Does My Early Retirement Plan Work?

Summary

Episode Summary: Does My Early Retirement Plan Work?

Podcast: Jill on Money with Jill Schlesinger
Date: June 12, 2026
Main Theme:
Jill Schlesinger answers listener Frank's detailed question about whether he and his wife can afford to retire at age 58, breaking down their current assets, expected expenses, retirement strategy, and the pros/cons of annuities. Jill and producer Mark provide candid, jargon-free advice on how to maximize financial security, manage risk, and keep flexibility in retirement planning.

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Key Discussion Points & Insights

1. Getting to Know Frank's Situation (03:51–06:01)

• Family & Career: Frank and his wife are both 52, with three children (twins, 20; eldest, 22, headed to graduate school). Frank works full time ($150k annual salary), wife works one day per week ($40k).
• Education Support: They paid for all three kids’ bachelor’s degrees but don't plan to pay for future graduate school.
• Retirement Saving:
  • Both max out retirement plans + Roth IRAs annually.
  • Assets:
    • $700k in traditional 401(k)s.
    • $100k in Roth IRAs.
    • $1.2M in rollover IRA (traditional).
    • $65k in brokerage.
    • $50k in cash.
    • $13k in an HSA.
    • $57k cash value in permanent life insurance.

2. Home & Real Estate Position (06:36–07:18)

• Home Value: $1.4M (Southern California), $190k mortgage at 1.75% interest (“That may be the lowest we’ve heard.”– Jill, 06:48).
• Intends to stay in the current home. No rental or vacation properties.

3. Current Spending & Retirement Income Plans (07:26–09:11)

• Expenses: ~$11,500/month (“Let’s call it 12 just for the heck of it.” – Jill, 07:36).
• Health Insurance: Would need to purchase from the marketplace if retiring early.
• No Pensions.
• Potential Post-Retirement Income: Maybe $20–40k/year (likely part-time or consulting between 58–62).
• Social Security Estimates:
  • At 67: Frank - $4,200/mo; Wife - $2,470/mo.
  • Plan: Frank will probably claim at 67, wife possibly at 70.

4. Proposed Retirement Timeline and Savings Projections (10:30–11:12)

• Six more years of working, adding to retirement and brokerage accounts.
• At 58, aim to create $12k/mo income from saved assets until Social Security kicks in.

5. Exploring a Deferred Income Annuity (11:12–13:17)

• Frank considers putting $1M into a deferred annuity, which would pay ~$8,500/mo for life to both Frank and his wife after six years.
  • “If I was to put...one million dollars into a deferred income annuity...it would give me about $8,500 a month for the rest of my life and my wife’s life.” – Frank (11:42)
• Jill's Reaction:
  • Not a fan (“It’s usually an expensive way to do it...I’m not giving up a million dollars of liquidity...it’s tough to get it out.” – Jill, 12:07)
  • Points out: You can achieve similar results through prudent withdrawals without high costs or loss of control. Annuity surrenders flexibility and may have higher fees.

6. Investment Management and Other Financial Considerations (12:55–16:08)

• Their investments managed by a financial advisor at 1% AUM, which is “not bad” per Jill.
• Reiterates: Annuities cost more, advisor also not a fan.
  • “It’ll cost you at least twice that to take the money out of the IRA and put it in a deferred annuity. I could almost guarantee.” – Jill (13:02)
• Jill explains “DIY annuity”: With $3M saved at retirement, could easily sustain $8,500/mo with systematic withdrawals.

7. Can Early Retirement Work? (15:37–18:34)

• “Do you think Frank’s game plan...can work?” – Jill (15:38)
• Mark: “Close. It’s very close...they’re going to have to spend down between when they call it quits and when they can get Social Security.” (15:54)
• Jill: Would work better if they either work a couple more years or secure more post-retirement income.
• Access to cash/flexibility retains importance since their children may still need occasional support.
• Suggestion: Surrender permanent life insurance for cash value and add to brokerage for more liquidity, rather than buy a new insurance product.

8. Roth Conversions and RMD Worries (18:52–19:41)

• Frank asks if he should start Roth conversions to avoid RMD “ticking time bomb.”
• Jill: “No, absolutely not. You will pull money out ... but you’re not going to convert. You don’t have enough cash to pay the price. You will need this money to live on.” (19:02)
• General action: Use traditional assets for income before Social Security, and RMDs will not be an issue if you retire before 70.

9. Final Advice and Engagement (19:46–20:30)

• Both Jill and Mark agree: Plan is plausible, but extending work to age 60 is much safer, especially since Frank doesn’t mind the job – just the commute.
  • “If he got to 60, I would feel a lot better.” – Mark (19:36)
  • “Me too. That’s exactly the number I’m thinking.” – Jill (19:39)
• Stay in touch, keep putting money away, consider cashing out old life insurance, don’t buy an annuity (“Don’t buy an annuity. Do keep putting money away.” – Jill, 18:35)

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Notable Quotes & Memorable Moments

• “My wife works one day a week. Oh, I love her schedule. Get me on that.” – Jill (04:45)
• “I hate it [the Cross Bronx Expressway].” – Mark (02:59)
• “Our interest rate is 1.75.” – Frank (06:42)
  • “Mark is being tortured right now. That may be the lowest we’ve heard.” – Jill (06:48)
• “Why? [consider the deferred annuity]” – Jill (11:21)
• “It’s an emotional reaction...You’re looking at this and saying, the insurance company will spit out this $8,500 a month. But...there’s a cost.” – Jill (13:23)
• “I don't trust him. I'm calling Jill. I'm going to shop around behind his back.” – Jill, joking about Frank’s advisor (15:09)
• “The commute sucks. That's a killer. But you get to listen to our show, so there's that!” – Jill (19:46)
• “I've consumed probably over 500 episodes in the past three months.” – Frank (19:51)

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Timestamps for Key Segments

• Frank’s Introduction and Financial Snapshot – (03:51–06:01)
• Home and Loan Details – (06:36–07:18)
• Spending, Insurance, Social Security – (07:26–09:11)
• Annuity Discussion – (11:12–13:17)
• Does the Early Retirement Plan Work? – (15:37–18:34)
• Roth Conversion & RMDs – (18:52–19:41)
• Final Advice & Signoff – (19:46–21:15)

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Takeaway for Listeners

Frank and his wife are in strong shape for early retirement, provided they keep saving, consider some flexibility (possibly working a little longer or part-time), and avoid unnecessary insurance and annuity products. Maintaining access to liquid assets and responding thoughtfully to changes (kids, expenses, unexpected events) are keys to sustaining their financial security.

Jill’s overall tone is direct, practical, and emphasizes empowerment through understanding — never just following a sales pitch or emotional impulse. As always, she makes retirement math approachable and avoids financial jargon, encouraging listeners to seek personalized, actionable advice.

Transcript

[Jill]

Hey gang, you know it's been a

[Mark]

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[Jill]

welcome to the Jill On Money Show. It's Friday, June 12th and we are here trying to help you navigate your financial journey, wherever that may lead you. Now I always say this but like sometimes when I'm driving I want the quickest, most direct route Happened to me yesterday. It's not like I really like to drive on the the major Deegan, which is one of these most horrendous roads in New York. I don't like to drive on the Cross Bronx Expressway.

[Mark]

I hate it.

[Jill]

But I needed to get home really fast. Other times I kind of want to meander whatever the route is that is in front of me, I like to

[Mark]

be able to choose.

[Jill]

That's what Mark and I do here on this program. We try to identify what is in front of you, the different ways to get where you want to go, and then you're going to determine what feels right. So if you want a little bit of guidance, just get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And if you would like to join

[Mark]

us on the air live, check the box.

[Jill]

Mark will do everything else while you are on the website. Do not forget to subscribe to the free weekly newsletter which comes out today Fridays, and that will also entitle you to our blog. Okay, let's get it going here. We've got Frank who's joining us from Southern California. Hello, Frank. What can we do for you?

[Frank]

Hey, Jill. Hey, Mark. How are you? I was curious. My wife and I were both looking to retire at 58 years old. We're calling today to figure out if we have the ability to pull the trigger in six years and give you a look at our assets. And I kind of wanted to run by my possible retirement strategy and see what you guys think.

[Jill]

I like this. Okay, so you're both 52?

[Frank]

Yes.

[Jill]

And you have kids?

[Frank]

Three kids, yes.

[Jill]

How old are they?

[Frank]

I got twins who are 20 and a 22 year old.

[Jill]

And 22 done, like launched or not graduated.

[Frank]

But now he's going to grad school to get his master's degree.

[Jill]

Oh, God. Are you paying for that? Sorry, sorry, I didn't mean to do that. I'm sorry, I'm sorry.

[Frank]

No, no problem. No, we just paid for the bachelor's degree for all three. They are all well aware of that.

[Jill]

Okay. And both you and your wife are working full time right now?

[Frank]

I'm working full time. My wife works one day a week.

[Jill]

Oh, I love her schedule. Get me on that. But how much do you earn?

[Frank]

About 150.

[Jill]

And what does she earn one day a week?

[Frank]

About 40k a year.

[Jill]

Okay. Are you both putting money into retirement plans?

[Frank]

Yeah, absolutely. I max mine out plus the additional and then we both do a Roth ira. We max out every year. As well.

[Jill]

Oh, great. Okay, so let's hear about the money you've set. You've already saved. So you've got a 401k, right?

[Frank]

Correct.

[Jill]

How much is in the traditional?

[Frank]

About $700,000 between my wife and I.

[Jill]

Okay, great. And what about Roth?

[Frank]

Probably about another $100,000.

[Jill]

Okay, great. So 700, 100. Is that it? For retirement accounts? Any old accounts floating around?

[Frank]

We actually have an IRA with $1,200,000.

[Jill]

Oh, actually, that's really very good for me to know. And that's also traditional, right?

[Frank]

Yes.

[Jill]

Okay. Brokerage account.

[Frank]

About 65,000 in there.

[Jill]

Cash floating around.

[Frank]

Cash is probably another 50 grand. Yeah.

[Jill]

Any HSAs, Health Savings Accounts?

[Frank]

13,000 in an HSA.

[Jill]

Okay, great. Any other. We'll talk about real estate in a second, but any invested assets? Anything else?

[Frank]

We have some permanent life insurance on myself and my wife, like a hundred thousand and two hundred thousand. And they have cash value of 12,000 for her, and then I have 45,000 for me.

[Mark]

All the surrender charges are done.

[Jill]

In other words, if you wanted to just blow out of these, you could without a penalty. Okay, yes. So pass. Surrender. Got it. All right, now let's see. How about your home? What would. What is your approximate value of your home?

[Frank]

About 1.4 million.

[Jill]

Oh, my God. Southern California, man. Is there a mortgage still?

[Frank]

Yeah, we owe about 190,000. And Mark, you're gonna love this. Our interest rate is 1.75.

[Jill]

Mark is being tortured right now. That may be the lowest we've heard.

[Mark]

I was gonna say that might be

[Jill]

the lowest one that you win that one point. Was it a 10 year? What happened?

[Frank]

I know. We redid it 20 years, and we have about eight years left on it now.

[Jill]

Oh, it's too bad. Don't you wish you borrowed more?

[Frank]

You know, I really, really wish I did.

[Jill]

I know everybody says that. Look, if I only did that. Okay, but you would never do. Do you want to stay in this home? Like, is this a house? Like, oh, yeah, we're here.

[Frank]

Yeah, absolutely.

[Jill]

Okay, cool. Any rental property, vacation property, anything like that?

[Frank]

No, that's it.

[Jill]

Okay, you ready for the hardest question? Which is how much do you guys spend right now?

[Frank]

Right now, our monthly expense is about $11,500.

[Jill]

Okay, let's call it 12 just for the heck of it. Now you guys want to.

[Mark]

If you are able to call it

[Jill]

quits at age 58, what are we doing for health insurance?

[Frank]

We would have to shop that out on the marketplace.

[Jill]

Okay, neither of you or do either of you, Are you entitled to a pension?

[Frank]

No, we're not.

[Jill]

Okay. And if you were to be able to get like, kind of get out at 58, would you do nothing? Would you. Would your wife keep doing her one day a week? Would you want to go to, like, do you have the kind of career where you could maybe do something, but not as much as you're doing now? What are you thinking?

[Frank]

We would probably do volunteer work.

[Jill]

No, that's not what I'm talking about.

[Mark]

I don't want.

[Jill]

I need to know the money making part.

[Frank]

Yeah, Yeah. I don't foresee much income. Maybe an additional 20 or 40,000 per year.

[Jill]

Okay. Okay. Not much, but something. Maybe. Maybe. Should I not count on it at all, or do you think that that's a reasonable bet?

[Frank]

I would say it's a reasonable bet.

[Jill]

So maybe from like, 58, how long should we have you make?

[Frank]

Two grand a month, probably 62.

[Jill]

Okay. Are you both in good health?

[Frank]

Yeah.

[Jill]

Do you have your Social Security estimates available?

[Frank]

I do.

[Jill]

67. Give me that. Age?

[Frank]

67, it is $4200 a month for me, and then for my wife would be 24, 70.

[Jill]

And were you planning to wait till age 70 or what do you think?

[Frank]

We'll probably both collect it. Well, one, I'll probably collect at 67. She'll probably collect at 70, or maybe both at 67.

[Jill]

Okay. And just looking ahead again, there's nothing besides the actual, like, we're going to pull back on working. Is there anything else that you have to consider in terms of, like, do you have aging parents that you need to think about? Is there, you know, is there something else that might change the nature of your game plan?

[Frank]

No. I mean, both my parents have passed, and her parents are. They're financially taken care of.

[Jill]

Would she potentially. Could she inherit some money?

[Frank]

I don't know, to be honest with you.

[Jill]

Oh, my God. Since I would ask this question immediately. Mark, did you ask, you know, this. This is like, really would be part of my. If I were dating again, which I hope I don't have to do ever, But I'd be like, oh, so tell me about your parents. And then I would sort of dig in a little bit. No, I'm just kidding. That's fine. We don't have to do that. So right now you say, let's say for the next six years, you both max out retirement accounts, you max out your Roths. Right. And then do you put extra money into the brokerage account on an ongoing basis?

[Frank]

Slightly. I would call it Maybe five grand a year.

[Jill]

So we have six years of getting some money into these accounts. You hopefully have six years of growth between, you know, your, your almost $2 million in traditional. And then you got your Roth and the brokerage. And so all that keeps going. Right, right. And then 58 comes along and you say, can we do this? Can we create 12 grand a year, a 12 grand a month in income? Can we do that from age 58 to 67 and then claim Social Security? Right. Is that, Is that about where we are?

[Frank]

Yeah, that's correct. And I kind of had a question for you guys regarding the possibility we're looking into doing like a deferred income annuity.

[Jill]

Why?

[Frank]

I wanted to know your thoughts.

[Jill]

Did you hear that? Did you hear what I just said? Oh, wow.

[Frank]

Yeah.

[Jill]

So what's the pitch? What's the pitch? Give it to me.

[Frank]

You know, actually I found this on my own. And I don't know if this is good or bad, but what it is, it's. If you, if I was to put this is. This is what it is. I put a million dollars into a deferred income annuity.

[Jill]

Yep.

[Frank]

Starting, you know, now, and give it six years of growth. It would give me about 8,500 bucks a month. The rest of my life and my wife's life.

[Jill]

Yeah.

[Frank]

And then we would leave the additional 1.1, 1.2 that's in there today, let that grow for the next six years, give us about 1.6, 1.7 at age 67, and then we can collect Social Security coming in. So I just want to know, what are your thoughts?

[Jill]

My thoughts are that it's usually an expensive way to do it. My bigger thought is I'm not giving up million dollars of liquidity. You can't. That's not your money anymore. Now it's the insurance company's money. And it's tough to get it out. And it's usually quite expensive, these policies. So I'm not a huge fan of them. Mostly, I mean, listen, I think they've gotten better because I think there are some low load or more affordable choices. But my biggest concern would be to take half of my liquidity and pop it into the hands of an insurance company. I'm not interested in that. Also, what are they going to do for you that you can't do for yourself? You can do the same thing. You can have your million dollars grow and without the fees. Are you managing this money yourself? Like that traditional $1.2 million IRA? Where is that?

[Frank]

No, that's with financial advisor.

[Jill]

And how much does the Advisor charge you?

[Frank]

1% of assets under management.

[Jill]

Not bad. It'll cost you at least twice that to take the money out of the IRA and out of your investments and put it into a deferred annuity. I could almost guarantee. Did you ask your financial advisor about it?

[Frank]

I kind of did, and he wasn't a fan of it either.

[Jill]

Oh, my God. So let me find someone who would be right.

[Frank]

I seem to be the only one

[Jill]

who's a fan because it's an emotional. This is a very emotional reaction. And I get it, because you're looking at this and saying, all right, let me look at my money that I have. For me, if I just do this, they'll spit. The insurance company will spit out this $8,500 a month. But what I'm saying to you is there's a cost to that, number one. And number two, you take that money and you just keep doing what you're doing. It will grow, and you'll be able to spit out the $8,500 a month that you need. You'll be able to do that. I want to approach this first from the idea of. It is very difficult to understand when you're in this place right now where you're 52 years old, like, what it means not to have access to your money when you might need it. And I think that's one big. That's the bigger part. The second part is like, well, what are they doing at an insurance company level that your financial advisor wouldn't be doing for you? But, well, they're. They're diversifying. They have access to this, then the other. So does your financial advisor. And you could set up a system where you're like, okay, for the next six years, we are investing. We're putting money away. Our assets are growing. Hopefully in six years, you know, our. Our 2 million becomes, I don't know, 2 and a half, 3. 3 million. Maybe it becomes 3 million bucks. And then you're telling me that we can't figure out a way to. From $3 million to push out, you know, a bunch of money every single. And maybe just withdraw it and get that money out of the IRA account and take that money out, and, you know, that's it. You will create your own annuity, essentially. That's what I'm saying. That's what I think is a better idea. Especially you, like the advisor.

[Frank]

Oh, yeah.

[Jill]

Good friend, Good friend. I don't trust him. I'm calling Jill. I'm going to shop around behind his back, all see that, Mark? You see how that works? I told some financial advisors, I said, I want you to know that you clients are calling us. I want you to know that because something's going on. And I think that if, if you hear it from me, you hear it from him. Mark, do you want to buy a deferred annuity? You want to pop a million bucks in there? No, he says no. Do you think that the game plan can work, though?

[Mark]

Do you think, Mark, that Frank's game

[Jill]

plan of six years of working and pushing money into these accounts, then the being able to generate a couple grand a month and then being able to claim Social Security, you think they have enough money to get it done?

[Mark]

Close. It's a similar to a call we had earlier in the week. It's, you know, over the next six years, this is going to be worth over $3 million. It's very, very close. They're going to obviously have to spend down between when they call it quits and when they can get Social Security.

[Jill]

Do you hate what you're doing, just out of curiosity?

[Frank]

No, no, not at all. I hate to commute, but I don't mind the job.

[Jill]

Oh, okay, fair enough. I mean, is there any way that you could commute a day less or a couple days less and keep working a little bit more? Or not really?

[Frank]

No. They made a mandate back.

[Jill]

I hate these guys, these stupid companies. I hate them so much. Okay, so let's say that, you know, just looking at the IRAs and the money that you have, like if you had $3 million, right, and we looked at, you know, a 4% withdrawal rate, right? So we just took some money out because you're young, maybe you would even do, I don't know, maybe you would do three and a half percent. But if you, you could do this, you could take the money out, you could pay the taxes, I can tell you how it works a lot better. It works better if you work a couple of years longer. That's number one. It works better if all of a sudden at age 58, you're like, you know what, Jill? I can make two grand a month. I'm making five grand a month. And that's fine. Between the two of us, we're making, we're pulling in 60 grand a year. So very similar, Mark said to a call we had earlier in the week, because part of the working, the doing the part time or getting some other income, it's not just the money that's coming in. It's not pulling as much out of these accounts. So do I think it's getting close? It's kind of close to working? Sure, sure. Yeah. Maybe one of the things that you do is, you know, instead of buying another insurance product like a deferred annuity, maybe one thing you should think about is just taking their permanent life insurance and grabbing that money out of those policies and adding that into your brokerage account and, you know, building that up. So I think that building the assets that are available to you, that are affordable, these are the things that you should be doing. You know, you get this younger one through school. It sounds like these kids are not like bleeding you dry for money. But I think that with kids in their 20s or maybe 30, I think that that's even another reason why I wouldn't want to actually annuitize anything. I would want to have access to my money. What happens? These three kids are going to get married. They're going to say, oh, we want a wedding. Can chip in. You say, I wish I could, except I have all the money in an annuity. Too bad, right? Right. I got to throw weddings for these kids. I'm just kidding. I think you're in good shape. You were in very good shape. Why don't we see how it goes?

[Mark]

Stay in touch with us.

[Jill]

Don't buy an annuity. Do keep putting money away. And do you guys have your estate documents done?

[Frank]

Yeah, we have a trust set up.

[Jill]

Oh, a trust.

[Mark]

Fancy.

[Jill]

Okay, sounds good. Anything else that is on your mind that we can help you with?

[Frank]

I'm always curious. You guys talk about the, the ticking time bomb, you know, from the RMDs. Do I want to start converting this money into. What are your thoughts?

[Jill]

No, no, no, no, no, no. Absolutely not. You will pull the money out. When you're 59 and a half, 60, you'll start, you'll pull the money out, but you're not going to convert. You don't have enough cash to pay the, the, the price. And you're going to need this money. You're going to need to live on this money. And these traditional assets, which are now 2 million, hopefully turn into 3ish. You'll, you're going to need that money and you're going to use that money to live on until you get Social Security. And I hope you don't run out, because if you could work a tiny bit longer, it's going to work better. Mark, what would make you feel better if he worked a little bit longer? What, what to what age?

[Mark]

I mean, if he got to 60. I would feel a lot better.

[Jill]

Me too. That's exactly the number I'm thinking.

[Mark]

And he doesn't hate his job either, you know.

[Jill]

Yeah, I know, but it's a commute. We're not.

[Frank]

I know.

[Mark]

The commute sucks. That's a killer.

[Jill]

That's, that's, It's a night under. But you get to listen to our show, so there's that.

[Frank]

That's true. I, I, I, I've consumed probably over 500 episodes in the past three months.

[Jill]

I love that about you, Frank. Keep going, keep going. We get, you know, all those back catalog episodes is great. We get paid on those, so that's good. Keep listening, Keep listening. Keep us in. Keep us in the loop. Okay? We're happy to help you out. So let us know if we can, you know, help walk you through and you'll Again, I think you're going to have more information over the next couple of years and, you know, we'll see. Maybe it can work. Maybe it can. So do not. Don't fret. We're good. We're going to get you there. Hey, are you like Frank and his wife? 52, Mark, you're so close to now you're getting closer to 50.

[Mark]

Just four years away. Four years.

[Jill]

I mean, I'm just saying, like, doesn't it seem strange? You remember how I used to say, like, what are you going to do with yourself? And like, you know, here we are. Here we are. Exactly. I understand that. These commutes are the worst. I hate these companies. I think they're so stupid. You have a guy who's like a good employee who would stay forever, and, like, there's some reason why you feel like you have to have people in the office. Such baloney. No evidence that you're more productive. None. Zero. Get over yourselves. All these. I think it's a control thing, Mark. I really do. I think it's like these bosses are just like, well, you know, we want to see people in the office anyway. Hey, get in touch with us. Let's get you out of that, that nonsense. Off that, off that big treadmill. Get in touch with us by going to Jill on money dot com. Click the contact us button, write us a note. And if you want to come on

[Mark]

the air live, check the box.

[Jill]

That's all you need to do. Mark will do everything else. Don't forget that we have all of the content that we produce living on our website, jillonmoney.com. you can subscribe to us here on the Odyssey app. Or wherever you find your favorite punch. It's Friday so want to do some thank yous? Our music is composed by Joel Goodman. Mark Tularsio is our executive producer and king of all things Web. We are distributed by the lovely folks at Odyssey. Please try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you on Monday.

[Narrator]

Nerds Today's episode is sponsored by NerdWallet's Smart Money podcast. Personal finance can feel like a pop quiz. You did and study for. This podcast is your study guide. On NerdWallet's Smart Money podcast, you'll hear from trusted journalists who explain the why behind major financial decisions. You'll get research backed insights and clear pros and cons. Whether you're planning a big purchase or just want to grow your wealth, make your next financial move with confidence. Follow NerdWallet's Smart Money podcast on your favorite podcast.

[Frank]

Apparently.