Seeking Financial Flexibility

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: Seeking Financial Flexibility
Date: December 9, 2025
Host: Jill Schlesinger, CFP® (with producer Mark)
Guest Caller: Lynn from Alaska

---

Overview of the Episode

This episode centers on a caller, Lynn, who is navigating mid-career financial planning and seeking strategies to gain flexibility and security as she and her husband approach retirement. Jill and Mark guide Lynn through issues surrounding pensions, Social Security (including the Windfall Elimination Provision), retirement savings, and the psychological/emotional trade-offs between financial goals and job satisfaction. The advice is practical, candid, and focused on real life circumstances, offering insights for listeners with similar questions about seeking flexibility before full retirement.

---

Key Discussion Points & Insights

1. Lynn’s Financial Snapshot

[03:42 – 04:41]

• Lynn (54) and her husband (52) both work full-time; children are grown.
• Husband will receive a defined benefit pension (PERS) of approx. $4,300/month at age 60.
• Lynn earns $75,000/year, husband earns $102,000/year.
• All kids are grown and independent.

2. The Retirement Metamorphosis and Desire for Flexibility

[03:42 – 04:01]

• Lynn’s goal is not a traditional “beach” retirement but having the financial flexibility to make other life decisions and possibly embark on a “next endeavor.”
• She wants the option to downshift or make employment changes without jeopardizing long-term security:

  “I’m starting to have a little bit of a metamorphosis when it comes to planning for retirement... to allow us some financial flexibility to make other decisions, a little next endeavor, a little look ahead.” – Lynn [03:42]

3. Understanding the Windfall Elimination Provision (WEP)

[05:39 – 07:59]

• Lynn is concerned about how WEP will impact her Social Security benefits, given much of her career is in higher ed (not covered by Social Security) and only 18 years with substantial SS-qualifying earnings.

• Mark explains she qualifies for SS with 10 years, but reduction under WEP depends on “substantial earnings” years.

• Jill clarifies:

  “When they calculate the amount... the windfall elimination, as it’s written right now, appears to apply either way. So regardless of what earnings record it goes against, you’re still going to get knocked down.” – Lynn [07:46]

• Lynn contemplates working more qualifying years to lessen the hit by changing the WEP reduction from ~40% (current) closer to 20%. She’s considering whether she should change jobs, stay in her field, or “crank” up SS-qualifying earnings:

  “I've got, you know, some working years left and I could work a few more years to have enough substantial earnings to change that percentage...” – Lynn [07:19]

4. Balancing Job Satisfaction vs. Maximizing Benefits

[08:00 – 08:15]

• Mark asks if Lynn enjoys her job. She responds:

  “I don't necessarily like the industry I'm in, but I like the type of work that I do... I just don't know that where I'm at is maybe the best fit.” – Lynn [08:05]

• Jill and Mark suggest not to endure an unsatisfactory job solely for maximum SS benefits, especially if it diminishes quality of life or mental health.

5. Current Savings, Debt, and Spending Needs

[08:51 – 10:39]

• Assets: $1,000,000+ in retirement savings (primarily pre-tax), $40,000 in Roth, $35,000 emergency fund.
• Debt: $275,000 mortgage on $525,000 house.
• No brokerage account.
• Annual living needs in retirement estimated at $100,000 (including taxes).
• Mark and Jill stress the importance of considering access to non-retirement (already taxed) money for greater flexibility:

  "We're going to need to have access to more money for you guys that has already been taxed... maybe to use instead of putting all that money into retirement." – Mark [13:07]

6. Evaluating Retirement Timeline & Income Gaps

[10:14 – 16:30]

• Husband’s pension ($4,300/mo) and Social Security (approx. $3,000/mo) will eventually suffice, but there’s a gap from ages 60-67 (pre-full SS).

• Lynn wants to have the option to make career changes within five years, possibly reducing income.

• Jill and Mark recommend:

  • Avoid focusing on paying off the mortgage early; prioritize cash flexibility and retirement savings.
  • Plan to work longer, perhaps in lower-stress, part-time, or more enjoyable roles, to reduce pressure on retirement assets during the crucial pre-SS years.
  • The later they can start tapping into retirement accounts, the stronger their overall plan will be.

• Memorable quote:

  “Even if you had to make a little bit less money for you as you make this shift, I'd be okay with that. As long as you're happier. Because if it meant that you could stay beyond five years, maybe it's seven years...” — Mark [15:20]

7. Job Change Considerations

[16:30 – 17:16]

• Lynn floats the idea of moving to a job with a defined benefit plan.

• Jill and Mark caution against putting the retirement plan ahead of job satisfaction:

  “Don’t go for the retirement plan or this plan or that. Get a job you like, because you are so lucky that…he’s got this defined benefit plan. You need to find something you like, actually want to be engaged with.” – Mark [16:53]

• The true driver should be finding “something where you feel like it’s... actually want to be engaged with. It matters less to me about what type of retirement plan you have.” – Mark [17:02]

8. Final Takeaways

[17:16 – 17:19]

• With current assets, future pension, and Social Security (even with WEP), Lynn and her husband are well positioned if they continue to work (albeit less or differently) through their early 60s.
• The focus should be on maximizing flexibility, maintaining happiness, and protecting against early depletion of assets by not making a sudden jump into retirement.

---

Notable Quotes & Timestamps

• “I’m starting to have a little bit of a metamorphosis when it comes to planning for retirement... to allow us some financial flexibility...”
  – Lynn [03:42]

• “When they calculate the amount... the windfall elimination, as it’s written right now, appears to apply either way. So regardless of what earnings record it goes against, you’re still going to get knocked down.”
  – Lynn [07:46]

• “I don't necessarily like the industry I'm in, but I like the type of work that I do...”
  – Lynn [08:05]

• “We're going to need to have access to more money for you guys that has already been taxed...”
  – Mark [13:07]

• “Even if you had to make a little bit less money for you as you make this shift, I'd be okay with that. As long as you're happier. Because if it meant that you could stay beyond five years, maybe it's seven years...”
  – Mark [15:20]

• “Don’t go for the retirement plan... Get a job you like, because you are so lucky that…he’s got this defined benefit plan.”
  – Mark [16:53]

---

Timestamps for Key Segments

• [02:54] – Main Show Begins (skip ads, intro)
• [03:42] – Lynn introduces her evolving retirement goals
• [05:39] – WEP and Social Security eligibility explained
• [08:00] – Discussing job satisfaction vs. benefits
• [08:51] – Current savings, debt, and asset overview
• [10:14] – Calculating retirement income needs
• [13:07] – Importance of taxable savings, not just retirement
• [15:20] – Advising phased, flexible semi-retirement
• [16:30] – Should Lynn seek another defined benefit plan?
• [17:14] – Episode wrap-up with final guidance

---

Tone and Style

Jill and Mark are practical, empathetic, reassuring, and honest. They balance the hard math of planning with sensitivity to emotional factors around work and life choices. Their advice avoids jargon, focuses on actionable steps, and emphasizes well-being and flexibility over rigid milestones.

---

Useful for Listeners Who…

• Fear running out of money if they downshift careers before full retirement
• Want to understand the Windfall Elimination Provision
• Are tempted to prioritize investment maximization at the expense of happiness
• Value straightforward, jargon-free financial advice with real-life context

---

Summary prepared for those seeking a comprehensive yet relatable breakdown of financial planning for flexibility, especially when considering non-linear or phased retirement paths.

Transcript

[Jill Schlesinger]

Everyone has their own reason for giving. Maybe it's to honor someone they love, to support a cause close to their heart, or just to make the world a little brighter. Whatever your reason, there's one way to do it better. A Donor advised fund from Daft Giving360 makes charitable giving simple, strategic and tax smart. Donate anything from stocks, securities and cash to non cash assets like real estate, life insurance and crypto. Contributions can be invested with the potential for tax free growth and then granted to any qualified U.S. charity. And you may qualify for a current year tax deduction on your contribution, but you don't have to make your grant decisions right away. No end of year scramble, no paperwork headaches, just smart flexible giving. All managed through an easy online dashboard. And there's no minimum to open an account. DaftGiving360 really does help you make a.

[Mark]

Greater impact on your terms.

[Jill Schlesinger]

Want to learn more? Visit daftgiving360.org you know how the Holidays Holidays can sneak up on you. Suddenly you're hosting a dinner or bringing a dish to a friend's party and you're scrambling. This year I decided to make my life easier and head straight to Whole Foods Market and honestly, it's my new holiday headquarters. Whether you're looking for show stopping mains like their bone and spiral cut ham or Heat n Eat sides from the prepared foods department that are seriously easy and delicious, Whole Foods Market has you covered. I stocked my pantry with all the 365 favorites too. Creamy mushroom soup, traditional stuffing and E even French style green beans. Perfect for classic holiday meals without breaking the bank. And don't even get me started on desserts. The holiday rum cake Buche de Noel? Yes please. Plus it's easy to grab something thoughtful for the host, cheeses and crackers, seasonal candles, cookie gift boxes, or even something from the floral department to make their table feel extra festive. You can order online for pickup or delivery in select zip codes, which is a total lifesaver. Shop for everything you need at Whole Foods Market. Your holiday headquarters episode is supported by what Should I Do with My Money? An original podcast from Morgan Stanley and like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries and dreams, asking questions like can I retire early?

[Mark]

Like really early?

[Jill Schlesinger]

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.

Welcome to the Jill on Money show. It's Tuesday, December 9th, and we are here listening to what is going on in your financial life and trying to help you get wherever it is you want to go. See, it's all about you. It's not about us. You tell us what you hope for, what you dream for. We'll see if it's possible. And if it's not, don't bum out. Maybe we'll find other routes to get.

[Mark]

You where you want to go.

[Jill Schlesinger]

May take a little longer, may not be ideal, but at least you'll know. Just go to our website, jillonmoney.com, click the contact Us button, write us a note, and if you want to join us live, check the box. Mark will do everything else while you're on the website. Don't forget to sign up for the free weekly newsletter. It comes out every single Friday. Mark does a great job with that. Right now, let's talk to Lynn from Alaska.

[Lynn]

I'm starting to have a little bit of a metamorphosis when it comes to planning for retirement. And retirement may not be, you know, full blown leisurely time on the beach, but to allow us some financial flexibility to make other decisions, a little next.

[Mark]

Endeavor, a little look ahead. So tell us how old you are, who's the we? What's going on in your financial life right now?

[Lynn]

So it's myself and my spouse, we both work full time, our kids are grown and out of the house. He qualifies for what's kind of old term, the PERS system, which is a defined benefit program. So we expect for him to have that and for that to be about just under $4,300 a month once he hits age 60.

[Mark]

How old is he now?

[Lynn]

So he is 52.

[Mark]

Okay.

[Lynn]

He's young and I am 54. I tell him that all the time.

[Mark]

How much does he earn right now?

[Lynn]

About $102,000.

[Mark]

And that defined benefit, does it require him to stay until he's 60? Is that where or just to claim it at 60?

[Lynn]

Just to claim it at 60. It starts to pay out at 60 and there's no benefit to delaying that claiming.

[Mark]

Okay, got it. And how much do you earn?

[Lynn]

About 75.

[Mark]

Are you also part of a pension system?

[Lynn]

Not currently. So currently I work in Higher education.

And I opted into their plan. And in the higher education, we don't pay into Social Security, so instead we get approximately about 3,200 a year in what the Social Security department considers to be pension funds.

[Mark]

Okay.

[Lynn]

And that's really kind of where I was going with my call today, was I'm a little concerned, trying to learn.

[Mark]

About wep, the windfall, the windfall elimination provision.

[Lynn]

As I'm trying to kind of look forward and plan ahead, I'm a little bit struggling with that. In the years prior, I only have about 18 years of what the Social Security considers substantial earnings. So you only need.

[Mark]

You only need 10 years. So that's okay.

[Lynn]

10 years to qualify. But when they look at WEP, they look at your total number of years as to the percentage that they discount you.

[Mark]

I got you.

[Jill Schlesinger]

So tell me what, like, okay, let's.

[Mark]

Just do some quick math right now. Is your husband subject to the WIP windfall elimination?

[Lynn]

No.

[Mark]

Okay. So for him, his full retirement age.

[Jill Schlesinger]

Right.

[Mark]

What's his Social Security benefit?

[Lynn]

At age 67, it would be just short of $3,000.

[Mark]

So for you right now, based on your record net of the windfall elimination, what does your Social Security record show.

[Lynn]

Prior to the windfall elimination? It'd be about 1500.

[Mark]

But then that gets knocked out, right? I mean, like, it gets reduced to.

[Lynn]

What.

According to their calculations, it looks like by about 40%.

[Mark]

I'm not sure. Like, I mean, so is your idea, like, bail out of what you're doing now so that you can, you know, crank on your record before you turn, you know what I mean? And, like, then make up for that?

[Lynn]

Right. So I've got, you know, some working years left, and I could work a few more years to have enough substantial earnings to change that percentage to something closer to, like 20%. Because as I understand it, the windfall elimination, even so, Social Security benefits can be paid out against my record or, you know, also 50% of the spouse, if that's higher.

[Mark]

Yep. Yes.

[Lynn]

When they calculate the amount. So the windfall elimination, as it's written right now, appears to apply either way. So regardless of what earnings record it goes against, they.

[Mark]

You're still going to get knocked down.

[Lynn]

Right.

[Mark]

Okay, let me ask you a very simple question. Do you like what you do?

[Lynn]

I don't necessarily like the industry I'm in. Okay. But I. But I like. I like the type of work that I do. I just don't know that where I'm at is maybe the best fit.

[Mark]

Because obviously, if you loved what you did. You'd be like, who cares? I'll just, you know, I'll eat the elimination. Right. Let's talk about the money you've saved so far, and then let's go back around to that to get back to, like, what you do next. All right, so right now you guys make 175 grand together. Right. Life is good. You feel comfortable.

[Lynn]

I'd rather not have debt. I'm understanding or coming around to the picture that with inflation being the way it is, that maybe having some debt and putting more money towards retirement savings might be a better financial decision.

[Jill Schlesinger]

Well, let's talk about some of the.

[Mark]

Assets and then we'll talk about the debt. So when you're talking about debt, are you talking about a mortgage?

[Lynn]

Yes.

[Mark]

How much is your house worth?

[Lynn]

About five and a quarter.

[Mark]

Okay. And how much remains on your mortgage?

[Lynn]

$275,000.

[Mark]

And what's the rate?

[Lynn]

$2,075,000.

[Mark]

Okay, let's go and do like, let's go from lowest risk to highest risk. Do you have an emergency reserve fund?

[Lynn]

Yes.

[Mark]

How much is in it?

[Lynn]

35.

[Mark]

And do you have a brokerage account?

[Lynn]

No.

[Mark]

Do you have retirement accounts and if so, what kind? Let's go through it. What do you got?

[Lynn]

Yes, so we have primarily Vanguard accounts, mostly in either, I lost the terminology, the goal type accounts, you know, retirement target date funds. Thank you. So mostly in that, also in some index funds.

[Mark]

How much is in your retirement savings right now?

[Lynn]

So all told, we have just over a million in total retirement savings.

[Mark]

Yep.

[Lynn]

Of that we have about 40 in Roth, the rest in all pre tax contributions.

[Mark]

How much do you think you need to live on each year? You know, you have this $175,000. What do you think are your, what's your need? If we're looking ahead at retirement, what do you think your need is?

[Lynn]

Once you factor in taxes, I think about a hundred thousand a year.

[Mark]

You mean factoring in like property taxes or actual, like income taxes?

[Lynn]

Factoring in income taxes. Okay, so trying to kind of figure out what our, what our end ballpark is for retirement years, I figure about 100K.

[Mark]

And I mean, you'll have 4,300 of your husband's defined benefit, right?

[Lynn]

About 50,000. Yeah.

[Mark]

Right. And then you'll have another 3,000 from Social Security eventually, at the worst case, maybe you'll have another 900 from yours. So you'll have 39. So I'm just going to do like there's two phases to this, right? There's phase 60 to 67 and then 67, you know, beyond. And at age 67 you have, you know, the 4300 plus 3900, which is, you know, it's not exactly right, but it's pretty close. From age 60 to 67 is where, you know, we have a gap. So here's my question. How much longer do you think you guys want to work?

[Lynn]

Well, we'd like to have the, the flexibility to make changes in about five years.

[Mark]

What do you mean by that? When you say in five years like that you would both make less money or. I mean five years.

[Jill Schlesinger]

He's only 52.

[Lynn]

I know he works very physically taxing jobs. So yes, we'd be looking at maybe making less money trying to give some flexibility there to. It's not going to affect his pension benefits because he's already kind of, you know, that's only going to go up from here. But I want to be able to give him the option or give us the option if one of us were to get disabled or, you know, stress wise, health wise. That's why I've been focusing on debt and trying to.

[Mark]

No, don't focus on debt, please. That is not where your focus needs to be. The focus needs to be that. And I'm not even so focused on your Social Security. I'm more focused on what you said after we talked about the windfall elimination, which is you don't love your job. So if you are going to plan on working for another five or six years, each of you doing something different, do you think between the two of you that you can basically make enough money just to pay for your needs? Do you feel comfortable with that?

[Lynn]

Yes.

[Mark]

Okay. Are you putting money into saving money in retirement right now? Are you, Are you putting a certain amount of percentage of income? Are you both maxing out how much are you saving right now?

[Lynn]

So we are putting money away. We are running about 50,000 that we're putting away in various types of accounts.

[Mark]

Wow, that's a lot.

[Lynn]

That's with the employer match. If you're just looking at what we put in, it's closer to 30.

[Mark]

But that's great. If you were to just both put in up to whatever the match is, what would that be? What would the amount be that you would have to fork over? Do you know what percentage or, you know, like where do they match? Where does it start? How much do you have to do? And then my idea is maybe to use. Instead of putting all that money into retirement, I think you're gonna need to put money in non retirement in some sort of brokerage account, potentially not pay down your debt. Please don't do that. But we're gonna need to have access to more money for you guys that has already been taxed. I think what you maybe should be considering is whether you want to just make a change, get a job that you feel more excited about, by the way, if it's a job that you like more, you might wanna work more, but that, you know, is it possible that if you're both sort of down, maybe not even downshifting, because it sounds to me like you want to, like it's just a different job. But if he is downshifting and he's making less money, then I think what's really becomes more possible is that you work into, you know, a couple years into your 60s. Because I am somewhat concerned that between 60 and 67, you, you know, you do need money, right? And a million dollars that you have in savings in retirement savings, if you think about it, that money that comes out of the retirement because it hasn't.

[Jill Schlesinger]

Been taxed yet, even if you pulled.

[Mark]

Out, let's say 40 grand a year, 30 grand a year, then that gets taxed and then that has to. Whatever that amount is, you have to be able to sustain yourselves based on the amount of money you're pulling out of your retirement savings, plus the $4,300 a month. And so I think you guys are going to have to work longer. Even if you make less money, I don't think you can go from making together 175 grand a year to like zero. I don't think that's happening in five years because I think you will run out of money if that's the case. I agree.

[Lynn]

That's. Yeah. The, my, my intent was to build us a, a savings, to fund us for a couple of years at least, and to work part time.

[Mark]

That would be my. I mean, so what I would think.

[Jill Schlesinger]

Is if, let's just say for five.

[Mark]

Years you're still kicking ass, right? And even if, you know, you don't have to, you don't have to change jobs, but if you want to change jobs, that's fine. Even if you had to make a little bit less money for you as you make this shift, I'd be okay with that. As long as you're happier. Because if it meant that you could stay beyond five years, maybe it's seven years. And if he could downshift and if you're both making enough money to support yourselves between the two of you, right? You would not be making any retirement contributions. So if you had from say, age, let's call it his 50. So five years from now he's 57, you're 59. If you can then work for like three or four, maybe five years and you are working part time and you're both happy and you're not killing yourselves and it's not physically demanding. The more you can delay dipping into that million dollar retirement savings pot, the better off you'll be. Because we know that once you get to Social Security, you're going to be fine, even with the windfall elimination. But it works so much better if you can delay dipping into these accounts. That's from my perspective at least.

[Lynn]

No, I definitely agree with that. I do. One of the opportunities would be to change into a job that also has the defined benefit plan.

[Jill Schlesinger]

I mean, don't go crazy.

[Mark]

It's fine if you do get a job you like, that's my number one recommendation, is try to find something where you feel like it's, don't go for.

[Jill Schlesinger]

The retirement plan or this plan or that.

[Mark]

Get a job you like because you are so lucky that you know he's.

[Jill Schlesinger]

Got this defined benefit plan.

[Mark]

You need to find something you like, actually want to be engaged with. It matters less to me about what type of retirement plan you have. I mean, if you want to go back and, you know, get a job like that and it happens to work, great.

[Jill Schlesinger]

But if not, don't go crazy.

[Mark]

I think you're going to be really, you're in very good shape.

[Jill Schlesinger]

It's just we need to have a.

[Mark]

Little more longevity for you.

[Jill Schlesinger]

If you've got something going on in your life and you need to think it through with someone else's guidance, Mark and I are here for you. Just go to jillonmoney.com, click the contact Us button and write us a note. You can subscribe to us on the Odyssey app or wherever you get your favorite podcasts. Don't forget to do something nice for someone else today. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

Other jewelers hate Stephen Singer. Why? Because Stephen Singer has the best real natural diamond stud earrings in America. Everybody knows gold and diamond prices are crazy right now. Gold is at the highest price in history. Lucky for you, Stephen Singer has locked in his diamond studs at the old prices. Steven has diamond studs available from a quarter carat all the way up to 10 carats total weight, all at the same perfect price as last year. Same incredible value. There's no better time to get a pair of diamond studs from Steven Singer Jewelers. This can't last forever. Each pair is eye flawless and near colorless. Beautiful stuff. They come with his safety silicone back so you never have to worry about losing them. And with his unbeatable full value lifetime trade in, you know your diamonds are always worth what you paid. All backed by the best guarantee in the jewelry business. A full 100 day 100% no hassle money back guarantee plus fast and free shipping. Experience the difference at Stevensinger jewelers online at ihatestevensinger.com that's ihatestevensinger.Com what's up world?

[Vaughn Miller]

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.