I’m 67, Am I Ok to Retire?

Summary

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Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode: I’m 67, Am I Ok to Retire?
Date: October 17, 2025
Host: Jill Schlesinger, CFP®
Main Theme:
Jill Schlesinger takes a listener call from “Sally,” a 67-year-old professional from Northern California, who wants to know if she’s financially secure enough to retire in the next year. The conversation covers Sally’s financial situation, including assets, income sources, living expenses, and retirement planning strategies. Jill provides tailored advice, focusing on maximizing Social Security, the advantages of Sally's frugality, and legacy planning.

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Key Discussion Points and Insights

1. Introducing Sally and Setting the Stage

[01:07-02:20]

• Jill invites Sally onto the show, creating a relaxed, friendly atmosphere imbued with reassurance.
• Sally’s main concern: Despite careful planning and apparently sufficient assets, she's haunted by doubts—echoing broader retiree anxieties:

  "We hear in the news ... people of a certain age don't have enough for retirement...there's always that little gremlin ... that says: Is it really time to retire?" — Sally [02:20]

2. Sally’s Financial Snapshot

[03:06-07:42]

• Age: 67; Working full time from home, earning $118,000/yr.
• Retirement Savings:
  • 401(k) (Traditional): ~$640K
  • IRA (Traditional): ~$285K
  • Restricted Stock (vested): ~$50K
  • Employee-purchased company stock: ~$30K
  • Pension lump sum: ~$190K (pays ~$1,200/mo.
• Social Security Estimates:
  • $3,752/mo at age 68
  • $4,382/mo at 70
• Expenses:
  • ~$3,600–$3,700/month
  • Living "below market" on rent, no debt, car paid off
• Personal Circumstances:
  • Single, no children, not supporting elderly parents, independent siblings

3. Evaluating Retirement Readiness

[07:54-10:02]

• Sally is considering “pulling the trigger” and retiring at age 68, in early to mid-next year.
• Jill emphasizes Sally's financial discipline and low spending:

  “You don’t spend any money...You can do whatever you want, Sally.” — Jill [08:30]

• Jill’s core advice:
  • Trigger pension at retirement (age 68): Take $1,200/mo.
  • Delay Social Security: Wait until age 70 for the higher benefit.
  • Bridge income gap with withdrawals: Take ~$50K–$80K annually from 401(k)/IRA to cover living expenses until Social Security kicks in. This reduces future required minimum distributions and manages tax exposure:

    “I would delay my Social Security to age 70 for two years. I would pull money out of my traditional 401k or IRA...Pay the tax that’s due, and then your future required minimum distributions will be diminishing.” — Jill [09:15]

4. Risk Management and Asset Allocation

[10:02-11:11]

• Company Stock: Jill recommends diversifying, selling some vested and employee stock to avoid “having an $80,000 bet on one stock”:

  “Even if you took some of it, like, early income...just so you don’t have that huge bet ... on one stock.” — Jill [10:52]

5. Legacy & Legal Planning

[11:11-12:21]

• Jill highlights importance of a will, healthcare proxy, and powers of attorney—even for people with no dependents:

  “It doesn’t matter. You don’t have to have dependents to worry about. It’s like, where’s your stuff going to go...?” — Jill [11:21]

• Sally admits she hasn’t taken care of this, but her employer offers free legal support:

  “Does your company offer [free legal]?...Do that. Definitely do that.” — Jill [11:17-11:19]

6. Mindset and Emotional Considerations

[12:06-12:36]

• Jill acknowledges that, for many, the challenge is psychological—believing you can retire:

  “Just also till you get your mind wrapped around the fact that you can retire, which I have a feeling you’re not going to really believe until it happens.” — Jill [12:25]

• Jill floats the idea of Sally negotiating for part-time work if she needs to “ease in:”

  “Give me half the money and I’ll just work half time...? Would you want to do that or not?” — Jill [12:17]

7. Wrap Up: Affirmation and Advice

[12:36-13:36]

• Jill confirms: Sally is “in great shape.”

  “Get ready to retire. It is happening because you have made it happen.” — Jill [13:09]

• Listeners are reminded that similar security is possible with saving and low spending—even without a huge salary or dependents.

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Notable Quotes & Memorable Moments

• “You don’t spend any money...I think you can do whatever you want, Sally.” — Jill [08:30]
• “I would delay my Social Security to age 70 for two years. I would pull money out of my traditional 401k or IRA...Pay the tax that’s due, and then your future required minimum distributions will be diminishing.” — Jill [09:15]
• "Should we take some of it? Even if you took some of it, like, early income...just so you don't have that huge bet, this $80,000 bet on one stock." — Jill [10:52]
• “You should only give [the job] up if you’re like, ‘I’m done.’” — Jill [12:06]
• “You do not have to be as in shape as Sally...Notice that she has saved a lot of money and she has very low expenses. Amazing.” — Jill [13:16]

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Timestamps for Key Segments

| Timestamp | Segment | |-------------|--------------------------------------------------------------| | 01:07 | Welcome and introduction of listener Sally | | 02:20 | Sally describes retirement anxiety | | 03:06 | Sally’s age, income, and retirement assets overview | | 07:54 | Sally's target retirement timeline and expenses | | 08:30 | Jill’s affirmation of Sally’s frugality and readiness | | 09:15 | Detailed advice on delaying Social Security, drawing down IRA| | 10:38 | Conversation on diversifying company stock | | 11:11 | Importance of updating will, beneficiaries, legal documents | | 12:06 | Approaching retirement gradually/considering part-time work | | 13:09 | Jill’s final affirmation and wrap up |

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Tone and Style

• Conversational, supportive, practical—Jill demystifies financial jargon, building rapport with Sally and listeners alike. She uses humor, directness, and empathy to make the advice approachable.
• Key message: With careful saving and modest spending, retirement security is realistic—even if you’re not sure you can “pull the trigger.”

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Resources & Next Steps

• For listeners: Jill encourages submitting questions at jillonmoney.com, signing up for the newsletter, and reviewing on-demand resources.
• For Sally: Draft estate documents using company-provided legal support, consider partial liquidation of company stock, possibly negotiate reduced work hours, and celebrate a financially secure retirement!

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Transcript

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[Jill]

Welcome to the Jill on Money Show. It's Friday, October 17th and we are here talking about all the things you want to do in your lives. See, sometimes we grant your wishes. Like you rub the bottle and out comes I dream of Jilly. It's not genie and I don't look that good certainly, but out I come. And then sometimes I can grant a wish, but sometimes it doesn't quite work out that way. So what I hope that you can do is instead of rubbing that little magic bottle that you can just give us a holler and see whatever is going on in your life and what you want to accomplish is doable. All you need to do is go to our website jillonmoney.com in the upper right hand corner there's a Contact Us button. You write us a note and if you'd like to join us live on the program, you check the box and Mark will do everything else because he's the best. While you are on the website, do sign up for the free weekly newsletter which will also get you our blog and also check out the videos, the resources. Our other show is called Money Watch. It's all there right on the website. Today we are talking to Sally who joins us from Northern California. Hi Sally, how are you?

[Sally]

Great. How are you?

[Jill]

Fantastic. What can we do for you?

[Sally]

Well, like a lot of people, we hear in the news and we read that, you know, people of a certain age don't have enough for retirement. So while I've been forecasting my what I believe will be my monthly income and my expenses and my portfolio, while it looks good on paper, there's always that little gremlin I guess in the back of your mind that says is it really time to retire? Do you really have enough money, so I thought I'd check in with you.

[Jill]

Okay. I think that makes sense to me. So why don't we do this? Why don't we go through what's happening in your life and we'll see kind of where you stand. So first of all, Sally, how old are you?

[Sally]

67.

[Jill]

And you're still working full time?

[Sally]

I am. I'm working from home, yes.

[Jill]

Wow. And how do you like working full time? Are you. Have you had it or do you like. We were just talking to somebody who's like 52 and he's like, I've had it. So I mean, I want to be clear that everybody's in a different place.

[Sally]

Yeah. No, I'm seriously thinking of pulling the trigger next year. But when you've been employed in the California area where there's, you know, been number of rifts.

[Jill]

Yes.

[Sally]

It's kind of hard to say, you know, bye bye to a job that seems stable.

[Jill]

Right. How much do you earn right now, Sally?

[Sally]

Annually? About 118.

[Jill]

Okay. I presume that you've been putting money away in a retirement account. So what kind of retirement account savings do you have?

[Sally]

I've got 401s and an IRA and I've also got some stock restricted and employee purchased.

[Jill]

Okay. So let's go one line item by line item. Okay. So 401, is this traditional or Roth?

[Sally]

It is traditional.

[Jill]

How much is in there?

[Sally]

About 640.

[Jill]

Okay. And Ira traditional or Roth also traditional.

[Sally]

And I've got about 285 in that.

[Jill]

Okay. There's restricted stock. Is any of it vested?

[Sally]

A good percentage of it? I would say about 50,000.

[Jill]

Okay. And you said you also have stock that you've purchased as an employee.

[Sally]

Correct.

[Jill]

How much? And it's the same stock? It's not two different companies?

[Sally]

No, no, it's the same stock, yes.

[Jill]

Okay. And how much is in that stock plan, that purchase plan?

[Sally]

That is about 30.

[Jill]

And the company's doing well right now?

[Sally]

Doing very well. I also have a pension I forgot to mention.

[Jill]

Oh, Sally, it's like my favorite word. It's like benign and pension. Two of my favorite words in the English language. Okay.

[Sally]

Y.

[Jill]

What's that look like?

[Sally]

It's about, I think 190, which I had planned to. One scenario was I was planning to use my Social Security and that pension with a lifetime payout to be my guaranteed monthly income.

[Jill]

What's the pension? If you like said, if you gave your notification at the end of this year. Okay. And you stopped working what is the pension payout amount as a lifetime? Yep.

[Sally]

It pays out a little under 1200amonth.

[Jill]

Okay, got it. Sally, I neglected to ask, are you partnered, married, single? Single. Okay. Kids? No kids.

[Sally]

No kids.

[Jill]

Parents you have to worry about.

[Sally]

No.

[Jill]

Siblings you have to worry about.

[Sally]

Yeah. But I'd rather not talk about that now.

[Jill]

You betcha. Nothing I should factor in, I guess, is what.

[Sally]

No, I think. I think it's pretty clean. Not bad.

[Jill]

Okay, got it. All right. The pension lifetime, you would take that even if, you know, essentially you're. You dropped dead on the second day after you started receiving it. And nobody else gets that money, Right?

[Sally]

Right.

[Jill]

Correct.

[Sally]

Yeah.

[Jill]

Okay. Because there is nobody else. Essentially.

[Sally]

Essentially.

[Jill]

Okay, Got it. At your. At age 70, what is your Social Security benefit at 70?

[Sally]

It's 4,382.

[Jill]

Wow. Okay, that's great. How much money do you spend right now?

[Sally]

Right now my expenses run about 3,600, 3,700amonth. I'm.

[Jill]

That's it?

[Sally]

Yeah. I'm, you know, I'm. Like I said, I'm a little frugal. I am below market.

[Jill]

Yeah.

[Sally]

Rent, so. Which is nice. Managed to.

[Jill]

But are you going to be able to stay below market?

[Sally]

Well, that's going to be the probably only variable in my plan.

[Jill]

All right. But good to know. So at this point, do you have other money besides the stock and the employee stock and the restricted stock? Any other money in savings or brokerage accounts?

[Sally]

I've got a small amount of like 17,000 in savings.

[Jill]

And there's nothing big coming up in terms of, like, what you'd have to spend money on?

[Sally]

No.

[Jill]

No.

[Sally]

Car's paid off.

[Jill]

Okay. And no other debt, right? No. Like, weirdo old, no school loan. Okay.

[Sally]

No.

[Jill]

So this is it. I got your life, right?

[Sally]

Yep.

[Jill]

In one little bitty piece of paper, I have your whole life. How much would you like to be able to just call it quits at the end of this year?

[Sally]

I was thinking of as soon as I hit 68, which would be maybe early next year. Early to mid next year.

[Jill]

Okay. And then you say goodbye and you're done working.

[Sally]

Yes.

[Jill]

And then would you immediately you trigger the pension? Right. That's your 1200amonth. Correct. And if you were to take your Social Security at that moment, what would that amount be at?

[Sally]

68 should run about 3752.

[Jill]

Okay. Do you have good life expectancy in your family? You feel like you're in good health? Where do you stand on that?

[Sally]

Yeah.

[Jill]

Continuum.

[Sally]

Yeah. My mom's 98. So I, I, oh, my gosh. The chances of me living in my 90s is pretty.

[Jill]

Okay. So this is the way I think about it. First of all, I think you can do whatever you want. Sally, you're. Because you don't spend any money. Okay. I think what I would do is I would keep working until you're 68. Just, that's fine. You give your notice. I think at that point you get your $1,200 a month pension. But then what I would do is I would start taking money. I would delay my Social Security to age 70 for two years. I would pull money out of my traditional 401k or IRA, either one. Okay.

[Sally]

Okay.

[Jill]

I would use that to live on. Because you're going to have to start taking money out of these accounts anyway, right? Yeah. So you might as well start getting that money out because, you know, assuming you know where you are right now, which is mostly, you mostly get taxed in the 22% tax bracket. Right. And then of course, the state of California will take their share. But I think it would be helpful for you start getting some of that money out. In fact, if you look at your pension amount of your 1200amonth, I think I probably would pull out something closer to like 50, $80,000 a year that hasn't been taxed yet just to get it out. You can live on it, pay the tax that's due, and then your future required minimum distributions will be diminishing. Right.

[Sally]

Okay.

[Jill]

And then once you that you're in such a weird situation, because honestly, once you get to age 70, it's golden. I mean, you have more money than you need. And then you're just going to have to start making sure that you take money out of those traditional assets so that you get the money out and, you know, hopefully stay in that 22% bracket over time, you're gonna have, you're gonna have no problem. I mean, I would say that the only other thing to consider would be what happens when you retire to the employee stock and the vested stock. Are you planning on selling it? Like, where do you want to go with that?

[Sally]

I believe I can keep it with the company and just allow it to.

[Jill]

Can we just take some of the money off the table, though? Like, what if the company rolls over and just, you know, like the market rolls over? You know what I mean?

[Sally]

Like, yeah, okay.

[Jill]

Should we take some of it?

[Sally]

Okay.

[Jill]

Yeah, we could. Even if you took some of it, like, early income. Yeah, okay, exactly. Just so you don't have that huge bet, this eighty thousand dollar bet on one stock. Right. You're in great shape. I mean, really great shape. Even though you don't have survivors. Do you have a will?

[Sally]

No. I need to take care of that, dude.

[Jill]

Does your company offer.

[Sally]

Yes.

[Jill]

Free legal?

[Sally]

Yes.

[Jill]

Oh, my goodness.

[Narrator/Advertiser]

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[Jill]

Definitely do that.

[Sally]

Okay.

[Jill]

Okay. You know, it doesn't matter. You don't have to have dependents to worry about. It's like, where's your stuff going to go right now? Who's the beneficiary of your retirement accounts? Your bust out siblings?

[Sally]

A couple of brothers. Yeah.

[Jill]

Okay, so is. Are you okay with that? Do you want them? Okay. And they're going to be like, will they be okay? Like they'll basically be the people who inherit your stuff, but just put it down on paper. Also, do you have somebody close by who can be your health care proxy?

[Sally]

Yes.

[Jill]

Okay, so that's it. Health care proxy, power of attorney, and then of course, the actual, you know, executor and, and the will. So those are the things you need to think about. But you're in such good shape. It's so funny because you're like, I'm so lucky to have a job. Maybe I shouldn't give it up. You should only give it up if you're like, I'm done. If you are happy or if they say, don't leave. Sally, what can we do to keep you? What would there ever be a time where you're like, okay, give me half the money and I'll just work half time? Would you want to do that or not?

[Sally]

I would probably do that. Yeah.

[Jill]

Just.

[Sally]

Just for a couple years. Just to. Until I hit 70.

[Jill]

Just also till you get your mind wrapped around the fact that you can retire, which I have a feeling you're not going to really believe until it happens.

[Sally]

Yeah, that's probably true.

[Jill]

Sally, you're in great shape. Anything else you need from us at this time?

[Sally]

No, I just really enjoy listening to both of you. You've been such a great source of information.

[Jill]

Oh, we really appreciate that. We love hearing from everybody. And you now know why? Because we just like to like interrogate you and learn all about you. Mark and I are voyeurs. That's why we love our journey jobs. So it's fantastic. Sally, get ready to retire. It is happening because you have made it happen. Now you do not have to be as in shape as Sally is. It could be that you, like, want to get to the Sally situation. Notice that she has saved a lot of money and she has very low expenses. Amazing. You don't have to make tons and tons of money to get yourself in a place where you can kind of achieve your goals. It's just that you have to be thoughtful about it. And I got a sense that Sally's the type of person who socked away money all along the way. But if you need some help with that, you want to get on the right track, 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 on the program, check the box. Mark will do everything else. Hey, while you're on the website, check out all of our content that lives there. Some of it is paid, some of it is free. And you'll see it. We've got all sorts of fun stuff. The free stuff that I love, the weekly newsletter that Mark puts together every Friday. It is super so awesome. So if you were a newsletter subscriber, you'd get your version today. Isn't that awesome? So Mark does such a good job with that. Check it out. All right. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. It is Friday, so we're going to do some business. Our music is composed by the wonderful Joel Goodman. Mark Teo is the best executive producer and king of all things web. We're distributed by the fine folks at Odyssey. Try to do something nice for someone else today. Change your work, change your wealth, change your life. Thanks for listening and we'll talk to you on Monday.

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[Nancy Cartwright]

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 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.