Trying Not to Screw It Up

Summary

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Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Trying Not to Screw It Up
Date: April 14, 2026

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Brief Overview

In this episode, host Jill Schlesinger consults with listeners Kay and Eric, a couple navigating major life transitions as they approach financial independence in their mid-50s. With their last child nearly out of high school, they seek advice on ensuring their prudent savings and investments are managed wisely as they contemplate next career steps, potential relocation, and the optimal use of pensions and retirement accounts. Jill breaks down actionable steps to help them "not screw it up" and ease their anxieties about the drawdown phase, all in her signature clear, jargon-free style.

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Key Discussion Points & Insights

1. Kay and Eric’s Current Situation

• Background: Both professionals, age 54, with high-stress jobs and a strong commitment to financial independence (committed to the "FIRE" philosophy).
• Income: Kay earns $225K/year, Eric earns $175K/year.
  • “We don't want to do something dumb and we have been really boring...save 30% of our net income and dollar cost average and put it in an index fund. Well, that's what we've done.” — Kay [01:34]
• Retirement Savings:
  • 401(k)s totaling ~$2.5M (pre-tax, with $350K in Roth).
  • Brokerage account with $2.1M.
  • Cash reserves: $230K.
• Children: Two, ages 17 and 19; college accounts of $200K for each.
• Home: Paid off, worth $230K.
• Pensions: Kay has a $2,100/month government pension starting at 62; Eric will have a state and federal pension (up to $3K/month at 60 if he works until then).
• Current spending: ~$10K/month, mostly on current lifestyle and kids' expenses.

2. Transition to Next Life Phase

• Timeline: Kay plans to transition careers in the next 11–12 months, considering a new job or endeavor (with an expected minimum income of $60–$75K/year).
• Geographic Flexibility: Considering relocation to a slightly larger or higher-cost area, but aware it may raise expenses.
  • “We do live in a low cost area, we would be assuming a cost even though we. We paid. The house is paid for.” — Kay [05:24]
• Pensions Strategy: Holding off on early withdrawals to maximize payouts, especially Eric's federal pension (doubles from $1,500/month at 57 to $3,000/month at 60).

3. Drawdown Strategy and Tax Planning

• No More Pre-Tax Contributions: Jill strongly recommends that, after Kay’s transition, both should stop making pre-tax retirement contributions.
  • “We have to stop with your pre-tax stuff. I think that what happens is for the years of 55 to 60, you guys keep, this is—again, we don't know what's happening tax law-wise. But let's pretend everything is the same.” — Jill [10:42]
• Switch to Roth and Brokerage: Any future savings should go into Roth IRAs (if allowed) or the taxable brokerage account.
• Withdrawal Discipline: Jill prescribes setting automatic withdrawals from retirement accounts to mimic income, preventing hoarding and supporting lifestyle needs.
  • “You’re going to make it an automatic transfer and you’re going to treat it like it’s income to you...If I have to rely on you to just pull the money out when you need it, you won't spend the money. And that's not good.” — Jill [11:47]
• Bridging Income Before Pensions: From 60 to 62, after Eric’s pension starts, draw necessary funds from retirement accounts to meet living needs.
• Cash Buffer: Keep 1–2 years’ living expenses liquid—approximately $250K in cash at retirement kickoff.
• Social Security: Delay claiming until age 70.

4. Emotional & Psychological Considerations

• Main Anxiety: Difficulty transitioning from “saving” to “spending” mode.
  • “Because you’re the types of people that know how to put money in. You don’t know how to take money out.” — Jill [11:45]
• Jill’s Assurance: Their careful planning earns them “a lot of opportunity,” and the systematic approach should alleviate their worries.
  • “There is nothing here that scares me about where you are. What scares you guys?” — Jill [13:50]
  • “I feel so much better just listening to you lay out the process because I can follow the directions... I feel like a weight has lifted.” — Kay [14:02]

5. Loose Ends and Best Practices

• Estate Planning: Documents are in place (“We do, actually.” — Kay [14:31])
• Life Insurance: Only term life policies, nothing unnecessary.
• Recognition: Jill commends their discipline and low-cost lifestyle.
  • “You are the dream for people on our program because, I don’t know, you guys make a lot of money and you are in a low cost area...You have bought yourself a lot of opportunity. So well done.” — Jill [14:40, 15:06]

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Notable Quotes & Memorable Moments

• On Living Beneath Means:
  “We live well beneath our means, obviously, that kind of place. We're very blessed that way.” — Eric [03:17]
• Addressing the Emotional Leap:
  “You’re going to turn your retirement account into an annuity...all we’re doing is automatically making sure it comes to you so you can spend it and have money and have fun.” — Jill [11:45]
• On Future Uncertainty:
  “If something changes, like tax brackets change or, or your plans change, anything that changes, we’re here for you.” — Jill [13:38]
• Listener Relief:
  “Now we have a plan, and I feel like a weight has lifted.” — Kay [14:10]

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Timestamps for Important Segments

• [01:34] – Kay and Eric share their financial background and discipline
• [02:46] – Details on retirement and brokerage account balances
• [03:39] – College funding for kids and home value
• [05:24] – Consideration of relocation and cost impacts
• [05:45] – Breakdown of pension values and timing
• [06:28] – Reviewing monthly expenses and lifestyle choices
• [08:09] – Eric considers the trade-offs of retiring before/after pension thresholds
• [10:42] – Jill instructs to halt pre-tax retirement contributions
• [11:45] – Jill outlines the psychological and logistical aspects of the drawdown phase
• [13:38] – Flexibility and contingency planning if tax laws or plans change
• [14:10] – Kay expresses gratitude and relief at the clear, stepwise plan
• [14:31] – Confirmation of estate planning and insurance
• [15:06] – Jill celebrates their financial diligence and opportunity

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Recap & Tone

This episode exemplifies Jill’s practical, empathetic approach. With a conversational tone, she dismantles the complexity of asset decumulation, gives concrete action items, and offers emotional reassurance. The conversation is candid, affirming, and offers a model for disciplined savers approaching the psychological shift of retirement.

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Transcript

[A]

Hey, gang. Now you know that we have not yet gotten into the merch business full time, but I was thinking about how easy it could be after I created these beautiful pullovers at vistaprint. I chose a pullover, but boy, the options are incredible. And what stands out is how vistaprint makes it simple for small businesses like ours to look professional without the headache. Their design tools are so easy to use, and if you need extra help, real people are ready to guide you. Whether you're creating merch, signage or thoughtful gifts for your audience, vistaprint helps you do it all quickly, easily, and within your budget. It definitely inspired me to think bigger about the podcast. So now we're looking at other items that we could customize. Maybe something like a water bottle. It's so easy. Vistaprint print your possible. Right now, new customers get 20% off with code NEW20@Vistaprint. Welcome to the Jill on Money show. It's Tuesday, April 14th and we are here answering your financial questions. If you've got one, just go to jillonmoney.com and click the contact us button. While you're on the website, don't forget to check out all of the content that lives there. We've got another podcast. It's called Money Watch. We drop that on the weekends. There's a blog, we've got a radio show, we've got videos, and we've got resources all there for [e-mail] right now. Let's talk to Kay and Eric. They're from the Mid Atlantic, so a

[B]

little bit of background. Eric and I turn 54 this year. We're both professionals, high stress job and I'm actually committed to the concept of find. There's some other things I'd like to do with my life experience and talent. And as we start looking at that transition, our final kid will be in college. We wanted to do a check because we don't wanna do something dumb and we have been really boring. You tell us to save 30% of our net income and dollar cost average and put it in an index fund. Well, that's what we've done. And so now we want to kind of give you the snapshot. And what do we measure now going forward? That we're transitioning.

[A]

Okay, that's fantastic. So tell us about your income level. So you said you're both in high stress jobs. So let's start with you, Kay. How much do you earn?

[B]

About 225.

[A]

Wow. All right. And are you maxing out your retirement contribution?

[B]

Yes.

[A]

And are you Doing the catch up also. So the extra money because you're over the age of 50.

[B]

Yes.

[A]

All right, fantastic. How much money is in your retirement account?

[B]

So the 401ks total for Eric and myself, about 2.5 million.

[A]

Whoa. That's going far. In the middle of the Atlantic coast. All right. And Eric is also maxing out his retirement, presumably. How much does Eric make?

[C]

175.

[A]

Is there other money besides the retirement assets that you've sucked away?

[B]

Yeah. So we have about 2.1 million in a brokerage account.

[A]

Okay. This is awesome.

[C]

We live well beneath our means, obviously, that kind of place. And we're very. We're very blessed that way.

[B]

Also, we follow directions really well. We really have been saving and dollar cost averaging. And because we listen to your show, Joe, we've been socking away cash. So we have about 230,000 in cash.

[A]

Wow. Wow. All right, well, you mentioned some kids, so how old are they and where are they?

[B]

So they are 17, almost 18 and 19. So I have a sophomore in college and a high school senior.

[A]

Okay, and the sophomore in college. Have you saved money for college or is it. Are you paying through cash flow?

[B]

No. So we saved it. We've got about 200 for each kid saved. Whoa.

[A]

Is that going to be more than you need? Are they going to. Well, is sophomore in state school?

[B]

Yeah, she's in state school and probably looking at grad school. And the younger one has aspirations of becoming an orthodontist. So.

[A]

Wait a minute. Stop right there. Who has a child who wants to be an orthodontist? You must have had an amazing orthodontist experience if your kid wants to be one.

[B]

So I have to tell you, because that kid has had one of everything wrong with her teeth starting from the day she was born. Her philosophy is I can guide anyone through it.

[A]

All right, let's talk about the game plan and the timing of the game plan. So, Kay, when you say you're committed to financial independence, next endeavor, when do we want this to happen?

[B]

So I'm giving myself the next, like 11 to 12 months to really start focusing on what my next position would look like. Also, because again, we don't want to make dumb mistakes going forward if we're not saving as much or if we need to be diffusing the tax time bomb or all these things that we hear about that we know we need to do, but we don't really know the steps to address it. So I need to take a lot of varied experience, start focusing a search a Location. And just to throw a little bit of a wrinkle, there is a possibility we would want to geographically relocate. Maybe not necessarily retire where we are right now.

[A]

Okay.

[B]

Maybe a slightly larger area. Not big, but it would. Because we do live in a low cost area, we would be assuming a cost even though we. We paid. The house is paid for.

[A]

How much is it worth?

[B]

Probably about 230. Are there pensions with these jobs? Yes.

[A]

Brilliant. Okay, tell us about the pensions.

[B]

So I have a residual government pension from a previous job that's probably going to be around $2,100 a month. And Eric is going to have two pensions. He's going to have a state pension and a federal pension. And his state pension right now is probably going to be about $1,500 a month. And you can explain your federal pension.

[C]

It depends on the years of service. But if I left at age 57, it would be about $1,500 a month. If I make it to age 60, it boosts all the way up to $3,000 a month.

[A]

Wow, that's a big difference. Let's see if you may not even need to. Okay, so today, under where we are today, living where you live, what do you think your expenses are?

[B]

So we spend about $10,000 a month.

[A]

Okay.

[B]

On everything.

[A]

Okay. And if you move to a different area, maybe that would be $12,000 a month. What do you think?

[B]

So we're actually grappling with that because right now a lot of what we spend a month is related to travel, sports and stuff to do with the kids that we wouldn't necessarily pay for. And we're assuming that we're going to continue to spend the same because it'll be like dating with money this time. So we're kind of stuck at the 10,000. And what we thought we might do is have like that oh, crap fund, like if something came across, you had to replace the refrigerator or something like that to kind of even it out until we really understand how much it does cost us to live.

[A]

And Kay, when you said your pension of $2,100 a month, when would that crank in? At what timing is this?

[B]

62.

[A]

62. Okay. And Eric's state pension, was that also a 60 or 62 or is that

[B]

a now it's a 62.

[A]

Eric, what is your ideal when you think about it? Like, is it 60? What's your really like in your heart? Pretend she's not sitting there next to you.

[C]

In my heart, I can go as soon as three years and 10 months. But it's very punitive. And I don't like the idea that if I leave early that they permanently reduce your pension. Then I would be first eligible in 20 years. So to answer your specific question, I like running the numbers at making it to age 57 when I would be eligible for a somewhat reduced pension. That's the first number we gave you. So in my heart, I probably will go to 60 just because I can't stand to leave that much money on the table.

[A]

Me too. And I, of course, don't have to do your work. But I felt the same way when you gave me the 1500 to 3000. I was Mark, I'm sure, was feeling that way now. The other thing is, though, I mean, if it's 60, then you're kind of stuck where you are for six more years. Kay. Are you okay with that?

[B]

Yeah.

[A]

Yeah. You could do that. Like, as long as you're doing your thing, like you do your. You, you do you. Eric, I'm going to go find myself in my fine environment. Right.

[C]

She's worked harder than me. She outearns me for the vast bulk of her career, so I defer to her.

[A]

Okay, so let's pretend. Let's just do this. Like, how we can try to do it. Let's say you're going to work for another year, okay? So Now, K, you're 55 and you're done working at this current job. Whatever you do next, you know, are you going to go on a Buddhist retreat for five years or do you think you'll make some money? Those are the only choices you have?

[B]

No, I'll make some money.

[A]

What? I mean, what's the least amount of money you could imagine making from, say, 55 to 60? Like, how much a year would you say? Like, oh, this is like a slam dunk. I can make blank a year.

[B]

75.

[A]

What if I even say 60? I'm just gonna say 60 for the hell of it. I don't want any pressure on you now. Eric's still making his 175, right? From 55 to 60, right. You can cover your needs, you can get your kids through school. You're like, done, right? So essentially what we're saying, from 55 to 60, you got plenty of money. You can float your needs, you can keep stockpiling some money. There's no debt to pay down. But the pressure's off, you K at this point, and you can do what you want. And it's. Everything is fine, and you don't even have to worry about putting money into a broke into the retirement account. I mean the two and a half million bucks that you guys have socked away, I presume it's pre tax, right?

[B]

Yeah. We only have 350 in a Roth, so the rest of it's pre tax.

[A]

Okay. Like there is a, there is a case to be made that you should convert. Okay. It's just that it soaks up the money that's in that brokerage account. We got to spend your money down. I don't know if you're going to feel great about that. I don't feel so great about that because I don't know where you're really going to land. So that would then mean, you know, of the 2 million or so, more than $2 million, that's pre tax. I think what I would suggest is that in a year, uk, whatever you make, you're not putting any more money into retirement. I'm not even so sure. Should Eric put money into a pre tax retirement account, Mark?

[B]

Pre tax? No, no way.

[A]

I don't think so either. I think we got to get, we have to stop with your pre tax stuff. I think that what happens is that for the years of 55 to 60, you guys keep. This is. Again, we don't know what's happening. Tax law rise. But let's pretend everything is the same. Live as you live from 55 to 60 with no pressure on putting money into your retirement accounts. I would instead pay the whatever taxes due and pop it in the brokerage account. Or if you wanted to, if you wanted to put some money away, put it in the Roth. Okay. And just make that Roth now from age 60 to 62. Right. Because we haven't started receiving any pensions or actually I should say that Eric's pension starts at 60. So then we have three grand a month from 60 to 62. And then you fund the difference by pulling money out of your retirement accounts to live on and pay the tax along the way. This is going to be so hard for you guys. I'll tell you why. Because you're the types of people that know how to put money in. You don't know how to take money out.

[C]

This is true.

[A]

Right? We're going to have to set it up so that. Let's just pretend it's like the beginning of your 60th year, right? You're 59, 60 years old. You look at your retirement accounts, your pre tax accounts and we know that you need, let's say you need seven grand net out of that in addition to your $3,000 a month from Eric's pension. Okay, so we're going to probably need to have you take about, let's call it $120,000 in your retirement accounts and put it in cash. And you're going to set something up at the beginning of the year and you're going to say ten grand a month is coming out of this account and going into our checking accounts. You're going to make it an automatic transfer and you're going to treat it like it's income to you. Like you pretend. You're going to say, oh, I'm just paying myself. This is great. You're going to turn your retirement account into an annuity. If I have to rely on you to just pull the money out when you need it, you won't spend the money. And that's not good. That's not the whole point of this. The point is that you have built this huge cash account. It's sitting in the ATM and all we're doing is automatically making sure it comes to you so you can spend it and have money and have fun. You'll have three grand a month that's taxable. You'll take ten grand from the retirement account a month. You make sure that money is in cash. You probably want two years. You're probably going to need at the beginning of your year that you turn 60, you are going to need to have like probably 250 grand in cash. You want two years in cash so you have it or maybe a year. It's really up to you. I just need to make sure you take that money out. And every year you are going to make sure you pull money out of this account and the amount will change when you're 62 and those two other pensions come into play and you're going to reduce that amount. But basically between age 60 and 70, you're going to use the money that's in the pre tax account to live on. You're going to pay the tax that's due and that's it. And you're going to claim your Social Security when you're 70. And we leave the option to come back and have you guys come back on the air. If something changes, like tax brackets change or, or your plans change, anything that changes, we're here for you. But this is so perfect. You can do this. There is nothing here that scares me about where you are. What scares you guys?

[B]

Actually, I feel so much better just listening to you lay out the process because I can follow the directions that makes me Feel a lot better. And now we have a plan, and I feel like a weight has lifted.

[A]

Thank you, Mark. I'm a dream maker today. Now, a few other odds and ends. Okay, number one, do you guys have your estate documents in place? Because I know you're two lawyers, which probably means no.

[B]

No, we do, actually.

[A]

All right, good. Excellent. And do you have any old life insurance policies floating around?

[B]

No.

[A]

Okay.

[C]

We have term life.

[A]

Good. I honestly feel like you are the. The dream for. For people on our program because, I don't know, I sort of feel like in many cases, you guys make a lot of money and you are in a low cost area. So that's true. But you've diligently socked it away. You don't live in a $2 million house, which is helpful. Right. I feel like there's going to be a real option for you to do something exciting in this next move.

[C]

Kay.

[A]

Let us know what you decide to do next. This is very exciting for us and we're excited for you. So congratulations. You really have bought yourself a lot of opportunity. So well done.

[B]

Thank you.

[C]

Thank you very much.

[A]

Are you weighing a big decision? Do you need a little assistance? Get in touch with us. Go to jillonmoney.com and click the contact us button. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. We always ask that you do something nice for someone else today. Change your work, change your wealth, change your life. Thanks so much for listening. We'll talk to you tomorrow.

[D]

Hi, my name is Lloyd Lockridge and I'm the host of a new podcast from Odyssey called Family Lore. In this podcast, I'm going to have people on to tell unusual and sometimes far fetched stories about their families.

[A]

I've heard my whole life that she invented the margarita.

[D]

And then we're going to investigate those stories and find out how much of it is true. He gets a patent one month before the Wright brothers. Oh, my God. Please follow and listen to Family Lore, an Odyssey podcast, available now on Apple Podcasts, Spotify or wherever you get your shows.