Help My Parents Plan for Retirement

Summary

Podcast Summary
Jill on Money with Jill Schlesinger
Episode: Help My Parents Plan for Retirement
Date: April 10, 2026

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Main Theme

In this episode, Jill Schlesinger helps a caller, Elise from New York, navigate the complex process of planning her parents’ retirement. The episode focuses on evaluating retirement income sources, Social Security claiming strategies, and consolidating scattered retirement assets—emphasizing transparency, simplicity, and risk management for people approaching retirement age.

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Key Discussion Points & Insights

1. The Family’s Situation (01:55–05:00)

• Background: Elise’s parents, both in their early 60s, have worked in the same jobs for about 40 years in a small town.
  • Dad: Hands-on, labor-intensive job; currently out on disability due to injuries, repeatedly returning to disability (03:10).
  • Mom: Long-time work-from-home, starting to burn out, aiming to retire at 62 (05:04).
• Challenge: Their previous financial advisor retired and the proposed replacements are product salespeople. Elise believes her parents need impartial planning, not more products.

2. Dad's Disability and Social Security (03:24–05:04)

• Jill clarifies whether the current disability is via workers’ comp, Social Security Disability Insurance (SSDI), or private insurance.

• Potential Income: If Dad retires now, he’d receive $1,915/month from Social Security at 62. Unknown on SSDI eligibility; Jill urges consulting HR and possibly an attorney to maximize benefits (04:34).

  “You have to see an attorney about that or at least talk to someone… Is the workplace being nice about it?” — Jill (04:37)

3. Estimating Retirement Expenses (05:48–06:22)

• Elise did a “deep dive” into her parents’ expenses, which were initially underestimated.

  • Actual monthly expenses: ~$4,400, (Aim for $5,000 for cushion).
  • Dad’s estimate: $3,700—Jill finds this underestimated (06:13).

  “Everyone has that same situation… What is the real-real number?” — Jill (06:06)

4. Asset Overview & Complexity (07:02–11:30)

• Annuities: Both parents were sold multiple annuities (~$118k, $58k, $12k, $53k), mostly fixed indexed, using prior retirement account rollovers.

  “That’s because if you have one [fixed indexed annuity], why not have a second?” — Jill, jokingly (08:46)

• Other Assets:

  • Dad: Small ESP, HSA ($1,400-$1,700).
  • Mom: IRA ($23k), current employer retirement plan ($121k; 20% Roth), $5k from old employer, ESP ($42k).

• Issue: Accounts are scattered; consolidation is key for clarity and manageability.

  “I think the other big thing is wanting to clean this up.” — Elise (10:58)

5. Social Security Claiming Strategy (12:01–16:58)

• Elise’s Dad’s Mindset: Strongly prefers claiming at 62, even though he’d have much higher benefits by waiting—$2,771/month at 67 vs. $1,915/month at 62.

• Jill’s Argument: Delaying to 67 is a “risk-free way to increase your benefit,” and aligns with Dad’s low risk tolerance. Bridge interim years using annuity income, gradually drawing them down until Social Security kicks in at full retirement age (FRA).

  “If you have a low risk tolerance, the reason that you would delay taking Social Security is that will be a risk-free way to increase your benefit… You cannot get risk-free money anywhere.” — Jill (15:00)

• Mom: More open to following advice; her 67 benefit would be $2,586/month (13:00).

• Notable Strategy: Annuitize contracts as Dad stops working, creating a steady income “bridge” to 67; do the same for Mom.

  “Let your father retire with dignity, knowing that he’s got his money.” — Jill (15:50)

• SSDI: If Dad is eligible, could pay up through full retirement age—potentially critical for their income plan (16:52–17:24).

6. Steps for Simplification and Consolidation (18:04–20:41)

• Find Fee-Only Advisor: Elise is seeking a CFP who does not sell products; Jill cautions that even fee-only planning can be expensive.

  “We don’t want product and we want someone to help you consolidate these accounts.” — Jill (18:36)

• DIY Consolidation: For those comfortable, Jill advises using a low-cost provider (Fidelity, Vanguard, Schwab, T. Rowe Price), rolling over pre-tax and Roth accounts into respective new accounts. Explains this is largely paperwork but makes long-term management vastly easier (19:17–20:40).

7. Family Communication and Emotional Reassurance (21:25–22:28)

• Jill stresses the importance of reassurance: Elise’s parents have saved enough if they follow her plan. If they claim Social Security too early, their future is less certain, but if they wait, “they’re going to be fine” (22:09).

  “They’ve saved enough. They’re going to be fine. They don’t spend that much money. If they wait until 67, they’re going to be fine. If they take it at 62, I’m not so sure.” — Jill (22:14)

• Mark adds: “62 does not cover their needs… Wait till 67, that’s going to cover their needs for the rest of their lives.” (22:42–22:54)

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Memorable Quotes

• On annuities:
  “That’s because if you have one [fixed indexed annuity], why not have a second?” — Jill (08:46)

• On Social Security strategy:
  “Risk-free money… Social Security is the lowest risk way to manage this process.” — Jill (15:00)

• On fixing inherited financial clutter:
  “I think the other big thing is wanting to clean this up.” — Elise (10:58)

• On tough love:
  “If you wait till 67 to claim, we think we can make it work. 62, not sure.” — Jill (22:28)

• On helping parents:
  “You’re doing such a mitzvah for your parents. Everyone listening should really take a note from Elise.” — Jill (20:41)

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Important Timestamps

• 01:55 – Elise introduces her parents’ situation
• 03:10 – Dad’s health, disability, and job status
• 05:57 – Actual vs. estimated monthly expenses
• 07:02 – Review of retirement assets and annuities
• 12:01 – Social Security claiming calculations
• 15:00 – Jill’s pitch for delaying Social Security as a risk-free move
• 18:18 – Planning vs. product-pushing financial advisors
• 19:17 – Steps for consolidating accounts
• 21:25 – Emotional assurance: “They’ve saved enough.”
• 22:28 – The hard truth: waiting is safer

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Actionable Recommendations

• Evaluate all potential income streams, especially claiming Social Security and SSDI at the optimal time.
• “Bridge” early retirement years by annuitizing existing contracts, rather than drawing from Social Security early.
• Consolidate scattered accounts through a reputable, low-fee institution, avoiding commission-based or high-fee advisors.
• Have honest conversations early—when parents are well—to set expectations, simplify the estate, and avoid crisis management later.

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Tone & Takeaways

Jill remains supportive, candid, and slightly irreverent throughout (“Oh my god, your dad is. Oh my. This guy’s a year older than I am!”). The episode’s practical, empathetic approach empowers listeners to ask uncomfortable questions, demystifies complex products, and stresses the importance of acting before a health or financial decline forces quick decisions.

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For anyone helping loved ones navigate retirement—or worried about their own—this episode offers a blueprint for reducing risk, maximizing lifetime income, and avoiding traps set by product-pushers in the financial industry.

Transcript

[A]

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[B]

Hi, Jill. Hi, Mark back there, too. I am coming on because I was recently at home visiting my parents, and they're getting ready for retirement. And I realized that they are in a transition moment. A woman that they were working with just retired, and they've been approached by another person to help them out. And I realize these are both people that kind of sell products, and I just think that that's not what they need. And so I just offered to help them clean up and figure out how we can get them prepped.

[A]

Okay. How old are they?

[B]

My dad is 61, and my mom.

[A]

Oh, my God. Your dad is. Oh, my. She's talking about them like, I thought they're elderly. This guy's a year older than I am, Mark. Are you kidding me? I just. I meant now I'm mad. Like my elderly parents. My aging parents. Oh, God. All right, Your dad is 61. How old is your mom? Younger than my mom is.

[B]

60. She just turned.

[A]

Oh, I could be your mother is what you're saying to me now. I feel terrible about myself, Mark, right now. All right, tell us a tiny bit about what their situation looks like.

[B]

So my parents, believe it or not, have both been at their jobs for just about 40 years. Each of them.

[A]

Oh, my God. So they're still working?

[B]

Yes, we're from a small town where it was kind of like you got the job and you stuck with it.

[A]

Okay.

[B]

My dad's job has. Is a hands on labor intensive job and it's actually been causing him some physical ailments in these past few years. So he was out on disability the other year and now he's actually back out in disability again because he's had some injuries and it's unclear whether he's actually like already retired, like if he ends up going back or not. But I think that's part of the impetus of this, figuring this out, how they can do this.

[A]

Okay, so just quick question about him. So when you say he's on disability, meaning Social Security disability or disability from work, where they're making a claim on long term disability through his workers working disability policy.

[B]

Workers comp.

[A]

Disability workers comp. Okay. If he were to go out and just be done, what would the amount of money he would be entitled to

[B]

be from Social Security at 62, it's $1,915.

[A]

But he would stay on workers. Doesn't he, wouldn't he then qualify for SSDI or not?

[B]

That's a good question. And I don't know much about that.

[A]

Okay. We definitely. You have to see an attorney about that or at least talk to someone. Is the workplace being nice about it?

[B]

Yeah, they've always been helpful. As soon as he has an injury and goes out.

[A]

Okay. All right, so someone there? Probably. I'm sure he's not the first person that this has happened to. I'm presuming somebody knows about this, right?

[B]

Oh, yeah.

[A]

Okay, so next up. Next question is about mom. Tell us about what she's up to.

[B]

Mom has is a long time work from home. She works on the phones. She is very vibrant and she is, I would say, becoming less happy with her job as the day goes by. But she Plans to work until she is 62 as well.

[A]

How much does she earn?

[B]

3340amonth.

[A]

3300. About a month. So what would the ideal time horizon be for both of them right now? Is to just be done immediately. Yeah.

[B]

For my dad, it's kind of figuring out, can he just be done? Like go. I'd hate to see him go back when he just keeps getting injured.

[A]

Yeah, I mean, that seems horrible. So let me ask you a different question. How much money do they spend right now? What does their expense level look like?

[B]

So this is funny. My dad gave me what he thought their expenses were and then I did a deep dive. And it is not what their expenses are.

[A]

You know what's so funny? It's everybody has that same situation. So tell us, what is the real number? The real real number?

[B]

4400.

[A]

All right, so even if we just said 5000amonth, right.

[C]

What did he tell you?

[A]

What did he think?

[B]

3, 700.

[A]

Okay.

[B]

He probably, I realized was the number basically if they both took Social Security at 62.

[A]

Okay, I got it. All right, so we'll go. Let's go into like what they have saved and what's really possible here.

[B]

Yeah.

[A]

So again, if they were both, I. I don't feel like your mom's going to be. She's not going to be done right now. You mean if he. If right. So how much can we assume she works at least till a couple more years or not.

[B]

He will work until 62. And then the other thing I should say is she is willing, she is interested in getting some part time work part time.

[A]

Like a thousand a month or two grand a month. What do you think?

[B]

Yeah, I would say like maybe two grand a month.

[A]

Okay, two grand a month, which would be helpful obviously from like 62 to 65.

[B]

Yeah.

[A]

If he. Are either of them entitled to a pension?

[B]

So my dad worked, the company he worked for did have a pension and then basically back in 2018 was when they were bought out. And so he was given all of his pension money and I had to move somewhere, which is how they got involved with this first financial person.

[A]

Okay. So that's why we have some rollover asset that was then sent. They. Someone sold them a product. Okay, so let's talk about their assets right now for a second. So first of all, what's the cash on hand that they have?

[B]

So in a savings account, high yield savings, they have basically just over $11,000.

[A]

Okay. And what about retirement accounts? So we had. We know about that rollover but what is. What is the value of the retirement account that has not yet been taxed? So traditional retirement accounts.

[B]

So that's where it gets a little confusing to me. Okay, so they were sold annuity products.

[A]

Okay.

[B]

So they've basically, between the two of them, have four different annuities.

[A]

Okay. And they're all. They were. But the source of all of those annuities. Those four annuities was a retirement account.

[B]

Correct.

[A]

Okay, so they haven't been taxed yet.

[B]

No.

[A]

Okay, so now what I need to know is the annuities that are in your father's name versus your mom's name.

[B]

Yeah. So my dad has a fixed indexed annuity that is about $118,000.

[A]

Fixed indexed. 118. Go, keep going.

[B]

Then he has another fixed index.

[A]

That's because if you have one, why not have a second?

[B]

Yeah.

[A]

Right. Okay.

[B]

The second one is around $58,000.

[A]

All right. Do you know when he purchased these?

[B]

Yes. So I. They gave me their logins, and they purchased these in 2018. So from my understanding is they can't get out of them until, like, 2028.

[A]

Not. No, not necessarily. That's not true. You can get out of them. There's different things you can do. You can annuitize them, you can take the money that was put in, but not the earnings. But there. There's ways to get money out of those annuities for sure. Okay. So don't freak out. And it's not like it's locked in. It's just kind of like it's locked in for a period of time with a surrender period. Usually that can be up to 10 years. It's usually more like seven. So now, next question. Mom's annuities.

[B]

Yes. So she's got a secure growth fixed annuity.

[A]

Sounds great.

[B]

Yeah. For just under. Just over 12,000.

[A]

Okay.

[B]

And then she's got a fixed indexed annuity for about under 53,000.

[A]

Anything. And so there's our four annuities. Two each, right?

[B]

Yes.

[A]

Okay. And is that it for all the assets? There's no IRA account? No. What do you got?

[B]

They've got more.

[A]

All right, so no more annuities, I hope. No, no. Oh, thank God.

[B]

My dad has an ESP account with his new company that basically just has just under $500 in it.

[A]

Okay.

[B]

And he has to keep that while he works at the company.

[A]

Okay.

[B]

Is what he told me. Okay. And then he's got 1400 and an HSA. And then my mom is more complicated.

[A]

Okay.

[B]

He's got about 23,000 in, like, a Voya IRA.

[A]

And is there a current retirement plan at work for mom?

[B]

We've got about 121,000, and about 20% of that is Roth. Then she has about 5,000 from an old employer that hasn't been rolled over anywhere.

[A]

Oh, my God. I can't believe you found all this stuff. God bless you. It's amazing.

[B]

I think the other big thing is wanting to clean this up.

[A]

Oh, yeah, totally.

[B]

And then the other thing she has is about 42,000 in ESP.

[A]

There's, like, little bits everywhere. My God.

[B]

They've gone through a lot of, like. Well, they've been at the same company. These companies have gone through different ownerships.

[A]

Yes, I see. And so they all have different little, like, benefits and.

[B]

Yeah.

[A]

Stuff there. Okay, so. All right.

[B]

And then one more thing.

[A]

Yes?

[B]

He's got $1700 in an HSA.

[A]

Okay. Is your father's disability a disability that I'm sorry to ask. This is a very crass thing to ask because I'm sure that this is not fun. That 61 year old has. Is out on disability. So first let me start by saying that stinks. However, I also am trying to get a sense of a claiming strategy for him. Is his health otherwise good? Is this more of like an orthopedic thing? Is this something where it would not impact his life expectancy, or would it impact his life expectancy?

[B]

More orthopedic and would not impact his life expectancy.

[A]

Okay, so tell me about his family history. Is. Did his parents live a long time?

[B]

Oh, yeah. His parents lived until their 80s and my. His great grandmother until her 90s.

[A]

Oh, wow. Okay. So if we could figure out a way for him to wait until age 67 to claim Social Security. Do you know what his Social Security benefit. I know you told me the 1915 number at 62. Do you know what his 67 benefit looks like?

[B]

$2,771.

[A]

Okay, great.

[B]

I tell you right now, Jill, he's done. So he's been so kind to me and my brother and helpful, but he's a very stubborn person and he's very set on taking his at 60.

[A]

62. Okay, well, we're gonna see if we can guilt them into it. So let's just see. What would your mom's benefit be? Would she do what we asked her to do?

[B]

Yes, she would be more keen to do what we asked.

[A]

What's her 67 benefit?

[B]

67 is 2,586.

[A]

2,586.

[C]

All they gotta do is wait till 67.

[A]

All they gotta do is 67. If we could get him. Okay, how about if I give him this situation? Try this on. Does he think these annuities are good or does he feel like I'm pissed? This guy bought sold me something I don't need.

[B]

What I said to him and he agrees is just. He didn't understand it and he didn't have anyone to help guide him. And they kind of thought this was more of a financial planner and instead they were just selling products. He's not mad about it. And he also agrees that they were probably sold these products because my dad has such a low risk tolerance. Okay, he was.

[A]

Okay, but wait, wait. That's good for me to know because here's what we're going to tell him. That if you have a low risk tolerance, the reason that you would delay taking Social Security is that will be a risk free way to increase your benefit over what we believe is your life expectancy. He might like this if we sell it to him this way. Meaning you took a bet and you said, I really want low risk. So what I would suggest is as soon as your father is retired, what we start to do is we annuitize these contracts. Okay. So you can essentially say, you can call up the insurance company and you can say, we would like to know what is the monthly or annual amount which would come out of these two fixed annuities. And you can just say we're interested in taking, like maybe we do the big One first, the 118. We want to get this emptied out between now and dad's age 67, and he'll get paid a monthly amount just like Social Security. It's essentially like getting a Social Security check. We're going to get that money out of this contract because it costs money to have it in there. And we're going to build the bridge to Social Security. So that bridge is coming because your father was really, you know, he is risk, he's risk averse. Maybe if we say to him it's like a more conservative approach to wait to claim Social Security because we know you're gonna get more money and that is risk free. That extra $800, $900 that he's going to get is going to come out without any. Is going to come to him risk free. You cannot get risk free money anywhere. So that's the way I would sell it to him. And you can play him this podcast if you'd like. You could play him this conversation and the same Goes with mom. I mean mom, if she's going to work until age 62, then from 62 to 65, she's working some part time stuff, right? No problem. She can either do that or not. She would do the same thing. She would be looking to get rid of to annuitize one of her two annuities before her age 67. They'll have plenty of money because once they get to Social Security, whatever annuity, they don't annuitize. We can keep annuity, we can just get that money out, we can consolidate all the other money and they're going to be fine. It's just this weird thing, five, six years where we want to let your father retire with dignity and knowing that he's got his money. But what you can say to him is if you claim Social Security early and then wait to take the fixed annuity money out, you are actually making a bet that costs you money and has more risk. Social Security is the lowest risk way to manage this process. Mark, do you, is that, are you buying that as like, do you think dad will buy in or not?

[C]

Well, maybe if he hears this, but. And they also have to really look into the SSDI part of this.

[A]

Well, absolutely. So what we, what I would do is talk to someone at work in the HR department and say, you know, how does this convert to Social Security disability claim? Which would mean that he would get his money up to, you know, until he is able to claim Social Security. I don't know, Mark, SSDI, does it only pay to 62?

[C]

It says it's usually available until the

[A]

applicant reaches full age, full Social Security age. So that would be good. So if he could get Social Security disability insurance until his age 67, oh my God, then he'll be so psyched. Right? But I still think even if he couldn't just really bang home that the money in the fixed annuity is costing him money. Right? It costs money to have it in that structure. Social Security doesn't cost you any money and it's building, building, building and then boom, that Social Security money is guaranteed and inflation protected. So what's better than that?

[B]

Nothing.

[A]

Nothing. So meanwhile on your side of it, you've got to start consolidating these, the variety of accounts that we have here. So I think that the first question is, are you going to do this yourself or are you going to get some help?

[B]

So that's the question. And I started, I went to the CFP website from your site and I actually found a woman who's not Far from where they live. Who I reached out and asked to have a call with her.

[A]

Okay.

[B]

She focuses on CFP plan, on planning and not selling products. There just so many people in there.

[A]

I know, I know. If she's going to do planning that that would be great. And if she's going to consolidate accounts, that would be great. Let me, you know, sort of warn you that even some of the it still could be expensive, you know what I mean? So I really want you to know that going in, whoever you decide to choose to work with with can help you with this. But we don't want product and we want someone to help you consolidate the these accounts. Where do you tend to manage your own finances?

[B]

I've got accounts at Betterment, which is where my rollovers are, my brokerage and then I got Vest Wells where my current retirement is.

[A]

If you're going to manage it, it's fine to do it at Betterment. If you want some help consolidating accounts, then I would look at a place like a Fidelity or a Vanguard or a T. Rowe Price or a Schwab where all you would be doing is taking as many accounts as possible and funneling them into one account. So most of your parents stuff is retirement, right? So you would want to figure out a way to say like okay, I have $121,000 in a current plan, right. And you said 20% of that is Roth. I have this voya ira. You want to get all the like money, all the money that hasn't been taxed in one IRA rollover at one of these low cost places, right. So you roll like to like traditional to traditional, traditional to traditional, Roth to Roth. And then when the ESP comes available, that too, I believe that's pre tax. So that would also get rolled into that. And any money that we don't annuitize in these annuities could also get rolled into that account without taking any distribution. If you go to a place like, you know, a Schwab, a Fidelity, a T. Rowe Price and you get someone on the phone, they're going to be like, oh my God, we want all these assets and then you'll have it. They'll help you do it. Like it's not like a hard thing to do. It just, it's a pain in the neck.

[B]

Yeah, it's just paperwork.

[A]

Exactly. So I think what is important for you is to feel like you have, you know, some help along the way. And that's, that's the issue, right, that you just need to know like Okay. I have someone who's going to help me with this, you know, like this paperwork fiasco. Right. So all that being said, I think you're doing such a mitzvah for your parents, and it's like, such a good thing. And everyone listening should really take a note from Elise that, like, while your parents are well and working, these are great conversations to have. If your father is reluctant to do the 67 Social Security, I would love to have a private conversation with him.

[B]

Okay.

[A]

Okay.

[B]

Yeah.

[A]

What do you think he'd be game?

[B]

You know, he might be.

[A]

Mark, do you think I can convince him? You are, Dude, I have convinced a lot of people. When I was an advisor, I was able to convince even the most reluctant people to do things like buy life insurance when they didn't want to. Like, you know, I was like, come on, if you die, what's going to happen to your kids? What's going to happen to your wife? Like, people always push back a little bit, but I don't know. I think we could do it.

[B]

Oh. He was sitting at his, like, local bank making no interest, and I was the one who moved them into high yield. And he was so resistant at the beginning, and now he's like, oh, thank God. Thank God you taught us about that. Like, this is amazing.

[A]

There you go. Give him that so you can give him that example.

[B]

Yeah. But I do feel like the thing my dad's going to want to hear is like, they've saved enough.

[A]

They've saved enough. They're going to be fine. They don't spend. They don't spend that much money. You know, they've saved enough, they've worked enough, and they don't. And they. If they wait till 67, they're going to be fine. If they take it at 62, I'm not so sure.

[B]

Yeah.

[A]

How about that?

[B]

That's good.

[A]

Mark, is that good? Let's play that little clip to them. Send that off to mommy.

[C]

That is the hard truth.

[A]

That's the hard truth. Okay, so if you wait till 67 to claim, we think we can work. Make it work. 62, not sure.

[C]

62 does not cover their needs. As things stand right now, what happens when they run out of their nest egg?

[A]

Exactly. So that's.

[C]

Wait to 67. That's going to cover their needs for the rest of their lives.

[A]

Yeah, most. You know the line.

[C]

Majority of it.

[A]

Yes, exactly.

[C]

And also, like I said, look into the ssdi.

[A]

Yeah. We want to make sure we get that. That has to be a big part of the strategy for sure.

[B]

Great.

[A]

All right. Okay. I'm excited for them and I'm happy that you got in touch with us. So if you are like Elise and you want to take care of your parents and do be a good kid and make your life easier, by the way, because it's all going to get complex and a little bit thorny if you wait till things go south. Get in touch with us. Go to jillonmoney.com bring your parents on the air with us. I'd love that. I love an intergenerational kind of conversation. Hit that Contact us button, write us a note. Let us know if you want to come on the air by checking the box. And of course, don't forget to check out all the content that lives on our website. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. It is Friday. Let's do some business. Our music is composed by Joel Goodman. Mark Telercio is the executive producer on King of All Things Web. We are distributed by the fine folks Folks at Odyssey, we always ask that you do something nice for someone else today. Change your work, Change your wealth, change your life. Thank you for listening. We'll talk to you on Monday.

[C]

Understanding power requires more than headlines. I'm Peter Hamby, host of the Powers that Be, a podcast from PAC examining politics, economics and media. To provide context, analysis and clarity without sensationalism, we ask how power operates, who benefits, and what's at stake. If you want to move beyond breaking news to deeper understanding, join us on the Powers that Be new episodes every weekday. Follow the Powers that Be wherever you get your podcasts.