55 With the Itch to Retire

Summary

Jill on Money with Jill Schlesinger – Episode 55: "With the Itch to Retire"

Release Date: August 1, 2025

In Episode 55 of "Jill on Money with Jill Schlesinger," hosts Jill Schlesinger, CFP®, and Mark Telassio delve into the complexities of retirement planning, addressing a range of listener questions that highlight common financial dilemmas faced by individuals approaching retirement age. The episode provides actionable insights and personalized advice, making it a valuable resource for anyone contemplating their financial future.

---

1. Balancing Retirement Plans: Veronica's Dilemma ([02:15])

Listener Profile: Veronica, a 40-year-old participant in a 401(k) plan with $75,000 invested, seeks guidance on choosing between a 403(b) and a 457 plan, and selecting an appropriate investment provider.

Discussion Highlights:

• Choosing Between 403(b) and 457 Plans: Mark suggests, “[04:05] ... you can use both, actually, and put a ton of money away.”
• Investment Providers: Jill emphasizes the importance of selecting low-cost providers, stating, “[04:27] ... choose options that give you access to index funds or a target date fund.”
• Avoiding Expensive Insurance Company Funds: Jill advises, “[04:27] ... steer you towards and away from the insurance companies... they can be expensive.”

Advice: Jill and Mark recommend maximizing contributions to both plans if possible and opting for reputable investment providers like Fidelity or Vanguard. They caution against high-fee insurance company funds, advocating for more cost-effective investment options to optimize retirement savings.

---

2. Managing High Incomes and Mortgages: Daisy's Strategy ([06:30])

Listener Profile: Daisy and her husband, both aged 55, have accumulated $1.5 million pre-tax in a 403(b) plan. They earn $300,000 annually and face a $450,000 mortgage at a favorable 2.75% interest rate. With college expenses for their two sons, Daisy contemplates reducing 403(b) contributions to bolster liquid savings.

Discussion Highlights:

• Balancing Savings and Expenses: Mark supports Daisy’s approach, affirming, “[06:50] ... having more money that builds up outside of this and also to allow you to breathe a little bit.”
• Future Savings Strategies: Jill suggests, “[06:50] ... consider a Roth once the kids are done with college.”

Advice: The hosts commend Daisy’s decision to prioritize building up liquid savings over additional 403(b) contributions during the children's college years. They recommend maintaining the low-interest mortgage and suggest transitioning to Roth contributions post-college to maximize tax-advantaged savings.

---

3. Tackling Credit Card Debt: Lenora's Solution ([10:15])

Listener Profile: Lenora faces $50,000 in credit card debt with interest rates soaring between 35–39%. She has an offer for an equity loan that wouldn't impact her current mortgage.

Discussion Highlights:

• Debt Consolidation: Mark advises, “[10:30] ... it is always better to take on the debt that has a lower [interest rate].”
• Preventing Future Debt: Jill emphasizes the importance of understanding the root cause, “[10:45] ... how did this credit card amass?”

Advice: The hosts support Lenora’s plan to utilize the equity loan to pay off high-interest credit card debt, highlighting the financial relief from lower interest rates. They stress the necessity of addressing underlying spending habits to prevent a recurrence of debt issues.

---

4. Navigating Late-Career Financial Pressures: Marie's Conundrum ([12:00])

Listener Profile: Marie, a 62-year-old earning six figures, carries a $652,000 family mortgage and $89,000 in student loan debt under the Biden Save program. Recent medical bills have depleted her savings, leaving her with a three-month emergency fund.

Discussion Highlights:

• Preserving Emergency Funds: Jill advises, “[12:30] ... do not blow through your emergency fund.”
• Adjusting Retirement Contributions: Mark recommends, “[12:45] ... drop your contribution to the minimum to get your match.”
• Leveraging Home Equity: Advice is given to consider, “[13:00] ... leverage some part of this house that you could maybe help pay off some of the loans.”

Advice: Jill and Mark recommend Marie maintain her emergency fund, minimize retirement contributions to secure employer matches, and explore leveraging home equity to manage student loan debt. They emphasize the importance of sustaining a financial cushion to navigate potential emergencies.

---

5. Assessing Retirement Readiness: Antonio's Queries ([14:00])

Listener Profile: Antonio, 55, and his wife, 56, are semi-retired with $1.6 million in a 401(k), $90,000 in a Roth, $40,000 in a traditional IRA, and $90,000 in stocks. They rely on Social Security and pensions, and Antonio seeks to retire with a target of $10,000 monthly spending.

Discussion Highlights:

• Feasibility of Retirement Goals: Mark cautions, “[13:43] ... Probably doable. Not a slam dunk.”
• Retirement Timing and Strategies: Jill explores options, “[13:57] ... Maybe we can make it work. But I don't think it's a 58. I think it's either 60 or 62.”

Advice: The hosts assess Antonio’s financial position, noting that while the assets and income sources are substantial, the $10,000 monthly target may be ambitious. They suggest delaying retirement slightly and potentially adjusting withdrawal strategies to align income with expenses, recommending a detailed personal consultation to refine the retirement plan.

---

Hosts' Insights and Conclusions

Throughout the episode, Jill and Mark emphasize the importance of personalized financial planning tailored to individual circumstances. They advocate for:

• Maximizing Tax-Advantaged Accounts: Leveraging plans like 403(b) and Roth IRAs to optimize savings.
• Managing Debt Wisely: Consolidating high-interest debts and avoiding future accrual.
• Maintaining Financial Flexibility: Building liquid assets to handle unexpected expenses without derailing long-term goals.
• Strategic Retirement Timing: Aligning retirement age with income needs and asset availability to ensure financial stability.

---

Get Involved

Jill and Mark encourage listeners to engage with the show by submitting their financial questions via jillonmoney.com and consider appearing on the program for personalized advice. They also invite listeners to subscribe to their Weekend radio show and explore additional resources available on their website.

---

Notable Quotes:

• Jill Schlesinger at [04:27]: “... steer you towards and away from the insurance companies... they can be expensive.”
• Mark Telassio at [06:50]: “... having more money that builds up outside of this and also to allow you to breathe a little bit.”
• Jill Schlesinger at [10:45]: “... how did this credit card amass?”
• Mark Telassio at [13:43]: “Probably doable. Not a slam dunk.”

---

For more information and to get your questions answered, visit jillonmoney.com.

Transcript

[Robert Half]

Need contract help for those workload peaks and backlog projects. You're not alone. Robert half found that 67% of companies surveyed said they will increase their use of contract talent. That's why their recruiters leverage their experience and use award winning AI to quickly find the skilled candidates you want. Learn about their specialized talent in finance, accounting, technology, marketing, legal and administrative support at Robert Half. They know talent. Visit roberthalf.com talent today.

[Carvana Representative]

Thanks for selling your car to Carvana. Here's your check.

[Carvana Customer]

Whoa.

[Time Traveler]

When did I get here?

[Carvana Representative]

What do you mean?

[Time Traveler]

I swear it was just moments ago that I accepted a great offer from Carvana online. I must have time traveled to the future.

[Carvana Representative]

It was just moments ago. We do same day pickup. Here's your check for that great offer.

[Jill Schlesinger]

It is the future. It's.

[Carvana Representative]

It's the present and just the convenience of Carvana. Sorry to blow your mind.

[Time Traveler]

It's all good. Happens all the time.

[Carvana Representative]

Sell your car the convenient way to Carvana.

[Jill Schlesinger]

Pick up.

[Carvana Representative]

Times may vary and fees may apply.

[Jill Schlesinger]

Welcome to the Jill on Money show. It's Friday, August 1st and we are here answering your financial questions. We are on this financial journey with you. There are many ways to get where you want to go. Our job, both me and Mark, we think of this as part of our jobs that we want to try to help you figure out the different ways to get you where you'd like to go and then ultimately you'll choose. But if we see something that's going on based on what you've told us and we think that you know, oh my gosh, you should shift things around, we'll let you know. But if you're in good shape, we'll help you know that as well. So if there is a concern that you have, maybe you are mid career and you'd really like to do something different. Maybe you're really wondering how is it that I can buy a house if I've been shut out of the market for so long? Or is it so foolish to give up a 3% mortgage rate to go into something else? Whatever is on your mind financially. Mark and I are here for you. We're both certified financial planners and we've been doing this for a while. So just go to our website, jillonmoney.com in the upper right hand corner there is a contact us button. You click that button. When you do so, a form will pop up and that is the email that we will receive. So check that out. By the way, if you get a chance, you can also listen to our Weekend radio show. Just a little factoid for you all to enjoy. It is our 750th radio show that we are broadcasting this weekend. We have been on the air doing this since 2011. So it was first the radio show, then this podcast, then. Then the Money Watch podcast. If you want to contact us and you want to look at all the other content that lives in the Jill on Money world, just go to jillonmoney.com okay, we have got to do some emails. So many are piling up. So thank you all to the shy people. It is really your turn. All right, this is from Veronica, who writes, I'm a relatively new listener, and I've binged most of the episodes. Oh, I love that. The question is, how do I choose between a 403 and a 457 plan? And. And how do I know which investment provider to use? She says I currently participate in 401k. I use a target date fund. Can I. And should I roll the money over from Lincoln Financial? I'm late to the game. At 40 years old with only $75,000 invested. Thank you for taking the time to read my email, Mark. You're the best. I went back and listened to older episodes, and it was so weird not hearing your input. I prefer the newer format that includes your advice and input much more than those early years. I'm not quite sure I'm ready to take the shot at being on the program live. So it's a big transition. Once I settle into my new position, I'm gonna definitely reach out to you. Mark, get yourself on the microphone. Let's talk. First of all, thank Veronica for her nice words about you.

[Mark]

Yeah, Veronica's my favorite listener right now. She's gotta come on.

[Jill Schlesinger]

Yeah, she gotta come on. We're gonna. She'll change her name. So, Mark, how do you think about the 403 versus the 457? You can use both, actually, and put a ton of money away.

[Mark]

Yeah. If your cash flow allows you to do that, you can max out both. I'm not sure what the situation is here. I would probably opt for the 403B. I'm guessing that one probably has a Roth option.

[Jill Schlesinger]

Yes, that's exactly right. So one of the things that I would look at, Veronica, is I know you say you've got a lot of options. Lincoln Financial, your old provider. Not a great provider. It's an insurance company. It's probably stuck in some very expensive types of funds inside of that. So ideally, what you would do is in the 403, you would choose what option gives you access to index funds or a target date fund? Either one. But if you have a plan that offers, I'm going to rattle off some names for you like a Fidelity or a Vanguard or a T. Rowe Price. If you have one of those, that's kind of where we're going to steer you towards and away from the insurance companies. This is not a slam at any future advertiser who would like to come and support this show, although some insurance companies have reached out to us and they then say you don't like us very much. It's not that I don't like insurance companies. I love insurance companies. When they sell straight up insurance, that's uncomplicated. What I don't love about many insurance companies and their products is they can be expensive. So what I think would be helpful would be to take whatever you have. Currently you can use a target date fund for 75 grand. It's okay. Roll it into the 403B. That will be your pre tax. But Mark is right. If you have an opportunity to use a Roth to start this new job, that's what we would suggest. So, Veronica, get back in touch with us. Mark's your favorite, is your favorite. I get that. No hard feelings. He's my favorite, too. All right, next up, Daisy. Here's what she says. Hi, Jill and Mark. I'm a new listener, Mark. I love all these new listeners. My husband and I are both 55. We've saved a million and a half dollars pre tax in a 403B. Okay, there you go. I think we earn too much for roth contributions at $300,000 a year. My husband will be entitled to a small pension of $500 a month. I will be entitled to $7,000 a month in pension payments after both of us are at age 63. Eight short years. Okay. They're going to have employer sponsored health insurance for life. So here's the issue. Daisy says we are house poor. We've got a $450,000 mortgage with a 2.75% interest rate. There's 24 years left. Our home is worth about $1.8 million. Okay. So she says we have reduced our 403 contribution to the minimum tax to obtain the match of 6% while we cash flow college expenses for our oldest son and four years for our youngest son. Blah, blah, blah, blah, blah. Okay. She says, I'm thinking that we would continue putting in 6% even beyond the college years just to increase our cash on hand instead of putting more money in the 403, especially considering those mandatory distributions later. Is this a good plan? Keep the house payment with the low interest rate and manage the mandatory distributions. Thank you, Daisy. Daisy, I think this is a great idea. Absolutely. And I would build up that money. And you look, you're going to have a few years here where you've got the kids and paying for college. That's a real deal. Right. But I definitely think having more money that builds up outside of this and also to allow you to breathe a little bit that I can get on board with. What I would also suggest to you is that if you have the ability, once the kids are done, maybe you're making a little more money. Maybe you consider a Roth. Maybe that's another way to put some money to work. But it seems like you're on the right track. This next question is from Lenora, who says I have a large credit card debt and has an offer for an equity loan that would not impact her current mortgage. $50,000. Question. Does it make sense for me to pay off my credit cards, which charge you ready for this, Mark? 39 to 35% if I can get a lower interest rate on the equity loan? Yeah, of course. But I'd want to know other things that are going on. How did this credit card amass? I really would like to know that, but without any further information. Yes. I think it is always better to take on the debt that has a lower. And hopefully, even if it's a. Even if it's a variable rate, it would be a lower rate than what you're paying, and then you can really start focusing on paying that down over time. I do really have an issue. Not an issue, but I have a concern that we don't want to start some big bad spiral into getting into debt again. So get back in touch with us so we can understand what else is going on. Okay. Marie writes, I'm 62 years old. The only debt that she has is a $652,000 family mortgage, of which I pay half. I work, I make six figures. But I also have you ready for this, Mark. $89,000 in student loan debt. She's 62 years old. It's currently in the Biden Save program. It's accruing interest starting now, as a matter of fact, August 1st. The save plan is going away next summer, so I can do another consolidation and be grandfathered into a lower payment plan and work to pay off the higher interest rate first and work my way down until it's all paid off. I figure it should take me about a year without any emergencies. Here's the dilemma. I had medical bills I've had to pay off, which depleted most of my savings. Do I use what little I have left of my savings to pay off my student loans or. Or do I make minimum payments until I die? Or do I take out a simple interest personal loan for $89,000? The compound interest has exploded. My student loans, six years of college, and all these years, you can imagine the interest. I only have a three month emergency fund. What is the plan of attack? I would not actually blow through my emergency fund. Here's what I would do. You still work. You make six figures. Drop your contribution. If you're making any contributions to retirement plans, drop that down to the minimum to get your match. That's it. Then the family mortgage. This is, I think because of a divorce. Do you own the home or is there something separate? Just like the previous question, would it be possible to leverage some part of this house that you could maybe help pay off some of the loans? And in general, I think that it is a bad idea to have zero savings if you're in your 60s. So I wouldn't do that. I'd like to hear more from you. The plan of attack for me would be no using up all of the money that you have in the three month emergency fund. Try to keep building that up, minimize the amount of money you put into retirement and keep whittling it away. It's going to be tough. Okay, here's a question from Antonio who writes. Oh, first, hi, Jill and Mark. Love the show. Nice mix of information and entertainment. Keep it up. I'm so entertaining. Antonio writes, my question is about retirement. I am 55. My wife is 56. She's semi retired. There's $1.6 million in a 401k, 90,000 in a Roth, 40,000 in a traditional 40,000 in HSA, $90,000 in stocks. I expect $2,800 a month from Social Security, 2,150 for my wife. Now check this out. He has a pension. Varying pension amounts based on his age of retirement. So let's go to like say age 62. If he were to do it at 62, he gets 4,300amonth versus next year where it would be $2,600 a month. They own their home, no mortgage, no other debt. I don't hate my job, but I can see the end in sight and would like to know how close I am to being Able to retire and spend. Ready for the number, Mark, $10,000 a month. So think about this, gang. He wants to spend 10,000amonth. We know the best idea here. Come on, we all understand this. There's going to be 3, $5,000 in Social Security about. And we know that if he waits till age 62, he gets $4,300 a month in pension. That's pretty close to the $10,000. Plus they've got this $1.6 million. That's good. That to me is the obvious, obvious way to manage this. I guess the question is, Mark, what would happen, you know, when someone says, I like my job, but I see the light at the end of the tunnel? Like, does that mean we should really look at that middle scenario where if he works for a few more years, he gets 3200? What would you think about that, Mark, if he chose to retire at his age 58, knowing they have that Social Security coming and this pension amount, what do you think about ten grand a month on that total?

[Mark]

Probably doable. Not a slam dunk. I'm not sure. The Social Security estimates that he provided, I don't know which age those are based on.

[Jill Schlesinger]

Right. I don't either.

[Mark]

I have a feeling it's taking it early. Ten grand a month, it's not a slam dunk.

[Jill Schlesinger]

No, it's a real number. So I'd love for you to get back in touch with us. Meaning maybe we can do this. Maybe it's age 60 and we come up with a scenario where you're pulling some money out at age 60. You delay, you don't take, you don't pull the trigger on the pension. Maybe you start pulling money out of that pre tax account. Maybe we wait till you grab your Social Security, maybe we can make it work. But I don't think it's a 58. I think it's either 60 or 62. And I'd love to hear back from you. Come on the program. We would be happy to look at this with you. And for those of you who are feeling a little bit like you want some help, you're scared to come on the program, just come do it. We'll change your name. It won't be a problem. It will be easy to do. All you need to do is go to jillandmoney.com, click the contact us button, write us that note, check the box. Mark will do everything else. While you're on the website, check out all of our content that lives there, and you can subscribe to this podcast as well as our Money Watch podcast on the Odyssey app or wherever you find your favorite podcast. Leave us a rating and review wherever you listen. Okay, it's Friday. Let's do some business. Our music is composed by Joel Goodman. Mark Telassio is our executive producer and the king of all things web. As I mentioned, we are distributed by the lovely folks at Odyssey. Try to 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 on Monday.

[WIX Representative]

It's time to turn your daydream into your dream job. WIX gives you the power to turn your passion into a money maker with a website that fits your unique vision and drives you towards your goals. Let your ideas flow with AI tools that guide you, but give you full control and flexibility. Manage your business from one dashboard and keep it growing with built in marketing features. Get everything you need to turn your part time passion into a full time business.

[Carvana Customer]

Go to wix.com hey there cats and kittens. It's Brian from the commercial break. The mediocre comedy podcast where my best friend Chrissy and I attempt to make sense of the world. We talk about the absurd, the the ridiculous and the stuff no one asked for like Internet weirdos, pickup artists and why everyone is obsessed with crystals and colonics. It's all gotta stop. The show is free, it's frequent and it's probably not for everyone. You can go to tcbpodcast.com, [e-mail] thecommercialbreak or check out the show wherever you listen to podcasts. We'll see you on the next commercial break. And best to you.