59 and Considering Retirement

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: 59 and Considering Retirement
Date: September 3, 2025
Host: Jill Schlesinger, CFP®
Guest: Roger from New Jersey (listener call-in)

---

Episode Overview

This episode centers on a candid conversation about retirement planning as Jill Schlesinger takes a listener call from Roger, a 59-year-old considering early retirement. Roger and his wife have saved diligently but are navigating uncertainties common to pre-retirees: Is it really “enough”? What about the years before Social Security and pensions kick in? What about finding meaning—and income—after a primary career? Jill walks Roger through the numbers, addresses emotional and practical concerns, and offers her trademark blend of humor, realism, and actionable advice.

---

Key Discussion Points

1. Roger’s Current Financial Picture

• Age: Roger is 59; his wife is 55.
• Employment: Both work; Roger earns ~$90,000, his wife earns ~$102,000 (New Jersey Board of Ed).
• Savings:
  • Roger’s 401(k): $1.76 million (pre-tax) (03:11)
  • Wife’s 403(b): ~$5,000 (started late)
  • Wife’s IRA: ~$16,000
  • Non-retirement brokerage: $66,000 (stocks, some withdrawn for daughter's wedding)
  • Emergency fund: $50,000 (cash in bank)
• Home: Estimated value $500,000; mortgage $250,000 (04:23)
• Projected Pensions / Social Security:
  • Wife: NJ Board of Ed pension eligible at 60, estimate provided by Jill: ~$60,000/year (based on a $102,000 salary and 25 years service) (02:57)
  • Social Security: Both expect ~$3,000/month each at full retirement age (04:38 & 04:49)

2. Retirement Income vs. Expenses

• Estimated Monthly Need: Slightly over $10,000 (05:02)
• Big Picture:
  • When both are receiving Social Security and her pension, income will meet/exceed expenses.
  • The challenge is bridging the income gap in the years between Roger’s retirement and when both streams kick in.

3. Timing and Readiness for Retirement

• Roger’s Plan: Wishes to retire “as soon as I turn 59 1/2” (six months away) (05:38)
• Financial Advisor Input: Roger met with an advisor who said they are "104% ready" to retire—but Jill pushes deeper, questioning if it’s truly comfortable without supplemental income in the interim (06:08)

Notable Quote

“If you could get 50 grand a year out of your 401k, 50 turns into, let's call it 38 or something. Right? Because that's going to be your tax situation... and maybe you sell the stock account out, but, you know, I still have a gap between today and when you can collect Social Security and that's what I'm trying to fill.”
— Jill Schlesinger (07:11–07:50)

4. Emotional & Lifestyle Considerations

• Mental Health & Satisfaction:
  • Roger dislikes his current job (“Do I hate my job? Yeah, I do … I absolutely hate being at home nonstop") (07:50–08:10)
  • Witnessing aging parents prompts him to value time over money:

    “I only have like 20 more years to run ... is it worth it? Why retire at 67, 65?... They (coworkers) just sound miserable. And I’m like, I want to be doing this job when I’m 70, so…”
    (08:24–08:47)

5. The Value of Semi-Retirement and Part-Time Work

• Alternative to Full Stop: Jill proposes that Roger might bridge the financial and personal gap with “fun and silly and stress-free” part-time work after leaving his current career (08:47–09:26)
• Benefits:
  • Supplement income, reducing withdrawals from retirement accounts.
  • Support emotional well-being and transition.

Notable Quote

“Could you do like something to make a few shekels every month?... if you could essentially ... make two or three grand a month... it works. And the less money you tap out of the 401k, the better.”
— Jill Schlesinger (08:47–09:14)

6. Planning For the Unknown and the Importance of Confidence

• Need for Reassurance: Despite solid numbers, Roger wants a “second opinion.” Jill notes this is very normal, especially because the stakes are so high (10:50)
• Estate Planning: In progress—Roger and his wife are updating wills and powers of attorney (11:46)

Notable Quote

“What I do want to be clear about is you're close enough that there was something inside you that wanted to actually talk it through.”
— Jill Schlesinger (10:50)

7. On DIY vs. Professional Financial Advice

• Roger’s Attitude: He tracks his own finances in a spreadsheet, manages his investments, and feels comfortable doing so.
• Jill’s Caution:
  • Don’t pay a pro for services (like basic investment selection) you can handle yourself.
  • Ensure any advisor provides real value—especially if you’re already detail- and fee-oriented (11:33–11:46)

---

Memorable Moments & Quotes with Timestamps

• (02:21) Jill on the “Younger Wife” Stereotype:
  “Well, she's not young enough to really make a big difference.”
• (07:50) Roger on Hating His Job:
  “Do I hate my job? Yeah, I do. I stopped traveling because I hated flying ... and now I’m finding out I absolutely hate being at home.”
• (08:35) On Not Wanting to Work Forever:
  “Why retire at 67, 65? ... They just sound miserable. And I'm like, I want to be doing this job when I'm 70, so...”
• (10:50) Jill on Seeking Reassurance:
  “What I do want to be clear about is you're close enough that there was something inside you that wanted to actually talk it through.”
• (11:46) On Estate Planning:
  “We're going to drop it off today, get our will updated and our power of attorney and our living will.”

---

Key Takeaways & Actionable Advice

• Retirement Readiness Is About More Than Numbers

  • Consider cash-flow timing: especially the pre-Social Security, pre-pension window.
  • Emotional satisfaction and peace of mind matter as much as what a calculator says.

• Bridging the Income Gap

  • Use a mix of partial withdrawals, non-retirement assets, and consider fun or less stressful part-time work to supplement income and reduce the draw on savings early on.

• DIY is Fine—If You’re Actually Comfortable

  • Don’t pay for professional management if you have the skills and interest to manage your own finances.
  • Do pay for specific guidance or planning if you encounter complexities or nagging doubts.

• Estate Planning Is Essential in Retirement Planning

  • Make sure wills, powers of attorney, and health directives are up to date.

---

Timestamps for Major Segments

• [01:53] Roger introduces his retirement scenario
• [03:09] Jill gets specific on retirement balances and assets
• [05:05] Discussion on income, expenses, and retirement feasibility
• [07:50] Roger expresses dissatisfaction with work
• [08:47] Jill suggests semi-retirement as a solution
• [10:50] Jill emphasizes need for emotional reassurance in decisions
• [11:46] Estate planning update

---

This summary distills the essence of the conversation while preserving the thoughtful, slightly irreverent, and practical tone of Jill Schlesinger’s advice. It covers both the technical and emotional sides of retirement decision-making, highlighting the most relevant questions, advice, and wisdom for anyone considering a similar leap.

Transcript

[A]

Need contract help for those workload peaks and backlog projects.

[B]

You're not alone.

[A]

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.

[B]

Hi, I'm Kristen Bell and if you know my husband Dax, then you also know he loves shopping for a car. Selling a car, not so much.

[C]

We're really doing this, huh?

[B]

Thankfully, Carvana makes it easy. Answer a few questions, put in your van or license and done. We sold ours in minutes this morning and they'll come pick it up and pay us this afternoon.

[C]

Bye bye Truckee.

[B]

Of course, we kept the favorite.

[A]

Hello other Truckee.

[B]

Sell your car with Carvana today. Terms and conditions apply.

[A]

Welcome to the Jill on Money show. It's Wednesday, September 3rd and we are here trying to provide you with unconventional and dare I say, entertaining insights on your money and your life. To do that, we ask that you do a little bit of work. Just go to our website, jillonmoney.com, click the contact us button and of course let us know if you'd like to come on the air by checking the box marked as everything else. Or while you're on the website, check out all the content that lives there. I especially have been excited about the free weekly newsletter which is now basically a substack subscription. So if you're on substack, just search for Jill on Money and you'll get the newsletter as well as the things that I write throughout the week. So check that out. Right now we're going to talk to Roger from New Jersey. Hello, Roger. How can we help you out today?

[C]

I'm looking at retiring. I'm 59 and I've done gap analysis couple of different places and the gap analysis says I can retire with what I've, what I've saved in my 401k. My wife and I both work. She has a pension but she's, she's younger than I am so she won't be.

[A]

So that was smart. So a younger wife? Yeah, yeah. How old is she?

[C]

55.

[A]

Well, she's not young enough to really make a big difference. When is her pension? Tell me, tell me some of the.

[C]

Details of her pension through the New Jersey Board of Ed. She can start collecting in like five more years.

[A]

So she would collect a pension at age 60 of how much?

[C]

That is a good, good clue. I don't know. A good question. Pensions, they have a formula based off your highest three years and.

[A]

But we don't know how much that is. Like how much does she earn right now?

[C]

About 102,000.

[A]

And how many years will she have in the system?

[C]

25 years.

[A]

I'm going to make it up. All right. I'm going to say it's 60 grand. How much do you earn, Roger?

[C]

About 90,000.

[A]

Will you be entitled to a pension?

[C]

No, mine's strictly a 401k.

[A]

How much money is in your 401k right now?

[C]

1.76 million.

[A]

Is it pre tax or is it post tax? This 401k?

[C]

Pre tax, yeah.

[A]

Okay. Does your wife also contribute to a retirement account? In addition to the whole pension, does she have either a 403 or some other savings plan? A 457 plan?

[C]

A 403, which we just started late. We didn't realize. The information we had early on wasn't clear. They didn't clarify. So we just started 403 like two years ago. There's minimal of about 5,000 in there.

[A]

Okay.

[C]

She also has a rollover IRA, that's about 16,000.

[A]

And do you have money outside of retirement that's invested?

[C]

I have some stocks that I've been trading. We also took some money out. My daughter got married, so we took some money out to pay for the wedding.

[A]

How much money is left in the, in the stock account right now?

[C]

66,000.

[A]

How about money that's like emergency reserve cash? Money markets, like non retirement? I mean, just the, just the, like what you could get your hands on quickly.

[C]

Right now, bank account is about 50,000.

[A]

Tell us about your house.

[C]

If you go on Zillow, it's worth 500,000 for this market and we owe 250,000.

[A]

Let's talk about Social Security. Will you and your wife both be eligible for Social Security?

[C]

Yes, my pia at age 67 is about 3,000. A little over 3,000 at age 67.

[A]

Okay. And what about your wife's?

[C]

I think it's about the same.

[A]

So it's really, it's kind of cool because probably. How much do you guys spend in. I mean, I presume you're both putting money away and doing all that, but what are your expenses? What do you think your need is for retirement?

[C]

It's about 10,000. A little over 10,000amonth.

[A]

So presumably when you're 72 and 70, you know, 73 and she's 67 and you're both collecting three grand a month for your Social Security, plus her pension, which is probably gonna be another five grand. A pretty darn close. Like that's when life is good for you guys, when you're both collecting Social Security and she's collecting her pension.

[C]

Right, right, right.

[A]

So what's the game plan if you were to retire? Like, and, and are we talking like when for you? You're 59, you're young. So how, when do you think you'd like to retire?

[C]

When I turn 59 and a half and.

[A]

Oh, geez. Okay, I got six months to go. All right, so what's, what is our game plan to get you through the next bunch of years? So you said your wife is 55 now, is that right?

[C]

Correct.

[A]

Okay, so she's 55, so she's going to work for another. If you retired right now. Right. Could you guys. And let's say she stopped putting money into retirement, could you guys live on her 102ish? Or you'd have to spend some of the cash.

[C]

No, no. Yeah, we, we, we talked to a financial advisor yesterday and he's like, wow, you're good. You're like 104% ready. So we're way above the curve. Well, no, I need to pay my bills. She doesn't have enough coming in to pay the 10,000.

[A]

And so what was your game plan to do that? Sell your stocks out in the non qualified account and use that for a year. And then what?

[C]

Well, yeah, that's why we're, we're talking to you, Joe, and financial advisors and like, you know, we don't know what.

[A]

I guess that you are looking at. And I'm thinking that when you said you looked at modeling, is that you're looking at. If I pulled 4 grand a month out of my 401k, I would pay tax on that. And then that would float a lot of the money that I need so that money would be available to help finance my share of the expenses. I mean, do you hate what you do? This is a question I ask people all the time. Because I don't want to be a pain in the ass about this. I am not clear that this works so great as everyone else seems to be. If you could get 50 grand a year out of your 401k, 50 turns into, let's call it 38 or something. Right? Because that's going to be your tax situation. Let's just call it 36. You get three grand a month essentially after tax out of your 401k. You know, that doesn't exactly give you what you need, but it's close. Ish. And maybe you sell the stock account out, but, you know, I still have a gap between today and when you can collect Social Security and that's what I'm trying to fill.

[C]

Yeah, exactly. And do I hate my job? Yeah, I do. I stopped traveling because I hated flying and I was home only for 48 hours. So I switched my jobs to be home more. And now I'm finding out I absolutely hate being at home, you know, non stop. You never leave, so. And then my father just passed away last year at 86. And I see my mom, she's getting older and. And I'm just like, wait a minute, I only have like 20 more years to run, you know, so.

[A]

Yeah.

[C]

Was it worth, you know, if I could retire at. Why, why retire at 67, 65. There's a lot of people on the team that are, they're old, they're. They're like 67. One people, one person, like 70. I'm like. And they just sound miserable. And I'm like, I want to be doing this job when I'm 70, so.

[A]

All right, let me ask you another question. Forget about that job. Could you do like something to make a few shekels every month?

[C]

Oh, yeah, yeah. No, you know, we talked about part time.

[A]

Yeah, that's what I'm thinking. Like it. Could you go and do. I don't know what you like to do, but if you could, if you could essentially like you quit when you're 59 and a half, right? She stops putting money into her 403B, just stops. Forget it, you're done. You gotta like stockpile some money, right? You are gonna now start pulling money out of your 401k and you're gonna take 3% in a given year. Let's call it out. You're going to pay the tax that's due and then to fund the difference, you're going to get some job that's kind of like fun and silly and stress free and you know, whatever. You're going to make two or three grand a month, if that. Okay, then it works. And the less money that you tap out of the 401k, the better. It is true that people die when they're 75 and it sucks. But statistically you live until you're 90, man. Or maybe 95, and that's a long time to have money last again. Do I think you could totally do this? You probably could. You want to make Yourself feel better because I hear you're, you know, there's no reason you're coming to us and asking our opinion if you felt 100% sure about the numbers. So if you're looking for the maybe the middle scenario is do a little part time work, figure out what it is you want to do, have some fun. You got five years before she's going to retire. If you can refrain from pulling money out of your retirement account, it's great. That's it. And I wouldn't go crazy. Do you have kids? Do you have grown kids?

[C]

Yeah, the two are in the army. One is married.

[A]

Wow.

[C]

Three kids.

[A]

And they're okay financially or do you think you're going to have to help them out?

[C]

Oh, no. Yeah, My daughter's a teacher. She's doing excellent. They live in Pennsylvania. And my other two are getting paid by the army. Army pays their officers in the army, so paid a good salary, so they're fine.

[A]

What I do want to be clear about is you're close enough that there was something inside you that wanted to actually talk it through. And when you're investing in either a financial planner or a retirement planning firm, you know, I want to know what you're going to get for your money. You're very, you are very good feel for these numbers. It does not seem like you are fooling yourself. Do you like to manage your own money?

[C]

Oh, yeah. I mean, I keep a spreadsheet. What goes in, what goes out, it significantly helps. And the financial advisor yesterday wants us to use their, their platform, put money over here. I'm like, well, dividend stocks, that's no big deal. I can pick dividends.

[A]

Right? That's what I'm saying. Like I'm not sure I'd go and pay for that service given the fact that you're sounding and you seem quite comfortable with your own ability to analyze and execute. Do you have your estate planning done?

[C]

That's what we're in the process of doing now and we just finished it. We're going to drop it off today, get our will updated and our power attorney and our living will.

[A]

Perfect. If you'd like to join us to talk about something going on in your financial life, it's very easy. All you need to do is go to our website, jillonmoney.com, click the contact us button, write us that note. And if you want to join us live, check the box. Mark does everything else. You can subscribe to us on the Audacy app or wherever you find your favorite podcasts. Please leave a rating and review wherever you listen. And of course try to lift someone up. Change your work, Change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.

[B]

Starting your own business can be intimidating. Suddenly you're wearing all the hats. Designer marketer, customer support, Shipping expert. It's a lot. That's where Shopify comes in. Shopify is the global commerce platform powering millions of businesses around the world and 10% of all e commerce in the US Shopify has your back. With hundreds of ready to use templates, you can launch a beautiful professional online store that looks and feels like you need content. Shopify's AI tools can help you write product descriptions, headlines, even enhance your product photos. Want to grow your reach easily? Create email and social media campaigns to meet your audience wherever they're scrolling. And with Shopify's world class support, you'll have expert help for everything. Turn your big business idea into With Shopify on your side, sign up for your $1 per month trial and start selling today at shopify.com OdysseyPodcast go to shopify.com OdysseyPodcast shopify.com OdysseyPodcast.