Retirement After 25 Years, What’s Next?

Summary

---

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: "Retirement After 25 Years, What’s Next?"
Date: August 21, 2025
Host: Jill Schlesinger
Guest/Caller: Giovanna from Florida

---

Main Theme

Jill Schlesinger speaks with Giovanna, a listener preparing to retire after a 25-year career. The conversation focuses on the emotional and financial logistics of retiring slightly early, how to strategically access savings, and considerations for sustainable post-retirement living. The main goal: evaluating whether Giovanna is financially set for retirement and how she should manage her assets and spending to ensure long-term security and satisfaction.

---

Key Discussion Points & Insights

1. Introduction to Giovanna’s Situation

• Giovanna is choosing to retire at nearly 61, a few years before her required retirement date.
• She is single but has a partner—important because finances are not combined.
• Key question: Is she ready (financially and emotionally) for this next chapter?

2. Giovanna's Financial Snapshot (04:22–05:32)

• 401(k)—Pre-Tax: $1.175 million
• Brokerage Account: $520,000
• Schwab Fund: $235,000
• HSA: $36,000
• IRA: $19,500
• High-Yield Savings: $50,000
• Checking Account: $30,000
• I Bonds & Company Stock: Approx. $2,500
• Home: Owned outright in Florida, valued between $350K–$500K
• No mortgage
• "That’s amazing. Is that all pre tax?" — Jill (04:41)

3. Expenses and Health Insurance (05:48–06:39)

• Estimated Annual Net Spending: $6,000/month (excluding taxes, including anticipated health insurance expenses)
• Health insurance is factored in at about $10,000/year
• Plans to potentially leverage lower-cost health care by living in Europe part-time

4. Partner and Living Arrangements (06:46–07:02)

• Giovanna covers all personal expenses herself; partner's finances remain separate
• Notably, $6,000/month figure is only for Giovanna (clarified at 06:59)

5. Post-Career Work and Social Security (07:18–07:53)

• No solid plans for part-time/consulting work
• Possible to return to career on a less full-time basis, but not ideal
• Social Security expected: Approx. $2,400/month

6. Real Estate & Rental Income Options (08:11–10:28)

• Giovanna’s home in a desirable Florida location could be rented seasonally
• Potential Rental Income: Up to $8,000/month in high season, or comfortably at $4,500/month
• Rental income could be a significant boost to retirement plan if needed

7. Strategic Withdrawal Plan (11:21–12:17)

• Jill’s Advice: Begin withdrawing from the 401(k) first, around $60,000/year
• Leverage lower tax bracket post-retirement; income drops from $250K/year to withdrawals
• “Instead of paying 32% in taxes, you pay 22%… That’s pretty nice.” — Jill (12:18)
• Coordination with Social Security at 67 to then reduce 401(k) withdrawals

8. Emotional Reflection and Transition (10:55–11:21)

• Giovanna acknowledges pride in her career, readiness to let go, and positivity about the transition
• Jill comments:
  “Usually people are holding on by…the old poster…that cat…‘hang in there’…You sound very upbeat about it.” (11:00)

---

Notable Quotes & Memorable Moments

• On Retiring Early:

  “I am choosing to leave a few years earlier than my required retirement date.”
  — Giovanna (03:39)

• On Savings:

  “401K as of today has 1.175.”
  — Giovanna (04:37)
  “That’s amazing. Is that all pre tax?”
  — Jill (04:41)

• On Expenses:

  “I spend six grand a month net to you, right?”
  — Jill (06:16)

• On Housing Flexibility:

  “I live in a beach community, so I could always…take some income from it.”
  — Giovanna (08:11)

• On Letting Go:

  “I worked pretty hard to get there, but it’s time for someone else to take my position.”
  — Giovanna (10:55)

• On Strategic Withdrawal:

  “You would take from your 401k a little bit at a time…you’ll be in a low tax bracket, so it’ll be easy.”
  — Jill (11:23)
  “If you took 60 grand a year out…instead of paying 32% in taxes, you pay 22% in taxes. That’s pretty nice.”
  — Jill (12:18)

---

Important Timestamps

• Giovanna’s career and reason for leaving: 03:19–03:45
• Full asset breakdown: 04:22–05:32
• Expense and budgeting overview: 06:03–06:39
• Plans for Social Security and rental income: 07:43–08:28
• Rental income feasibility: 10:05–10:28
• Withdrawal and tax planning advice: 11:21–12:18

---

Overall Tone & Takeaways

Jill maintains her signature blend of empathy, wit, and practical frankness, giving clear, jargon-free advice while also offering emotional support. Giovanna is both thorough and positive about her transition, showing careful preparation and an openness to new experiences and flexibility in retirement. The episode is a case study in how detailed preparation allows for an empowering, confident approach to major life changes.

“All right. Very exciting. I’m excited. Send us a picture from wherever you land in those three months! It’s very cool.”
— Jill (12:27)

---

Final Thoughts

If you’re contemplating retirement and unsure about your readiness, this episode breaks down the process—from calculating basic expenses, assets, and expected income, to thinking creatively about generating extra cash from existing resources like your home. Jill’s advice: Plan your cash flow, know your taxes, and ensure emotional as well as financial preparedness for the big transition.

---

Transcript

[Jill]

Hey gang. You know, it's one thing when I'm at work and there are professionals doing my makeup, but when I'm home, I want something different. I want simplicity. Merit is a minimalist beauty brand created to streamline your routine with clean, high performing products that are impossible to mess up. Merit is designed for people who want to look polished without spending hours in front of the mirror. Merit makes beauty feel effortless. Merit's products are clean, vegan, cruelty free, and made with skin care ingredients that support your skin long after your makeup comes off. In fact, Merit makes it easy to get ready in five minutes or less. That's right up my alley. There are curated sets and essentials that fit seamlessly into any lifestyle. Are you ready to simplify your routine? Head to meritbeauty.com and get their signature makeup bag free with your first order. That's meritbeauty.com need contract help for those workload peaks and backlog projects? You're not alone. Robert half found that 67% of companies surveyed said they will increase their use of contract talent. That's why their recruiters leverage their experience and use award winning AI to quickly find the skilled candidates you want. Learn about their specialized talent in finance, accounting, technology, marketing, legal and administrative support at Robert Half. They Know Talent. Visit roberthalf.com talent today welcome to the Jill on Money Show. It's Thursday, August 21st and we are here trying to help you figure out what comes next in your financial life. And for each of you, that means something different. So to get a little bit of a customization, you should 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 live, just check the box. Mark will do everything else. While you're on the website you can check out all of the great content that lives there. Our free weekly newsletter. You can check out the other podcast called Money Watch and the radio show and videos and resources all there for you. And also we have a subscription service. It's called Jill on Money live free for 45 bucks. For the next 12 months you'll get four quarterly live webinars, the entire back catalog of those webinars, as well as bonus audio and video content. Our next webinar is going to be focused on estate planning. And you know what we're going to do? We're going to have a shrink join us. And we're doing that in September, on September 10th. And I think it's going to be very enriching for people. I really think this is one of those things that people forget to do or put off. And we, we're going to get you off your little moment of I don't know what to do and who do I want to leave my money to? And we're going to help you get to that other level. And remember, you can only join us live if you are a member of the subscription service. Okay, that is enough about us. Today we are joined by Giovanna who is on the line from Florida. Hello there. How are you? What can we do for you?

[Giovanna]

I'm fine, thank you very much for asking.

[Jill]

What's going on?

[Giovanna]

I'm getting ready to leave a career that I've had for almost 25 years and I'm not quite sure what to do.

[Jill]

Really. What is the reason that you're going to be leaving that career?

[Giovanna]

I think it's been long enough.

[Jill]

In other words, it's your decision, not someone is not. No one is deciding for you. You're not letting go?

[Giovanna]

No, no, no. I am. I am choosing to leave a few years earlier than I required retirement date.

[Jill]

Okay, and how old are you, Giovanna?

[Giovanna]

I'm 60, almost 61.

[Jill]

Okay, 60, almost 61. And will you be entitled to any pension when you do this? No. Okay. It's okay. Are you married, single, partnered?

[Giovanna]

I'm single, but partnered, I guess.

[Jill]

Okay, how will do you guys combine your money or not? No. Okay, so we're going to forget about that person. So, so congratulations that you have a partner, but we have no access to their money, so we don't really care. How have you saved your money over these 25 years? Tell us a little bit about that.

[Giovanna]

I have saved most of my money in a 401k. I have a brokerage and I have some like extra stocks and T bills or I bills, I guess, and just I bonds, I bonds.

[Jill]

How much is in the 401k?

[Giovanna]

401K as of today has 1.175.

[Jill]

Okay, $1.175 million. That's amazing. Is that all pre tax? Is it traditional? Okay, all pre tax. How much is in the brokerage account?

[Giovanna]

520.

[Jill]

Okay. And you said you've got some stocks, some other stuff on the side.

[Giovanna]

I have a Schwab account that has 235 that's in some type of a fund and I have an HSA for 36,000, an IRA, a regular IRA for 19.5. Savings of just 50k is in a high yield savings account. And then 30,000 is in a checking account.

[Jill]

Great.

[Giovanna]

And then I have an I, bonds and, and some company stock which is worth about $2,500.

[Jill]

Okay. Do you own your home?

[Giovanna]

Yes.

[Jill]

How much would you say it's worth?

[Giovanna]

I live in Florida, so it's whatever somebody wants to pay that day.

[Jill]

Give me a guess.

[Giovanna]

350 to 500.

[Jill]

Okay. And do you have a mortgage?

[Giovanna]

Nope.

[Jill]

Okay. And when you look at your spending right now, even if you and your partner go away and do your stuff, but like what your share of spending on a monthly basis. Do you have an idea about what that is?

[Giovanna]

Well, we did it on an annual basis. I think it's 6,000. And that's. We added everything we could possibly think of to put in there.

[Jill]

6,000Amonth.

[Giovanna]

But I did not do taxes. Like real income taxes.

[Jill]

Yeah, yeah, but you're saying I need. I spend six grand a month net to you, right?

[Giovanna]

Yes.

[Jill]

Okay, got it. What will you do for health insurance after 25 years?

[Giovanna]

Well, I put in money in my account to buy it, in my taxes to buy it.

[Jill]

Okay.

[Giovanna]

So I thought it would cost about $10,000 a year.

[Jill]

Okay. And is that included in that six grand a month expense number?

[Giovanna]

Yes.

[Jill]

Oh, great. Okay, fine.

[Giovanna]

Or I can move to Europe.

[Jill]

Okay, well, I'm all in on that.

[Giovanna]

At least for six months out of the year.

[Jill]

The 6,000. The 6,000amonth. Is that just you or both you guys combined?

[Giovanna]

Ish me. Ish both of us combined. So.

[Jill]

So you're not on the hook for the full six grand. You're not on the hook for it by yourself then?

[Giovanna]

Yes, I am.

[Jill]

Oh, you are.

[Giovanna]

Okay, that's what I'm working from.

[Jill]

Okay, that's fine. That's totally fine. And will you have, I mean, after the 25 years and doing this career that you love or liked or whatever you have around that. Is there any part time work that we should count on in your future?

[Giovanna]

I can return to my career after I'm going to be on a little bit of medical leave. I can return if I wish, but it's not something that's a very part time able. I can lessen my hours, but it requires a pretty full commitment.

[Jill]

All right, and so you're pulling the plug like at the end of this year or like at the end of this month? Just out of curiosity.

[Giovanna]

Tomorrow.

[Jill]

Tomorrow. Here we go. We're done. You will be entitled to Social Security, right?

[Giovanna]

Yes. And I forgot to look that up. I think it was like 2400 or something.

[Jill]

Okay. That's great. So that's a part of it, right? No plan to sell your house or anything you're gonna, or the 350-500,000 dollar dwelling, does that stay intact? Should we just presume that you have some or do you want to sell it and, and really move to Europe and like do something different?

[Giovanna]

No, I assume that I would just rent it. I live in a beach community, so I could always have something, take some income from it.

[Jill]

Oh, okay. Should we count on that or do you want to just kind of run some numbers without that?

[Giovanna]

Without it that I might need to. Once you do your numbers.

[Jill]

All right. All right, so let's, let's say that, okay, you've got this 401k which you know you can access, right. So if we have that 401k and we start pulling some money out right. Right now, then we have to do that until you're age 67. And then you'd have to pull a little bit more money out, obviously. I mean a little bit less money out because you'll have your Social Security and you know, you have saved a bunch of money. You know, the, the, let's see, 7, about 750 between the stocks and the brokerage account, 1.175. There's some savings, a little IRA. It would be great. I'm going to give you like you, your. As if I were your sister. Right. I would say this is a great idea, but I hesitate to, to mention the fact that if you are carrying the 6,000amonth and that really is just all you, and yet you're covering your boyfriend, girlfriend, whoever, person, partner. I would also say, like, if that number starts to swell up, this is not going to work very well. And if the person has the ability to contribute, that would work a lot better.

[Giovanna]

Okay, Makes sense, right? Yeah.

[Jill]

Okay. I think this is interesting. The other idea is that like when I think about having the house, when you look at rental income that, let's say at the end of this year, you're done and then you, or whatever you, and you rent your condo out. Paint me a picture of what life looks like when you do that. Do you, do you say, okay, I live in Florida, so I have to do it for, for the winter months. So how much money do you think you could get from renting it out for the winter months?

[Giovanna]

I rented it for $8,000 a month.

[Jill]

That makes it so much better.

[Giovanna]

But that's only, you know, it doesn't mean I'd do it every month for 8,000 no, no, no, no.

[Jill]

But I'm just saying, like. Like, is that usually like January, February, March?

[Giovanna]

So I could. If I. I figure that if I had it for $4,500 a month, I would be fine.

[Jill]

Yeah. I mean, listen, any money like that rental income will really make this work, especially before you collect Social Security. So if you're willing to do that and, you know, leave your. Your beautiful, like, Florida existence for those months and collect that money and figure out someplace else to go that's cheaper, then it really does work a lot better. Are you feeling, like, nostalgic about your 25 years in your career?

[Giovanna]

Yeah, I mean, I worked pretty hard to get there, but it's time for someone else to take my position.

[Jill]

What a. What a kind thing to say. Actually, that's very nice. Usually people are holding on by the, you know, clawing their way and holding on as they're, you know, like, they look like that cat that used to be that old poster. You'll remember this because you're my age, where it would say, hang in there. That's kind of what most people feel like at the end of their careers. You sound very upbeat about it.

[Giovanna]

One question. Where do you start taking the money from?

[Jill]

First, I think that for you, you would take from your 401k a little bit at a time, because that is money that you're going to have to take out 15 years in the future, and you might as well start getting some of the money out right now. And you'll be in a low tax bracket, so it'll be easy.

[Giovanna]

All right.

[Jill]

You know, you'll be in a. You'll be. How much were you earning at? Like, you know, as of now, like, what's the. What's your tax. What's your taxable income right now?

[Giovanna]

Probably around 250.

[Jill]

Yeah, you'll be in a little single bracket. Yeah. But it, you know, if you're single in 250, that means a lot of your money is being taxed at 32%. Like, it'll be pretty nice and sweet for you. You're going to be like, oh, I'm gonna pull. Let's say you pulled. Let's say you took 50. Or let's say you took 60 grand a year out of your 401k. Right. That hasn't been taxed yet. That would mean that you, instead of paying 32% in taxes, you pay 22% in taxes. That's pretty nice.

[Giovanna]

That would make a big difference.

[Jill]

Right. So I think you pull from that 401k. Like 60 grand a year is what I'm thinking. Thank you. My, my. Maybe even. Okay.

[Giovanna]

I like having roads.

[Jill]

All right. It sounds good. It sounds good. All right. Very exciting. I'm excited. Send us a picture from wherever you land in those three months. It's very cool. All right. Thanks for joining us. Hey, if you are looking, if you're done, if you're ready to call it quits and you're looking for your off ramp, give us a Holler. Go to jillonmoney.com, click the contact Us button. Let us know if you want to come on the air by checking the box. Don't forget, by the way, we talk a lot about people who are slowing down. If you're just starting out in your career, we want to hear from you too. I don't want it to just be this is not a retirement show, it's a money show. So whatever it is you want to do, we want to be there for you. So just go to jillonmoney.com, click the contact us button and we would be so happy to help you out. Ah, so good, Mark. So fabulous. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen. And of course we ask that you lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

[Narrator]

You say you'll never join the Navy, that living on a submarine would be too hard.

[Giovanna]

You.

[Narrator]

You'd never power a whole ship with nuclear energy, never bring a patient back to life or play the national anthem for a sold out crowd. Joining the Navy sounds crazy. Saying never actually is. Start your [e-mail] America's Navy forged by the Sea Every week on the Moth podcast we hear from incredible people who have found their own voice.

[Giovanna]

There's this little bit of wisdom people say all the time, you know, that you should live in the moment. Let me tell you something. There is nothing worse than being forced to live in the moment.

[Narrator]

The Moth podcast features real people telling their stories live on stage to connect and learn from them. Follow and listen to the Moth on the Free Odyssey app or wherever you get your podcasts.