Finalizing My Exit Plan at 65

Summary

Jill on Money with Jill Schlesinger

Episode: "Finalizing My Exit Plan at 65"

Date: July 9, 2026

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Episode Overview

In this episode, Jill Schlesinger, CFP®, helps listener Amy from the Bay Area finalize her retirement exit plan as she looks towards leaving her tech career at age 66. Amy and her retired husband want to know if their finances can support their lifestyle—especially while holding onto their two homes. Jill, alongside producer Mark, reviews Amy's assets, income sources, spending, and options, offering practical advice and reassurance on the next steps towards a comfortable, stress-free retirement.

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Key Discussion Points & Insights

1. Amy’s Retirement Readiness: Background and Concerns

[04:19–06:37]

• Amy, 65, works in Bay Area tech with a base salary of $230,000 and a $40-$50k bonus.
• Husband is 72 and retired; receives $2,200/month in Social Security.
• Amy seeks a “double or triple check” on her finances after being laid off previously, which disrupted her savings confidence.
  • “I thought I had a good plan a few years ago and then got laid off… so it kind of threw me off… Lost ground in terms of not being to save money and kind of drawing on stuff.” (Amy, [06:10])

2. Current Asset Breakdown and Retirement Accounts

[07:15–08:25]

• Brokerage: $190,000, with concentration in a few big stocks.
• Roth IRA: $110,000 (current), $185,000 (old).
• Rollover IRA: $300,000.
• Variable Annuity (funded from IRA rollover): $300,000 initially, now about $430,000; still under surrender charge for 1.5 more years.
  • “No one buys an annuity when you're feeling great… there's no way. It's like, ‘Oh, yeah…’” (Jill, [07:46])

3. Property Holdings

[09:05–09:32]

• Primary residence in San Francisco, worth ~$2.2 million; $320,000 mortgage (3% interest).
• Second home in wine country, worth ~$1.2 million. Amy loves this property.
  • “I know that if I sold one, it kind of fixes things, but I kind of want to keep both.” (Amy, [09:52])

4. Spending and Social Security Planning

[10:06–10:29]

• Current monthly spending: ~$9,000.
• Social Security expected: Amy estimates $4,100/month at 67; $5,100/month at 70.
• Jill leans toward maximizing benefits by delaying Social Security to 70:
  • “I think 70 seems like the right number for you.” (Jill, [21:13])
  • Amy is concerned about bridging the gap before benefits kick in: “I was hoping 67, but… 70 seemed to be the answer.” (Amy, [12:18])

5. Work “Off-ramp” & Part-time Options

[11:31–11:45]

• Amy may switch to part-time after full time ends: “I'd like to do a kind of part time afterwards, and the company offers that.” (Amy, [11:31])
• Jill cautions about relying too heavily on this: “Of course, it’s part time while everything is good…then we’re in some horrible recession, and then we go, ‘Did we say part time? No.’” (Jill, [11:45])

6. Recommended Retirement Income Strategy

[12:24–14:29]

• Use the rollover IRA for annual withdrawals (~$100,000/year) to supplement husband's Social Security, covering most expenses until Amy files for Social Security.
• Consider annuitizing the variable annuity after the surrender period; it could serve as reliable income.
• Roths should be left untouched to grow and be used last.
• Both homes make for a tight, but doable, plan. Selling one (especially wine country home) is a powerful Plan B:
  • “If one of those [homes] goes, you’re 100% great.” (Jill, [14:26])
• Part-time work would make keeping both homes more feasible; otherwise, selling one relieves pressure.

7. Real Estate as Plan B

[14:29–16:50]

• Jill and Mark lean toward selling the wine country home for liquidity, emphasizing aging-in-place in the city.
  • “I always think…the place that you have in a city as you get older is usually the place where you want to be, but maybe it’s not. I don’t know.” (Jill, [15:35])
  • Suggests not renting out the wine country house: “No, I don’t… I’m not into that either.” (Jill, [16:54])
• Amy agrees she doesn’t want to rent to strangers.

8. Concentrated Brokerage Accounts and Actionable Moves

[17:32–18:25]

• Amy has large positions in two individual stocks.
• Jill recommends trimming positions to reduce risk and rebalancing for more diversification.
  • “Take half of a position off… then you’re protected.” (Jill, [18:03])
• Amy is convinced: “Just convinced me.” (Amy, [18:23])

9. Estate Planning and Possible Inheritance

[18:25–21:07]

• All estate documents are in order.
• Amy expects to inherit ~$500k from her mother eventually, but it's not part of the core plan.
• Jill’s advice: Do not use inheritance to pay off low-interest mortgage (3%). Instead, add to investments and increase flexibility:
  • “I absolutely would not pay down a three-something note, anything under 4%. Absolutely not.” (Jill, [21:13])

10. Psychological and Emotional Aspects of Retirement

[06:10, 21:08–21:23]

• Jill acknowledges the emotional impact of late-career layoffs and transitions, emphasizing the value of having a clear plan B for peace of mind:
  • “If you need a plan B, get in touch with us… It is freaky. It does something to you.” (Jill, [21:08])

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Notable Quotes & Memorable Moments

• Jill on buying annuities out of fear:
  “No one buys an annuity when you're feeling great… It’s like, ‘Oh, yeah…’” ([07:46])
• Amy on keeping both homes:
  “I know that if I sold one, it kind of fixes things, but I kind of want to keep both.” ([09:52])
• Jill on real estate in retirement:
  “It’s a great asset, looks beautiful on your balance sheet, but it can’t pay the bills.” ([16:49])
• Jill on downsizing exposure to individual stocks:
  “Take half of a position off… then you’re protected. …You’ve protected against the downside.” ([18:03])
• Jill on flexibility and control:
  “Don’t trust the man—not the husband, I mean the man you work for. And plan accordingly. You got your plan B.” ([21:08])
• Jill on Social Security strategy:
  “I think you should wait till 70 unless something really weird changes in like the next couple of years, health wise.” ([21:13])
• Amy on her confirmations:
  “It’s confirmed. Couple things, so that’s good.” ([21:26])

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Timestamps for Key Segments

• Amy’s Intro & Goals: [04:19–06:37]
• Asset Overview: [07:15–08:56]
• Property Discussion: [09:05–09:32]
• Monthly Expenses & Social Security: [10:06–10:29]
• Part-time Retirement Options: [11:31–11:45]
• Withdrawal & Income Strategies: [12:24–14:29]
• Real Estate as Contingency: [14:29–16:50]
• Brokerage Investments Advice: [17:32–18:25]
• Inheritance & Mortgage Strategy: [19:38–21:07]
• Final Assurances & Emotional Support: [21:08–21:26]

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Summary Takeaways

• Amy is well-positioned for retirement, provided she is flexible about real estate, income withdrawals, and possible part-time work.
• Selling one home (especially the wine country property) offers a powerful safety net.
• Diversifying concentrated stock positions and delaying Social Security to age 70 are both wise moves for long-term stability.
• A clear plan B (real estate sale, possible inheritance) gives Amy emotional confidence in a period of big transition.
• Jill’s advice is practical, direct, and empathetic, focusing not just on numbers but on the realities of aging, work, and life transitions.

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For listeners facing similar crossroads:
Jill and Mark encourage ongoing planning, flexibility, and the value of having a contingency—whether that’s your home, your investments, or just the knowledge you can always reach out for a second opinion.

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To get your questions answered or appear on the show:
Visit jillonmoney.com, click "Contact Us", and specify if you want to be on the air. Sign up for the free weekly newsletter and check out their live programming for deeper dives.

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Best Quote to Sum Up Jill’s Tone:
“You've done everything right. Don't trust the man. Not the husband—I mean the man you work for. And plan accordingly. You got your plan B.” ([21:08])

Transcript

[A]

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[B]

Hi. Thanks, guys, for taking me on this morning. I appreciate it.

[A]

Sure. What's up?

[B]

So I wanted to do a double check, probably more like a triple check, to kind of see if I'm ready for retirement.

[C]

80.

[B]

I'm not 85. I'm 65.

[A]

Wow. I mean, first of all, 85. I was like, you're still working and you're 85. That's a lot. That's amazing. Okay. So amazing. You're still working at 65. Do you like what you do?

[B]

It's okay. I'm in tech.

[A]

Okay.

[B]

Bay Area tech.

[A]

Yep. And have you been in IT for your whole career?

[B]

This is actually my second career. I was in different aspects of technology before, but more on the consumer side. So now it's a B2B.

[A]

Okay, and are you thinking about this, like, right this second, like, what's our time horizon here?

[B]

So my time horizon would be lovely if I could aim for end of next year.

[A]

Okay, so we're talking at the end of 2027, right? Yep, yep. And then you'll be 66 at that time.

[B]

That's right.

[A]

Okay, got it. Okay. Are you married, single, partnered?

[B]

Married. And he's retired? Yep.

[A]

Old man. Well, how old is he?

[B]

He's 102. No, he's 72.

[A]

He's 72. Okay.

[B]

That's right.

[A]

And. And does he. Or will you have any pension benefit?

[B]

No pension, unfortunately.

[A]

Mark, finally, we've broken the chain. We had three pension questions this week, so we're just want to talk to regular old people who don't have pensions. Okay, so right now, why do you need a double triple check? Like you, it sounds like I can just hear it in your voice. You sound very organized. And so I'm guessing you have a bunch of money. So is there something that is holding you back from feeling confident in your own numbers?

[B]

Yeah. So I thought I had a good plan a few years ago and then got laid off, which is not unusual for being in tech and a certain age. Um, so it kind of threw me off, Joe, for a couple of years. Lost ground in terms of not being to save money and kind of drawing on stuff. So that's the reason why I'm kind of skittish about things. And I've been working since I was 15, so it feels unusual to maybe just kind of call it quits, but.

[A]

Yeah, I get that thinking about it.

[B]

Yeah.

[A]

Okay, well, how much do you earn?

[B]

Right Now I'm at 230 base with a 40k 50k bonus, which seems likely this year and has been for the last couple of years.

[A]

Okay, Bonus. Great. Do you also get awarded stock? I don't know if you're working for a private or a publicly traded company.

[B]

No stock. No stock.

[A]

All right, so your husband receives Social Security, correct?

[B]

Correct.

[A]

How much?

[B]

22.

[A]

2,200amonth. A month or 22 grand a year?

[B]

A month.

[A]

Okay, 2,200amonth. Got it. What have you guys saved?

[B]

Brokerage. It's 190 or so.

[A]

Okay.

[B]

And it's with a couple of big stocks which I would like to ask you about, too. Current Roth is 110, and I have a Roth IRA at 185, a rollover IRA for 300. And I was freaked out a few years ago when I lost my job. I opened an annuity which is grown. I'm sorry. Yeah, I know that.

[A]

No, I just. I like that you're just like. I was freaked out, and I think that this happens. No one buys an annuity when you're feeling great. There's no way. It's like. It's like. Oh, yeah. No. Okay, so the annuity, it's a non qualified annuity, meaning it is.

[B]

It was transferred from an ira.

[A]

Okay, so it's a qualified. Okay.

[B]

Yes.

[A]

And how much is in there for 30?

[B]

I started with 300 on that, so.

[A]

All right.

[B]

It's okay.

[A]

When did you buy it?

[B]

I bought it two and a half years ago.

[A]

All right, so we still have surrender charges that you have to deal with

[B]

for about another year and a half.

[A]

Okay. And is it a variable annuity or a fixed annuity?

[B]

Variable.

[A]

Okay, what about your current retirement account?

[B]

That has 110 in it. It's a Roth.

[A]

Oh, that's the current one. Okay. And what about. Is this all for you or does your husband have another. Do we have other.

[B]

No, he's. He's got maybe 100 laying around, but

[A]

not a lot in retirement.

[B]

Mm.

[A]

Okay.

[B]

Yep.

[A]

Anything else in terms of investment accounts?

[B]

No more investments. Just emergency kind of safe money. About 75.

[A]

Okay. And do you guys have kids?

[B]

No kids.

[A]

Okay. And how about a house? Those Bay Area prices are kind of crazy.

[B]

Yeah. So we were lucky. We have a home, and it's in the city. It's worth like 2.2, but we still owe money on it. Yeah, we still owe money about 320 or so. And then we also have a second home that we don't rent that's worth like a million to.

[A]

Wait a minute. What's the second home? Like a ski place or something like that?

[B]

It's a wine country type.

[A]

Oh, nice. And you love it?

[B]

I love it, Jill.

[A]

So, okay, if you said in a year from now. Right. And you're ready to, like, rock and roll, is your desire to hold both of these properties or is there some sort of real estate transaction that you think will happen?

[B]

I want to hold on to both. I know that if I sold one, it kind of fixes things, but I kind of want to keep both.

[A]

How much money do you guys spend in a given year?

[B]

Given month is like 9,000, 9,000.

[A]

Okay. And if you were to retire next year, can you tell us what your Social Security benefit would be at 67 or at 70?

[B]

At 67 would be about 41.

[A]

Okay.

[B]

And at 70, about 51.

[A]

Okay. How's your health? Good. Yeah. Okay, good. And your husband? Also good.

[B]

Yep.

[A]

Okay. Anything else that we should know about that is on that balance sheet of yours?

[B]

No more assets. That's pretty much it.

[A]

Okay, got it. So when you said that you were spending some of the money when you were, you know, in that interim period between jobs, where did you draw it from? Was it from your cash? Was it from your brokerage? Where did you pull from?

[B]

It was from cash.

[A]

Okay. So that's why there's 75. And right now, I presume. Are you. Are you maxing out your Roth? Right now?

[B]

I am.

[A]

Okay, so that's the 110 maxing out. And is it your desire that it's next year, we're done, or is it like, I could work next year. I could then kind of get a. Kind of. Get a little bit of a halftime, kind of like, do you want to have a sort of a. A sliding down, or do you want to be abrupt? Done.

[B]

I'd like to do a kind of part time afterwards, and the company offers that.

[A]

Oh, great.

[B]

Yeah, I know. It's kind of interesting, so I might do that. But it's. You just never know.

[A]

I know you don't really trust business. It's like, yes, of course, it's part time while everything is good, and then we're in, like, some horrible recession, and then we go. Did we say part time? No. So most likely you want at least let's look at the numbers to say, all right, what happens if it's next year? Right, right. And if it's next year and you can hold off, I guess that the. The. The most important thing is that we need to get you to your Social Security age. Right.

[B]

Mm.

[A]

I'm leaning 70. I. I don't know about you, or were you thinking 67 or 70?

[B]

I was hoping 67, but when I keep on looking at these numbers, 70 seemed to be the answer.

[A]

You know, it's. Because that way, you know, you can take. You know, your spend can be covered by just pulling out. Whatever. I'm just going to give you, like, let's just do a round number. Let's say you take out from that rollover account 100 grand a year, and we just get rid of it, we deplete it, and you pay the tax that's due. You're pretty close to your nine grand a month. Right. On your spend, because it's like 100 with his 2,200amonth. And, you know, maybe you'll have to do a little bit from the brokerage, but you can. I'm hopeful that you can leave your Roths alone. And by the way, your husband, his retirement is pre tax.

[B]

No, it's after.

[A]

Oh, it is. Okay. So he's. So that's Roth.

[B]

Yes.

[A]

So we'll just get rid of that rollover and that'll be done. You'll get rid of it. You're going to have to get rid of it anyway. Right. Might as well use it then. That gets you to your annuity period. And then if you look at that annuity, it may be worth it to annuitize it just to get the money and get your cash flow, and that'll take you through whatever else you need, like again in a year and a half when the surrender period is gone. And it's a very short surrender period. We're sure about that. Four years.

[B]

It's 20, 28 March.

[A]

Okay, great. And then you might want to look at that. You could literally use that and try to kind of annuitize that, get you through whatever else you need, or you can roll it over and use it to help get you to your age 70. Once you're at 5,100amonth, plus your 2,200amonth, you're, you know, you're. You're in good shape there. That's. That's like, you know, you got 7,300. The thing is that I hate to tell you this, but I'm going to tell you what, you know, that obviously all of your wealth is not all of it, but so much of your wealth is in these two homes. Yep. So I don't know if you have really thought about whether or not maybe you can maintain them for a while, for the first five years, seven years. But, you know, the way that this works beautifully is if one of those goes, you're 100% great. Mark, which one do you want to sell? You want to sell the wine country, or you want to sell the city?

[C]

No, I want to be in the city. So I'll sell Wine Country.

[A]

You're selling wine country. I'll sell wine country, too. Meaning that it's just like too much money that's at stake there. So it's, it's just a. It's a real it's game changer, frankly. Now it can also be that, you know, instead of doing that, if you really want to keep both, that maybe you can keep both because if you work part time, you don't have to take as much money out of the qualified accounts then and that have not been taxed yet and it can stretch it out a little bit more. So in other words, if it's like, oh, you know what, I retire next year and I will, you know, Instead of making 230 plus 40 or 50 grand, what I'll do is I'll make half that and maybe not even have the same bonus. But, you know, if you made 100 or 150 grand total and then you're really not having to touch any of the money in retirement accounts, then maybe you can keep it. It's just, it's going to be a trade off somewhere if you really want to be done. Done. I'm, I don't know. I don't know. I'm sort of thinking that one of those places goes. And you know, frankly, I always think that the, the place that you have in the, in a city as you get older is usually the place where you want to be, but maybe it's not, I don't know. And like, if you're like, oh, my doctors are in the city and that's where I want to be and you know, my friends are really in the city and we can always like go glom off somebody or stay in a hotel and, you know. Mark, have you ever been to the wine country?

[C]

Yeah. In California? Sure. Yeah, I've done that. Yep.

[A]

You want it? You want to, you know, should we, should we make the play to be in the wine country? I mean, there's fires there. I'd rather be in the city.

[C]

No, I want to be in the city drinking my wine.

[B]

Okay.

[A]

Exactly. Don't you have friends who have houses also? You can sponge off them. Wouldn't that be nice?

[B]

Probably can try. Yeah.

[A]

And you can go and you can stay in a hotel, you can Airbnb. I don't know. It's a, it's at least something worth considering. It's like, well, would I rather work part time for a couple of years? If it's possible. But in the back of your head, you should always know, plan B. I can just, I can sell that second home or sell the primary, whatever, wherever you want to be, and you're, you're golden. But the problem with the real estate is like, it's a great asset. It looks beautiful. On your balance sheet, but it can't pay the bills.

[B]

Right.

[A]

Would you ever rent the. The wine country house?

[B]

No.

[A]

No. Yeah, I don't stuff either. I'm not into that either. Someone just made an offer for me to rent something. I'm like, no, I don't want you. My stuff. I love you, but no, I think you're very close, Mark, don't you agree so close on this?

[C]

Yeah, they're. They're basically right there. And it's nice knowing that they have

[A]

the solution if it comes to that, if ever again. If that's necessary. Is your husband totally chill about this?

[B]

Yeah, he doesn't care one way or another.

[A]

Yeah. He's like, whatever. Whatever you want.

[C]

Bed.

[A]

That's what I. Yeah. Mark cares. You'd be surprised how much he cares.

[C]

I would care a lot more about this. Yeah.

[A]

Yeah. These are the kinds of things he does care about. I think that you're in good shape. Can we just talk a little bit about the brokerage account and the stocks you have in there? What do you. What do you have and why? You just don't want to sell because you have a capital gain, so it's done really well.

[B]

Those are the two. The names that you've heard.

[A]

Of course,

[B]

it's. It's a capital gains for sure. But also, I think there's still upside on it.

[A]

But take some. One, take some of the money. Money off the table. Big deal. Yeah, just a little bit. Just so that you're not so exposed. Just some. Even if it's like, oh, you know what, how much is in there? You said there's a hundred and ninety thousand dollars. Take half of a position off. Take half. Just take half of it and pay some capital gains and. And then reallocate. Then you're protected. You still have upside, but you've protected against the downside. It's not saying. Yeah, it's not so bad.

[B]

Just convinced me. Yeah.

[A]

All right, good. Do you guys have your estate documents

[B]

done, all checked off? Yep.

[A]

All right. I think you're in very good shape. I really do. And Amy, you know, again, as Mark said, the nice thing about this is that in the back of your head, you know, you have a plan B. And to me, that is kind of the way that you can get through this next year and you guys can really, like, let it sit a little bit, you know that there's an answer. You can do this in a year. If you were talking to the company and, you know, they're like, you know, we want to lock you down and get you give you a one year contract for the year after you. Okay, great, fine. And if you really say I want to be completely free of work, I don't want to be, I don't want to be tied to that, then I think you're in a situation where you could basically say, well, we can always sell a house and it's fine. And you'll, you're going to pay some capital gains on that also, guess what? You really are. So one way or another, you're going to pay some capital gains, you're going to free up some money and you're going to go live your life and it's good. And I think you should wait till 70 unless something really weird changes in like the next couple of years, health wise. But I think 70 seems like the right number for you.

[B]

So if I get well, I know I'm getting something from my mom. My mom's very healthy at this stage and there's some.

[A]

Is she healthy and wealthy, which is like a great combo.

[B]

She's okay. She does all right. And we, we should already told us what's happening afterwards. So would you take some of that money to pay off?

[C]

How much money are we talking?

[A]

Wait a minute. Pay off the mortgage? No. What's the mortgage interest rate?

[B]

3? No,

[A]

definitely not. But if you're. How much money are we talking about? Mark asked the right question about cash

[B]

is probably like half a million and.

[A]

All right, well, half a million gives me a little bit more. So no, what you would do is like, she's healthy and everything is good, but if like, if something happened to her, you'd have that half a million, you add it to your brokerage account, you're in great shape. That, that helps a lot. If that happened before you retired, if that happened in the next year, that would help you walk into retirement and then you wouldn't have to sell the second home. But if it didn't and you were just kind of keeping this in the back of your head knowing that you're going to have a half a million or, you know, more or less, whatever, a few hundred thousand. And the longer she lives, the less you'll get, obviously. Right, because she'll need her money. But you know, your retirement is not predicated on receiving that money. If you had that money, I absolutely would not pay down a three something note, anything under 4%. Absolutely not. If you told me it was like six and a half maybe.

[B]

Right, right. Okay.

[A]

You're in great shape. You really are. You're right on The Cusp. You've done everything right. Don't trust the man. Not the husband, I mean the man you work for. And plan accordingly. You got your plan B. I think you're in good shape. I really do.

[B]

Okay.

[A]

You feel okay? Yep.

[B]

Yep.

[A]

All right, good.

[B]

It's confirmed. Couple things, so that's good.

[A]

All right, good. All right, listen, get, get in touch with us if there's any issue over the next year. But I think you're on the right track. And if everybody listening, if you're out there and you've got kind of had a surprise thing, like when you lose your job and you're 60 and you're in your 50s, it is freaky. It does something to you. So I understand that if that's the situation you're in, if there's. You need a plan B, get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note if you'd like to join us on the air, just check the appropriate box. We'll get you on the air. Don't forget to sign up for the free weekly newsletter, which comes out tomorrow Fridays. And you'll also get our blog. And of course, don't forget to subscribe, follow and promote our sister broadcast, which is called Money Moves. And you can get that as well as this program on the Odyssey app. You can find us wherever you find your favorite podcast. Please leave us a rating and review. Wherever you listen, we always ask that you lift someone up. Change your work, change your wealth, change your life. Thank you for listening. I'll talk to you tomorrow.

[B]

Foreign.

[A]

Hey there, it's Jill Schlesinger. I'm launching a new show. It's called Money Moves, and your money is going to move. We're going to help you make better financial decisions. We're going to call out the B.S. you're finding all over social media. We're going to give you actionable guidance to make your financial life clearer, less stressful. We're going to answer you your financial questions and take the mystery out of your financial life. Follow and listen to Money Moves with Jill Schlesinger. Wherever you get your podcasts.