On Track for FINE?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode: On Track for FINE?
Release Date: March 3, 2026

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Episode Overview

In this episode, host Jill Schlesinger takes a listener call from Dean in Colorado, who is contemplating “FINE”—Financial Independence, Next Endeavor—within the next four to five years. Dean is seeking Jill’s guidance on whether he and his wife are financially ready to scale back their work lives, and has questions about how to handle his wife’s TIAA retirement accounts, as well as general withdrawal strategy anxieties. The discussion explores financial planning for high earners without children, strategies for decumulating savings, and the psychological hurdles of moving from accumulation to drawdown.

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Key Discussion Points & Insights

1. Dean’s Financial Profile

• Ages: Dean is 51, his wife is 46.
• Employment: Dean works part-time ($100k/year), his wife works full-time ($300k/year).
• Monthly spending: About $12,000.
• No children.
• Noteworthy assets:
  • $500,000 in wife’s old TIAA account (split $300k in 403b, $200k in 401a)
  • Dean’s old 401k: $400k
  • Wife’s current 401k: $80k
  • Both own Roth IRAs: $400k combined
  • Dean’s Roth 401k: $350k
  • Joint brokerage: $1.9 million (self-managed)
  • House: $1.1 million, mortgage outstanding: $750k at 3.5%
  • HSA: $30k
  • Cash: $80k in money market, $20k in checking
• Family support: $750/month to in-laws (included in their $12k monthly spending).

[04:26] Jill (A): “Oh, much easier planning. And how are you living on 400 grand a year between the two of you?”
[04:33] Dean (B): “Very well. We have probably a monthly spend of about 12,000.”

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2. Planning for FINE: Evaluating Early Semi-Retirement

• Timeline: Both want to reduce to part-time (or consulting) in 4-5 years.
• Projected income in semi-retirement: Minimum $150k/year, possibly more depending on split.
• **No significant new expenses expected.
• Current plan factors in post-job health insurance and steady spending.

[07:13] Jill: “So in four years and you weren't doing part time... Is your wife on that game plan or...?”
[07:21] Dean: “I think she would go down to either consulting or part time. So we would both probably do part time because I think it's just more sustainable for us.”

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3. TIAA Account & The Annuity Question

• Dean seeks guidance: Should they annuitize the $200k 401a sub-account?
• Jill’s take: The account size is not large enough to make annuitization particularly valuable versus staying flexible with withdrawals.
• **Jill advises a self-managed withdrawal strategy over purchasing an annuity.

Memorable Quote:
[10:42] Dean: "It seems without a pension, which is a guaranteed amount of money you can say you're going to spend, I'm gonna have a hard time convincing myself that I have to just keep working to fund myself as opposed to pulling money out."
[10:50] Jill: “Okay, I'm gonna do it for you… your goal—and this will maybe appeal to your planning persona—your goal is to drain those accounts by the time you're 75 years old, that is your goal.”

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4. Withdrawal/Decumulation Strategy

• Stop extra retirement contributions: After scaling back, stop maxing retirement accounts and start using savings to fund lifestyle.
• Use brokerage funds first to supplement reduced income until age 59.5.
• At 59.5+, focus withdrawals on tax-deferred accounts ($900k+ between them).
• Goal: Systematically draw down pre-tax retirement savings before Social Security, ideally eliminating RMDs later on.
• Set a withdrawal “salary” each year: For example, withdraw $100k/year, pay the tax, and live on that.

Actionable System:
[13:47] Dean: "Taking it as a distribution just to live off?"
[13:49] Jill: "Yeah, exactly. Okay, get it out. Be done with it. Let's get rid of that money. You'll never have to do a—I mean, wouldn't it be awesome not to have any RMDs? Be incredible."

[15:20] Jill: “Just pull it out. Use it. You make your own annuity with no costs involved... The discipline is: just make sure, bro, in your brokerage account, you set up an automatic monthly transfer of $10,000... At the end of December, free up $100k, liquidate it, and instruct them to send you $10k/month.”

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5. Emotional/Psychological Considerations

• The struggle is not with math, but with permission:
  • Dean, like many savers/DIY planners, finds the “decumulation” phase emotionally difficult.
  • Jill emphasizes systematizing withdrawals to sidestep emotion.

[16:57] Jill: “I know that if you were giving this advice to somebody else, you could see it very clearly, but there'd be no emotion. No, exactly. And that is how we have a role in your life, which is without the emotion, you would be able to do everything perfectly. But sadly, we're human beings…”

• Plan for flexibility: If in a few years things change (e.g., wife wants to work longer or spend less), reevaluate then.

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6. Other Notable Insights

• Insurance needs: Health insurance post-job is already built into their spending plan.
• **No additional significant real estate or investment changes planned.
• Estate planning: Up-to-date, in place.
• Jill’s encouragement: Life is short; you have “permission” to enjoy what you’ve saved.

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Notable Quotes & Moments with Timestamps

• On spending needs:
  • “[04:33] Dean: ‘Very well. We have probably a monthly spend of about 12,000.’”
• On psychological roadblocks:
  • “[10:42] Dean: ‘It seems without a pension... I'm gonna have a hard time convincing myself that I have to just keep working to fund myself as opposed to pulling money out.’”
  • “[16:57] Jill: ‘I know that if you were giving this advice to somebody else, you could see it very clearly, but there'd be no emotion.’”
• On creating your own “annuity:”
  • “[15:20] Jill: ‘Just pull it out. Use it... You make your own annuity with no costs involved.’”
  • “[13:49] Jill: ‘Get it out. Be done with it. Let’s get rid of that money. You’ll never have to do a—I mean, wouldn’t it be awesome not to have any RMDs?’”

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Key Takeaways for Listeners

• If you’re planning for FINE, systematize withdrawals from your savings; treat your retirement accounts as self-made pensions.
• Don’t let emotional hang-ups about “touching principal” stop you from living your planned post-career life.
• Annuitization has a role, but for sizable, flexible portfolios, disciplined self-withdrawal is often superior.
• Set up regular, automated withdrawals to replace a “paycheck”—a practical and psychological bridge.
• Financial independence is as much about emotional readiness as having “enough” assets.

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Important Segments with Timestamps

• Listener profile, assets, and goals: [03:35–08:31]
• Discussion of FINE timeline and health insurance: [07:13–08:11]
• Withdrawal and annuitization strategy deep-dive: [09:18–16:56]
• Addressing emotional side of decumulation: [16:57–19:06]

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This episode demonstrates Jill Schlesinger’s clear, pragmatic approach to financial independence: focus on what you truly spend, build a withdrawal system you can stick to, and don’t let fear override financial logic. For high earners or super-savers hesitating at the threshold of the next phase, Jill’s message is clear—give yourself permission to use what you’ve built.

Transcript

[A]

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[B]

I'm well. Thanks for having me on.

[A]

Sure. What's happening? How can we help you out?

[B]

Well, I'd like your opinion on whether I'm on track for. Fine, you know, financial independence, new endeavor in the next, say, four or five years. And then specifically some options for a TIAA account that my wife has from an old job. What to do with it, whether an annuity makes sense. Lots of questions, and I'm sort of an analysis paralysis about it.

[A]

Oh, man, you got that spreadsheet rocking. And then all of a sudden you're like, wait, I don't know what I want to do. So let's start with easy information. Dean, how old are you?

[B]

I am 51.

[A]

And how old is your wife?

[B]

46.

[A]

And you're both working full time?

[B]

My wife works full time. I work part time.

[A]

How much do you earn part time?

[B]

I earn about 100,000 part time.

[A]

And what about your wife? Full time?

[B]

300.

[A]

Okay. You have kids?

[B]

No kids.

[A]

Oh, much easier planning. And how are you living on 400 grand a year between the two of you?

[B]

Very well. We have probably a monthly spend of about 12,000.

[A]

Okay, let's talk about the money that you've squirreled away. The old TIA account that was your wife's. What's in there?

[B]

It's 500,000 total, split up between a 403B and a 401A.

[A]

Are they treated as separate accounts, though, those two?

[B]

They sort of are. In terms of the rules as to what we can do with the money? Yes.

[A]

Okay. You can annuitize each of them as separate annuitization schedules.

[B]

You can combine them or annuitize the 401A.

[A]

Okay. And so what's in the 401A?

[B]

It's about 200,000.

[A]

Okay, got it.

[B]

And so 300 for the 403B.

[A]

Perfecto. Okay. What other savings have you done? You guys both have retirement plans currently? Yeah.

[B]

So I have an old 401k which is valued at 400,000.

[A]

Okay.

[B]

Her current 401k, which is relatively new at her new job, is valued at 80,000.

[A]

Okay, so she has some old stuff somewhere. Okay, what else you got?

[B]

And then we have Roth accounts in total. So we both have Roth IRAs, which in total is 400,000.

[A]

Great. Amazing.

[B]

And then I have a current Roth 401K at my employer, which is 350,000.

[A]

350 in a Roth 401K brokerage accounts?

[B]

Yeah. 1.9 million.

[A]

Oh, all right. One mark. I love the mark. The mark giggles with delight. He loves that in a brokerage. And are you guys managing that yourselves?

[B]

I manage everything myself.

[A]

Yep. Okay. He's a big do it yourselfer. Okay. Is that it for the financial side of the world? Can we go into real estate or is there anything else you have invested

[B]

an HSA at 30 house.

[A]

How much is it worth?

[B]

1.1.

[A]

Mortgage or no mortgage?

[B]

Mortgage outstanding at 750 at 3.5.

[A]

Do you love this house? Is this like the house you want to be in?

[B]

It's going to be for a while until we downsize at some point in the future, but for sure, like the next 15, 20 years.

[A]

Yeah. Do you guys have responsibility for anyone else? So parents, siblings, anyone else? I know you don't have kids, but do you feel like there's anyone else you need to take care of?

[B]

We do help out my in laws and that that money is sort of lumpy, but on average probably about 750amonth.

[A]

So if I said in the 12. Okay, so that's good. Good. Perfect. I was going to say do I need to. Okay, let's say that we. You say in four years you want to do something different. Is your wife on that game plan or is it we just talking about you like losing your money?

[B]

No, I think she would go down to either consulting or part time. So we would both probably do part time because I think it's just more sustainable for us.

[A]

Okay, so in four years and you weren't doing part time. Right. Let's say, you know, you're 55 and she's 50.

[B]

Yeah.

[A]

What about life health insurance that is

[B]

going to be included in the 12? Because right now she has some travel expenses because her job is based in another location and so she has to pay for that. So once that job is up, we just converted that money that we would spend to cover the health insurance. So it still includes the 12,000 that we've allocated.

[A]

So I like that. This is like. It's 12. It's 12, Jill. Get over it. It's a thousand bucks a month either way. Great. Okay. And anything else on the horizon that we should know about before our four years is up? Anything else, like a big expense or anything else that you see that would change some of the dynamics here?

[B]

No, there would be expenses for the house, but those are expected. So nothing, nothing drastic there.

[A]

Okay. And you have just a plain old savings, high yield savings or checking savings, what you got?

[B]

Yeah. So that sits in our. Basically we have 80,000 currently in a money market account as part of the brokerage.

[A]

Okay.

[B]

And then we have about combined 20,000 in checking.

[A]

Okay. You will both be, you know, obviously very young when you retire and go into semi retirement. But if in four years you were both working part time or doing something different, what do you think? I mean, you're doing it already because you're working part time.

[B]

Yeah.

[A]

Would you, would you think like your part time income would go down and then what do we think she could earn just like. And make. Be conservative?

[B]

Yeah, I think 150 would be the low end, but it likely will be more. But I think, I think 150, we

[A]

would manage with that for the two of you.

[B]

Yeah. To earn. I think I might go down more or she may go down much more and I continue at the current rate. We would work that out, but I think 150 is the right number. Conservative income. Yeah.

[A]

Okay, so in other words, if you did that and you could do that for how many years? Like when we'll do financial independence. Right. You are going to be financially independent. So if you're 55 and she's 50, what's the, what's the clock look like after that? Is that five more years, do you think?

[B]

Probably a maximum of five more years.

[A]

Okay, so it's even less.

[B]

Yeah.

[A]

Okay. Three to five years.

[B]

Yeah. Yeah.

[A]

Okay, that makes sense. All right, so in that time, the bulk of your expenses you pay for just with your income. Let's say you just do it for a few years. Right. You can certainly fill in the blanks with your Brokerage account. Got plenty of money there. And then by the time you are 59 and a half, or if you're still working, you know, it is possible that you can take money out of a retirement plan while you're still working if you wanted to. And you're fine. You're totally fine. Tell me about the question regarding TIAA about the annuitization. In some respects, since only 200 is really the annuitization part of it. Right. I'm sort of, like, not that interested. It's not going to be that much money.

[B]

Yeah. So the bigger philosophical question I had is it seems without a pension, which is a guaranteed amount of money you can say you're going to spend, I'm gonna have a hard time convincing myself that I have to just keep working to fund myself as opposed to pulling money out.

[A]

Dude, what's. Oh, so you're saying, like, oh, my God, I cannot possibly take money out because I don't have the discipline to do that. Okay, I'm gonna do it for you.

[B]

That's what I'm worried about.

[A]

All right, I'm gonna do it for you. I'm gonna do it for you right now. So, first of all, when you're 55, do you think you. You currently have this job and you're putting money into your Roth 401K right now, right?

[B]

Yes.

[A]

How much are you putting in the max?

[B]

$32,500.

[A]

All right, well, stop doing that. In four years, you will no longer do that, and you will live on that money. You will use that money to actually live on. You don't need to keep putting it into the 401k. You don't. Absolutely don't have to. So now you're just gonna, like. All I'm doing is just trying to kind of chill out a little bit, give you the cash flow so you don't panic. By the time you get to 59 and a half, which is only if, let's say, even, you know, a few years later, you pull some money out of the brokerage account, and then your job is going to be making sure that of that half a million dollars that your wife is in there, you are going to pull out a bunch of money every year from her accounts. From your. You have a. You said you have an old 400,000. That's traditional, right?

[B]

Correct.

[A]

So those. Okay, that million dollars. 900,000, your 400 traditional. Her 500 tiaa. Your goal. And this is going to be. This will maybe appeal to your planning Persona. Your goal is to drain Those accounts, by the time you're 75 years old, that is your goal. Now what you're going to do is you're going to say, well, you know what we have to do, each of us, you know, maybe you'll start with you, because you'll be getting there first is we're going to take $100,000 a year out of these accounts and pay the tax on it and live on it. If you're 55 and you're working for three or some years, you're going to pay whatever you need to pay for. You use a little bit of the brokerage account when you're 59 and a half. That account, that's 400 now, which may be 600 for all I know, or 500 or, you know, whatever it is, that's the money you're going to attack first. You're going to pull as much money as you want as you can out of that even before you claim Social Security. I almost would love it if you guys could get out of all of this taxable money, not the money that has not yet been taxed, and do that before you claim Social Security. Just get it out and you'll be able to do this. I mean, honestly, even if you said, you know, you're going to basically pay the tax that's due, you're used to paying the 24% bracket, take the money out, get all that money out, fund, and if you're not living on it, put it in the brokerage account. But maybe you just say like, well, you know What? We need 50 grand a year, we need 80 grand a year. Whatever it is you need, you pull it out. That's what you're living on. I don't think that annuitization is going to do you that much good. I think what you have to do is sort of discipline yourself and say, I live on this money. So whatever I take out of my retirement account, that is my money, that is my pension. I am going to use that to live on. And that's how you treat it. Maybe that money never goes even in your brokerage account. Maybe just goes in your high yield savings account. And you're using it to live on because.

[B]

Taking it as a distribution just to live off.

[A]

Yeah, exactly. Okay, get it out. Be done with it. Let's get rid of that money. You'll never have to do a. I mean, wouldn't it be awesome not to have any RMDs? Be incredible. Yeah.

[B]

And, you know, given my asset allocation, most of that money in the Tax deferred spaces and bonds. So I imagine it's not going to grow terribly over the period of time that I'm before I start pulling it out. But it may grow some.

[A]

The funny thing is about this money that has not yet been taxed, it's weird how it just gets away from you, right? So now it's 900, and then if you do nothing in seven and 10 years, all of a sudden it's a couple million. And now you're like, oh, no, now I've got all this money I have to take out. So I think that just pulling the money out, you don't need to convert it. You will never have to touch your 401k. You can pull it out and be disciplined. And you know, whether it's. I mean, if. Even if it's like some people will set it up as just send me income every month. If that's better for you, what you can do is you can say to. You can say to yourself, here's how I would manage it. I know I'm going to pull 100 grand out, okay. I'm going to make sure at the beginning of the year that I free up 100,000. I got some bond funds, I'm going to sell them, I'm going to sell out the bonds. I'm going to have $100,000. I'm going to make an instruction, send $10,000 a month to my bank account. Boom, done. And make that what you live on.

[B]

Yeah. So this is helpful. Not even to think about what do I do with this possibility of annuity. Just pull it out as I would for living expenses.

[A]

Just pull it out. Use it that you make your own. This is how you'll make your own annuity with no costs involved. I mean, by the way, TIA Cref has a great annuity product. If you're in it. It really does. But. But I don't even think you need to do that. I really don't. I think you pull the money out. This is your. How you live. This is something that many people have to contend with as they age and as they retire. It's like, I am so good at accumulating. I cannot figure out how to decumulate. I cannot figure out how to get the money out to my. I don't give myself permission, Right. So that is how, you know, annuities are always sold. They're not purchased. The reason why some people really like the idea of an annuity is that, you know, some salesperson will be like, well, don't you want consistent income? Yes. But you can do that yourself if you're disciplined. The discipline is. Just make sure, bro. In your brokerage account, you set up an automatic monthly transfer of $10,000 so that at the end of December of any given year, you say, I'm freeing up 100 grand. Because I know I'm going to need 100, 120,000, whatever it ends up being. I know I'm going to need this money over the course of the subsequent year, free that money up. Do not have it invested, because that's how you whipsaw yourself. If you keep it invested, then you're gonna freak out when the market goes down. You say, oh, I won't take it this month. You don't have to do that at the end of the year, be disciplined. You have whatever you need for the next 12 months, you liquidate it. It sits in the money market. You say to the company, now, send me $10,000, $9,000 a month. Just send it to me. Goes to your checking account. Live on it. That's what you're gonna live on.

[B]

Okay.

[A]

I don't think we'd have to do anything else. I really don't. You guys have estate documents? We do. It's so funny, Dean, because I know that if you were giving this advice to somebody else, you could see it very clearly, but there'd be no emotion. No, Exactly. And that is how we have a role in your life, which is without the emotion, you would be able to do everything perfectly. But we're. Sadly. We're human beings, and I can't do anything about that except to give you the guidance and almost. We want to set up the systems that will allow you to do the things you want to do. By the way, I think it is highly possible that you kind of. You futz around for a couple of years and you're fine, and that you can even say, get back in touch with us and say, like, here's where I am. What do you think? Like, it may not be that it's. In four years. It might be something different. And it might be that your wife's like, hey, I can't go from 300 to 50. I really. I need an interim step. So maybe she's going to keep. Maybe for her, she'd be like, I want to work a little bit longer full time, but then I want to make no, nothing. People have very different ways of approaching this. Some people need, like, an interim step. Maybe your wife's like, I'd rather work full time for a Few extra years and then never have to work again, which is also going to be an option for you guys.

[B]

So within that time frame that we talked about, it doesn't seem out of possibility in that four to five.

[A]

No.

[B]

If she wanted to do that.

[A]

Yeah, no, definitely not. I don't. I don't see that as a problem. Yeah, you know, I think that you factored in all the things you need to factor. And also if she's in a job and she's traveling and it's exhausting and she's like, I'm all over this. Like, I get that, man. I just traveled for work last week and it's like, it's just drag. It's a hassle, and it takes something out of you that's a little bit different than your regular old job, which takes enough out of you anyway. So I think that life is short. You got it. You got the money, there's no kids. Keep yourselves occupied. If she thinks she's like, I don't really want to do. I don't want to do a part time gig. I'd rather work a couple of extra years full time then. Then let's see how that goes for her.

[B]

Okay, sounds good.

[A]

I like this. I like this plan. I'm excited. I'm gonna go execute it for myself now. And I'm older than you guys, so maybe I'll just go ahead and do that. Except my spend. My spend's a little bit more. That's the problem. All right, Dean, good luck. Keep in touch with us. If you are like Dean and his wife, you've got a lot of money socked away. You can't give yourself permission to stop because you're just. Your program in your brain does not allow you to enjoy the fruits of your labor. Get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note, let us know how we can help you out. And we really. There might be a lot of different ways to get where you want to go. It's not something that you have to do on your own. We can help you out. So please just let us know how we can help you out. And of course, while you're on the website, check out all of the content that lives there, including our free weekly newsletter, comes out every Friday. And you can subscribe to us here at Jill on Money, as well as our other podcast, Money Watch on the Odyssey app, or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen. And of course, do something nice for someone else today. Change your work, change your wealth, change your life. Thanks for listening I and we'll talk to you tomorrow. Hey gang. I just made a first time ever purchase on behalf of the pod. I was so psyched because Mark and I don't do a lot of promotional materials, but I was able to create a branded sweatshirt. Yep, a Jill on Money branded sweatshirt with vistaprint. Now I'm not usually good at these things, but vistaprint means made it simple to bring this idea like, oh, wouldn't it be cool if Mark and I could create some sweatshirts that we'll try out and maybe the listeners would want to get them as well. They've got these great design tools. They have fast shipping human support if you need a little guidance along the way. Because the sweatshirts were so easy to execute, now I'm thinking about doing some other stuff. Maybe there's some baseball caps or I don't know, other fun stuff that you guys would want. You'll let us know. There's a reason that over a million people trust Vistaprint for their small business print needs. Vistaprint print your possible right now, new customers get 20% off with code [e-mail].