Is Retirement in 2027 a Possibility?

Summary

Podcast Summary: "Is Retirement in 2027 a Possibility?"

Podcast: Jill on Money with Jill Schlesinger
Host: Jill Schlesinger (featuring Mark, producer/co-host)
Date: December 17, 2025

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Episode Overview

In this episode, Jill Schlesinger takes a listener call from Bradley in New York City, who is considering retiring at age 62 in 2027. The conversation dives into Bradley’s financial health, his retirement assets, outstanding debts, and his plan to generate passive income from his duplex. Jill provides practical, actionable advice on managing high-interest debt, leveraging home equity, and preparing for a smooth transition to retirement, all delivered in her trademark approachable and down-to-earth style.

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Key Discussion Points

1. Bradley’s Retirement Goal and Work Intentions

[04:26]

• Bradley, age 60, hopes to retire at 62 to take a year off, retrain, and re-enter the job market in a new capacity.
  • “I like to do. I would really like to do something else. I don’t want to quit the work scene altogether. What I like to do is I like to retire, take maybe a year off, retrain myself, and then go back into the market again.” – Bradley [04:50]
• He is single and currently fully employed making $130,000/year.

2. Retirement Savings

[05:44]

• Bradley has a TIAA retirement account with about $730,000.
• No additional pension expected; coworkers have used TIAA annuities to simulate pension income.
  • Jill notes the TIAA annuity option is “very good and reasonably priced.” [06:11]
• Jill is cautious about “annuitizing” now, wanting to ensure Bradley retains liquidity.

3. Recent Financial Setbacks and Liquid Savings

[06:58]

• Bradley withdrew $100,000 from his TIAA account in November to pay bills.
• He now holds approximately $80,000 in checking.

4. Real Estate Assets and Income Potential

[07:31]

• Owns a duplex in NYC, valued at ~$800,000, with a $370,000 mortgage at 4% interest.
• Plans to renovate the unoccupied top floor to create rental income for retirement.
  • Estimated $5,000 for renovations, but Jill is skeptical about such a low figure for NYC costs.
  • “Get out of here. You can’t do anything in New York for $5,000 in an apartment. Come on.” – Jill [08:00]
• Won a housing lottery in 2001 which means the property is relatively recently renovated.

5. Debt and Monthly Expenses

[08:40]

• Outstanding liabilities include:
  • HELOC (Home Equity Line of Credit): $130,000 at 6% (variable)
  • Credit Card Debt: ~$30,000
  • Personal Loan: $20,000 at 20% interest
• Combined monthly expenses = $6,200

6. Jill’s Action Plan: Debt Elimination and Cash Flow Management

[10:13 – 15:24]

• Top Priority: Use savings to immediately pay off high-interest debts:
  • $30,000 (credit card) + $20,000 (personal loan) using the $80,000 available in checking.
    • “If you didn’t have the credit card debt or that personal loan… do you feel like you could manage your cash flow better?" – Jill [10:53]
  • Mark strongly agrees: "I mean, you know, 20% interest rate on the personal loan. I’m sure the credit card is probably, maybe even higher. So I would get rid of those asap." – Mark [13:07]
• Rationale: Eliminating $850/month in debt payments will significantly ease Bradley’s cash flow and set him up for future savings.
• Home Improvements:
  • Fund new roof and top floor renovations via additional HELOC draw, not cash savings. Retain ~$30,000 as emergency buffer.
  • Jill and Mark both feel the HELOC is a justified tool here due to its lower rates relative to the personal loan/credit card debt.
    • “I would use the HELOC to pay for the new roof and the top floor... That is what it’s there for.” – Jill [12:10]

7. Future Rental Income: Game Changer?

[13:25]

• Potential rent for the top apartment: about $3,000/month (possibly reduced to $2,000 after management fees).
  • “Oh, my God. You got to get this done. Definitely." – Jill [13:28]
• Jill advises Bradley to contact management companies for realistic net rental projections.

8. Retirement Viability and Next Steps

[14:30]

• The ability to retire in two years hinges on:
  • Eliminating expensive debt
  • Accurate rental income estimates
  • Keeping sufficient liquidity, avoiding premature full annuitization of TIAA
• Jill recommends Bradley focus now on:
  • Clearing high-interest debt
  • Finalizing cost estimates for property upgrades
  • Researching rental management fees and rental market rates
  • Building savings over the next one or two years as debt burden lessens and rental income begins.
  • “Once you clean that up, I think you’re going to feel a lot better.” – Jill [15:26]

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Notable Quotes & Moments

• Jill on debt repayment:
  “Of the $80,000 that’s sitting in savings, the first thing that I think you need to do is before you even start renovating the top floor, is take 30 grand and pay off the credit card debt immediately. Just get rid of that.” [09:43]
• On using a HELOC for renovation:
  “I would use the HELOC to pay for the new roof and the top floor… That is what it’s there for. And then I’d keep that 30 grand in place.” [12:10]
• Realism on NYC renovations:
  “Get out of here. You can’t do anything in New York for $5,000 in an apartment. Come on.” [08:00]
• On the psychological impact of debt:
  “I think that the credit card debt and the personal loan has become, like, a bigger issue on this… because that’s a big chunk of money.” [11:22]
• Closing advice for similar listeners:
  “If you are listening to this and you are like Bradley and you need an off ramp, then you want to clean up your balance sheet. That just means cleaning up some of the debt that’s sitting out there with some of the assets that you own and you’re not sure about the next step, get in touch with us…” [15:26]

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Timestamps for Key Segments

• Listener Introduction/Retirement Goal: [04:20–05:06]
• Retirement Assets Discussion: [05:18–06:11]
• Withdrawal and Savings: [06:58–07:27]
• Property & Home Equity: [07:31–08:29]
• Debts & Monthly Expenses: [09:04–09:43]
• Detailed Debt Repayment Strategy: [10:11–13:14]
• Rental Income & Renovation Planning: [13:25–14:30]
• Is Retirement in 2027 Possible? Final Recommendations: [14:30–15:26]

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Conclusion

Jill emphasizes the importance of cleaning up high-interest debt and making informed decisions about home equity and passive income as foundational steps before considering retirement. While retiring in 2027 is possible, concrete numbers on rental potential, renovation costs, and improved cash flow will help Bradley – and listeners in similar situations – make a truly informed decision.

Tone: Friendly, encouraging, jargon-free, practical, direct

Host’s Closing Message:
“Change your work, change your wealth, change your life. Thank you for listening and we’ll talk to you tomorrow.” [16:57]

Transcript

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[Jill]

Welcome to the Jill on Money show. It's Wednesday, December 17th and we are here trying to provide you with unconventional and hopefully entertaining insights on your money and your life. And we do this by making you do some work. Sorry I Don't want to do any work. Jill, why are you making me do work? Because this whole show is about you and what's going on in your life. So what we need to happen is we need you to go to our website, jillonmoney.com when you're on the website, all you need to do is click the contact us button. When you click that button, a beautiful little form will pop up, and that form is the email that we received from you. Mark, how's the email inbox doing right now?

[Mark]

Let me give you a real time update. The inbox is at 3,000, 945.

[Jill]

All right, we have 4,000 people who have sent emails, and that's not great, but, you know, there's only so much we can do. If you want to jump that line. You can click the box that says you would like to join us on the air live. Now, some of you click the box, and then Mark follows up, and then you disappear on him. He hates that. So if you'd like to come on the air, let us know. It's so much more fun for us when you join us. Join us because we don't want to hear ourselves drone on. And certainly Mark has to hear my voice so much. Must be agonizing for you, dude. I'm sorry. In that respect, it's so much better of an experience when you come on the air with us, and we love it when you do. So make sure that you check the box if you'd like that. Also make sure that you sign up for our free weekly newsletter, which comes out on Fridays, and that will also entitle you to the blog post. And I usually do once or maybe twice a week. Sometimes. Depends. Depends how I'm rolling that day, that week, that that month. Sometimes more, sometimes less. Okay. Today we are talking to Bradley, who joins us from New York City. Hello, Bradley. How are you today?

[Bradley]

I am well, thank you. It's nice to meet you.

[Jill]

It's great to have you with us. What can we do for you?

[Bradley]

Okay, I'm 60 years old. I'd like to retire at 62.

[Jill]

Okay. So want to retire in two years?

[Bradley]

Yes.

[Jill]

Okay, great. Are you thinking about retirement because you're kind of burnt out. You're done. Are you thinking about retirement for some other issue? Like what's the genesis of the I want to retire now. Ish.

[Bradley]

I like to do. I would really like to do something else. I don't want to quit the work scene altogether. What I like to do is I like to retire. Take maybe A year off, retrain myself, and then go back into the market again.

[Jill]

That's so cool. I love that idea. Okay, so you're 60 years old, got a couple years, we'll look at a little off ramp to figure out what happens next. And Bradley, are you single, married, partnered?

[Bradley]

Single.

[Jill]

Okay. And right now you are fully employed. How much do you earn?

[Bradley]

129, 0, 41.

[Jill]

Can I just say 130. Come on, let me do that. I'm going to round up, you earn 130,000. And are you putting money in a retirement account?

[Bradley]

I am. But what's nice about my retirement, it's a tiaa and my job makes contributions too.

[Jill]

Oh, nice. So how much money is in the TIAA account?

[Bradley]

Roughly around 730,000.

[Jill]

Wow, that's great. Will you also be entitled to a pension beyond that retirement fund in tiaa?

[Bradley]

No, it'll only be tiaa. Some of my co workers, what they've done was they've created an annuity to sort of simulate that pension.

[Jill]

Right. So the tiaa, for a lot of people listening, you may not be as familiar with TIAA cref. A lot of colleges, universities, hospitals, they were part of the TIAA CREF system. And, and the TIAA side is an annuity. And actually these are very good and reasonably priced annuities. So what Bradley's talking about is that you could take 730,000, the whole thing or some portion of that and annuitize it, building out a retirement income stream for a long period of time. Sometimes it's a period certain, like 10 years or 20 years. So that's certainly an option. Now, Bradley, do you have other money that's saved either inside of a retirement account or outside of a retirement account?

[Bradley]

Back in November, I really needed, I had bills that had to be covered. So what I did was I withdrew about 100,000 out of my TIAA to cover that. So right now I roughly have about $80,000 in my, in my account that.

[Jill]

You took a withdrawal and you'll pay the tax on that. In other words, you didn't take a loan. Right?

[Bradley]

Right. It was a withdrawal, yes.

[Jill]

Okay, so the 80,000 is in savings.

[Bradley]

Right now it's in my checking account.

[Jill]

Okay. Do you have to pay any more bills out of that 80,000 or not?

[Bradley]

I have a home that's still in mortgage, it's a duplex, a two family.

[Jill]

Okay.

[Bradley]

I don't rent the top floor, but I'd like to do some renovations to take care of that so that I'll have Some type of passive income in retirement.

[Jill]

Huh? How much do you think you'll need to spend to get the. The top floor rentable?

[Bradley]

It's not. It's not a lot. Maybe. Maybe 5,000.

[Jill]

Get out of here. You can't do anything in New York for $5,000 in an apartment. Come on.

[Bradley]

I was lucky enough back in 2001 to win a lottery through Housing Preservation and Development.

[Jill]

Okay.

[Bradley]

Where they renovate properties that were. That were pretty bad off. You're buying it at market value.

[Jill]

Got it.

[Bradley]

So the house itself is literally like only 20 something years old. So I think I can. I think I can get it back in shape.

[Jill]

Okay. What do you think the house is worth right now?

[Bradley]

Around 800,000.

[Jill]

And there's a mortgage that remains, right?

[Bradley]

Yes.

[Jill]

How much?

[Bradley]

370.

[Jill]

What's the interest rate on the mortgage?

[Bradley]

4%.

[Jill]

Even if you said of the 80 grand in savings, let's say you had to spend 10 of that for. To get the rent to make the top floor rentable, what do you think? Any other bills besides that? Money that need. That, you know, that. Of the 80 grand in savings, anything else you have, like a credit card bill or an auto loan, anything else outstanding that you need to use that money for?

[Bradley]

Well, I do have a HELOC.

[Jill]

What's that? How much is that?

[Bradley]

About 130,000.

[Jill]

Interest rate is what, variable?

[Bradley]

It's around 6% now.

[Jill]

And that's the only other outstanding liability you have?

[Bradley]

I do have credit card and also a personal loan. My monthly bills right now come to about 6200.

[Jill]

And how much. Wait, how much is outstanding on the credit card debt?

[Bradley]

About 30,000. Maybe.

[Jill]

Between the two, the loan and the credit card debt.

[Bradley]

I do have a HELOC and of course, credit card bills. I'm really. I'm giving you a very rough ballpark.

[Jill]

Yeah, yeah, yeah. But if you're telling me you got 30 grand in credit card debt right now, yes. Okay, so of the $80,000 that's sitting in savings, the first thing that I think you need to do is before you even start renovating the top floor, is take 30 grand and pay off the credit card debt immediately. Just get rid of that. How much is the personal loan? I'm not talking about the heloc. But you said a personal loan. Was that separate from the HELOC?

[Bradley]

Yes.

[Jill]

How much is that?

[Bradley]

$20,000.

[Jill]

What's the interest rate on the personal loan?

[Bradley]

Oh, wow, it's high. About 20%.

[Jill]

We have $80,000 that's in savings. If you didn't have the credit card debt or that personal loan, what would your expense be? What would the expenses look like for you?

[Bradley]

The personal loan monthly is 363.

[Jill]

Okay.

[Bradley]

The HELOC is 714.

[Jill]

And the credit card maybe.

[Bradley]

Maybe about 500amonth in a credit card.

[Jill]

Okay. So if we got rid of the credit card and the personal loan, we would save about 850 bucks a month out of your 6200. Right. And we'd get rid of this problem. So could you support yourself on your $130,000 a year? Can you just. If you didn't have the credit card debt and you didn't have the personal loan, if that was just gone. Okay. Do you feel like you could manage your cash flow better without, you know, seeing anything, you know, compound? Like, how do you feel about that? Can you do that?

[Bradley]

Yes, I can. I really believe I can. I guess one challenge I didn't. I forgot about is that I will need a new rule. That's one item.

[Jill]

I think that the credit card debt and the personal loan has become, like, a bigger issue on this, you know, because that's a big chunk of money. That 850 bucks a month. I think that if you removed that from your cash flow and we could get rid of that, you already took the withdrawal. And even though I don't love having just 30 grand in savings, I almost would prefer that because I feel, like, the pressure right now if, like, if you had 30 grand in savings and you spent. How much is the new roof? Did you do that already or. You're going to have to do that.

[Bradley]

I'll have to get an estimate on that.

[Jill]

All right, so we have a new roof. We also have the renovation for the top floor. One thing that I would consider is that the HELOC. Can you draw more down on the HELOC at 6% or not?

[Bradley]

Yes, I can.

[Jill]

I would. Mark, tell me if you agree with this. I would use the HELOC to pay for the new roof and the top floor. So you have the 80 grand that came out that it's from the retirement account. Of that 80, I would immediately pay off that credit card debt and that personal loan. I would not use that cash to pay for any house stuff. I would use the HELOC to pay for that, for the new roof and the top floor. That is what it's there for. And then I'd keep that 30 grand in place. Then when you look at your TIAA contribution, how much are you putting in there right now?

[Bradley]

$75 a month, but my job is putting in around $1,200 a month.

[Jill]

Do they put that in regardless of what you contribute?

[Bradley]

Yes.

[Jill]

Mark, what do you think about using this money, the cash, to pay off the credit card debt, the personal loan? We keep the 75 month going into TIAA and let the company do the heavy lifting and see where we stand in a couple years. How do you feel about this right now?

[Mark]

Yeah, 100%. I mean, you know, 20% interest rate on the personal loan. I'm sure the credit card is probably, maybe even higher. So I would get rid of those asap.

[Jill]

Yeah, ASAP is right.

[Mark]

I'm curious, Bradley. What, What? You know, when the renovations are done and you think about renting this place out, any idea what you expect to get in rent?

[Bradley]

I would say about $3,000 a month.

[Jill]

Oh, my God. You got to get this done. Definitely.

[Bradley]

But I'm not. I'm not a landlord. I. I need a. I need a management company to. To. To. To manage the rent, the repairs, and. And, you know, okay. For me.

[Jill]

All right, well, then it won't be three grand a month. Maybe it'll be $2,000 a month. You know, maybe that's what it'll be. You have to find out what that is. But at the very least, here's what I think needs to happen for today, Bradley. Number one is paying off those two big chunks of debt at the high interest rate. Then get the estimates of the new roof, what it would cost to get the top floor. And then you also need to. Once that's done, you'll talk up to management companies and see what they would charge you to do the things you need to get done, and then you'll have this passive income. Now, what I'm not sure about is I don't know if it's two years or four years for you. A lot of this depends on what the rent is going to be from the top floor. Because if you can get the, you know, again, if we drive down your cost of, you know, you sort of living your Life down to 5,400amonth because those two other pieces are done. We build up your. Because you're not spending money on the credit card debt and the personal loan. You build up your savings. You keep putting money in savings, and, you know, two years from now, if you're 62 and the rental income is, you know, three grand a month coming in, and it only costs $500 for you to actually pay the management company, then we have more information to Think about retirement. I don't think we have all the information yet. I'll tell you what I would not do. I would not turn your TIAA into an annuity necessarily, because then you have no, absolutely no liquidity. You don't have access to money if something else is going on. So I'm not so sure that that's the best idea.

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[Jill]

I just don't know. It's a definite. You know, I would normally not say, like, oh, take money out of your tiaa, but I think in this case, having this outstanding debt, you know, you've got like, once you clean that up, I think you're going to feel a lot better. So why don't you get some of this information about the cost of the new roof, the cost of the top floor renovation, maybe even have a realtor come in and give you a sense of like, hey, how much money could I get for renting this out? And maybe you start renting it out, you know, sooner rather than later, and that helps build up your savings. That could also be a great benefit to you. And then we go from there. So get us that information and I think that we can probably help you out a little bit more, give you a little more guidance. And if you are listening to this and you are like Bradley and you need an off ramp, then you want to clean up your balance sheet. That just means cleaning up some of the debt that's sitting out there with some of the assets that you own and you're not sure about the next step. Get in touch with us. Go to jillonmoney.com click the contact us button, which is in the upper right hand corner, no matter where you are on the website. And of course, write us a note. But if you'd like to come on the air live, please check the box and Mark will do everything else. Hey, don't forget to sign up for the free weekly newsletter when you cut onto the website. We love that newsletter and we love having those subscriptions and it's free, so you'll love that too. You can subscribe to us on the Odyssey app or wherever you find your friends favorite podcasts. Please leave us a rating and review wherever you listen. And of course, we like to ask that you lift someone up. Just do something nice. It's a good time of year to do it anyway. You should do it no matter what time of year it is. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

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[Von Miller]

Is Von Miller, Super Bowl MVP, chicken farmer, and now host of Free Range. This is a show where I go off the field and off the script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet, deep dives, the conversation, this is your podcast. Join me every Wednesday. Follow and listen to Free Range with me, Von Miller everywhere. You get your podcast.