Can I Retire in Four Years at 60?

Summary

Podcast Summary: Can I Retire in Four Years at 60?

Jill on Money with Jill Schlesinger
Date: June 9, 2026
Guest: Jane from the Midwest
Host: Jill Schlesinger

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Episode Overview

In this episode, Jill Schlesinger, CFP®, takes a call from Jane, a 56-year-old listener from the Midwest, who is eager to retire at 60 due to job burnout and health concerns stemming from work-related stress. Jill walks Jane through her financial situation, discussing her assets, expenses, retirement planning, and the feasibility of retiring in four years. The episode focuses on real-world retirement planning, the challenge of early retirement with no pension, and strategies for bridging the gap to Social Security and Medicare.

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Key Discussion Points & Insights

1. Jane’s Motivation and Background

• Reason for Wanting Retirement: Jane feels "a bit fried" (04:34) from a stressful job that is negatively impacting her health.
• Personal Situation:
  • Single, no children, no pets (allergic)
  • Two financially stable, aging parents; possible but modest inheritance (05:15)
  • No imminent financial family obligations

2. Jane’s Financial Snapshot

• Retirement Accounts:
  • $1.6M in 401(k) (mostly traditional, $71K in Roth) (05:33–05:50)
  • $21K in Roth IRA (backdoor contributions) (06:03)
• Brokerage & Liquid Assets:
  • $415K in brokerage (05:55)
  • $207K + $77K = $284K in high-yield savings (06:16–06:28)
  • $14K in checking (07:45)
• Home Ownership:
  • House worth ~$650K, with $80K mortgage at 4.125% (07:10–07:23)
• No pension (08:12)
• Income & Savings:
  • Maxes out 401(k) + catch-up (08:34)
  • Regular additions to brokerage from bonuses (10:37)
  • Total annual savings (incl. bonuses): $100–150K+ (11:02)

3. Spending and Retirement Projections

• Current Spending: ~$9,000/month (07:53), not including health insurance
• Adjusted Retirement Spending: Likely $10,000/month to include healthcare (~$120K/year) (12:09–12:14)
• Healthcare: Intends to use ACA exchange before Medicare at 65 (08:24)

4. Longevity and Health Considerations

• Family Longevity:
  • Mother's side: late 70s
  • Father's side: into 90s (09:01–09:15)
• Jane’s Health: Chronic issues worsened by job stress; concerned about future mobility (09:16–09:25)

5. Social Security Strategy

• Estimated Benefits:
  • At 67: $4,008/month (11:33)
  • At 70: $5,119/month (11:36)
• Strategic Consideration: Delaying benefits until at least 67/70 could materially boost monthly income

6. Jill’s Retirement Analysis and Recommendations

• Shortfall Challenge:
  • Need to withdraw roughly $120–150K/year (plus taxes) from savings for ~7 years pre-Social Security to cover expenses and healthcare (12:13–12:14)
  • Building the nest egg for four more years will help, but market risk remains
• Bridge Income Solution:
  • Strongly recommends Jane seek a less stressful, part-time job after 60 to:
    • Defray early retirement withdrawals
    • Possibly secure health insurance
    • Maintain routine/structure (14:25)
  • "If you could figure out how to make $50,000, $60,000 a year and maybe do something where you get health insurance, I think that will defray so much of the cost of those first few years." – Jill (13:37)
• Savings Strategy Adjustment:
  • Advises Jane to move a portion of her high-yield savings ($150K of $300K+) into investments for better growth (15:47)
  • Suggests gradual dollar-cost-averaging if Jane is nervous about markets (16:17)

7. Psychological & Lifestyle Considerations

• Importance of Transition:
  • Jill emphasizes that “going from what I’m doing now to nothing… there’s no way,” highlighting the challenge of abrupt retirement for high performers (14:30)
  • Partial retirement or a career pivot can provide financial relief and support well-being

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Notable Quotes & Memorable Moments

• On financial conservatism:
  "I like a person who fears Armageddon. My kind of gal." – Jill (06:28)
• On risk aversion in investing:
  "I'd be much richer if I had a better risk tolerance… but I wish I weren't. But that is definitely how I…" – Jill (06:36)
• On partial retirement:
  "If you could figure out how to make $50,000, $60,000 a year and maybe do something where you get health insurance, I think that will defray so much of the cost of those first few years. And then I think you can do it." – Jill (13:37)
• On making a gradual transition:
  "I can't imagine going from what I’m doing now to nothing…there’s no way." – Jane (14:30)
• On shifting high-yield savings to investments:
  "300 grand is a lot. Even if they can do, that's a lot of money to have on hand. So…could you live with 150 and get the other 150 invested? That would be great." – Jill (15:47)
• On work-life balance:
  "Change your work, change your wealth, change your life." – Jill (17:04)

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Timestamps for Key Segments

• [04:12]–[05:22]: Jane introduces her retirement concerns and personal situation
• [05:33]–[07:45]: Detailed review of Jane’s account balances and assets
• [07:53]–[08:14]: Spending patterns and lack of pension
• [08:24]–[09:25]: Health insurance and health/longevity considerations
• [10:37]–[11:09]: Bonus saving strategies and risk-averse cash management
• [11:27]–[11:41]: Social Security estimates
• [12:09]–[14:25]: Jill calculates retirement drawdown needs and the value of supplemental income
• [15:34]–[16:17]: Discussion on re-allocating excessive cash savings to the market
• [14:30]–[14:32]: Jane affirms psychological need for a gradual retirement (“There’s no way [I’d quit abruptly]”)

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Actionable Takeaways

• Jane is well on track to retire in four years, but a “soft landing” (via part-time work) is advised to cover healthcare and reduce portfolio drawdown risk.
• Gradual portfolio rebalancing from high-yield savings to investments is recommended to keep pace with retirement needs.
• Jane’s disciplined saving and conservative financial management put her in a strong position, but continued incremental planning (and flexibility) are key.

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Conclusion

Jill reassures Jane that her plan is close to viable, especially if she incorporates some post-retirement income to ease the transition and mitigate early withdrawal impacts. The episode ends on a supportive note, encouraging listeners facing similar pre-retirement burnout to plan both financially and emotionally for a balanced next chapter.

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For additional resource links, live webinar info, and archive access, listeners are directed to jillonmoney.com.

Transcript

[A]

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[B]

Hello, Jill and Mark. Thank you so much for taking my call. Of course. So I'm, I'm 56, and I'm wondering if the first question is if 60 is if I can retire at 60.

[A]

Are you fried? Are you unhappy? Like, what's the. What's the source of the I want to get out at 60 question?

[B]

It's a bit fried. Stressful job. And stress is, I think, having an impact on my health.

[A]

I hate that for you. Yeah.

[B]

Yeah.

[A]

Okay. Are you married? Partnered? Single?

[B]

Single. No kids.

[A]

Okay. Pets?

[B]

No pets. Allergic.

[A]

Oh, my goodness. Okay. All right. But it's just you. And so in some respects, that makes it kind of easy. Unfortunately. No one else saving for you, but hopefully you save enough for yourself. So. Oh, let me ask you this. Do you have aging parents that you have to think about?

[B]

I have two that are left, and they're financially okay.

[A]

Does that mean you might inherit some money?

[B]

Perhaps, but maybe not probably much because there's several of us siblings.

[A]

All right. This is when you really say, like, oh, if I were an only child. No, I'm just kidding. All right, so, Jane, let's talk about the money that you have saved. Tell us a little bit about that.

[B]

Okay, so I think the first one is my biggest one, and that's my 401k. Currently I've got about 1.6 million.

[A]

Wow. Great. Awesome. Is it mostly traditional?

[B]

Yeah. The only part That's Roth is $71,000.

[A]

Okay. What else? $1,600,000. What else you got?

[B]

I also have a brokerage account of $415,415.

[A]

Okay, great. What else?

[B]

I have a, I've been doing a backdoor Roth IRA at $21,000.

[A]

Any cash? Like, you know, kind of a slush fund for yourself, something I do, Yeah.

[B]

I, I've been a little nervous with the volatility recently, so I have probably way too much in my high yield savings accounts. One is at 207 and the other's at 77.

[A]

I like a person who fears Armageddon. My kind of gal. Right, Mark?

[B]

That's what I figured. We're, we're aligned there, Jill.

[A]

Yeah, I, I, I'd be, I always say to people I'd be much richer if I had a better risk tolerance. I really would be. I thing is, you may be like me in that since you said three careers. I'm willing to take risk in a career like that. I'll make take a risk for, but I'm kind of wimpy when it comes to investing. It's too bad, but I wish, I wish I weren't. But that is definitely how I.

[B]

Well, especially as you're kind of trailing towards the retirement piece then, you know. Yeah, I used to be all stocks. Now my 401k, 70, 30.

[A]

Oh, okay. That seems quite reasonable. Do you own your home?

[B]

I do.

[A]

How much is it worth? Would you guess?

[B]

About $650,000.

[A]

Okay. Is there a mortgage outstanding?

[B]

Yes. $80,000.

[A]

That's it?

[B]

That's it.

[A]

Okay. What's the interest rate?

[B]

It's currently 4.125. It is an arm next, or the adjustment will be in 2032.

[A]

Okay, so you're good. You're good. All right.

[B]

Yeah. I mean, I've resisted all urges to pay that off.

[A]

Yeah. Well, let's see how you, you know, maybe eventually. Any other assets that we have not covered here?

[B]

Well, I have 14,000 in a checking account.

[A]

Okay. What about the big question? How much do you spend?

[B]

Well, that's a really good question. I think it's probably an average of 9,000 okay.

[A]

And is that. That's not going to change for any reason? I mean, I guess if you didn't have the retirement, the mortgage. But nine is probably a decent number, right?

[B]

I think so.

[A]

Will you be entitled to any pension?

[B]

Unfortunately, no.

[A]

Okay. And if we could figure this all out and you do reach the age of 60, how would you then get health insurance?

[B]

Yeah, I'd have to go to the exchange and purchase it.

[A]

And how much are you contributing right now to your big humongo? 401k.

[B]

I max it out and do the catch up.

[A]

How's your health? Just like, how are you in your, like, longevity? Is there any health issue that might change how we would approach your Social Security claiming strategy?

[B]

For me, I think as far as, like, the parentals on the mother's side, she and her family for the most part pretty much have lived into their upper 70s and that's it. On my dad's side, their longevity is there. I mean, he just turned 80 and they're in there. His parents died in their 90s. For me.

[A]

Let's talk about you.

[B]

Yeah, for me. So it's a mixed bag there for me. I have some chronic issues that I deal with and I think stress from my job is making them worse.

[A]

Yeah.

[B]

And it could end up affecting mobility and, you know, so I don't. I don't want to.

[A]

I get you. So, Jane, if you were to work for four more years, is there any way that you could work part time or, you know, scale back but have some money coming in?

[B]

Yes, I thought about that. I thought about doing something that would be part time at least, so that. Or even a less stressful new career.

[A]

Okay. Look at her changing again. Four. Four is good. Okay.

[B]

It's about time. Okay.

[A]

And so right now, again, we have no idea what markets are going to do, but you have just over 2 million. I'm not even going to talk about the, the cash on hand, but you got 2 million bucks. If you work for four more years, that 2 million will grow. Plus you're putting a lot of money away. Right. Because you're doing the catch up. Is there any other money that you're putting away? Like, if I looked at your cash flow right now, I didn't really ask you how much you earn right now, but, like, if I just looked at the cash flow. Are you adding money to your brokerage account on an ongoing basis?

[B]

Yes, I get some bonuses at work and I tend to throw those into the brokerage account. Except for recently, I've thrown it in high Yield savings. Because I've been nervous.

[A]

Because you're a wimp. I love that. Again, we've already covered. Would you say that in addition to this, whatever, 32 grand you'll put away this year? 32. 5. How much more are you putting away?

[B]

That's a good question. I would say probably maybe 100 or 150.

[A]

Wow.

[B]

Yeah.

[A]

Holy smokes.

[B]

So I'm trying to build these things up.

[A]

I mean, well, you're doing a great job. So if you say so, we'll have 130 grand for four more years or even, let's just say three more years. Right? That's great. That's really good. Right. Have you looked at your Social Security benefit yet?

[B]

Yes.

[A]

What do you look at for 67 and 70, just out of curiosity?

[B]

67. It's $4,008.

[A]

Okay.

[B]

Let's call it $4,000 and 70 is 5,119.

[A]

Wow. What a jump, huh?

[B]

It's a big jump.

[A]

I guess it would depend really, about how you're feeling, but. Okay, so here's what we have to do. We get you done at 60, right? You've got, let's say, 2.3 ish, $2.4 million building up. Building up. We have to pull money out of that until we get you to age 67 again. You said $9,000 a month. Does that 9,000 include your health insurance or not?

[B]

No.

[A]

Okay, so it's really 10. Let's do 10.

[B]

Okay.

[A]

So we got to pull out 120 grand a year from your accounts, which is fine. I mean, we do need to get money out of that 401k account. Might as well pull it out, right? If we pulled out 150 grand, it's probably more like 180, because we have to pay tax on it. I know you hate that, but it does happen. So we have to do that for seven years. Then you would have to claim Social Security. Then that's 4,000. It's close. Here's what I think, Jane. I think that your job in the next four years is to keep doing your terribly stressful job, but hopefully take a deep breath while you're doing it, and know that from 60, if you could figure out a way to earn just a little bit of money, even if it was like a different career, a different something. You know, like, if there was a way that you could scale back, okay, make some money. You know, you make. You obviously make a lot of money. But I think that if you could figure out how to make 50, 60 thousand dollars a year and maybe get. Do something where you get health insurance. I think that will defray so much of the cost of those first few years. And then I think you can do it again. If you figure out this, this may change for you, Jane, because it may be that, like you've killed it over the next four years. You didn't save, you know, 130 grand. You saved 200 grand a year. The markets were on fire. Everything looks like. I'm not saying you can't do it. I'm just saying that where we are today, if we were to be somewhat more conservative, just about the future, I would think that having some income from 60 to 65 just to get you to those Medicare years and not take quite as much money out of the retirement accounts, then I think it will looks a lot better. Again, not saying it's impossible. I just want to give you kind of like the, the best possible hope to get you there. And I think that's the right approach, which is, you know, it may work out great today. I would count on trying to figure out what could I do for some bunch of years less stressful, but making some money.

[B]

I agree with that. How does. I can't imagine going from what I'm doing now to nothing.

[A]

Zero. Right.

[B]

Right.

[A]

Okay.

[B]

There's no way.

[A]

So, all right, so this is not the worst news. I haven't been a dream crusher, right?

[B]

No, not at all. Not at all.

[A]

See that, Mark? I thought I was a dream crusher. But Jane, you. Have you done your estate planning? Have you.

[B]

Of course.

[A]

All this? Yeah, of course. She says, come on, don't be silly.

[B]

I have on my estate plan.

[A]

All right. And is there anything else that you need from us at this point? I think you're in great shape. And even if you stopped 60, 62, you worked a little bit and things are really good. Like you might say, maybe you figured out a way and you don't make as much money for the next four years. Maybe you can talk to the bosses and see, like it's so stressful. So this. If you really want me to work longer, then you know what, then I can do it. If. But you got to ease up on where I am today. But I don't know if that's the kind of place you work. You know, with my place, it would be like, goodbye.

[B]

I'll see what I can do with that.

[A]

Yeah, I don't know. We'll see.

[B]

One other, one other question that I had with the money I have in my high yield savings.

[A]

Yeah.

[B]

And I know you and I are aligned on the conservative approach, but, I mean, I realize now I've got close to 300 in high yield savings, and I should probably pop it in brokerage, is what I'm thinking. Or at least a portion of it.

[A]

Yeah, yeah. And you don't have to do it all at once. If you're freaked, you know, you can say. But you know, you can Dollar cost average a little bit every month. You could say the next, when I get a bonus. If you're. Instead of putting it in the high yield savings, you can put it in the brokerage. But, you know, I think that having, you know, 300 grand is a lot. Even if they can do, that's a lot of money to have on hand. So maybe half that. Could you live with 150 and get the other 150 invested? That would be great.

[B]

Okay, that would be great. I can do that.

[A]

All right. Just a little at a time. It's no problem. Yeah, you can do 20 grand a month. Just dollar cost average if you get. If you get nervous about it.

[B]

Okay.

[A]

All right.

[B]

That sounds good.

[A]

All right, Jane, go get them, girl. Go find. Thank you so much. Go find that off ramp. If you're like, Jane, you need a little off ramp. You're fried. Oh, man. People are fried right now. And I hear it. I get it. And doesn't. You know, it's interesting, Mark, We. We often will hear from people who are fried and they're in their 50s, sometimes they're in their 40s. Kind of depends what you do. And if you need to try to figure out your next best move, get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And if you want to come on the air, check the box. Mark will do everything else. Don't forget that all of our content [e-mail] so that's where you should be bookmarking us. Do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening, and we'll talk to you tomorrow. Are you really buying a car online on Autotrader right now?

[B]

Really? At a playground? Yeah, really. Look at these listings from dealers.

[A]

Wow, your search can really get that specific.

[B]

Really?

[A]

And you just put in your info

[B]

and boom, car's in your budget. Mom needs a second. Honey, you can really have it delivered. Really? Or I can pick it up at the dealership. One sec, sweetie. Mommy's buying a car.

[A]

Mommy, I think your kid is walking up the slide.

[B]

Kyle.

[A]

Again?

[B]

Really?

[A]

Auto trader? Buy your car online.

[B]

Really?

[A]

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