At What Age Would I Be Able to Retire?

Summary

Episode Summary: At What Age Would I Be Able to Retire?

Podcast: Jill on Money with Jill Schlesinger
Date: January 21, 2026
Host: Jill Schlesinger, CFP®
Producer: Mark
Theme: Real listener questions about retirement age, investing strategies, and financial advisor fees, with practical, jargon-free guidance.

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Main Theme & Purpose

In this episode, Jill Schlesinger and her producer Mark dive into listener emails, focusing on retirement readiness—especially around the question: “At what age would I be able to retire?” Jill parses the financials, asks the tough follow-ups, and gives actionable advice on everything from target retirement age to questions about long-term care, advisor fees, and pension decisions. The tone is empathetic, direct, and reliably irreverent, cutting through complexity to help listeners take practical steps with their money.

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Key Discussion Points & Insights

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1. Case Study: Katherine’s Retirement Readiness

[03:30 – 09:30]

Background:
Katherine, 52, married with 2 teens, wants to know when she can feasibly retire. She earns $195k/yr, has $851k (mostly pre-tax) in retirement, $227k in joint taxable investments, and hefty emergency savings, but no pension or property. Monthly expenses are $10–12k (with $6k rent in NYC), and college savings are solid at $342k (529 plans). She’s not planning to retire in the next 10 years.

Key Considerations & Jill’s Analysis:

• Retirement Accounts & Savings Rate:

  • Contributes 14% of salary plus $31k (catch-up) annually.
  • Large chunk in traditional pre-tax accounts; some Roth, healthy liquidity.
  • No pension; has a 414(h)—a little-known public sector retirement plan.

• Household Expenses:

  • Unusual division—husband covers rent, Katherine covers all other expenses.
  • “His situation is more unpredictable. He owns his own business.” (06:33)

• Katherine’s Central Question:

  • Should she plan for retirement at 65, 67, or 70+?
  • Wonders if expenses will drop in retirement.
  • Concerned about long-term care insurance and not burdening her kids.

Jill’s Candid Take:

“I think you should target 67. You got to get these kids through school, right?...Then you'll use some pre-tax money for the few years in between and then you’ll get this big chunk of [Social Security].” (09:08)

• On Expecting Lower Expenses in Retirement:

  • “I doubt that. I would never just—everyone listening—don’t presume that unless you are paying for something like out-of-pocket, that definitely will go down. I think we should always presume you’ll spend exactly what you’re spending today.” (07:06)

• On Social Security Timing:

  • Advises deferring until 70 if possible for higher benefits.

Mark’s Observations:

• Wishes Katherine joined on-air for more details, especially about her husband’s finances since the marital finances seem so separate.

  • “Is she asking us will she have enough to cover her expenses or the whole thing?” (08:43)

• Even with incomplete info, Mark estimates:

  • “She’s going to have around $3 million when she’s 64...Yeah, that'll probably get her to what she needs.” (08:50)

Open Questions Jill Wants Answered:

• Why do Katherine and her husband file taxes separately?
• What’s behind their financial separation?
• “Katherine, get back in touch with us.” (09:08)

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2. Financial Advisor Fees: Are You Paying Too Much?

[10:30 – 12:30]

Melinda, retired with $330k, wonders about an advisor fee of 1.25% (about $4,000/year), versus the 0.75% internal fees she’s currently paying on her funds (all at Fidelity).

Jill’s Blunt Ruling:

“The acceptable fee is zero if all they’re doing is actually managing money. That’s my feeling.” (11:00)

• For standard asset allocation, Jill says Melinda should stick with index funds (even suggests the Fidelity Go robo-advisor at 0.3%) if she wants hands-off help.

• “No, you don’t [need someone moving money around].” (11:22)

• Mark interjects:

  “Gotta be actively managed because I have one of those same funds, and it’s basically free.” (11:14)

• Jill:

  “They're not gonna be able to find the top and the bottom of the market—nobody can.” (12:18)

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3. Should I Use RSUs to Buy Rental Real Estate?

[12:31 – 13:30]

John, 56, is tech-rich in restricted stock units (RSUs) and wondering if he should sell some for a $1M rental property to diversify away from stocks/bonds.

Jill’s Take:
Focus on liquidation and diversification—but a $1M rental is a major commitment. Instead, she recommends:

• “Maybe you sell the RSUs anyway and just like peel off some of that consolidated position.”
• “If you want liquidity, you could certainly sell RSUs to get that big bet off the table.”
• Not enough info on John’s full circumstances:

  “I don't know anything about you. So if you want liquidity...” (13:24)

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4. Should I Elect a Pension Annuity or Lump-Sum Rollover?

[13:40 – 15:40]

Jeff has a defined contribution pension, 401k, and brokerage account. Should he take an annuity for guaranteed lifetime income or roll the pension to an IRA? He’s confused why Jill warns about annuities, yet loves pensions.

Jill Distinguishes:

• Pensions often provide lifetime income with low costs.
• Retail annuities usually come with high annual fees (2–3% or more).

“Here’s the question...if you had a million dollars in your 401k and you say, ‘I want to take half of it, buy an annuity, lose the access to the money...Would you pay 2.5% a year for that? I wouldn’t. And that’s what a lot of annuities cost.’” (14:30)

• Each tool can work, but cost matters:

  “It's very important that we would look at the cost of what that annuity is and what your alternatives are.” (15:24)

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Memorable Quotes

• On Retirement Planning Realism:

  “Don’t presume [expenses will go down], unless you are paying for something that definitely will. I think we should always presume you’ll spend exactly what you’re spending today.” (07:06, Jill)

• On Financial Advisor Value:

  “The acceptable fee is zero if all they’re doing is actually managing money.” (11:00, Jill)

• On Annuity Fees:

  “Would you pay 2.5% a year for that? I wouldn’t. And that’s what a lot of annuities cost.” (14:30, Jill)

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Notable Moments & Recommendations

• Jill and Mark’s candid banter about financial plans that seem “very separate,” highlighting missing info in listener scenarios. (08:21–08:49)
• Jill’s recurring plea for listeners to come on-air for deeper, more helpful conversations.
• Mark’s technical contributions and quick clarifications, such as on 414(h) plans and Fidelity fund fees.

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Timestamps for Important Segments

• Listener Katherine’s Retirement Scenario: 03:30 – 09:30
• Advisor Fees and Value: 10:30 – 12:30
• RSUs for Rental Property Decision: 12:31 – 13:30
• Pension Lump Sum vs. Annuity Buy: 13:40 – 15:40

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Final Thoughts

This episode is a masterclass in honest, practical financial advice. Jill and Mark walk through complicated family, career, and retirement decisions, always emphasizing the need to ask tougher questions, keep costs low, and make only the moves that serve your specific circumstances. If you want actionable guidance with no sugarcoating, this episode delivers.

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Transcript

[A]

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[B]

Yeah, I haven't even come across that in my cfp. Continuant Ed.

[A]

Hold on a second. Let's just. We gotta google this. Hold on. Standby people.

[B]

414 Plan, state and local government employees exclusively.

[A]

Yes. Okay, here it is.

[B]

And no pension.

[A]

That stinks. Okay, all right, we're going to get back to this. So it's a. Whatever. It's a retirement plan for state employees and city. Okay, catch up. Goes into a deferred 457 plan. 31 grand in 2025. So 14% of her salary plus 31 grand. Then also a Roth IRA through a backdoor. Oh boy, isn't that incredible? She and her husband file their taxes separately. Hmm. Something's going on there. But again, because Katherine, you're not coming on the air with us, I can't ask the follow up questions. Okay. On average they spend 10 to 12 grand a month. 6,000 goes to rent. And by the way everybody, I just want to point this out. She's in New York and six grand is a rent stabilized apartment.

[B]

It seems high.

[A]

Well, I don't know if she has a three bedroom. It's not right because she has a 16 and a 14 year old. Okay, so six grand rent, the rest is their expenses. Husband and I split the expenses where he is responsible for rent. She takes on the rest. I consider his portion of the expenses. Right, that's six grand a month. That's a liability because while I have a stable job, his situation is more unpredictable. He owns his own business, he's got variable income. Both kids are going to College. They've saved $342,000 in 529 plans. Boy, I wish I had some of that money for retirement. I am not planning to retire in the next 10 years. At least. Okay, good. And she says, I know it's impossible for me to do so, but how about this question mark? Should she be prepared to work until 65? 67 or 70, maybe even beyond. Assuming I continue to contribute at the same rate as today. Social Security at 67. That's all I care about, gang, is 4 grand. It's about 5,100. At 70, she says, I assume that my expenses will decrease in retirement. I doubt that. I would never just everyone Listening. Don't presume that unless you are paying for something like out of pocket, that definitely will go down. I think we should always presume you'll spend exactly what you're spending today. She's in good health. Longevity in her blood. She is. Estate documents that have been drafted, but she's got to revise it when each kid reaches 18. I'm also considering whether now is the right time to buy long term care insurance. I don't want to burden my children in the old age and would prefer to live independently as long as my health would allow. Okay, Mark, come on the microphone. What do you think about Katherine?

[B]

I wish Kathryn was on the microphone with us because this whole thing seems very separate to me. Like she gives us her income and her retirement savings. But clearly the husband's working because he's covering the rent. But I don't know what he's making. I don't know what he has saved. And their monthly spend. I'm assuming that's both of them.

[A]

Let's just say it's 12 grand a month. Half he covers, half she covers.

[B]

Right. So is she asking us will she have enough to cover her expenses or the whole thing?

[A]

Let's say the whole thing.

[B]

You know, she's contributing, you know, let's just say $40,000 a year. She's going to work for another decade. I put in 12 years. She's going to have around $3 million. When she's 64, she will. I have no idea about her husband. So, you know, is that going to get her? Yeah, that'll probably get her to what she needs. When you factor in Social Security at 67.

[A]

Here's what I'm thinking. I'm thinking I want you to come back on the air. But here's what I really think from your very specific questions. I think you should target 67. You got to get these kids through school, right? So we know she's got a 14 year old. So we got like seven years more, right? She says, I know I have to work 10 more years. So let's say that she retires when she's 67. Okay? She'll test it. You know, Katherine, you'll keep running these numbers, but I think in your head I think you should target 67. I think that most likely you'll defer. You'll wait to claim your Social Security until you're 70. You'll use some of that pre tax money for the few years in between and then you'll get this big chunk of money. We would love for you to get in touch with us and tell us more about why you and your husband have such different. Why you're filing separately and what's really going on. There's a possibility when you file separately that maybe someone had to declare bankruptcy. Or maybe there's a situation where people will be on income driven repayment plans for their own loans well into the future and that maybe having filing separately makes sense. I don't know. Let's get to an easier question. Katherine, get back in touch with us. Okay. Melinda wants to know what is an acceptable fee for a financial advisor? Okay, let me just start by saying this. The acceptable fee is zero if all they're doing is actually managing money. That's my feeling. No, if they're just going to be money managers, don't hire somebody. But here is what Melinda says. She was quoted one and a quarter percent, which would be approximately $4,000 a year for the approximate $330,000 invested in mutual funds from a reputable advisor. The current funds that I have are about 0.75%. Wow, that's high. She's got a few different Fidelity funds. Why is that so high? I'm going to just look.

[B]

Got to be actively managed because I have one of those same funds, and it's basically free.

[A]

Okay, so she has management of three index funds. She says all she has is 330 grand. It's all she has. She's retired. She thinks her fund fees are high. Do I need someone to be watching and moving as times indicate? No, you don't. Then she says, my husband had made poor choices and doesn't have much invested. She's 70 years old, and she will have to start withdrawing at 73. I mean, look, one and a quarter percent is not terrible, but I'm not sure why you need this. I think that what you might need is, like, if this is the. The situation where you're thinking like, hey, I need someone to move my money around. No, then it's not worth it. Maybe what you should do is frankly be with. You know, you own Fidelity Funds. Just keep your money at Fidelity and maybe use the Fidelity service. What's that called again? I always forget. Mark. Gosh.

[B]

Fidelity Go.

[A]

Fidelity Go. Maybe you have a Fidelity Go account and you just let them do it. It'll be like 0.3%, but no, I don't think so. I don't think it makes sense to pay one and a quarter percent. No, I do not. And they're not gonna be able to find the top and the Bottom of the market, nobody can. Okay, John wants to know, should I sell some restricted stock units in a technology company in order to buy real estate? My mindset is that I would be balancing my portfolio so that I am not just 100% in stocks and bonds. I'm 56. I'm well ahead of my retirement goals. I'm wondering, the trade offs, taxes, loss of dividends, future gains. Should I use my RSU money to buy a rental property to create steady rental income in the future? The property in mind is a million dollars. Come on, John. I have a lot to ask about this. I mean, if you're really worried about just being in stocks and bonds, maybe you sell the RSUs anyway and just like peel off some of that consolidated position and maybe you can create a brokerage account and maybe inside your 401k you can you add some other asset classes. I don't know if I would buy rental real estate. I don't know anything. Like, I don't know anything about you. So if you want liquidity, you could certainly sell RSUs to like, get that big bet off the table. That might be something very, very interesting. Okay, this last email is from Jeff, who says he wants to know about payout options for defined contribution plans versus a traditional annuity purchase. Hi, Jill and Mark. Thank you for the helpful perspective and insight you share with your listeners. I have a general question. It just doesn't seem to get enough airtime. In addition to my 401k, as well as separate money in a brokerage account, I also have a defined contribution pension plan available to me upon retirement. No cola. I may consider the annuity option when the time comes instead of a lump sum to be rolled over because it would provide some guaranteed lifetime income. Okay. I don't think you would be opposed to that choice because after all, Jill loves pensions. But isn't that really the same thing as someone just buying an annuity with a 401 disbursement? After all, both types of lump sums could be rolled into an IRA for liquidity, which I know Jill also loves. My confusion is based on the fact that on your show you often frown upon annuities, but pensions are typically embraced. Can they be considered the same thing? What am I missing? Hopefully you appreciate that this question is philosophical, so I didn't put any numbers around it. Okay, here is what you're missing. Annuities. Many annuities, not all of them have wildly high fees. That's what we're missing. So here's the question that we would look at Jeff in your situation, which is if you had, let's just say you had a million dollars in your 401k and you say, you know what? I want to take half of it, buy an annuity, lose the access to the money. Right? I lose my money and I don't have that access to that money. I've lost that liquidity and I turn on an income generating machine. Sounds great. Would you pay 2.5% a year for that? I wouldn't. And that's what a lot of annuities cost, 2, 3% a year. So it's not a bad idea. But I think in isolation it could work. But it's very important that we would look at the cost of what that annuity is and what your alternatives are. Whereas with a pension, you have this lump sum that you could roll over and do whatever you want with or a stream of income. And that is very different than, and has a much different cost structure associated with it. So I hope that helps. Okay, if you've got a question, if you've got something going on, philosophical, concrete, doesn't matter, go to Jill on money dot com, click the contact us button. Of course, let us know if you'd be willing to come on the air live with us, because we'd love to have you. Don't forget to sign up for the free weekly newsletter and subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review. Wherever you listen, and we ask that you lift someone up today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. 2026 is calling and it's your year to launch that business you've been dreaming about. We all have ideas, talents, or projects we keep putting off. But the magic happens the moment you take action. Don't let another month slip by. January is short, and the fastest way to turn your vision into reality is to start your business with Shopify. 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If you're interested in what's happening with all the places where you consume sports, the sports media podcast has you covered.

[B]

I've been turning down interviews all week. Coda Copy reached out. Oprah, George, Stephanie. So I said no. I was booked on the Deitch podcast before the Taylor Swift phenomenon. I must live up to my responsibility.

[A]

Listen wherever you get your podcasts.