Retirement Planning Checkup at 65

Summary

Jill on Money with Jill Schlesinger

Episode: Retirement Planning Checkup at 65

Release Date: September 18, 2025

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Overview

In this episode, host Jill Schlesinger CFP® is joined by Bob, a listener from Boston approaching age 65, for a detailed retirement planning checkup. Bob seeks Jill’s guidance as he navigates key life and financial changes, including the recent loss of his mother, an inheritance, decisions about his job, and the best tactics for drawing down assets as he approaches full retirement at 70. The episode is a hands-on, candid discussion about transitioning into retirement, using inheritance wisely, optimizing Social Security, and finding a satisfying balance between work and life.

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Key Discussion Points & Insights

1. Bob’s Situation: Retirement Planning at 64-65

• Continued full-time work planned until age 70; considering a possible career change or at least a change in work conditions.
• Enjoys the travel aspect of his job, but dislikes the management and working conditions at his company.
• Recognizes generalist background and is concerned about how well it translates in today’s job market.
• Considering hiring a “really good resume writer” if pursuing a job change, mindful of resume screening technology.
  [04:54]

Notable Quote:

“I’m not so hot on the management I work for or the conditions that I work under. So I have been contemplating a possible career change. Although with only...five years of full time to go, I’m not sure that’s an easy thing.” – Bob [03:49]

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2. Inheritance & Estate Questions

• Recent loss of his mother; he and his sister are co-executors and are “completely in sync.”
• Main inheritance: His half of a $220,000 IRA (Required Minimum Distributions, RMDs, already started) and about $30,000 from cash and tax refund after estate settlement.
• The IRA must be distributed within 10 years, not necessarily in equal increments. Jill emphasizes flexibility in timing the withdrawals to optimize tax strategy.
  [07:15]

Notable Quote:

“10 years to get the money out does not have to be equal. Can be in one fell swoop. It could be in five years when you have less income… it’s really up to you.” – Jill [07:15]

• Jill offers a public service reminder for listeners about estate planning:

“If you have aging parents and they do not have their estate documents done, please, please let them get that done. It will make your grieving a lot easier.” – Jill [08:25]

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3. Bob’s Financial Snapshot

• 401(k): $1,160,000, with about 97% traditional, 15% contribution rate, includes a 4% match.
• Emergency fund: $32,500 split across CDs.
• Other savings: $12,000 for condo repairs, $19,000 for car expenses.
• Home: Condo valued at ~$300,000, $61,000 remaining on mortgage at 4% interest.
• Salary: 2024 income of $80,800 (salary), $87,400 with bonus.
• Spending: ~$3,000 monthly, $3,500 for planning, Jill encourages $4,000/month for comfort.
• Social Security projection:
  • Age 67: $3,058/month
  • Age 70: $3,798/month
    [11:39]

Notable Exchange:

“With 1.16 million...you have all—you’ve done a great job.” – Jill [11:47]
“Maybe this is not just about a career change. Maybe this is just about you being able to work less or changing other parts of this…you don’t have to make that much to support yourself. You don’t spend a lot of money.” – Jill [12:20]

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4. Career Change, Downshifting, and Building a Safety Net

• Jill's guidance:
  • Bob has the freedom to leave if unhappy; his financial discipline gives him flexibility to downshift or even stop working for a while and “dribble” withdrawals from the inherited IRA.
  • Jill encourages Bob to “start dribbling some of that money out and using it” if he takes time off between jobs, optimizing for tax efficiency by drawing from low-tax-bracket years.
    [13:46]
  • Using years with lower income (possible gap between jobs or part-time work) to withdraw more from inherited IRA.

Notable Quote:

“If for some reason, like at some year where you’re like, ‘Oh, I’m not going to stay here,’ you know, that’s when you get the money, when your income goes down. Right. And…the thing that’s going to be a little bit funny with you is that at age 70, you’ll have that Social Security income. So it would be kind of interesting for you to try to get some of the money out a little bit at a time.” – Jill [16:11]

• Bob expresses intention to work part time after 70 for structure, purpose, and some travel money.
  [14:26]

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5. Inherited IRA Strategy and Roth Conversions

• Bob’s question: Could he take the inherited IRA withdrawal, pay taxes, and put the remainder into a Roth IRA?
• Jill’s answer: Not ideal. Better to increase 401k Roth contributions at work if cash flow allows; otherwise, use the cash from withdrawals to build up a brokerage/savings cushion for upcoming needs instead. [18:13]

Notable Exchange:

“It’s a little cute for me, honestly. You can just put more money into your Roth 401k at work. I would just…put it into your cash and your brokerage account and build that up and have that available to you rather than have it in the Roth environment…” – Jill [18:28]

• Bob aligns with this, stating his goal to build a larger emergency fund for unexpected expenses or future assessments.
  [19:19]

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6. Closing Encouragement & Takeaways

• Jill lauds Bob’s preparation and gives her signature stamp of approval:

“If you are feeling comfortable and you wanted us to just give you…the Jill and Mark papal and Jewish girl blessing, we are doing that in spades. You’ve done a really wonderful, wonderful job, truly...you gave yourself options. So well done, Bob.” – Jill [17:24]

• Final advice: Bob should be kind to himself as he deals with his mother’s estate and consider options at work without stress—he has effectively bought himself flexibility through years of careful saving and planning.

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Memorable Moments & Notable Quotes (with Timestamps)

• “People really, they don’t know what to say, so they say silly things like that. Anyway, I’m just very sorry.” – Jill, on condolences after a loss [05:41]
• “If you’re the type of person who can manage that – philosophically…it sounds like you’re a real worker. So I guess I’m asking you, do you feel like you can give yourself permission to just say, ‘I’m done at this thing, let me find out the next thing to do?’” – Jill [13:46]
• “I don’t see myself entirely not working anymore. I can see myself easily doing part-time work…” – Bob [14:30]
• “There’s nothing bad that can happen to you. You’ve done a great job of saving. You should be comfortable with where you are.” – Jill [15:43]
• “You take your time with the mom’s estate and be nice to yourself…no matter what, you will have options. Not because we’re giving you options, because you gave yourself options.” – Jill [17:36]

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Important Timestamps

• [03:03] Bob introduces his situation and asks about retirement planning at 65
• [04:54] Career satisfaction, job market concerns, resume writing
• [06:01] Bob’s inheritance and estate planning after mother’s passing
• [07:15] Inherited IRA: rules and flexibility in withdrawals
• [08:50] Bob’s current retirement and savings details
• [11:39] Social Security projections at 67 and 70
• [13:46] Discussion on transitioning out of the workforce and flexible withdrawal strategies
• [14:26] Bob’s post-70 work plans and reasons to keep active
• [16:11] Jill's analysis of inherited IRA withdrawals around Social Security
• [17:56] Q&A: Converting inherited IRA distributions into a Roth IRA
• [19:19] Emergency fund strategy and building cash positions

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Final Thoughts

This episode provides a relatable, practical roadmap for anyone approaching retirement—or inheriting assets—while giving the reassurance that careful financial habits offer not only future security but also the freedom of choice in later years. Jill’s blend of expertise and empathy offers Bob—and listeners—actionable advice and genuine encouragement for navigating major life transitions with confidence.

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Transcript

[Jill]

Want to quickly create and execute trading strategies to help keep up with the markets. With Fidelity Trading Dashboard, you can access live data, advanced charting, portfolio insights, and automated alerts all on one screen. We streamlined the trading experience so you can build and place trades better. Your Fidelity Trading Dashboard is ready now. For free, visit fidelity.com tradingdashboard Investing involves risk, including risk of loss Fidelity Brokerage Services, LLC Member NYSE SIPC I want to tell you about another podcast I Can't Get Enough of. Giving Done Right is all about how to make an impact with your charitable giving and tackles the question every donor is asking, how can I make the biggest difference right now? With shifts in federal policy and funding in flux, nonprofits and civic institutions are struggling and your giving matters more than ever. You'll hear from philanthropic experts and major donors who reveal how to maximize impact on issues from protecting democracy to to supporting immigrants in crisis. Whether you give hundreds or millions, this show delivers knowledge that turns good intentions into real results. You can listen to Giving Done Right wherever you get. Podcasts welcome to the Jill on Money show. It's Thursday, September 18th, and we are here trying to talk you through whatever is going on in your life that impacts your financial life. Now, please note that I start with your real life, not with your money. This is a very important concept to me. We are not in the business of trying to help you accumulate as much as you possibly can for no particular reason. We, Mark Talercia, the best executive producer in the world, and I are doing this program because we first of all, we're voyeurs and we love to hear your stories. But we also want to help you get where you want to go, where you want to go, not where someone else thinks you should be, not because your parents told you to do this or because you think about this in some way. What is it that you wish to accomplish? And then when you tell us that we're going to try to help you get there, maybe with a few different options, maybe with a little bit of humor, but we are going to focus on you. And that means you've got to do a little bit of work. I'm sorry, you've got to go to our website, jillonmoney.com click the contact us button, write us a note, and if you'd like to join us on the air, you check the box. Mark does everything else while you're on the website. Just bookmark it and that way you can come back anytime. But at the very least, you should sign up for our free weekly newsletter. It Comes out on Fridays. And by doing this, you'll also be getting blog posts that I post put up there and you can just stay in touch with us. Okay, so that's kind of a fun thing to do. Today we are chatting with Bob who joins us from Boston. Hello Bob, how are you?

[Bob]

Hello, Jill and Mark. Great to talk with you.

[Jill]

What's going on? How can we help you out?

[Bob]

I am approaching 65. I'll turn 65 next May. And at a time when a lot of people are considering retirement or actively moving into retirement, I am looking to work full time for another five years until I hit 70. Looking for a checkup on my finances and see if I'm on the right path and see if there's any changes I should consider making between now and then.

[Jill]

Well, first of all, I love the idea that you're willing to think about at least full time for another five years. Now do you want to keep doing what you're doing or do you want to have a different kind of off ramp, easier job? What are you thinking?

[Bob]

Well, that's, that's one of the big questions for me. I like a lot of what I do. I do get to do a lot of, a lot of travel, which is very rewarding and interesting. I'm not so hot on the, on the management I work for or the conditions that I work under. So I have been contemplating a possible career change. Although with only, you know, five years of full time to go, I'm not sure that's an easy thing. And also in today's job market, I am someone, I have a two year degree. I am more of a generalist. There are a lot of different things that I do and that kind of stuff doesn't matter, translate well into today's resumes and how they're machine read and things like that. So one of the things I've been doing is keeping my eyes open for like a really good resume writer if I'm going to go down this path.

[Jill]

That's interesting. Okay, that's kind of cool. So let's talk a little bit about your financial wherewithal to make this kind of change. So you are 64 right now. Are you single? Are you partnered? Are you married?

[Bob]

I am single, no kids. And recent big life event that affects my finances a little bit and my life in a larger way is that my mother passed away about two weeks ago.

[Jill]

Oh no. I'm so sorry.

[Bob]

Thank you. Thank you.

[Jill]

It's terrible. That's a lot to take on. You know, I always like when People are like, Molly, she was old, she had a good life. And I'm like, yeah, it's still my mom, still my dad.

[Bob]

Exactly.

[Jill]

Such a. People are so funny. I just said this to Mark over before we came on the air. I'm like, people really, they don't know what to say, so they say silly things like that. Anyway, I'm just very sorry. Do you have siblings?

[Bob]

I have one sister.

[Jill]

Okay, so who's managing the estate disposition and like the administration per the will?

[Bob]

We are co executors. Everything comes to us. We are, we see very much eye to eye on this stuff.

[Jill]

Great.

[Bob]

And yeah, we have been going through some of the administrative stuff. And yeah, we're like, you know, completely in sync with each other. And we will get to the point where, you know, once we go through 20, 25 taxes and things like that, at some point next year, we will just split everything down the line, down the middle.

[Jill]

And what do you think that will amount to for you? Your share of that?

[Bob]

So the biggest chunk of it is there is a IRA that our mother had, which currently has a balance of 220,000. RMDs were already being taken from that. And so I'm looking for some input on what to do with it. What I can do with it. I've done a little research. It seems to me that we've got 10 years to. To move that money elsewhere.

[Jill]

10 years to take it out, not to move it elsewhere. You can move it wherever you want right now, but you can. 10 years to get the money out does not have to be equal. Can be in one fell swoop. It could be in five years when you have less income, you know, when you're 70, you know, so it can be. It's really up to you. Okay, so that's the, the biggest chunk. Anything else? Is there a house or something that.

[Bob]

Is no property, no house, nothing like that. There are some four bank accounts and 20, 25 tax refund coming. And when that's all said and done, I'm thinking there'll be maybe around 30,000 for each of us somewhere in there.

[Jill]

Okay, let's get back to you. So now we have that single event which. And by the way, can I just give you a little unsolicited advice about the administrative process? It is what it is. It takes some time. Work through it and you'll get there. It's good that it's the two of you seeing eye to eye for everybody else. If you have aging parents and they do not have their estate documents, Done. Please, please let them get that done. It will make your grieving a lot easier. Instead of you cursing them after weeks and months of going through a lot of nonsense, you will just say, I love you so much. Thank goodness you took care of everything. Okay, that's my public service announcement for the estate planning out there. Okay, now next for Bob. What about your savings? What have you done?

[Bob]

Savings. So 401k. I have 1,1600,000. Roughly 97% of that is in a traditional 401k. I contribute 15%. So that's about a little over $12,000 a year going into the Roth company. Match is 4%. One for one on the first 4% that I put in, that goes to the same funds that my Roth money goes to. But those are pretax, so you have.

[Jill]

A lot of money that's saved. What about non retirement accounts or IRAs that you have that are outside of the retirement account through work?

[Bob]

So no other retirement accounts? I do have. I have an emergency fund of about 32,500 that is in two CDs that I just keep renewing. I have two cash accounts that are. One is designated for condo repairs and improvements. That is currently 12 grand. The other is for car repairs and savings for my next car that is currently 19,000.

[Jill]

Tell me about the condo. What's it worth?

[Bob]

Based on recent sales in this building, say 300K.

[Jill]

And is there a mortgage on it?

[Bob]

Yep, there's a mortgage. I have 20 years left. The remaining balance is 61,000 and it's 4% interest.

[Jill]

Okay. And you like it there? You want to stay there?

[Bob]

Yeah, I can't really do any. You know, if I were to sell this, it's not like I could do any better in this immediate area.

[Jill]

But you don't have. You're not telling me. Oh, you know what I want to do? I want to sell it and go move to South Carolina or something.

[Bob]

No, no, no plans like that.

[Jill]

Okay, got it. Okay. And we talked about the fact that you're been in this job. You like what you do. You don't necessarily like the conditions. How much do you earn right now, Bob?

[Bob]

2024. Salary was 80,800. Gross pay for 2024 was $87,400. That's with some bonus money mixed in there.

[Jill]

What do you spend on an annual basis or a monthly? Either one.

[Bob]

Monthly. I would say it's around 3,000. I would say for planning purposes, I would go with 3,500.

[Jill]

I'm going to go four. Come on. Can't you live a little? Geez. Okay, so what does your Social Security benefit look like? You can give me 67, you can give me 70. You can give me both. Do you know that number?

[Bob]

I do. 67 is 3058 and 70 is 3798.

[Jill]

So you are in great shape. Obviously you don't spend a ton of money. You know, I'd be interested in this. I know that you say, oh, I just have a two year degree. I'm a generalist. Right. With 1.16 million. I have to say, like, you have all, you've done a great job. And even in this job market, I do think that someone who has your experience. But not just experience, Bob, and it's not just about, you know, writing a great resume or getting on LinkedIn. Although believe me, I would get friends with, like, if you have nieces, nephews, friends, whatever, like young people to help you on that, I would be really interested to see what you could find that's out there through your own network, you know, depending on, like, what's out. I don't really feel like I am not inclined to have you be in a situation where you're gutting it out because you don't have to. You have really done a great job. And so when you say, you know, I dislike the conditions under which I work, I'm like, well, why do you have to stay there? And maybe this is not just about a career change. Maybe this is just about you being able to work less or changing other parts of this. You know, you don't have to make that much to support yourself. You don't spend a lot of money. And so there is a case to be made where I would say, okay, you know, I'm 64 years old, I'll give them, you know, at the end of the year, I call it quits. Let's just pretend this is the case. Next year, what happens is you, you know, you'll be able to inherit some of these assets from your mom. Right? And so if you think about it like that IRA that you inherit, if you stopped working next year and you're like, well, I have no income, it's going to take me a while to find a job. I would just start dribbling some of that money out and using it. And I might, you know, maybe I would take, maybe in 20, 26, I'd take 50 grand out of there, okay, and just, you know, pay the tax that's due. You'll be, essentially, you'd be in the 12% tax bracket, maybe even you take out 40 grand, you pay the tax it's due and you live on it, so be it. Fine. And do the same thing the next year. And then you give yourself some time to find something else. I don't know if you're the type of person who can manage that. Philosophically. It sounds like you're a real worker. So I guess I'm asking you, do you feel like you can give yourself some permission to just say, I'm done at this thing, let me find out the next thing to do?

[Bob]

I see that happening more when I hit 70.

[Jill]

Okay, 70.

[Bob]

I don't see myself entirely not working anymore. I can see myself easily doing part time work and that could just be one. It's tough to, to give me something to do to keep me busy, to, to give me some routine. Also to bring a little extra money in that I can use for, for travel. Because that's, that's a big thing for me is, is being able to do that. And a couple things about my current position is my company was sold last year and I'm starting to see some, some positive turnaround.

[Jill]

Oh.

[Bob]

In the way things are going. So.

[Jill]

So you kind of want to stick around to see what happens.

[Bob]

Yeah. You know, I'm not at the, at the one bad meeting and I walk out the door stage.

[Jill]

Okay. Okay.

[Bob]

It's. And, and I really like certain things. I really like the travel. I do in part because I go to the same, a lot of the same places over and over again. And so I have people who are not just colleagues but their friends. And I'm not, I'm not ready to, to give that up at this point. So.

[Jill]

Okay, I am, I am down with that now. I get it. Okay. So what I, here's what you need to know. You're not at the one bad meeting away yet, but you are for our purposes. There's nothing bad that can happen to you. You've done a great job of saving. You should be comfortable with where you are. I would think about the money from the IRA that you will inherit. I think I would start using that up. You'll have a 10 year time clock, right. To get through that. You'll have to start taking that money out at some point. If for some reason, like at some year where you're like, oh, I'm not going to stay here, you know, that's when you get the money, when your income goes down. Right. And you can. The thing that's going to be a little bit funny with you is that at age 70, you'll have that Social Security income. So it would be kind of interesting for you to try to get some of the money out a little bit at a time. You'll do it out over the next 10 years, but then you still will have your required minimum distributions from your own retirement account. So, okay, you'll do it. It's fine. You'll just pull the money out. I mean, if you. It's just that because you have a lot of money in there, you've been working a long time, you'll deal with it, it'll come out. And so your required minimum distributions essentially, plus your Social Security are going to be fine. That's it. You'll be done. No sweat. All done. As long as you know you are. If you are feeling comfortable and you wanted us to just give you sort of the, the Jill and Mark papal and Jewish girl blessing, we are doing that in spades. You've done a really wonderful, wonderful job, truly. And so I think you have a lot of options. You take your time with the mom's estate and be nice to yourself, and maybe you're not going to feel like, oh, everything's so great and hot and dandy at work, but no matter what, you will have options. Not because we're giving you options, because you gave yourself options. So well done, Bob.

[Bob]

Excellent. Thank you. I have one question about the inherited, inherited ira.

[Jill]

Okay.

[Bob]

My thought was to take the rmd, pay the tax on it, obviously, and then put the remainder of each RMD into a Roth IRA at the same institution that that IRA is currently at. Does that sound reasonable?

[Jill]

Well, in other words, what you're saying is I pay the tax that's due, and because of my income level, I am entitled to make a. A contribution to a Roth IRA in addition to my 401k? Is that what you're telling me?

[Bob]

Yes.

[Jill]

I mean, it's a little cute for me, honestly. You. You can just put more money into your Roth 401k at work. I would just. I would actually just put it into your cash and your brokerage account and build that up and have that available to you rather than have it in the Roth environment, if you want. If your cash flow is so good that you're like, I have plenty of money, and I just then put more money into your Roth 401K at work.

[Bob]

Okay. Okay, yeah, maybe. Yeah, I'll look at that. Yeah. Because the other option is to. Is just to put this into savings or high yield savings or cd. Because one thing I do want to continue working on is building up a pile of cash for the future for, you know, if I ever have assessment in my condo building or need to pay for health care and things like that.

[Jill]

So see, I agree with you. I would much rather build up that cash position and I think you're in a perfect situation that's a great use of those funds. So that's absolutely what I would do. So I think you're in really good shape. And again, if you need any help along the way, we're here for you. Bob from Boston, thanks for joining us. If you are like Bob and something's going on in your financial life, you're thinking about a change, a shift, a downshift, some way to get yourself to the next place. Give us a Holler. Go to jillonmoney.com, click the contact Us button, Write us a note if you'd like to come on the air. Check the box. Mark will do. Everything else. Don't forget to check out all of the wonderful content that lives on our [e-mail] including our subscription service Jill on Money Live, where you have access to quarterly live webinars, the back catalog of those webinars as well, well as bonus audio and video content. It's all for 45 bucks for the next 12 months, so check that out. Okay? You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Put your hands metaphorically on someone's back. Reach out to someone, connect to somebody. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. Hey gang, here's the thing about wine. Some of the best bottles are not sitting on a store shelf. They're being crafted at small independent wineries. But those wines can be so hard to find sometimes. I wish I had a personal sommelier to guide me to find the best wines I normally wouldn't be able to access. Where's that handcrafted pinot that I've been craving? Well, Psalmsation's expert team seeks out incredible wines from top independent producers. These are bottles that you will not find in stores and on shelves. They aren't mass produced wines. They're handcrafted with care, using pure ingredients and meticulous winemaking. Whether you want a single bottle, a guided tasting experience, or an entire wine club membership, Psalmsation makes it easy to elevate your wine experience. Shop their [e-mail] jillonmoney that's somsation.com jillonmoney hi, I'm Nancy Cartwright. You may know me better. As the voice of Bart Simpson on Simpsons Declassified, we're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers, the celebrity guests? Be sure to follow and listen to Simpsons declassified wherever you get your podcasts.