Terrified of Making the Wrong Move

Summary

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Podcast Summary: Jill on Money

Episode: Terrified of Making the Wrong Move
Date: November 6, 2025
Host: Jill Schlesinger, CFP®
Guest/Caller: Chris (West Coast, anonymous location)

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Brief Overview

In this episode, Jill Schlesinger takes a listener call from Chris, who is wrestling with big financial decisions following a family inheritance and a self-imposed retirement. Chris and his wife are facing anxieties about their financial choices, especially with a background of inconsistent financial luck, dependent adult children, and a now-complex asset portfolio. The conversation dives into details of Chris’s assets, expenses, and future plans, with Jill guiding him through practical steps, risk assessment, and actionable options—all in Jill’s signature direct, supportive style.

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Key Discussion Points and Insights

1. Chris's Situation and Family Context [03:12–04:10]

• Chris is 60; his wife is 57. Chris is not working (caring for ill parents until their passing), while his wife works part-time mainly for benefits, earning ~$22,000/year.
• They have two adult children (ages 24 and 22), both still living at home and not fully financially independent.
• Chris: “Wife and I are huge fans. …Our background has had its ups and downs and so we’re maybe a little more cautious than most might be.” [03:16]

2. Asset Breakdown (Pre-Inheritance) [05:02–08:45]

• Primary Home: Worth ~$850,000, paid off.
• Two Rental Properties:
  • Rental #1: ~$600,000 value, $170,000 mortgage (ARM, ~6%+ interest, cash flow-neutral).
  • Rental #2: ~$575,000 value, $30,000 mortgage (fixed at 4%, generates $1,300/month in true cash flow).
• Investments: $1 million in a brokerage account (all stocks); $28,000 in an old 401(k); $140,000 in a money market account; $50,000 in cash.
• Additional Real Estate: A beach house ($1.1 million, no mortgage) intended as a retirement home.

3. Impact of Inheritance and Spending Concerns [08:45–10:33]

• Recently inherited ~$2.2 million, resulting in a combined ~ $3.2 million in investable assets.
• Estimated monthly spending is around $12,000, which includes caring for adult children.

4. Future Plans and Options [08:53–11:14]

• Current plan: Eventually sell the primary residence and move to the beach house full time within 1–2 years.
• Open to selling one or both rental properties if circumstances change.
• Chris expresses doubts about his investment management skills and diversification, citing their self-directed experience since the 1970s.

5. Portfolio Concentration and Risk [10:01–16:17]

• Major concern: All $1 million in brokerage is in eight individual stocks.
• Jill highlights the risk: “Eight stocks, $3.2 million. That’s too much in each one of those stocks.” [15:11]
• Jill recommends reducing stock concentration—suggests moving at least $1 million into broader ETFs or index funds, even if it triggers taxes.
• Chris and Jill discuss lack of bond exposure and the pros/cons of self-management vs. hiring an advisor, especially with tax and estate complexities after inheritance.

6. Health Insurance as a Retirement Obstacle [12:45–14:35]

• Wife’s job provides the family’s health benefits.
• If she retires, family coverage could cost upwards of $20,000/year out-of-pocket, especially given their income/assets make ACA subsidies unlikely.
• Jill’s pragmatic advice: “If she doesn’t hate her job, I’d keep doing it for a while…You should investigate it. …You’ll have some sticker shock.” [13:15; 14:23]
• Kids’ lack of independence adds to the urgency to plan for their eventual decoupling from parents’ health insurance.

7. Estate Planning Needs [14:36–15:01]

• Chris admits their estate planning is incomplete but underway.
• Jill affirms importance: “Great. All right, that’s good.”

8. Encouragement and Closing Thoughts [17:12–17:30]

• Jill reassures Chris: “You made it sound like you were some sort of screw-up. Doesn’t sound like it. …You guys have the money you need, which is great.”

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Notable Quotes & Memorable Moments

• On Real Estate Management:
  • Jill: “Oh, my God, you have so much real estate. That’s why you can’t work. …The properties keep me busy.” [07:50]
• On Diversification Anxiety:
  • Chris: “It’s spread over about eight individual stocks.” [15:09]
  • Jill: “…That’s too much in each one of those stocks. …I might reduce the positions” [15:11]
• On Health Insurance Shock:
  • Jill: “It’s going to be expensive to get coverage for the four of you. You should investigate it. …Wait till after November 1 and the marketplace opens. …You’ll have some sticker shock.” [13:39–14:35]
• On Financial Confidence:
  • Jill: “I think you are in really good shape. …You guys have the money you need, which is great.” [17:12]
• On Consideration of Professional Help:
  • Jill: “It may be worthwhile talking to somebody just because you’ve got a lot going on in this balance sheet. …There’s some concentration risk…maybe you should pay someone to manage the money for the near term just to get this process handled.” [16:15–17:05]

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Timestamps for Important Segments

• Chris introduces his situation: [03:12]
• Asset rundown and real estate discussion: [05:02–08:45]
• Discussion of inheritance and monthly spending: [08:45–10:33]
• Kids’ dependence and logistical challenges: [04:18–04:53]; [08:19–08:30]
• Portfolio concentration concerns: [10:01–16:17]
• Health insurance issues: [12:45–14:35]
• Estate planning needs: [14:36–15:01]
• Advisor vs. DIY debate: [16:00–17:11]
• Jill’s closing encouragement: [17:12–17:30]

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Overall Tone and Takeaways

• Tone: Supportive, no-nonsense, and practical. Jill highlights both risks and opportunities without alarmism. She encourages self-reflection, professional input, and planning over panic.
• Takeaway for Listeners: Even in a solid financial position, complexity from real estate, dependent children, and inheritance can be overwhelming. Seek diversified investments, research large expenses like health insurance, and don’t fear getting professional help for peace of mind.

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Transcript

[A]

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[B]

Like can I retire early?

[A]

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.

[B]

Welcome to the Jill on Money show. It's Thursday, November 6th. I cannot believe that I am saying November, but here we are into the.

[A]

Last two months of the year, just.

[B]

Weeks before you shut your brain off and get subsumed by holidays and fun and anxiety. Which is all the same when you're dealing with your family, isn't it? If you would like an escape during those holiday times, you want to think about something larger than how am I going to get the gift for the kid or the kid's teacher or whoever in your life. Why don't you give us a Holler? Go to 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 will do everything else. Hey, while you're on the website. There's so many things that are there that are great. We've got our sister broadcast, which is called Money Watch, which airs on Saturdays and Sundays. We go a little bit deeper with people on some of their financial planning topics. We also have a blog. We've got a radio show. There are videos, there are resources, and. And of course, the free weekly newsletter, which Mark compiles every Friday, might have missed a story during the week. Mark will find it for you. So check it out. Everything lives on the jillonmoney.com website. Today we are talking to Chris, who is in an unidentified parking lot on the west coast to maintain his anonymity. Hello, Chris. Welcome to the show.

[C]

Hello. Wife and I are huge fans. Thank you.

[B]

We are delighted to have you. What's going on? How can we help you out?

[C]

Well, my wife and I have a few questions about moving forward. She still is working. I haven't worked in a while since my parents got ill. They. They have both recently passed and with that. Yeah, left us with an inheritance in addition to what we have. We think we're in pretty good shape, but our background has had its ups and downs and so we're maybe a little more cautious than. Than most might be. And so we'd like to get your thoughts on. Can I stay? Not working? I've been doing my best to live my best life recently and she loves her job, but with, I think, love to join me. So there. There you go.

[B]

Okay. Chris, how old are you?

[C]

I am 60.

[B]

Okay. How old is your wife?

[C]

57.

[B]

And do you guys have kids?

[C]

We have two adult kids that I haven't completely launched yet, but yes. They're almost 24 and 22.

[B]

When you say haven't completely launched, in what manner do you help them out? Right now?

[C]

They still live with us, so food mostly.

[B]

Right. Come on. That's not. That's even. That's. Do they have jobs?

[C]

No, no. One is finishing last semester of school and the other one has been taking some online classes from home.

[B]

Oh, brother. Okay, so that's like a real number, though. And it also means you can't, like, leave your house because you have, you know, the four of you still.

[C]

Well, right. Yeah. Yes.

[B]

Right. Okay. So how much does your wife earn?

[C]

About 22,000 a year. She works mostly for the benefits.

[B]

Okay. With your up and down, you know, you said like sort of up and down financial history. Why don't you tell us a little bit about what you guys have been able to save? What do you have Right now for before the inheritance.

[C]

Oh, before the inheritance, we have our primary home. We have.

[B]

How much is that house worth?

[C]

About $850,000.

[B]

Okay, welcome to the West Coast. Is there a mortgage on it?

[C]

No, it's paid for.

[B]

Okay, what about retirement assets?

[C]

We have about $1 million in a brokerage account.

[B]

We keep going.

[C]

Oh, we have two rental properties also.

[B]

Wait, so no IRA, no 401k? No 403?

[C]

No, none of that.

[B]

Okay, got it. Okay, two rental properties. So let's do rentals. Okay, number one, the first one. How much is it worth?

[C]

About $600,000.

[B]

Okay, mortgage or no mortgage?

[C]

We owe about $170,000 on that one.

[B]

What's the interest rate?

[C]

It was an arm. Our credit wasn't the best. So right now it's about 6ish, a little over 6.

[B]

Okay, is that fixed now or is it keeps continued to be adjusting?

[C]

It is still adjusting.

[B]

Okay, how does that rental property, number one, how is that cash flow?

[C]

It's a push.

[B]

Okay, now rental property number two, what's that worth?

[C]

That's worth about 575. About $30,000.

[B]

Okay, what's the interest rate?

[C]

That one is about 4.

[B]

Okay, how's that cash flow?

[C]

Oh, that cash flow is fantastic.

[B]

Monthly, Real cash flow. Don't tell me about depreciation or anything. Money in the checking account.

[C]

Money in the checking account monthly is about $1,300 a month.

[B]

Okay, what about savings for you guys?

[C]

Savings? Well, we have money market with about 140,000 in it. Cash is about 50,000. Oh, and there was. I apologize. There was an old retirement fund with about $28,000 in it.

[B]

Okay.

[C]

The 401k.

[B]

Okay, you said 140,000 in the money market, that's in addition to the million, or is that within the brokerage in addition? Okay, got it. Good. So 140 money market, 50 savings. $28,000 in an old 401.

[C]

Yes.

[B]

Do we have it all?

[C]

No, there is. We have a beach house that we would like to retire to.

[B]

Oh, my God, you have so much real estate. That's why you can't work. You can't go back to work.

[C]

The properties keep me busy.

[B]

Yeah.

[C]

Yeah.

[B]

All right, so the beach house, how much is that worth?

[C]

About 1.1 million.

[B]

Wow. And is there a mortgage on that?

[C]

No, there's no mortgage on that.

[B]

Okay. Can't wait to visit now.

[C]

It's beautiful.

[B]

Incredible. And so is the game plan, like, hey, sell primary, live in the beach house full time?

[C]

Yes, we would eventually. Yes, that Would be the goal is eventually to sell our primary and move to the beach.

[B]

How so? When do you think that's going to happen? We got to get these kids launched for real. Right.

[C]

Well, part of us are thinking, well, maybe they just stay. They can adult in our house and we just.

[B]

I have a better idea. I've got a nice rental for them. So do you rent the beach house now?

[C]

No, no. Right now we back and forth.

[B]

Okay. We've got most everything pre enhanced inheritance accounted for now.

[C]

Yes.

[B]

Okay. How much money did you inherit?

[C]

About $2.2 million.

[B]

You ready for the most important question of all? How much money do you guys spend?

[C]

We spend about. With all that's going on, about $12,000 a month.

[B]

And are you open to selling a property here and there, like the rental property? Either. Both of those properties?

[C]

Yes.

[B]

You are. Okay. Do you have somebody who helps manage the brokerage account or are you doing that?

[C]

No, it's just me.

[B]

How do you feel about that? You feel like you can do it? You good?

[C]

Well, I guess that's why I'm calling. I felt okay. We've had been in the stock market since the 70s really. And we've seen portfolios go up and we've been through the crashes and all of that. And I think our biggest concern is are we diversified enough, you know, Social Security. Thinking I'd probably wait till 70 is my information there. You know, the rental incomes, do I pay off the houses? Do we sell out some stocks for ETFs? Do we. I mean the.

[B]

Hold on a second. Is the million that's in brokerage right now, all stocks?

[C]

It is actually.

[B]

And are they all like big. Are they big time, long term capital gains?

[C]

Yeah, yeah. I would say the basis. So with the inheritance and what we have, we're about 3.2 million total? Something like that.

[B]

Yeah.

[C]

And the basis probably is something a million less than that.

[B]

Hold on a second. Why are you talking about the basis of the inheritance? Didn't you get a step up or did you inherit money that was like. Did somebody gift it to you first?

[C]

It was a step up, but it's done well in the time that we've had it.

[B]

Oh my God.

[C]

Yeah.

[B]

So we got 3.2 right now. We have an eventual. Eventual. You'll get to four because you got the house because you are going to sell the primary eventually.

[C]

We will. Yes.

[B]

All right, so we got. So there's four. I don't know why we keep rental number one. I mean honestly, like I was sort of joking about the kids. But like if the kids wanted to move there and just like pay for the mortgage, that's fine. But like it doesn't seem like that's a great property. Are you attached to it or not.

[C]

Really, no, no, not really.

[B]

So it looks to me like, you know, I don't know really. When you, when are you thinking about the sale of the primary for real?

[C]

I would say probably in the next one to two years.

[B]

Okay. So 4 million is not a bad number for me to look at. Okay. And so, and then if we also, eventually you don't, you're not going to have to go back to work. Okay. I think this is a no brainer, I really do. Because ostensibly, again, I know that the kids are an important part of this because you've just got to get them launched. But like, I think that you can very comfortably be able to count on producing, I don't know, 12 grand a month from the portfolio. There will be extra money that you have to, you know, throw at that $4 million once you get your rental sold off. I don't even know, you know, I'm not even looking at the, the second rental. Like is, is that a pain in the neck? Is it good? I mean it works because you have so, you know, the mortgage is cheap. But is it, is it a pain in the neck to operate? If you move to the beach full time, is this a place that's going to be harder to manage? Will we have to hire a management company? So what do you think about that?

[C]

No. The beach is only about an hour and a half from there and the renters that we have in the homes, we rent them for below market. They've been there for years and I spend most of my time really just depos putting the money in the bank. They're wonderful renters. Yes. They treat them like their own.

[B]

The other thing to think about is with your wife, is she going to continue to work for the benefits?

[C]

Well, that was, I guess part of the question too. That's mostly why she's working right now. But I think that if she felt good about we just pay our own way with that, that she'd be happy to help me move to the beach a little bit quicker.

[B]

But it will be expensive to find health insurance like that. Then your 12 grand a month spend is going to increase.

[C]

I'm assuming you're covering the kids too, right?

[B]

Right.

[C]

Right now we are, yes.

[B]

Yeah, that's a real expense. Like for family coverage. Right now if you had to go out and buy your Platinum plan on the marketplace. It's weird because you have brokerage account money and it's going to generate income. It's not going to be huge income, but like it's going to be a couple. I got to imagine that it's going to cost you 20 grand to get family coverage for the four of you.

[C]

Right.

[B]

So if she doesn't hate her job, I'd keep doing it for a while. And I think you ought to find like, do some research in the interim. Doing some research about like, what would my healthcare option be until we turn. Each of us turned 65. I don't, I really wouldn't do anything until we got these kids launched and getting their own health insurance. So it might be a couple years or you're going to have to set aside some of your money that you are inheriting and make sure that, you know, for all I. Maybe it's just that like, gosh, you know, the, the money that comes from rental number two is really health insurance money. Plus, plus some. But it's going to be expensive. It's going to be expensive to get coverage for the four of you. You should investigate it.

[C]

Okay.

[B]

Wait till after November 1 and the marketplace opens. Presume you're not going to get any tax credits. But you'll see, like, don't. You'll have some sticker shock and you should look and see what those numbers are.

[C]

Okay, thank you.

[B]

Now, did you do all of your own estate planning?

[C]

My estate planning is not complete right now. We are working with a group to take care of that.

[B]

Great. All right, that's good. What else do you need to know? Oh, you know what? You asked and I didn't answer. You were sort of like, should I sell my low basis stocks? When is this one account now? Is there 3.2 in one account or are there two separate accounts? Inheritance plus old brokerage.

[C]

It's all in one account right now.

[B]

Are there any losers in this account?

[C]

No.

[B]

And it's all individual stocks or a little bit of everything?

[C]

Yeah, it's spread over about eight. Eight individual stocks.

[B]

Eight. That's it.

[C]

That's it. That's. That's part of the anxiety.

[B]

You know, I think you're going to have to sell some of them or some portion. I'll tell you what, I would think it might be helpful if you even just you looked at these eight stocks, you know, sort of brutally honest and say like, I have too much exposure. Eight stocks, $3.2 million. That's too much in each one of those stocks. So I might reduce the positions. The ones where you have. Do you have. I mean, I don't know what they are. We don't have to go stock by stock. I would reduce that. I would try to get at least a million dollars that is outside of those eight names. And even if you have to pay the tax, I really would.

[C]

Perfect.

[B]

Okay. ETFs, index funds. Is there any bonds in there?

[C]

No.

[B]

How do you feel about bonds?

[C]

I don't know much about bonds.

[B]

I'm just thinking. I know you want to do this yourself. Are you interested in talking to a financial advisor or not?

[C]

Sure.

[B]

Ish.

[C]

Or not really, I'm open to it.

[B]

I mean it may be worthwhile talking to somebody just because you got a lot going on in this balance sheet. You've just inherited this money. I think that there's some concentration risk in your assets right now. It might be worth it for you. Especially because you said you've had sort of an up and down history that maybe you should pay somebody and maybe you should pay someone to manage the money for like the near term just to get this process handled and then you would take it over after. I don't know. But I might think about talking to somebody who can walk you through what you have, listen to it and maybe have a different view on how you should be investing and how you should be thinking about your rentals. Because there's tax issues to manage and then there's tax issues on the inheritance. And if you do it all at once, you're going to get slammed.

[C]

Right. Okay.

[B]

Right. So I think it's worth talking to somebody or at least considering it. How about that?

[C]

That sounds great.

[B]

I think you are in really good shape. Your parents did a wonderful job. You guys have done it. You made it sound like you were some sort of screw up. Doesn't sound like it. I mean really, I thought I was like, oh, all right. But you really sound. It's good. It's really good. Like you've, you guys have the money you need, which is great. So that's it. We're done with you. So if you are like Chris and there's a real life changing event, an inheritance could be a negative event also. It could be something different in your life if the kids are still on the payroll and you want to try to figure out how to juggle everything. Get in touch with us. Go to jillonmoney.com, click the contact us button, which is in the upper right hand corner. Write us a note. Check the box if you want to join US Live. We're happy to chat with you. And don't forget there's all sorts of thing on the things on the website including subscription service. Jill on Money Live we have our upcoming webinar with Janet Davis. She is a Certified Financial Planner fee only planner and she is going to be with us talking about year end tax and financial planning. Oh my gosh. So much to do. But you've got to be a member of Jill on Money Live to join us. 45 bucks for the next 12 months. You'll get this upcoming webinar on November 19th. There'll be three more after that. The back catalog Bonus audio and video content.

[A]

Woohoo.

[B]

Way to go. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[A]

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[D]

It's Vaughn Miller, Super Bowl MVP, chicken farmer, and now host of Free Range. This is a show where I go off the field and off the script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet deep dives the conversation. This is your podcast. Join me every Wednesday. Follow and listen to Free Range with me, Vaughn Miller. Everywhere you get your podcast.