Caller)]

I do have a pension, but it's only going to be like 500amonth.

[Jill Schlesinger]

Okay, well, at least it's something.

[Richard (Caller)]

Yeah.

[Jill Schlesinger]

And if you were to get out of this job, would you do something else? Would you be willing to maybe, you know, make less money doing something else? Just getting some money in the door for another bunch of years?

[Richard (Caller)]

Absolutely not.

[Jill Schlesinger]

No. Did he answer that quickly enough? I mean, okay, absolutely not. So are you independently wealthy? Is what we need to actually answer. So the question I have for you is how have you saved for retirement so far?

[Richard (Caller)]

I've always, you know, my parents have always told me that, you know, it's to start saving right away. And I've been putting 24% into my Roth 401K.

[Jill Schlesinger]

How much is in there right now?

[Richard (Caller)]

Right now it's 870.

[Jill Schlesinger]

Are you married?

[Richard (Caller)]

Partnered, Single, unmarried, childless and single.

[Jill Schlesinger]

Unmarried, childless and single. So we're just taking care of you, which is kind of makes it a little bit simpler. Right. Besides the 401k, what other assets do you have saved?

[Richard (Caller)]

I just have a brokerage account with $26,000. That's it. And then I just have. I mean, I have a savings account with $3,000 or I guess my emergency and $5,000 in a treasury money market account.

[Jill Schlesinger]

Okay. Do you own or rent?

[Richard (Caller)]

I own my house.

[Jill Schlesinger]

How much would you guess it's worth?

[Richard (Caller)]

Maybe around 5:30.

[Jill Schlesinger]

Do you have a mortgage?

[Richard (Caller)]

I do have a mortgage. It still has $184,700.

[Jill Schlesinger]

And what's the interest rate on that mortgage?

[Richard (Caller)]

2.625.

[Jill Schlesinger]

Wow. And how long do you have left on it?

[Richard (Caller)]

It's supposed to end in 2041.

[Jill Schlesinger]

So we got some time. We got some time. So if you were to like, retire right this minute, if you could retire at this minute, how much money would we need to actually pay for your bills and live your life?

[Richard (Caller)]

I think I'm around like between 6600, 500, something like that. I know I could not retire right now. That's not realistic.

[Jill Schlesinger]

Okay, as long as I know that, you know that. But would you like to be able to. To have the ability to retire early? And if that's the case, since you do want that, I know that. What are we shooting for? How many more years?

[Richard (Caller)]

Well, I was hoping like at around 60, I could actually slow down at work and maybe instead of the 24% that I'm putting in, I could reduce that. So I could reduce work. And, you know, I mean, a dream would be like 62, but I know, you know, I don't know what Will be available healthcare wise. So, I mean, if I have to stay until 65, let's try to do.

[Jill Schlesinger]

This the way you want to do it. Let's pretend that at age 60, you. All right, so right now you make how much working full time and disgruntled.

[Richard (Caller)]

Around between 85 and 90,000.

[Jill Schlesinger]

Okay, what would happen? Can you forget. Let's forget that you put any money away Once you're age 60, could you reduce the amount of work you do? Could you actually reduce the amount of work you do so that. So you're. Instead of making 85 or 90, what would be the amount. Amount that you could make and maintain health insurance?

[Richard (Caller)]

I probably end up with maybe 70 or something. I'd probably end up going down to.

[Jill Schlesinger]

Okay, and so at 70,000, at age 60, you would say, I'm going to stop putting money into my retirement account. Let's just pretend that. And you can live on this 70,000, not 100%, because I know your expenses are a little bit more than that. But let's just say that that's doable. Could you reduce it further at age 62? In other words, can you. Can you kind of like say at 60 I go to 70 grand, but then at 62 to 65, I go to, I don't know, 40 grand? Could you do that?

[Richard (Caller)]

I do have the ability to do that, but I'm kind of afraid that I wouldn't be, you know, I mean, is that enough money for me to make sure I pay my house bills and stuff like that?

[Jill Schlesinger]

You're going to be able to do that? Don't worry. We're going to. We're going to make sure you can do that because we would then try to start dipping into maybe some of this retirement money at age 60 to give you that 60 to 65. Do you know what your Social Security benefit is at age 67?

[Richard (Caller)]

Around 3,300, it says.

[Jill Schlesinger]

Do you have the 70 number? Are you in good health?

[Richard (Caller)]

Yes.

[Jill Schlesinger]

Okay, what's this? Do you know the 70 age 70 number?

[Richard (Caller)]

I think it was 4,000 and change.

[Jill Schlesinger]

Okay, so 4,000. Okay. All right, Mark, I'm talking here with our man Richard. He is miserable. We cannot let him be miserable for 10 more years. We just can't. What can we do to get him to age 60 in a more reasonable way and help him continue to save? But maybe not even. Maybe we should stop putting 24% away. Maybe we need to be building up the savings and brokerage. What's your view on this, Mark?

[Mark (Co-host)]

I mean, that's a possibility. But if he is gonna work until he's 68 years from now and he's keep saving at his current rate, you know he's going to have conservatively 1.6 million by the time he's 60.

[Jill Schlesinger]

So then at age 60, at 1.6 million he goes to making 70 grand a year. Okay. And then could, could we essentially take some of the money out at that time? Just not a lot, but a little bit of money out of the pre tax part of his retirement funds and make sure he can float his six to $6,500. And remember the $6,000 in eight years is going to be more. Right. We have to account for inflation, but we're kind of giving you back of the envelope guidance. Do you think that that's kind of the game plan, Mark, to say put money away now, keep putting it away, let the money grow and then at age 60, reduce the schedule, stop putting money or just put money into the mat like to get up to the match but start pulling money out of the net non tax portion of it, meaning the traditional part of it.

[Mark (Co-host)]

Yeah, 100% he'll be able to do that. And he's not even going to be withdrawn, you know, say 3% he's going to be pulling out less. So it was really if he's willing to work and it sounds like he is, there's really, there's not a lot of problems here.

[Jill Schlesinger]

So can you get on board with that? I just worry that if you're like so burnt out right now that you're going to have to do eight more years of this. It makes me worried.

[Richard (Caller)]

We're just knowing that I'll be able to like reduce, you know, the amount of time that I'm putting in. I mean it would be make things so much better.

[Jill Schlesinger]

Well, I think you'll absolutely be able to do that. I think that that's not the problem. I think the real problem is how we can make your life a little bit better today. Do you feel like, do you feel under pressure financially right now?

[Richard (Caller)]

Right now I have a car loan and I've been making double payments on it. And I'm thinking, well maybe instead of that double payment I should put some of that money to either emergency or and some of it to brokerage.

[Jill Schlesinger]

Yeah, I mean, what's the car loan? You didn't mention that. I guess I didn't ask about it. How much is the interest rate on the car loan?

[Richard (Caller)]

It's 4.9. It's $337,000. Is the payment, but it's for six years. Okay.

[Jill Schlesinger]

When's that up?

[Richard (Caller)]

In 2031. I mean, I just got the car this year.

[Jill Schlesinger]

Okay. Oh, very nice. I don't know about paying that off so fast. Like, I would just try to give yourself some flexibility. I wouldn't make double payments on that, certainly. I. I would prefer. Frankly, I would much prefer you having a little bit more breathing room. It seems like you're making yourself a little. You're putting the pressure on yourself, and I'm not sure whether it's worth it. It would be far more interesting for you to give yourself a little grace here and to allow yourself to, like, breathe and live, Especially if you're not, you know, if you're feeling bad. You know, I feel like that's the issue here. Like, if you're really feeling like, oh, my God, this is terrible right now, I don't want you to be in that place. I really don't. So I'd like to try to give you the ability to, you know, breathe and live and not have such pressure on yourself. Do you think you can do that?

[Richard (Caller)]

Yeah, I mean, I'm looking forward to doing that.

[Jill Schlesinger]

Are you the kind of person who gets a tax refund every year?

[Richard (Caller)]

Yes.

[Jill Schlesinger]

When you get that tax refund, a couple of things that I would suggest to you. One is, I would suggest that you take that money and just bank it. Do not put it away into that car. Don't pay off the car loan. Just put it in the bank and give yourself like that. Oh, okay. I see. This is. I have this now. It's like, I can make this work for myself. Like, that's. I want you to just give yourself some breathing room, because it seems to me you're putting a lot of pressure on yourself. A lot. And you don't need to. You really don't.

[Richard (Caller)]

Yeah, I mean, I have some vacation time coming up, so, I mean, I'm kind of looking forward to relaxing a little, kind of resetting for the next year is coming up, so.

[Jill Schlesinger]

Oh, my God, this poor guy. Okay, I think you're in good shape. Do you have anyone else you have to take care of besides yourself? Like you said, you know, you're. You're single and everything, but you have parents who are alive. Is there anyone else you have to take care of?

[Richard (Caller)]

No, my parents, they're fine. They have their place to live, and, you know, I have a sister, and she's fine, so.

[Jill Schlesinger]

Good. Okay. I think you're gonna be okay. Let's get you to 60 and then reduce that amount of work, and then you'll be back in touch with. Maybe things go even better, and you're like, oh, it's 59 and a half, and I can do it. But we have to get you to this place where we can slow you down a little bit. You know, we really also have to see a little bit of, like, what's available for you in terms of medical coverage between 60 and 65. And so if it's like 60 to 62, I work. But 62 to 65, there is some coverage that is, you know, I can make work for me or that you say, you know what? I know I said I'd never work again, but maybe you would work if it was, like, a fun thing. I don't know. I'm just. I want to look at. You're saying no, but it wouldn't be in the same job. Yeah, Mark, he's not buying what I'm selling here. Do you hear that? Not.

[Mark (Co-host)]

And you're typically the. The salesperson.

[Jill Schlesinger]

I know, I know. And. All right, well, we're going to hopefully get you where you want to go. Do you have any other questions right now?

[Sponsor/Announcer]

No.

[Richard (Caller)]

You. You've helped so much. Thank you.

[Jill Schlesinger]

All right, well, we appreciate it, and we thank you for getting in touch with us. So if you are like Richard and you hate what you do, I want to hear from you. I want to get you out of this. Totally. I really, really want you to feel like we can brainstorm a little bit, at least. You know, one of the nice things is when you come on the program, we can talk about and we can hear from you, like, how are you feeling about this? How do you think about looking at it at 60 or 62? And, like, we can workshop this with you. So get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note. If you want to join us live, check the box, and we're going to help you get one wherever you want to go, but you got to get in touch with us. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Don't forget, you should lift someone up. You should do this every day, but do it today especially. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

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[Nancy Cartwright]

Jill on money hi, I'm Nancy Cartwright. You may know me better. As the voice of Bart Simpson on Simpsons Declassified, we're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers, the celebrity guests? Be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.