Is Early Retirement an Option for Me?

Summary

---

Jill on Money: "Is Early Retirement an Option for Me?"

Date: June 2, 2026
Host: Jill Schlesinger, CFP®
Guest/Caller: Marie from Western New York

---

Episode Overview

In this episode, Jill Schlesinger takes a live caller, Marie, who is contemplating early retirement at age 58. Together, they explore Marie’s finances, motivations, and strategies for retiring before the traditional age, as well as the pros and cons of claiming Social Security early. Jill provides practical advice on how to bridge the gap until Marie turns 62, how spending and work flexibility can impact her retirement readiness, and the importance of estate planning.

---

Key Discussion Points & Insights

1. Marie’s Background and Motivation

• Marie: 58 years old, single, no kids, recently started a new job
• Why consider early retirement?
  • Wants more control over her time and to pursue interests outside of work
  • Not driven by workplace burnout, but by a desire for autonomy
• Jill’s Reaction:
  • “I like a woman with a lot of things to do, I gotta tell you. I mean, I really do.” [04:59]

---

2. Marie’s Current Financial Picture

• Income: $90,000–$100,000/year

• Pension: $200/month, starting now (her “cappuccino budget”)

• Retirement Savings:

  • Traditional IRA: $365,300
  • Inherited IRA: $67,000 (required minimum distributions apply)
  • HSA: $7,000
  • Brokerage: $60,000
  • 401(k) at current job: $1,400
  • 401(k) from previous job: $125,000 (plans to utilize Rule of 55)
  • Emergency Fund: ~$35,000

• Housing:

  • Owns home (wants to stay)
  • Mortgage: $16,000 remaining at 3.62%
  • Home value: $300,000

---

3. Retirement Income Planning

Social Security

• Earliest claim at 62: $1,700/month (Marie conservatively estimates $1,400 after Medicare taken out)
• Jill’s Advice: Consider delaying Social Security for a higher monthly benefit if health allows.
  • “I want to know if this is like you—there are certain hills I’m not going to die on. If you’re like, I’m taking it at 62 no matter what…” [06:24]
• If health is a concern: Drawing at 62 may be reasonable
• Jill urges Marie to check SS benefits at 65 and 67 for comparison

Retirement Withdrawals & Work

• Short-term Plan (58–62):
  • Use Rule of 55 to withdraw from $125k former 401(k) without penalty
  • Supplement by earning $1,000/month through part-time work (Marie agrees this is reasonable) [09:10]
  • Spend $2,500/month (includes health care, which is covered)
• Jill’s Analysis:
  • The $125k will be “drained” by 62 to cover living expenses [11:21]
  • After 62, Social Security will cover part, and the rest comes from retirement/brokerage accounts

Spending Rate & Flexibility

• Jill: “The only way to really change the calculation here is to really focus on what you can control: When do I retire, and what do I spend?” [13:32]
• Marie’s Budget: $2,500/month (conservative, includes health care)
• Jill’s Recommendation:
  • Ideally, work two more years to add savings and shorten the period of heavy withdrawals before Social Security
  • Even after 62, consider earning $1,000/month for more financial cushion

---

4. Important Planning Considerations

Social Security Claiming Age

• Jill: “You’d be surprised that the numbers [Social Security benefit] start to go up pretty dramatically” at 65 and 67. [14:35]
• Marie: Will check her benefit estimates for later ages

Estate Planning

• Jill: “Do you have your estate documents? You got a will?” [14:37]
• Marie: No, plans to get it done within a few months
• “Why? I liked you. All of a sudden I liked you and then I turned on you. Vicious. Get that done.” [14:44]

---

5. Notable Quotes & Memorable Moments

• Jill, playfully, about the small pension:
  • “Is that like your cappuccino budget?” [04:32]
• On prioritizing time in retirement:
  • Marie: “I want more control over my time. There's other things that I want to do that work is just interfering in.” [04:51]
• Jill on managing withdrawal period risks:
  • “If you worked for even just a couple more years, it would prevent you from pulling money out of the 401(k). You’d save a little bit more money and then you could do the same scenario and then see if it works.” [13:48]
• Jill on estate planning:
  • “All of a sudden I liked you and then I turned on you. Vicious. Get that done.” [14:44]

---

Timestamps for Key Segments

• [03:56] Caller Marie introduces her early retirement question
• [04:38] Marie explains her reasons for wanting to retire early
• [05:21] Discussion of Marie’s retirement accounts and pension
• [06:01] Social Security planning and discussion of ages/strategies
• [07:41] Clarification of 401(k) accounts and use of Rule of 55
• [08:48] Decision to supplement early withdrawals with part-time work
• [09:50] Marie’s plan for covering expenses from 58–62
• [13:32] Jill highlights levers Marie can use (working longer, spending, timing Social Security)
• [14:37] Importance of estate planning
• [14:54] Marie agrees to act on estate documents

---

Actionable Takeaways

• Check Social Security estimates for ages 62, 65, and 67 before deciding when to claim.
• Consider working two more years, if possible, to bolster retirement savings and reduce drawdown risk.
• Maintain part-time income after retirement to relieve pressure on savings.
• Get estate documents (will, healthcare proxy, power of attorney) in place soon.
• Plan spending carefully—$2,500/month is reasonable given current assets, especially with health care covered.

---

Conclusion

Jill encourages Marie—and listeners—to take an honest, nuanced look at retirement readiness, emphasizing controllable factors like spending and retirement age, and the outsized impact Social Security timing can have over the long term. Marie leaves with clear action items and encouragement to secure her financial—and personal—future.

---

Transcript

[A]

Today's episode is brought to you by alma. I think a lot of people put off therapy not because they don't want help, but because finding the right therapist feels like such a process. I know I've experienced that, digging through options, trying to understand insurance, and not knowing if I'd actually click with someone. ALMA simplifies all of that. They've built a network of over 26,000 therapists nationwide, and you can browse their directory without signing up. You can filter for exactly what you're looking for, whether that's someone who shares your background, specializes in something specific, or takes your insurance. Clients with insurance pay $20 on average, and 98% of Alma therapists accept insurance. And with their free insurance cost estimator, you'll know exactly what you'll pay before your first session. Most people find their match on the first try, and 95% connect with a therapist within a week. Over 80% of people report female feeling better within six months. Get started now at helloalma.com money that's helloalma.comm o n E Y. You know, I always say to make smart financial decisions. So let me ask you this. What exactly is that old car in your driveway doing for you right now? Seriously, is it an extra car nobody drives anymore. Maybe it doesn't run. Do you keep saying you'll sell it one weekend and suddenly it's been two years and meanwhile it's taking up space, costing you money, and slowly becoming part of the landscape? Here's the easy solution. Donate it to Cars for Kids. And yes, it's that Cars for Kids, the one with the jingle you absolutely know already. 1877 cars for kids. Here's why people love to donate to Cars for Kids. It's ridiculously simple. You go to carsforkids.org Jill that's cars with a K. Answer a few simple questions and you're done. The they'll come, pick up the vehicle for free, tow it away, handle the paperwork, and you'll receive a tax deductible receipt. Done. Cars4Kids has been doing this for over 30 years and has accepted more than a million vehicle donations. So if you've got a car you're not using, turn it into something meaningful. Go to carsforkids.org Jill that's cars with a K. And fair warning. Now that jingle's going to be stuck in your head for the rest of the day. Welcome to the Jill on Money show. It's Tuesday, June 2nd, and we are here answering your financial questions. If you have One, all you need to do is go to our website, jillonmoney.com in the upper right hand corner, there is a contact us button. Click that button, write us a note. And if you'd like to come on the air live, check the box. Mark will do everything else. While you're on the website, subscribe to our free weekly newsletter. Comes out on Fridays. And you also should check out our subscription service called Jill on Money Live. Now, this is where you plunk down a whopping $45 probably is like the same as filling your tank right now. $45 for the next 12 months. And you know what? You're going to get four live webinars. You'll also be entitled to go behind our paywall and check out the bonus audio and video content. You can also look at the back catalog of our webinars and our upcoming webinar later this month. Wednesday, June 17th. Social Security expert Heather Schreiber. She is fantastic. She has every factoid about the Social Security system at her fingertips. So if you'd like to join us again, go to Jill on Money, the website. Scroll down. You'll see Jill on Money Live. Subscribe. And if you feel like I don't want to make a commitment, you can always buy the single webinar for 15 bucks. So you won't be able to participate live. That's all right. Maybe so. Check that out. All right. Now let's get to you. We are joined by Marie from Western New York. Hello, Marie. How are you?

[B]

Hi, Jill. I'm doing well. Thank you for taking my call.

[A]

Of course. What's going on?

[B]

So I am looking at early retirement and it would be a modest retirement. I think I know what you're going to say, but I'm going to run the numbers by you anyways, if I may.

[A]

How old are you?

[B]

I am 58.

[A]

Okay. Married? Single? Partnered?

[B]

Single.

[A]

Okay. Kids? No kids.

[B]

No kids.

[A]

Are you, when you think about your early retirement, are you entitled to a pension?

[B]

A small. And I'm actually starting it now. It's actually. I actually forgot about that, too. Yes. It'll be $200 a month.

[A]

Okay. So it was that like your, your cappuccino budget.

[B]

Exactly.

[A]

Right.

[B]

Exactly.

[A]

Okay. So are you thinking about retirement because you feel kind of burnt out, like I'm always interested in the why. So tell us a little bit about what's been going on for you.

[B]

I want more control over my time. There's other things that I want to do that work is just interfering in it.

[A]

I like a Woman with a lot of things to do, I got to tell you. I mean, I really do. Okay, so how much are you earning right now?

[B]

I earn 90 to 100.

[A]

Do you have a retirement plan at your current employer?

[B]

Oh, I do, but it's okay. There's 1400 in there. I just began with them recently.

[A]

Okay, okay, so tell us about the money you have saved already.

[B]

Okay. Every. Everything I'm telling you right now is traditional IRA.

[A]

Okay.

[B]

Okay, so there's 365, 300 in traditional 67 in an inherited HSA, 7,000.

[A]

Wait, wait. When did that person. When did that person pass away? In the inherited 16.

[B]

So I don't have to liquidate it. I can take, like, I'm already getting money. They have to give me a certain percentage every year.

[A]

So $365,300 and $67,000 in the inherited IRA.

[B]

Correct. HSA $7,000, brokerage, $60,000.

[A]

Okay.

[B]

Emergency fund, 35. Ish.

[A]

Okay, great.

[B]

I went on the Social Security site. If I were to take Social Security early, which I'm looking at doing, it would be 1,700, but I would only factor in 1,400 because of Medicare. So I want to be conservative and just say 1400amonth, but that wouldn't be until 62.

[A]

Do you happen to have the number for age 67?

[B]

I don't have that. I mean, I did, because I'm never

[A]

going to convince you to do that.

[B]

Well, you're not asking.

[A]

I mean, I just. I want to know if this is like you. There are certain hills I'm not going to die on. If you're like, I'm taking it at 62, no matter what. Could you be convinced potentially?

[B]

Oh, I. I'm absolutely open to being convinced.

[A]

Okay, great. All right, that's good. Let's keep going.

[B]

Okay.

[A]

So what about your home? Do you rent or do you own.

[B]

I own my home. There's approximately 16,000 left on the mortgage, but it's such a low interest rate. That's why I don't want to liquid. I was going to liquidate from the brokerage to pay it off, but I.

[A]

What's the rate?

[B]

362.3.62.

[A]

Okay. What's the house worth?

[B]

300.

[A]

Do you want to stay there?

[B]

I do.

[A]

Okay, good. Great. Okay. And are there any other assets that we have not talked about?

[B]

No.

[A]

Okay.

[B]

No. Fine.

[A]

All right. You're single, you're no kids, you got yourself to take care of. How much money do we need to generate for you every Month. Not like it's a struggle, which you just want to be able to spend.

[B]

I was looking at 2,500amonth. What my. What my original plan was. Oh, I think I missed something. Did I tell you about the 401k?

[A]

Tell me. You mean that 1400.

[B]

The 1400 is in my current employer's 401k. That's correct. I do have other money in another 401k. That amount is 125,000. I'm leaving it.

[A]

Look at you skipping over 125.

[B]

No. Oh, just. Just a pocket change. Right.

[A]

No problem.

[B]

I wanted to leave it there because I wanted to exercise and I'm able to do it with this plan. I wanted to exercise the rule of 55. So my plan was between 55 and 62. To use that 125.

[A]

Are you going to make any money in those interim years? If I looked at your, you know, you're 58 years old. Right. And if you exercise the rule of 55 in the old 401k. So are you intending to say that you need the whole $2,500 a month from that old 401k from age, your current age 58 to 62, or will you have other money to consider, like other income? Are you going to do something part time, you're going to have some fun? Just wondering.

[B]

I think I am. Minimally, like maybe to the tune of 16. 16,000 a year.

[A]

All right, let's say a thousand a month.

[B]

Okay. From employment. From employment would be okay? Yeah, that'd be fine.

[A]

Yeah. Like if you said, I'm gonna spend 2,500amonth, but I'll figure out a way to make 1,000amonth at least from age 58 to 62. Is that fair?

[B]

Yeah, no, that's totally fair.

[A]

You feel comfortable with that?

[B]

I do, I do.

[A]

Okay, so now from the old 401k, the $125,000 account, you would take money out every year, Right. And maybe you'd take out like 2,500 bucks a month, $3,000 a month. We'll see. You'd pay tax on it. You live in a high tax state, New York, so we know you have to pay taxes, but you live on whatever that is, that thousand of income plus whatever you take from the 401k until age 62, when you would potentially claim Social Security. Does that seem like the sort of general game plan? Seem.

[B]

Okay, that that was my plan. And then at 62, presuming Social Security is probably not going to be enough at 1400. At that point, I would then access the rest. Yeah, yeah, yeah.

[A]

Traditional. Okay, let me ask you a couple questions.

[B]

Okay. How's your health right now? It's good, but I have. I've had some setbacks recently.

[A]

Okay. The reason I asked that is not, like, to be coy. It's because if your life expectancy is not great because of either your health history or your current health, then drawing at 62 might make sense. For real. Will you have health care? Like, what's going to happen if you said, you know, you called it quits right now? How are we paying for health care from age 58 to 65?

[B]

I do have that covered.

[A]

Oh, okay.

[B]

Yeah.

[A]

So that's covered even in the $2,500 a month, right?

[B]

Yes, that's covered.

[A]

Okay. Okay, so game plan. Let's go back $1,000 a month of some income from age for the next four years, plus you take a distribution from your old 401k, that 125,000. Maybe it's going to be, like I said, maybe it's $3,000 a month so that you have 36,000 bucks plus your 48, that you have, like, 48,000 of gross income. You pay your taxes. You boil it down. You have plenty. You got your $2,500 a month. No problem. Good. Right.

[B]

Right.

[A]

You feel good about that?

[B]

I do, but I. I don't know how I could do it based on the numbers you said, like, if I. If I took out 3,000 from the 401k, we're gonna get rid of that

[A]

401k, that's going to be drained by the time you get to be 60, 62.

[B]

Right? Right. That's my plan. Okay. Yes. Yeah.

[A]

So that's done. Okay. Now what's left? You're 62 years old. Right. And at 62, maybe you don't want to work at that thousand dollars a month. Or should we? What do you think?

[B]

I would like to be conservative and say, yeah, I don't want to work at it. And if I do want to work, then I have extra money.

[A]

Okay. So then we have 62 onward. We have, I'm just saying 1700 because that's the gross amount. I know you have to pay for health care, but let me do 1,700amonth for your Social Security. Okay. And then we basically need to come up with more money coming out of your accounts to kind of make it work. There's two ways to think about this, okay? Depending on, like, really how you feel and that is one. Hey, I keep working. Let me put some more money away in the old 401k, then I don't have to start drawing down, but I want to get towards, you know, I need a few. You need a few more years. Okay? Partially because. Not because you spend so much money, but we just want to keep pushing some more money into savings and also shorten the time. I would like you to find out what the benefit at Social Security would be at age 67. See, the problem with 62 is again, and it really does depend on your health. So I don't want to get in your head about this. If odds are you're not going to live past 80, then you should claim whenever you decide to call it quits at work. So 62, 63, 3, 64 is fine. Right? But if you really are overstating that and you think you're going to, eh, you know what, I talked to my doctors. I'm probably going to live till I'm 80. I'm going to live till I'm 85. Okay, if that's the case, then I'd rather you, I'd rather see what the number is at 67. Put it this way, if you worked for even just a couple more years, it would prevent you from pulling money out of the 401k. You'd save a little bit more money and then you could do the same scenario and then see if it works. You know, hey, if I work two more years, what would happen? And 60, I make the same thousand dollars a month from 60 to 62 or 63. And then now we're starting to talk. I need a little bit more of a cushion. That's what I think. It doesn't mean you have to spend less, but I think if the, the only way to really change the calculation here is to really focus on what you can control. When do I retire? Right. And what do I spend? If you really think that you're 2500 is the 2500, that's that, then you've got to make a decision about whether you say, hey, am I going to work longer full time or am I going to commit to saying whenever I stop working I need to work, not just till I'm 62, I need to work till I'm 65. Those are the kinds of things that you can control.

[B]

How much more do I need?

[A]

It's a little bit of a moving target where we are today. I think you need a, I think you need two more years of work. And then I still Think you need to commit to kind of create $1,000 a month of income. You should look at maybe. What would your Social Security payment be, say at 65 and then 67. And I think you'd be surprised that the numbers start to go up pretty dramatically.

[B]

Okay, I can do that. I can do that.

[A]

Do you have your estate documents? You got a will?

[B]

I do not. And I will be getting that done in the next few months.

[A]

Why? I liked you. All of a sudden I liked you and then I turned on you. Vicious. Get that done. Do you have a legal service benefit through work?

[B]

We don't. No. No. I'll go to an attorney. I know it's old. Yeah, I'm gonna. I'm gonna do it that way.

[A]

Good. Okay, Marie, go off and get ready for football season. I know that you're probably a Buffalo Bills fan. Cause you're Western New York. So I'm just gonna assume that for everyone else listening. Are you thinking about calling it quits? Do you need a little guidance? Do you not trust the calculator that you're seeing on the website? I know we are good like that. We're like the set of eyes and ears that work on your behalf. Get in touch with us by going to jillonmoney.com, click the contact us button, write us a note. And if you would like to join us live, check the box. Mark will do everything else. And just make sure you check out all the great content that lives on our website. So much fun. You can subscribe to us on the All Odyssey app or wherever you find your favorite podcast. Try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[B]

Are you really buying a car online on Autotrader right now? Really? At a playground? Yeah, really. Look at these listings from dealers. Wow, your search can really get that split. Really? And you just put in your info 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.

[A]

Mommy's buying a car. Mommy, look.

[B]

I think your kid is walking up the slide. Hi, Ol.

[A]

Again? Really?

[B]

Autotrader?

[A]

Buy your car online?

[B]

Really?

[A]

Hi, this is Jill Schlesinger, CBS News business analyst, certified financial planner, and the host of the Jill on Money podcast podcast. Beginning, middle or end of the year, it's always a great time to take control of your financial life. And the Jill on Money podcast is here to help your questions make it possible for me to provide unconventional and entertaining insights on your money and, more importantly, on your life. Follow and listen to Jill on Money wherever you get your podcasts.