In Our Mid 50s, Can We Retire?

Summary

Podcast Summary: "In Our Mid 50s, Can We Retire?"

Podcast Information:

• Title: Jill on Money with Jill Schlesinger
• Host/Author: Audacy
• Episode: In Our Mid 50s, Can We Retire?
• Release Date: May 5, 2025

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Introduction

In this episode of "Jill on Money with Jill Schlesinger," host Jill Schlesinger delves into the complexities of nearing retirement in one’s mid-50s. The episode features a candid conversation with listeners Jane and Matt from Arizona, who are contemplating retirement within the next year. Jill provides insightful guidance on decumulation strategies, tax implications, investment management, and health insurance considerations to help Jane and Matt navigate their impending retirement with confidence.

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Guest Introduction and Retirement Goals

[03:15]
Jill Schlesinger: “Okay, today we are talking to Jane and Matt. They join us from Arizona. Hello, you two. How are you?”

Jane and Matt from Arizona: Jane and Matt are both 54 years old, soon to be 55, and have been long-time listeners of the show. They are planning to retire within the next year and seek Jill’s expertise to fine-tune their decumulation strategy, especially concerning their tax-deferred assets.

[03:28] Matt: “So longtime listeners and have been thinking about this, and we're coming upon retirement, we think within the next year, probably less than that... we just don't want to go into it blindly. We're trying to do all of our prep on our side so, you know, we can compare notes with [our financial advisor] and, and just looking for an unbiased opinion on what we're facing.”

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Financial Overview and Assets

Jill begins by assessing Jane and Matt’s financial portfolio to understand their readiness for retirement.

[04:15]
Jill Schlesinger: “Okay. How old are you guys?”

Matt: “54. Soon to be 55. Both of us.”

Key Financial Assets:

• Pension Lump Sum:
  [04:26] Matt: “I will have a lump sum pension that's going to pay out over the summer... about $30,000.”

• 401(k):
  [04:52] Matt: “$1,500,000 in a 401.”

• Stock Plan (RSUs and Options):
  [04:58] Matt: “That's approximately, let's say 55 grand.”

• Traditional IRA:
  [05:14] Matt: “Husband has a traditional IRA at $850,000.”

• Roth Account:
  [05:20] (Clarification Needed)
  Matt: “It's a Roth. That's 80 grand.”

• Brokerage Account:
  [05:29] Matt: “It's just over a million dollars.”

• Health Savings Account (HSA):
  [05:49] Matt: “Approximately $32,000.”

• Cash Savings Outside Brokerage:
  [06:04] Matt: “$110,000.”

• Real Estate:

  • Primary Residence:
    [06:09] Matt: “Worth $625,000, paid off.”

  • Short-Term Rental Property:
    [06:26] Matt: “Approximately $625,000 with a remaining mortgage of $385,000. Planning to sell this fall, potentially netting around $200,000 after taxes.”

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Decumulation Strategy and Rule of 55

Jill emphasizes the importance of a strategic decumulation approach to ensure a sustainable income in retirement.

[12:11] Jill Schlesinger:
“Do you want to invoke the rule of 55 to start pulling money out of that 401k that has not yet been taxed? [...] Part of a decumulation strategy is kind of like, it's sort of twofold. What we know is you have a bunch of money, right? Most of your money has not been taxed yet.”

Explanation of Rule of 55:
The Rule of 55 allows individuals aged 55 or older to withdraw funds from their 401(k) without the early withdrawal penalty. Jill advises leveraging this rule to begin decumulating retirement funds in a tax-efficient manner.

[12:13] Matt:
“I would certainly consider that.”

Strategic Withdrawals:

• 401(k): Utilize Rule of 55 to withdraw funds gradually over the next decade to meet the monthly expense target of $10,000.
• Traditional IRA: Continue growth for the next 10 years, tapping into it post-401(k) depletion.
• Social Security: Plan to claim benefits at 67 or delay until 70 for increased monthly payouts.

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Tax Implications and Professional Guidance

Jill underscores the necessity of understanding tax obligations, especially when liquidating assets like rental properties.

[07:44] Jill Schlesinger:
“[...] make sure you have a CPA or a tax filing service or person you work with. [...] When you sell [the rental property], [...] you depreciated it. So just know that there could be some tax due.”

[17:49] Matt:
“We just redid the will. We're set there.”

Jill’s Advice:

• Engage with Professionals: Ensure continuous collaboration with a CPA to navigate tax implications effectively.
• Avoid Unnecessary Products: Stay clear of products like annuities unless explicitly beneficial, as Jill warns against them even when suggested by fiduciary advisors.

[15:42] Jill Schlesinger:
“[...] Do not buy any product. [...] even fiduciaries could probably make a case that you guys might want to consider an annuity. [...] It’s not the right thing for you. [...] If this person happens to bring up an annuity, you need a new advisor.”

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Health Insurance Considerations

Navigating health insurance post-retirement is a critical concern for Jane and Matt.

[08:39] Jill Schlesinger:
“So what's the game plan on that? Are you guys thinking Affordable Care Act for 10 years? Kind of.”

[08:45] Matt:
“We’re exploring options like crowd-sharing services due to narrow networks and challenges in finding comprehensive coverage.”

Jill’s Recommendations:

• Stockpiling Cash: Allocate proceeds from the house sale and HSA to cover health insurance premiums and potential medical expenses.
• Alternative Coverage Options: Investigate options like Affordable Care Act plans or crowd-sharing services to ensure adequate health coverage without resorting to additional employment.

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Investment Management and Advisor Selection

Effective management of existing investments is pivotal to sustaining retirement funds.

[15:24] Jane:
“Our advisor manages the traditional IRA and the brokerage account with minimal fees, at about 1% of assets under management.”

Jill’s Guidance:

• Fiduciary Standards: Ensure the financial advisor is a fiduciary who prioritizes Jane and Matt’s best interests.
• Cautious Investment Choices: Avoid risky products and stick to mutual funds or other stable investments as currently managed.
• Guard Against High-Fee Products: Be wary of advisors suggesting products that may not align with long-term financial goals, such as annuities.

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Estate Planning and Final Preparations

Jill emphasizes the importance of having comprehensive estate documents in place.

[17:49] Matt:
“We just redid the will. We're set there.”

Jill’s Final Tips:

• Ensure Up-to-Date Documents: Regularly review and update wills and life insurance beneficiaries to reflect current wishes.
• Comprehensive Coverage: Verify that all aspects of estate planning are addressed, including trusts if applicable.

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Key Takeaways and Conclusion

Jill Schlesinger provides Jane and Matt with a clear, actionable roadmap to transition smoothly into retirement:

1. Leverage the Rule of 55: Begin strategic withdrawals from the 401(k) to meet monthly expenses without penalties.
2. Manage Tax Implications: Work closely with a CPA to minimize tax liabilities, especially when selling assets.
3. Ensure Health Coverage: Utilize proceeds from asset sales and HSAs to secure comprehensive health insurance.
4. Select the Right Advisor: Choose fiduciary advisors and avoid unnecessary financial products that may not align with retirement goals.
5. Estate Planning: Maintain updated wills and life insurance policies to ensure estate preferences are honored.

[17:53] Matt:
“Our biggest... trying to avoid any unforced errors as we move forward.”

Jill’s Final Advice:
“[...] avoid buying products you don’t need and ensure your financial strategies are aligned with your long-term goals.”

Jane and Matt expressed satisfaction with the guidance provided, feeling more confident in their retirement plans and equipped to avoid common pitfalls.

[18:27] Jill Schlesinger:
“Thanks so much for getting in touch with us. [...] Change your work, change your wealth, change your life.”

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Notable Quotes

• Jill Schlesinger on the Rule of 55:
  [12:11] “Part of a decumulation strategy is kind of like, it's sort of twofold. What we know is you have a bunch of money, right? [...]”

• Matt on Avoiding Additional Income Needs:
  [15:09] Matt: “We haven’t counted on additional income.”

• Jill's Warning Against Annuities:
  [15:43] “Do not buy any product. [...] If this person happens to bring up an annuity, you need a new advisor.”

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Conclusion

This episode serves as a comprehensive guide for individuals in their mid-50s contemplating retirement. Through Jane and Matt’s real-life scenario, Jill Schlesinger illustrates the critical steps and considerations essential for a secure and fulfilling retirement. Listeners gain valuable insights into managing assets, understanding tax implications, ensuring health coverage, and selecting the right financial advisors to support their retirement journey.

For personalized advice or to discuss your own retirement plans, visit jillonmoney.com and reach out through the "Contact Us" button.

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Subscribe and Connect:
Stay updated with future episodes by subscribing on the Odyssey app or tune into the sister broadcast, Money Watch. For more resources and expert advice, visit jillonmoney.com.

Transcript

[Jill Schlesinger]

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[Matt]

Hey, Jill. We're doing well. How are you guys?

[Jill Schlesinger]

What's happening? What's going on? I mean, Scottsdale, so nice. All of Arizona. I'm a big fan of Tucson also. So what is it that we can do for you? How can we help you out today?

[Matt]

So longtime listeners and have been thinking about this, and we're coming upon retirement, we think within the next year, probably less than that. And so assuming all the models we've run and the scenarios, I feel like we're there, you know, ready to step away. I want to do something different. I know that typically you're, you know, thinking, well, what do you want to do next? I have ideas. It's retiring to, not retiring from. But the biggest thing I think we want to nail down is our decumulation strategy because we're pretty knee deep in some tax deferred assets. We have a meeting with our financial advisor coming up, and we just don't want to go into it blindly. We're trying to do all of our prep on our side so, you know, we can compare notes with him and, and just looking for an unbiased opinion on what, what we're facing.

[Jill Schlesinger]

Okay. That's awesome. How old are you guys?

[Matt]

54. Soon to be 55. Both of us.

[Jill Schlesinger]

So young. Wow. Will you be guys be entitled to pensions?

[Matt]

I will have a lump sum pension that's going to pay out over the summer. The company has decided to do the lump sums instead of. They froze it years ago. So I think that they're just unburdening themselves.

[Jill Schlesinger]

Okay, and how much will that be, that lump sum?

[Matt]

About $30,000.

[Jill Schlesinger]

And then what other retirement assets do you have, Jane, that this lump sum would be added to?

[Matt]

401K. Do we want to start there?

[Jill Schlesinger]

Sure, why not?

[Matt]

$1,500,000 in a 401.

[Jill Schlesinger]

Not taxed yet.

[Matt]

Correct.

[Jill Schlesinger]

Okay.

[Matt]

I do have a stock plan with some RSUs and options for 20, 25 that vests. That's approximately, let's say 55 grand. That's going to dump into there.

[Jill Schlesinger]

Okay.

[Matt]

Husband has a traditional IRA at 850,000. We do have a joint Roth.

[Jill Schlesinger]

What do you mean a joint Roth? There's no such thing.

[Matt]

Okay, well, it's a, it's a Roth.

[Jill Schlesinger]

You have. Someone has a Roth. It's either in your name or his name.

[Matt]

Correct. That's 80 grand.

[Jill Schlesinger]

What about the brokerage account? What do you got?

[Matt]

It's just over a million dollars.

[Jill Schlesinger]

So we've got the lump sum payout. Your traditional. There's a little Roth. There's a traditional IRA in Matt's name. And we have the brokerage account. The stock plan's going to get added to the brokerage account. Any other assets that are in invested accounts?

[Matt]

There is an HSA of approximately 32,000.

[Jill Schlesinger]

Oh, that's great. When I look at like the cash accounts, do you include like the cash on hand inside of that brokerage account or do you have something outside of the brokerage account that's cash or cash.

[Matt]

Equivalents savings outside of that? $110,000.

[Jill Schlesinger]

You guys own your home?

[Matt]

We do, yeah.

[Jill Schlesinger]

How much Is it worth?

[Matt]

625. Paid off.

[Jill Schlesinger]

How. How paid off? Great. How is the room for me and Mark? Can we visit?

[Matt]

Well, we, we do have another property. You could stay at a few.

[Jill Schlesinger]

Oh, where's the. So rental property?

[Matt]

It is. It's a short term rental right now and we're considering selling that actually. I think we've made the decision to sell it this fall. So that's another.

[Jill Schlesinger]

How much is that worth?

[Matt]

Approximately 625.

[Jill Schlesinger]

Oh two 625s. A pair of 625s. And is there no mortgage on that one either?

[Matt]

There's a mortgage on it of 385,000 remaining.

[Jill Schlesinger]

Did you buy it, you know, at a much lower value?

[Matt]

No, not really. I mean, it's appreciated. It's appreciated some. Since we purchased it.

[Jill Schlesinger]

Are you declaring the short term rental income as rental income flowing through on your tax returns?

[Jane]

We are, Jill, but it's been, you know, here's one of the challenges we've been facing. So it's, it approximately costs about, let's say 38k for the rental. One season we were able to break even here. In the recent seasons it's probably brought in around 20k and we do shut it down over summer and when we go back to visit family and so forth. So it's. Yeah, it's.

[Jill Schlesinger]

It Costs. So the only thing that I just want to point out, since you're going to sell it in this year, is make sure you have a CPA or a tax filing service or person you work with.

[Matt]

We do. We just had a conference with her about this. Yes.

[Jill Schlesinger]

Fabulous. Because she's going to tell you, well, it may not feel like you've made a lot of money, but I depreciated it. And now when we sell it, I have to capture the depreciation. So just know that there could be some tax due, that's all. It doesn't mean you shouldn't do it because you've got a lot of equity. Right, right. And so it'd be nice to unlock that equity as you approach your retirement. Right. So, you know, whatever, 240, let's say it's 200 grand you'll net.

[Matt]

I think that's fair. Yeah.

[Jill Schlesinger]

Okay. So that'll go into the brokerage account, which is fabulous. So that's another 200,000 from house sale. Is there anything else you want to do with that money? Are you going to tell me that, you know what, in the summer we want to go north and we want to invest that $200,000 from the house proceeds to buy something else or not?

[Matt]

No. We were, you know, thinking of, you know, we're going to have to pay for health insurance in some. In some form. Pretty much trying to stockpile, you know, cash.

[Jill Schlesinger]

So what's the game plan on that? Are you guys thinking Affordable care Act for 10 years? Kind of.

[Matt]

You know, the networks are so narrow. We're not having good luck finding, you know, you can get coverage, but to get care is a whole nother equation. You know, there's some other options of crowd sharing type services that we're looking into. So there's.

[Jill Schlesinger]

But neither of you wants to get another job. You're not going to be baristas to get health insurance is what.

[Matt]

No, no. Highly unlikely.

[Jill Schlesinger]

All right, so you're saying, let's look at that house proceeds, that $200,000, plus whatever's in the HSA. We're going to burn that up. That's going to pay for health care? Essentially, yes. All right. This is great. Do you have kids? Grown.

[Matt]

No kids.

[Jane]

No kids.

[Matt]

No kids. We're dog people, but no dogs currently.

[Jill Schlesinger]

It's hard to have dogs in Arizona. I knew this because I had friends who lived in Scottsdale and it was traumatic getting the dog used to the hot weather, basically meaning that in the summer they had to get that dog up very, very Very early and walk the dog.

[Jane]

Yeah, you do have to adjust getting up early and. Yeah, so that is a challenge.

[Jill Schlesinger]

All right. But I think you should get a dog. Okay. Now, in terms of your spending, what is it that you. And again, let's presume that the short term rental is sold. Now tell me what you think you spend on a monthly or annual basis.

[Matt]

Ten grand a month.

[Jill Schlesinger]

That's it?

[Matt]

Yes.

[Jane]

Yeah, that's on the high end. It can range 8 to 10. So instead of picking 9, let's. Let's go with 10.

[Jill Schlesinger]

Let's go with 10. I like that. All right, so let's do some math. Mark, are you ready to math with me? It's going to be fun. So, mark, we have 3.7, 3.7. Or wait, total. Or let's do traditional first. Don't even include that Roth. So that's. We have the, the 1.5. Right. And then the 850. Right. That's our, that's our, like what we're on the hook for in terms of RMDs. Correct. There's nothing else. Okay. It's 1.5 plus the lump sum payment. It's 880 and 1.5. Okay, Mark, let's grow that for. Let's grow that for 10 years. Tell me what you got at age 65 at that point. Yeah, you're north of 4 million. All right, so that would be 4 million at age 65. Okay, I'm just looking at this now. So then we have the brokerage account and the Roth account. When you're looking at your strategy, and I'll talk about decumulation in one second. What are you thinking about in terms of claiming Social Security? Are you going to claim at age 67?

[Jane]

You know, we have, you know, we're certainly. We're not married to it or we do have the numbers of what the benefit would be.

[Jill Schlesinger]

All right, what's your benefit at 67 or 70?

[Matt]

So it's 67 for me. It's 3300 and it's 3100 for him.

[Jill Schlesinger]

Okay, 3300 and 3100 at 67. And what about at age 70 for you guys?

[Jane]

Roughly say, I think 4000. I looked at the estimates recently, so.

[Jill Schlesinger]

Okay, yeah, instead of 6400, about eight grand. Okay, the question is, and I'm going to ask Mark this, Do you want to invoke the rule of 55 to start pulling money out of that 401k that has not yet been taxed? Mark, if the plan allows It.

[Jane]

I would certainly consider that.

[Jill Schlesinger]

Yeah, that's. So have. So part of a decumulation strategy is kind of like, it's sort of twofold. What we know is you have a bunch of money, right? It's most. Most of your money has not been taxed yet. There is a rule that allows you, if your plan allows it, to take money out of. To tap money out of a 401k before the age of 59 and a half, as early as age 55, hence the rule of 55. And you could pull money out of that account a little bit at a time. Okay. And that is a pretty interesting idea for you guys because you would avoid having that money pile up, pile up, pile up, Be forced to take the money out. You get the money out sooner, live on it. Because we have to replicate this. 10 grand a month, right? So if you pulled 150 grand out or so, and you paid the tax that's due, you're in the 22% tax bracket, and you live on what you pull out of that 401k, that's pretty good. That's pretty close there. And if you did that for, let's say, 10 years, and you essentially started to deplete your 401k slowly but surely over the next 10 or 12 years, then you get to age 65, 67, then the Social Security benefit kind of kicks in. You have the money that's in the brokerage account. You also have the old traditional IRA that's still bubbling up because we can only tap money from the 401k and invoke the rule of 55. You can't do it with a traditional IRA.

[Matt]

Okay?

[Jill Schlesinger]

So I think that when we talk about decumulation for you guys, we would say, how about we live on your 401k? If again, you have to check to see if you're allowed to use the rule of 55 in your plan.

[Matt]

They do recognize it.

[Jill Schlesinger]

They do. Okay, fantastic. So essentially, I would use that, take all the money out of that as I possibly could over the next, say, 10 years. You'd essentially get. You know, I think you'd probably deplete it over 10 years or so. Maybe a little bit. I don't know. It'll depend on markets. But let's just say you get. It's done. But the traditional IRA will have. Will continue to grow over the next 10 years. You could use that if you wanted to. Once the 401k is depleted, you then turn to the traditional IRA, start using that, and then once you are claiming Social Security either at 67 or 70. We're now, like off to the races because we haven't touched your brokerage account and we haven't touched the traditional IRA or the Roth. Now, is there any idea, like you said, okay, we're going to retire, too. Is there any hope, dream of making a little bit of cash on the side or not?

[Jane]

You know, we want to volunteer more with our, with the rescue organizations. So it's. Yeah, we hadn't really.

[Matt]

We haven't counted on additional income.

[Jill Schlesinger]

That's fine. You don't need to. I mean, if it happened, it happens. You know what I mean? Like, that's fine. Please don't feel like you have to. I think it works. So the advisor that you're meeting with, does that person manage the traditional IRA and the brokerage account?

[Jane]

Yes.

[Jill Schlesinger]

Okay. What kind of investments are in those accounts? Are they mutual funds? Are they. Are they. Yes. Okay. How do you pay this person?

[Jane]

So he is a fiduciary. It's a minimal fee.

[Jill Schlesinger]

Okay.

[Jane]

Yeah.

[Jill Schlesinger]

Okay. Okay. And it's like 1% of assets under management. Exactly.

[Jane]

Yes.

[Jill Schlesinger]

Okay. If for some reason this person says, I have a great idea, let's take that 401k, or let's take your traditional IRA and invest it in an annuity. Do not do anything like that. Do not buy any product. Do not buy any product. I want to say this three times. Ready for your third time? Please, do not buy any product. Even fiduciaries could probably make a case that you guys might want to consider an annuity. Because they would say, look, we'll take that traditional ira. We'll, you know, invest it for a few years, but then we'll start pumping money out. It'll be a guaranteed monthly income. There can be a shock and jive on this. It's not the right thing for you. I'm going to tell you that right now.

[Jane]

Okay.

[Jill Schlesinger]

So if this person happens to bring up an annuity, you need a new advisor.

[Matt]

Okay, Noted.

[Jill Schlesinger]

All right. All right. Now, what else do we need to know about this? Does this plan seem reasonable to you? I mean, the health care thing is a big deal, so I'm going to leave that to you guys. But you got to have coverage. We want to make sure you have, you know, 10 years of coverage. And I think you're right that, you know, you're going to need 10 or 15 grand just for that. So that's why I think it's good that you have that. The house proceeds to pay for that.

[Matt]

Yeah. No, I think. I think that this makes sense. It's, you know, confirming what. What we're thinking. You know, our biggest. Aside from the planning is just trying to avoid any unforced errors. I guess, moving forward, you know, you tend to.

[Jill Schlesinger]

Well, you know, I don't think there'll be an unforced error if you avoid buying product. I think the only unforced error would be someone convincing you that you need something that you probably don't need. Also, an unforced error might be if an advisor were like, oh, let's roll your 401k over to your traditional IRA. But you lose the ability to invoke the rule of 55. Okay, that would be the unforced error.

[Matt]

All right, makes sense.

[Jill Schlesinger]

Now, what about. Do you guys have any estate documents? Done. You're going to be traveling. You have everything all set?

[Matt]

We do. We just redid the will. We're set there. And.

[Jill Schlesinger]

Great.

[Matt]

We've got our life insurance in place.

[Jill Schlesinger]

Who's getting all the money? Exactly. Where's that insurance going? Where is it going? Come on.

[Jane]

Based on statistics, Jane. Will.

[Jill Schlesinger]

Jane and her second husband Will. That'll be very nice for them. Excellent. I. I just recently told my wife I thought it would be I because we have a friend who has found love after a deceased spouse. And I said, you know, honey, what I really want is for you to wear black for the rest of your life and be miserable. She goes, thank you. That's very nice to know. I'm glad.

[Matt]

Honesty is the key to a long and healthy marriage.

[Jill Schlesinger]

That's right. Exactly. I want everyone to be happy. All right, Jane, Matt, Arizona, go have some fun. Stay cool. Put on your sunblock. Thanks so much for getting in touch with us. If you guys are listening to this and are like, oh, rule of 55. I want to know if I can do that. Give us a holler. Maybe it's something else going on in your. In your financial life or your broader Life. Go to jillonmoney.com, click the contact us button, write us a note. If you want to join us on the air live. Check the box. Mark will do everything else. Don't forget, you can subscribe to this show on the Odyssey app. You can also subscribe to our sister broadcast called Money Watch, both of them available through the fine folks at Odyssey. Do me a favor and lift someone up. Change your work, change your wealth, change your life. Thank you for listening. Don't drink too much tequila tonight, because we're going to talk to you tomorrow. Hey, gang. I was a small business owner. I know how hard it is and starting your business should actually be simple. Now you can get more when you start your business with Northwest Registered Agent, your entire business Identity in just 10 clicks and 10 minutes. Northwest registered agent provides more privacy, more guidance and more freedom to run your your business from anywhere. If you want to build your business while keeping your personal information secure, Northwest is the partner you need. In just 10 clicks and 10 minutes. They'll form your business. Create a custom website and set up your local presence wherever you need it. Don't wait, protect your privacy, build your brand and set up your business in just 10 clicks in 10 minutes. Visit northwestregisteredagent.com Jill and start building something amazing. Get more with Northwest registered [e-mail] Jill when you're with Amex Business Platinum, you have the card that helps businesses dream bigger, get a flexible spending limit that adapts with your business and earn 1.5 times Membership Rewards points on select business purchases so you can stock up on what you need to take your business further and get rewarded for growing bigger. That's the powerful backing of American Express. Not all purchases will be approved. Terms apply. Learn [e-mail] AmEx Business.