Feeling Stuck as I Approach Retirement

Summary

Jill on Money with Jill Schlesinger

Episode: Feeling Stuck as I Approach Retirement
Date: December 30, 2025
Guest: Jackie (Caller from Nevada)

---

Episode Overview

In this episode, Jill Schlesinger takes a call from Jackie, a 63-year-old listener from Nevada, who is feeling stuck as she approaches retirement. Jackie is anxious about her investment choices after moving all her assets into “safe havens” following a market downturn years ago. Jill walks Jackie through a comprehensive review of her retirement readiness, breaking down her income sources, assets, and options for managing the emotional and practical challenges of transitioning into retirement.

---

Key Discussion Points and Insights

1. Jackie’s Retirement Snapshot

[02:58 – 07:20]

• Jackie, 63, plans to retire around age 65, currently working part-time (earning ~$12,000/year).
• Income sources in retirement:
  • Small pension: $800/month
  • Business income: ~$2,000/month, business equity valued at ~$500,000
  • Husband’s Social Security: $1,500/month (he's been retired ~6 years)
  • Jackie’s future Social Security: ~$2,600/month at full retirement age, $3,000/month at age 70
• Estimated monthly expenses: $6,000
• Assets:
  • Jackie’s 401(k): $430,000 (in stable value fund)
  • Husband’s 401(k): $200,000 (also in stable value)
  • Cash/non-retirement accounts: $200,000 (bank), $400,000 (brokerage, in stable value)
  • Home: Paid off, valued at ~$600,000
• No children, planning to leave assets to family (sister, nephew); no pets.

2. Current Asset Allocation and Risk Aversion

[06:37 – 07:32]

• Post-market crash, Jackie and her husband moved nearly all assets into stable value or cash equivalents due to fear of losses.
• Jackie wants to do “better” but is hesitant and lacks confidence re-entering the market.

3. Encouraging Strategic Allocation & Accepting Volatility

[10:58 – 13:49]

• Jill suggests a gradual approach to re-investing:
  • Start by shifting a modest portion (e.g., 10–25%) into equities and bonds.
  • “Your allocation would literally be 10% fixed income, 10% equities, and 80% stable value. Do you think you could live with that?” (Jill Schlesinger, 12:43)
• Jackie responds positively: “Not when you put it like that.” (12:43)
• Jill encourages making these changes within the old 401(k) accounts to start, emphasizing it's okay to proceed slowly: “It's like a little bit like we're dipping your toe in the water.” (13:51)

4. Social Security Strategy

[13:56 – 16:44]

• Jill analyzes the pros and cons of delaying Jackie’s Social Security to age 70:
  • Maximizes benefit significantly (from ~$2,600 to $3,200/month)
  • Requires drawing down savings to cover the income gap ($100,000 over 3 years)
• Jill: “Can you give yourself permission to spend the hundred? Because it’s kind of nice to get that guaranteed big bump up to maximize your Social Security benefit.” (14:45)
• Jackie: “Yeah, well, that's what it’s for. But it’s like, oh, yes, I know, I know. Run out.” (16:50)

5. Emotional Challenge of Spending Down Savings

[16:50 – 17:20]

• Jill discusses the psychological hurdle many retirees face: the transition from accumulating to decumulating assets.
  • Jill: “There’s a fancy term for this in financial planning… it’s the problem of the accumulator versus the decumulator. It’s a very hard transition.” (16:56)
• Jackie agrees, acknowledging the difficulty.

6. Tax-Saving Strategy: Roth Conversions

[09:34 – 09:58]

• Jill suggests converting a portion of the husband’s IRA to a Roth IRA while still in a low tax bracket.
  • "Only convert enough so that you'd stay in that 12% tax bracket because your income is low... Or you don't have to. You really don't have to.” (10:01)

7. Estate Planning Reminder

[17:34 – 17:47]

• Jill urges Jackie to complete her estate planning (wills, documents).
  • Jackie: “Well, that’s on the to-do list.”
  • Jill: “All right, let’s put that higher up on the list.” (17:44)

---

Notable Quotes & Memorable Moments

• On Facing Retirement Fears:
  "I really would like to get back in there, but I'm afraid. I'm afraid to lose the money and I don't know exactly what to."
  — Jackie (07:32)

• On Rebalancing Investments:
  “If I looked at your total assets... all I’m asking you is could I put 100,000 of that million in stocks? Can I put 100 of that million into bonds? ... That doesn’t seem like a lot to me.”
  — Jill Schlesinger (12:10–12:43)

• On Delaying Social Security:
  "It’s kind of nice to get that guaranteed big bump up to maximize your Social Security benefit. Most people can’t afford to do it… but it will require you to spend down some of your money, and you’ve got to be okay with that."
  — Jill Schlesinger (14:44–14:56)

• On Emotional Hurdle of Drawing Savings:
  "The problem of the accumulator versus the decumulator. It’s easy to accumulate... It’s a much harder transition to go from putting money in to taking money out."
  — Jill Schlesinger (16:56–17:12)

• On Estate Planning:
  “Let's put that higher up on the list.”
  — Jill Schlesinger (17:44)

---

Timestamps for Key Segments

• Jackie's Background & Income Sources: [02:58 – 07:20]
• Asset Allocation History & Motivation: [06:37 – 07:32]
• Strategy for Gradual Portfolio Risk: [10:58 – 13:49]
• Discussing Social Security and the Psychology of Spending Down: [13:56 – 16:50]
• Roth Conversion & Tax Planning: [09:34 – 10:01]
• Estate Planning Message: [17:34 – 17:47]

---

Tone and Style

Jill remains characteristically warm, straightforward, and jargon-free while guiding Jackie. She balances empathy for Jackie’s emotional struggles with practical, actionable advice, encouraging a step-by-step and manageable approach to financial change.

---

Summary Takeaways

• Jackie is in a strong financial position with multiple income sources and substantial savings.
• Her “stuck” feeling is rooted in risk aversion and emotional difficulty with shifting from saving to spending—incredibly common among new retirees.
• Jill recommends a gradual reentry into the market with a small allocation to stocks/bonds, possible strategic Roth conversions, and considering delaying Social Security for a higher benefit.
• Emotional readiness for decumulation and completing estate planning are highlighted as equally essential retirement tasks.
• "Let me know how it goes. I want a screenshot of when you pull the trigger and buy some stocks." — Jill Schlesinger (17:23)

---

For listeners approaching retirement unsure about investment moves or spending down savings, this episode offers reassuring, stepwise strategies and underscores the emotional as well as financial aspects of retirement planning.

Transcript

[RingCentral Announcer]

RingCentral will completely transform the way you work. It gives you built in AI across all your business conversations. Your phone System has an AI receptionist that answers calls 24 7. Your video meetings have AI that takes notes instantly. Even your contact center has AI so you can help customers faster. It all comes together in one reliable platform for effortless AI communications. See for [e-mail] RingCentral Voice of your.

[Jill Schlesinger]

Business Today's episode is supported by what Should I Do With My Money? An original podcast from Morgan Stanley and Like Jill on Money. This podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries and dreams, asking questions like can I retire early? Like really early? And how do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and it's shifting how I think about my money. Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player and feel empowered and supported. When it comes to managing your life and finances, your business identity is everything that shows what your business is about, from what customers see to what they don't. Like legal paperwork where website security and state licenses get more for your business. More privacy, more tools, more guidance with Northwest Registered Agent. They're the largest registered agent and LLC service in the US with over 1500 corporate guides. Real people who know your local laws and can help you and your business every step of the way. Northwest is your one stop business solution. Don't wait. Protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes. Visit www.northwestregisteredagent.com paidjill and start building something amazing. Get more with Northwest registered [e-mail] paidjill welcome to the Jill on Money Show. It's Tuesday, December 30th and we are here talking to you about whatever is on your mind for financially and sometimes you've got big life decisions that you're making. You may not even realize how it impacts your financial life. Sometimes you get in touch with us talking about something very specific and then we expand into something completely different. So if you've got something cooking, get in touch with us. Go to jillonmoney.com, click the contact Us button, write us a note and if you'd like to join us live, check the box. That's what Jackie did. She joins us from Nevada. Hello, Jackie. What's going on? How can we help you today?

[Jackie (Caller)]

Well, I'm getting ready to retire. I'm 63 years old and I have lots of things on my plate. The number one thing probably is years ago when the market kind of crashed and burned and went around. I put my investments in safe, safe havens. And so now, because my husband and I, we felt like, well, we made this money, we earned it, and we can't afford to lose anything. So, you know, everyone always says to stay the course. What goes down must come up. And so I'm stuck. I feel like I need to do better at that.

[Jill Schlesinger]

Okay, well, but tell us a little bit about the retirement and, and what your retirement might look like. For example, you say you're going to retire. Will you be entitled to a pension?

[Jackie (Caller)]

I have a very small pension that's probably about $1,000 a month. Sorry, 800amonth.

[Jill Schlesinger]

Do you have any other sources of income besides a pension? And we'll talk about Social Security, but anything else, like a rental property, anything like that?

[Jackie (Caller)]

There is a business that is worth about $2,000 a month and equity on that is about 500,000.

[Jill Schlesinger]

That's great. So you'll have $2,800 a month guaranteed. Not guaranteed, but pretty much a guaranteed, it sounds like. And when are you really thinking about. You said a few years. Are you thinking like 67 or more?

[Jackie (Caller)]

Honestly, right now I'm working very part time, like two days a week. And I'm thinking once I get my Medicare and everything in place, I'd like to retire at 65.

[Jill Schlesinger]

How much right now do you need to live on? Like, what would you say if you were estimating your expenses? What do you think you need?

[Jackie (Caller)]

Well, I would say probably around maybe 6k a month.

[Jill Schlesinger]

And you, have you mentioned a husband? Is he still working?

[Jackie (Caller)]

No, he's retired about six years. And his Social Security is $1,500 a month, 1500amonth.

[Jill Schlesinger]

What will your Social Security benefit be when you retire at your full retirement age?

[Jackie (Caller)]

Probably about 2,600. Well, 70 would be 3,000, but I'm forget that.

[Jill Schlesinger]

Let's see, let's look at the 2,600. Okay, we look at this and I look at you and I say, okay, there's the pension, there's the money from the business. There's your husband's Social Security, there's your Social Security. Right. And those are the sources of retirement income, right?

[Jackie (Caller)]

Well, I have 401 Wait, wait, wait, wait, wait.

[Jill Schlesinger]

We're going to do that 401 in one second. But to be clear, you guys are in pretty good shape because I'm looking at the 2,800. The 800 from the pension, the business income of 2,000. There's 2,800. Your husband has 1,500 dol a month in Social Security. You, at age 67 will have $2,600 a month. So when I eyeball this, I'm looking at, you know, total income at your age 67 is pre tax, $6,900 a month. That's great. I mean, you're almost covering everything. I know it's not exact, but you're covering a lot of your base expenses because some of this will be taxed. I get it. Okay, now let's talk about the assets. Let's talk about that 401k. How much money in there?

[Jackie (Caller)]

About 430,000.

[Jill Schlesinger]

That's your 401k. Does your husband also have any retirement savings?

[Jackie (Caller)]

Yes, his 401k is about 200,000.

[Jill Schlesinger]

Now, is all of the money in the two 401k accounts? Are you telling me is it cash? Is it bonds? Like where like when you said we kind of like got rid of the risk. Was it everything?

[Jackie (Caller)]

Mine is in like vanguard, a stable value fund, and he rolled his over into a stable fund.

[Jill Schlesinger]

Okay, so there no problem. Very simple. That's the money. Okay, how about money in the bank or non retirement savings or investments in the bank?

[Jackie (Caller)]

Maybe 200,000.

[Jill Schlesinger]

That's awesome. And nothing else, right? No other like weirdo strange brokerage accounts or anything like that?

[Jackie (Caller)]

Yeah, there's one for about 400,000.

[Jill Schlesinger]

Whoa. Is that also in stable value?

[Jackie (Caller)]

Yeah, I got scared on that too.

[Jill Schlesinger]

When did you get scared? I just interested in the timing of this. Just out of curiosity.

[Jackie (Caller)]

Gosh, I'm thinking it's been at least maybe 5 years. I went stable on my 401k a lot earlier than I did on the brokerage account. I mean, I. I really would like to get back in there, but I'm afraid. I'm afraid to lose the money and I don't know exactly what to.

[Jill Schlesinger]

What it would be like. You don't know where you would move if you were to move? Okay. Is there anything else that we should know about? Do you have grown kids?

[Jackie (Caller)]

No kids.

[Jill Schlesinger]

No kids. Okay. Do you have pets?

[Jackie (Caller)]

No pets.

[Jill Schlesinger]

Wow. Who are you going to leave all this money to?

[Jackie (Caller)]

Family, sister, nephew?

[Jill Schlesinger]

Everyone better kiss your butts because you're gonna have a lot of money left over. Tell us about your, where you live. Do you own your home?

[Jackie (Caller)]

Yes, our house is paid off.

[Jill Schlesinger]

How much would you say it's worth?

[Jackie (Caller)]

Well, I looked the other day. Zillow says about 600,000, but that's probably a little negotiable.

[Jill Schlesinger]

You're not moving though. You're happy where you are.

[Jackie (Caller)]

Happy where we are. We're going to stay here as long as we can.

[Jill Schlesinger]

You're in great shape. You are in fantastic shape right now. If you looked at your taxable income, are you receiving that small pension yet, that $800 a month?

[Jackie (Caller)]

Well, no, and that's something I wanted to ask you about. I was thinking maybe I could access that pension and that would pay for my cobra because in March I'll be losing my insurance. I thought, well that's a good idea to use the money for that.

[Jill Schlesinger]

Yeah, sure, you can take the pension, get the money and yeah, use it for cobra. That's fine. The taxable income that you guys are receiving keeps you. I'm pret sure you, you're probably in, I don't know, maybe mostly the 12% tax brackets, maybe the 20. How much do you earn right now on this part time income?

[Jackie (Caller)]

Probably I'll make 12,000 this year.

[Jill Schlesinger]

Okay.

[Jackie (Caller)]

I have my Magi number from last year that I used for my to look into insurance. Would that help?

[Jill Schlesinger]

Yeah, how, what's that?

[Jackie (Caller)]

Last year it was 78,000.

[Jill Schlesinger]

Okay.

[Jackie (Caller)]

But I worse more last year. So it's going to be quite a bit lower I think this year.

[Jill Schlesinger]

Okay. How would you feel about converting some of your husband's IRA? How old is he?

[Jackie (Caller)]

I'm sorry, 70.

[Jill Schlesinger]

I mean you could convert some of his money into Roth money because you're going to be in a low tax bracket. If that's a pain in the neck to you, I understand it. You don't have to. But you could convert some of that money from a rollover IRA into a Roth ira. Possible. I'm just putting it out there.

[Jackie (Caller)]

So if you roll it over then you can convert it to Roths.

[Jill Schlesinger]

And so then.

[Jackie (Caller)]

But then when does he pay taxes on it?

[Jill Schlesinger]

Yeah, he has to pay tax on it, which is why you'd use some of that brokerage account money to pay tax on it. You don't do it all at once. I mean a little bit at a time. Only convert enough so that you'd stay in that 12% tax bracket because your income is low. And as you said, if you made if your AGI last year was 78, let's say this year it's like 60. You could take 20 grand a year until you start taking your own Social Security and convert some of his retirement money. Or you don't have to. You really don't have to. It's just like one of those things where you don't. You're not really investing for anyone in the future. It's just nice in case tax rates go up on you in the future. That's all you will. You would also be minimizing the distributions that you take. But, you know, you could do that. You could just start taking some of the money out of his account. Anyway, I put that out there as a planning idea because I would be remiss if I didn't tell you that's a possibility. All right, the more interesting thing going on for you guys is what do we do with all this cash? Let's just talk about your retirement account alone. Let's say out of that $430,000, could you stomach pudding? I don't know. Let's say. Let's say I bargain with you. We'll keep half of it in stable value. We'll put a quarter of it in stocks and a quarter of it in bonds. How would that make you feel? It will still fluctuate, so I'm going to just give you that. It won't fluctuate as much as the overall market, but it would still fluctuate.

[Jackie (Caller)]

Okay, I'll think about that.

[Jill Schlesinger]

Here's why. You're young, right? And while I'm happy that you have saved so much money and you are going to have income, it is entirely possible that you are going to live for 30 more years. In that case, the stable value, which has done right by you certainly in the last year is going to start to be a problem because we're not growing any part of your portfolio. So if I looked at your total assets, which are, forget about the bank account, even like the brokerage, the, the rollover IRA and the 401k, you've got a million dollars. And all I'm asking you is could I put 100,000 of that million in stocks? Can I put 100 of that million into bonds? Your allocation would literally be 10% fixed income, 10% equities, and 80% stable value. Do you think you could live with that? I think you could. That doesn't seem like a lot to me.

[Jackie (Caller)]

Not when you put it like that.

[Jill Schlesinger]

That's what I'm trying to do. I'm trying to get you to, like, buy. Buy into my plan. It might make looking at your actual 401k plan a little unnerving to you day to day. So don't do that. But if we do it, I think we should do it in your. In your 401k. We'll do that. We'll do the machinations inside of your 401k to start.

[Jackie (Caller)]

Now, let me ask you this. 401k is from a previous job, so I'm not making any contributions.

[Jill Schlesinger]

Doesn't matter. Okay. Because it's just sitting there at Vanguard. Right. So you can still change your allocation. So in that 401k, the old 401k you had, no one's told you how to move it, so you can just keep it. If it works out okay. You might do the same thing in your husband's old 401k as well. You might say, take a little piece of that and say, well, you know what I'm going to do? I'm going to put, you know, 25,000 into stocks and 25,000 into bonds.

[Jackie (Caller)]

That's the waters.

[Jill Schlesinger]

Yeah. I just wanted you to guys to get used to being invested again without feeling like you're giving away the farm. Mm.

[Jackie (Caller)]

Well, that kind of makes sense to me.

[Jill Schlesinger]

Yeah. And it's like a little bit like we're dipping your toe in the water.

[Jackie (Caller)]

I just want to.

[Jill Schlesinger]

What.

[Jackie (Caller)]

What do you think about my Social Security? When do you think?

[Jill Schlesinger]

Well, you know, I think it's interesting. I'm sort of leaning towards. I kind of want to see what it feels like for you to be retired. Okay. You're healthy, right?

[Jackie (Caller)]

Yes.

[Jill Schlesinger]

You have longevity in your family or not?

[Jackie (Caller)]

Yes. On one side. Yeah, absolutely.

[Jill Schlesinger]

I mean, you can afford to delay your Social Security until age 70, but it will require you to spend down some of your money, and you've got to be okay with that. You could say, you would literally be saying to yourself, okay, between the bank and the brokerage account, I've got $600,000 if I delay my Social Security for three years. Let's see. Did you have your age 70 number at hand?

[Jackie (Caller)]

3200.

[Jill Schlesinger]

Gosh, that's a nice bump, isn't it? It really is. And especially if you have longevity. Well, here's what it would require of the money that's sitting in the bank brokerage. That's 600,000. You'd have to say, I'm going to spend $100,000 of that to pay for our expenses between now and the time I claim Social Security. Can you give yourself permission to spend the hundred? Because it's kind of nice to get that guaranteed big bump up to maximize your Social Security benefit. Most people can't afford to do it because they don't have the money to live on between the time they retire and the time they can claim.

[Jackie (Caller)]

So there would be capital gains tax involved in that brokerage account?

[Jill Schlesinger]

No, because you said that brokerage account is in the stable value fund, isn't it?

[Jackie (Caller)]

Well, it is, but it was an inherited thing, and when it was making money, I was paying a lot of capital gains taxes.

[Jill Schlesinger]

Yeah, but wait a minute. You sold that. You sold the account out, Right? In other words, you sold the assets in that account, that stable value, it's in your name now, right? Yes. You inherited it when?

[Jackie (Caller)]

Oh, gosh, 20 years ago, 15 years ago.

[Jill Schlesinger]

Okay, so what you're saying is that while it was invested, you had to pay capital gains along the way, right?

[Jackie (Caller)]

Yes.

[Jill Schlesinger]

Okay. Then you got spooked. You sold everything. Right. And you went to the stable value fund. So the only capital gains you would have would be the growth of the stable value fund. You've already paid capital gains in this account.

[Jackie (Caller)]

Okay.

[Jill Schlesinger]

So if you could give yourselves permission to spend 100 grand out of the 600 that you have in cash or stable value between the bank and the brokerage, I would be inclined to do that. The problem is, this is emotional, because what I'll tell people is, okay, you're going to spend the money and then they'll call back, But I have a hard time spending that money. Think of it as, this is your pension, okay? You've saved all this money, and now you're basically saying to yourself, okay, send me 30 grand a year from the brokerage account because I'm going to need that to live on. That's your pension payment from yourself.

[Jackie (Caller)]

Yeah, well, that's what it's for. But it's like, oh, yes, I know, I know. Run out.

[Jill Schlesinger]

This is the problem. There's a fancy term for this in financial planning. It's the problem of the accumulator versus the decumulator. It's easy to accumulate if you're like a diligent, hardworking person. You're keep. You know, you live within your means, you accumulate. Right?

[Jackie (Caller)]

Yeah.

[Jill Schlesinger]

It's a much harder transition to go from putting money in to taking money out. It's a very hard transition.

[Jackie (Caller)]

I. I understand completely. Yes, that's. That's us.

[Jill Schlesinger]

But I think you're going to do it. Let me know how it goes. I. I want a screenshot of when you pull the trigger and Buy some stocks.

[Jackie (Caller)]

All right, all right.

[Jill Schlesinger]

Makes sense.

[Jackie (Caller)]

Makes sense. Thank you so, so much.

[Jill Schlesinger]

Great. You got your, by the way, do you have that estate planning done? You got that good stuff done?

[Jackie (Caller)]

Well, that's on the to do list.

[Jill Schlesinger]

All right, let's put that higher up on the list. Okay. Okay.

[Jackie (Caller)]

All right. Thank you guys so very much.

[Jill Schlesinger]

If you need some guidance, maybe some mentoring or coaching, get in touch with us. We can help sort through whatever's going on in your financial life. Just go to jillonmoney.com, click the contact us button, write us a note. And of course, check that box if you'd like to join us on the air while you're on the website. Check out all the stuff that lives there. We've got another podcast called Money Watch. We've got a blog. We've got resources all [e-mail] you can subscribe to us on the Odysee app or wherever you find your favorite podcasts. Don't forget to do something nice for someone else today. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

[RingCentral Announcer]

Ringcentral will completely transform the way you work. It gives you built in AI across all your business conversations. Your phone System has an AI receptionist that answers calls 24 7. Your video meetings have AI that takes notes instantly. Even your contact center has AI so you can help customers faster. It all comes together in one reliable platform for effortless AI communications. See for [e-mail] ringcentral voice of your business what's up?

[Draymond Green]

It's Draymond Green. I'm back for my 14th NBA season and my podcast, the Draymond Green show is back too. This season I'm breaking down games, reacting to the biggest NBA stories and sitting down with teammates, rivals and culture shapers. And trust me, I'm not holding back on the court or on the mic. Two new episodes every week. New segments, big conversations, real basketball talk for the real hoop heads. Listen to and follow the Draymond Green show wherever you get your podcast. We're back. We're better. Let's get it.