44 Years Old, $2 Million Saved – Why They're Still Hesitant to Downshift

16 Dec 2025 · 56 min

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Afford Anything Podcast Episode Notes

Episode Title

44 Years Old, $2 Million Saved – Why They're Still Hesitant to Downshift

Episode Number

#669

Host

Paula Pant

Guest

Joe Solcihai

Date

Latest Episode Release

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Episode Summary In this episode, hosts Paula Pant and Joe Solcihai engage with listeners who have significant financial queries regarding investments, retirement accounts, education funding, and effective money allocation strategies. They answer three main questions from listeners named Slade, David, and Graham, exploring concepts such as downshifting career paths, college funding options, and tax-efficient investment strategies.

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Key Topics Discussed

  1. Slade's Transition to a Downshifted Career
  2. Background: Slade, 44, plans to downshift his career in the next 5-7 years while raising his 11-year-old daughter.
  3. Financial Situation:
  4. $685K in a brokerage account.
  5. $1 million in traditional retirement accounts and $370K in Roth IRAs.
  6. Annual expenses: $115,000.
  7. Questions:
  8. Should they shift towards bonds to de-risk their investment?
  9. Should they consider a 72T distribution to access retirement funds early?

Key Insights

  • Taxable Brokerage Allocation: Hosts advise focusing on the taxable brokerage account and adjusting asset allocation to reduce volatility while maximizing growth potential.
  • Opinion on 72T: Paula expresses hesitance towards using 72T due to the mandatory long-term withdrawals which could impact financial flexibility.
  • Investment Strategy: Suggestion to consider value stocks instead of bonds to mitigate risks without locking in smaller growth opportunities.

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  1. David's College Funding Dilemma
  2. Background: David has a high school senior and is considering the best account to withdraw from for college expenses.
  3. Financial Situation:
  4. $60K in a 529 college savings plan.
  5. $200K in a 457(b) plan from a former employer.

Key Insights

  • Recommendation: Paula suggests utilizing the 529 plan first since it's specifically allocated for educational expenses, allowing the 457(b) to remain as a flexible safety net.
  • Legacy Considerations: Discussion on whether David wishes to establish a family educational trust for potential future grandchildren through the 529 plan.

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  1. Graham's Tax-Efficient Investment Strategy
  2. Background: Graham questions how to balance investments in taxable accounts while avoiding capital gains taxes.

Key Insights

  • Asset Swap Strategy: Graham proposes a workaround for managing asset allocation without incurring capital gains taxes through an "asset swap."
  • Involves selling equities in taxable accounts while simultaneously reallocating bonds from pre-tax retirement accounts.
  • Flexibility vs. Complexity: Hosts highlight the strategy's efficiency but caution against the potential complexity and behavioral challenges it presents for the average investor.

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Key Takeaways

  • Planning for the Future: Emphasizing the importance of planning for future financial needs, particularly in terms of retirement and education funding.
  • Behavioral Finance: The conversation touches on the psychological aspects of financial planning, including how emotions and behaviors can impact investment decisions.
  • Flexibility in Financial Strategies: Importance of maintaining flexibility in investment strategies to accommodate life changes and unexpected financial needs.
  • Tax Efficiency: The necessity to consider tax implications when planning withdrawals from retirement accounts and allocating investments.

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Additional Resources

  • Free Book: Download "Escape" at [affordanything.com/escape](http://affordanything.com/escape).
  • Community Engagement: Join discussions on the topics covered in this episode at [affordanything.com/community](http://affordanything.com/community).

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Conclusion This episode of the Afford Anything podcast provides listeners with valuable insights into financial planning, offering a blend of practical advice and theoretical concepts that help navigate complex financial situations. Through listener questions, Paula and Joe illustrate the importance of creating a tailored financial strategy that considers personal goals, tax implications, and market conditions.

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Transcript

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0:00Joe, it's been a minute. Welcome back from Europe. Well, thank you. I made it back safely. The Christmas markets, however, are devastated I'm gone because I felt like between my mom, my spouse, and I, the GDP of the EU is going to be just fine. You are single-handedly responsible for GDP growth in the EU. When you come home with seven of those Christmas market mugs and you're like, why seven? Why not one? But every single one you go to, you're like, oh, that's pretty too. You know what? We could just bring these out around the holidays because God knows I love to store crap for 11 months and bring it out for just one.

0:38Well, you've got one mug for every day of the week. That's good. It's like I'm starting my Advent mug collection. I don't know. Well, maybe. Hopefully not. Well, speaking of days of the week, I don't know how to segue that. We've got some great callers today. That has nothing to do with days of the week. Welcome to the Afford Anything podcast, the show that knows you can afford anything, not everything. The show covers five pillars, financial psychology, increasing your income, investing, real estate, and entrepreneurship. It's double I fire. I'm your host, Paula Pant. I trained in economic reporting at Columbia.

1:11Every other-ish episode, unless Joe's on vacation, I answer questions that come from you and I do so with my buddy, Joe, who has been absent for a little, he's been traveling. I have been. Welcome back. Thank you. I also kept up the dad jokes, though, just for you. So you know what you call a paper airplane that doesn't fly? What? Stationary.

1:41And with that, we will hear our first question today, which comes from Slade. Hi, Paula and Joe. This is Slade in Virginia. I have a few details I'd like you to hear to see if you could help guide me into the next steps or some reallocation of my brokerage account. My wife and I are both 44 years old and have an 11-year-old daughter. In the next five to seven years, we are both looking to downshift in our careers or find something that pays much less. We would like your thoughts on withdrawal order and allocation. We spend about$115 ,000 a year. Currently, all of our tax-deferred and tax-free retirement are allocated in about 60 % S &P 500 funds, 15 % international, 15 % small cap, and about 10 % mid-cap.

2:26We have about$1 million in traditional retirement and$370 ,000 in Roth. We also have about$36 ,000 in HSA and$75 ,000 in 529s. Our taxable brokerage, however, is worth about$685 ,000 and is split between about 85 % S &P 500 funds and 15 % small cap. Over the next five to seven years, while we continue to work our current jobs that pay well, if we want to live off our taxable brokerage after that, should we start to heavily work bonds into that allocation to de-risk? Should we consider a 72T? Looking for any guidance to help make this possible? Thanks so much. Slade, I love your question. And first of all, congratulations on building such a healthy portfolio and on having such clear, well-thought-out goals.

3:15I love the foundation that you're starting with. Personally, and Joe, we have not discussed this ahead of time, so I'm curious to see if we fall into the same camp here. I am actually not a huge fan of the 72T in Slade's situation because they have so much in taxable brokerage accounts and they've got enough time until their goal and their goal involves taking significantly lower paying work, but there's still going to be some income coming in and their annual cost of living at 115 ,000. That's a very, given the balances that he's talked about and given the whole set of circumstances that I've just outlined, a fairly achievable number.

3:57Based on all of that, I'm not a huge fan of the 72T. I think I'd like to focus on the taxable brokerage portion. What do you think, Joe? I tend to agree. Here's the one piece of information, Slade, that we don't have that would help me with 72T, which is when you talk about the difference between what you're making now and what your income stream's going to be later, I don't know what that delta is. So I don't know how much we're trying to take per year. And I'll tell you why that's important is that when it comes to 72T, one fun reason to take 72T, I like working fun into 72T because anybody who knows this knows it's not that fun, but it gives you some opportunities for some clever financial planning.

4:44So if you use some software and you look out, you project out later on with your traditional retirement accounts, there are some hurdles that you're going to need to overcome later. Number one, there's going to be taxation of your social security. And this just assumes things stay the same. Number two is there's this little thing that we probably won't get into today, but people should look it up called IRMA, which is another tax-ish hurdle that can be caused by taking too much money out of your traditional retirement account. So what I get worried about, Paula, is that the traditional retirement account might grow too big.

5:25And if it does, we might cause some tax problems down the road by not tapping it. Now, the cool thing with 72T is you can segregate your retirement accounts. Let's talk about what this is first. So 72T for people like, what the hell are you even talking about? What this question revolves around is, should I take my money in traditional retirement accounts and tap it legally and without penalty before 59 and a half? People have probably heard that you can't do it before 59 and a half. Cool thing is you can, but you have to follow some specific rules. And basically what the IRS makes you do is turn it into a pension.

6:08And that pension has to run for at least five years or until 59 and a half, whichever is longer. So at 44 years old, if Slade goes at 50, Slade will need to continue to take this, quote, pension for nine and a half years, for 10 years. If you want a super deep dive into 72T, go all the way back to episode number 94. It's funny to state a two-digit number now that we're at, what, 600 and something. But if you go all the way back to affordanything.com slash episode 94, we do a deep dive into SCP-72T. That's awesome. That's great. Well, and you know what's cool is it is like riding a bike. Once you know it, once you know it, you got it.

6:56I mean, episode 94, it doesn't matter what episode number it is because it's a training thing that, frankly, probably doesn't need to be done again. It's an evergreen topic, right? Well, that's what I meant. Yeah. It's not like the first Friday macroeconomic episode when I'm, you know, here's the inflation data. Well, you know, it's not something that changes every month. It's very steady. You can tell them just back from vacation. I use 84 words. Paula uses two evergreen topic to explain the mess of words that I had just before that. But the deal is, is that Paula, Well, I think you could use 72T in a cool way.

7:35So what most people think with 72T, and this is where people get it wrong, is that you got to take all your retirement accounts and turn it into a pension. Well, what's cool is you can segregate your retirement accounts and only use a piece of it. So I could 72T this one fund over here and not 72T these other fund. And that gives me the opportunity to build a small quote pension ish stream of income that comes out between now and age 60. I reduce my taxation after age 60 because I keep that retirement account value smaller, a little smaller. and I then am able to do some tax planning today, get the money that I need today.

8:22And that also leaves some of that brokerage money available for later, which is also pretty cool because that brokerage account represents flexibility. Now, like you, I don't think they're going to spend on all the brokerage account. I don't think they will, but I'd love to know how much money they think they're going to make and use a conservative number, how much money you think you're going to make. and then maybe see about a hybrid of I'm going to spend most of the money through my brokerage account. But then I'm also going to, because I did some projections of the future of how much money I'm going to have to take out of this later.

8:57If those numbers are problematic way down the road, I could do some cool planning at age 50 to lessen the load after 60, 65, 70, 75 years old. Yeah. I mean, so fundamentally, right, they're 44 right now. They're talking about doing this within five to seven years. Let's split the difference and say six years. They do it at the age of 50. And we're trying to plug this nine and a half year gap from 50 to 59 and a half. again with 685 ,000 in the taxable brokerage rule of 72 assuming that the market does in the next six years what it did in the last six years which we can't necessarily assume that but there's a pretty good chance that taxable brokerage account is going to be over a million by the time they turn 50.

9:48I think there's a reasonable likelihood that it'll be around a million. And so we're trying to plug in nine and a half year gap with a million bucks in taxable brokerage when their annual spend is 115 ,000, adjust that for inflation by the time they turn 50. It seems like they can, especially given that even if they earned a pretty small incomes, I think they could do the whole thing out of taxable brokerage. Oh no, they could easily do it out of taxable brokerage. My question wasn't around that. When And I said, I want to know what the Delta is. My question is, how big do I make that 72T to avoid further taxation?

10:25Further taxation down the road. Let's be clear. I'm not worried at all about making it. Slade, you're going to be fine. You're going to be great. Love your allocation, by the way, the way it is right now. I think it's fantastic. We can talk about how you switch that over. But yeah, the 72T thing, I don't like doing it generally. but in this case, because also when you talk about the rule of 72, Paula, that 1 million in a traditional account by the time he gets to 59 and a half is also going to be double. Yeah, it's going to be 2 point something million dollars sitting there. Yeah. So if we go to tax expert, I mean, uh, my friend Ed slot wrote this book, you know, the tax time bomb.

11:07I'm looking at this time bomb possibly with that traditional retirement account. So I'm just trying to diffuse that bomb and use 72T that way. Now, the good news, Slade, let's go through the good news. You could pay all these additional taxes, and I think you're still going to be fine. So this is really much more advanced planning that we're talking about, much more advanced tax planning we're talking about. You could do none of that, and you're going to be okay. You're going to be fine. So then the question comes around, what are your legacy goals? What are your really beyond your lifetime goals with your money?

11:45And that's when financial planning gets even more exciting, Paula, because Slade and his family may be able to change the world. The other thing to note, Slade, your daughter's 11 right now. Six years from now, she'll be 17. She'll be on the verge of moving out, going to college. Your annual expenses will likely drop at that time. I mean, your college expenses are going to be high, but the 529 covers that. But your day-to-day, the amount of groceries that you have to put in the fridge, the cost of clothing, the cost of all of those miscellaneous daily cost of living items, a lot of that will likely shrink right at the time that you're making this transition.

12:30So I think it's wise to plan for your annual spending to remain at 115 where it currently is. but I think there's also a decent probability that that annual spend might shrink. Yeah. Without any lifestyle change at all. Yeah. Without any meaningful feeling that it'll change. Yeah. Joe, I know you experienced that when your twins went to college. Oh my God. When my son left home, my grocery bill just shrunk by so much. University of Texas had a food program along with his dorm. And when I saw that number, I laughed. I'm like, you're going to to lose. My son will eat that and more. What's amazing is for people that know him and you've met him, Paul, he's not a big dude, not a big dude, but he could put it away in college course.

13:18So could I, but it's a whole different story. Yeah. The metabolism of an 18 year old. Yeah. Yeah. So jealous. Now I look at a Cinnabon and I gained 10 pounds. Can we talk about the switch in allocation? Yeah, let's do it. There is this problem, Slade, that I think of as the bond problem. On one hand, you hit the nail on the head, you're reducing volatility. On the other hand, you're locking in much smaller opportunities for growth. And you're also creating some tax issues if you just hit this straight forward. If you just change over some of your funds and your brokerage account to bonds, you create additional taxes and you lock in really suboptimal returns.

14:07The issue with bonds that I have is that whenever I think about a portfolio, I always think of bonds as something I'm trying to have as few of as possible while also not wrecking my ability to meet my goals. I would want to talk more about risk tolerance here and how you react to changing markets. And based on your current asset allocation, this money in the S &P 500, small cap to mid cap, your diversification looks really good to me without doing a lot of analysis, just looking at it. I think it looks great. I do think that you need to back off. So your gut feeling of, okay, the plane's coming in for a landing.

15:02I need to back it down. I think you're right on there. But how much do we back down? And how do we back it down? I think revolves again, Paula, around whether he uses 72T. Because if he uses 72T to diffuse the time bomb, that money's going to be an income stream that he has to take. Then we can do some of this volatility lessening inside of his traditional retirement account. And then we end up with kind of the best of both worlds. Now, if we don't think there's going to be a huge tax bill, if he goes through and he does this research that I'm talking about and it's not going to be a big deal.

15:42Right. Then maybe I go ahead and I put bonds in the account if we want it to be straightforward. We got a great call from Graham Slade. Hold on. Graham's going to explain. this whole thing to you later on, some foreshadowing of later in the episode. Of later in the episode. Yeah. Graham's going to give you kind of the 201 way you could do this and pay less tax. But straightforward wise, I didn't even know that's that straightforward wise. Boy, I'm rusty. Yeah, straightforward wise. Yeah, sure. Yeah. I declare that a word. But to be straightforward about it means you're going to run into some volatility.

16:20So let's go down the ladder first. The first thing you can do is traditionally value stocks have had less volatility than growth stocks. So without going all the way to bonds, right, I could take more of a value oriented tilt because during lean years, value stocks are going to go down less than growth stocks will. So remove some of the growth from your portfolio, go more toward a value bent. But we know, Paula, that utilities, utility stocks, much more conservative, but you don't have to play the bond game. When I look at sectors, the utility sector might be something that he looks at. It's kind of a halfway.

17:03I see people go full force from stocks over to bonds. And I think you can do that with some money. But I think you can also lessen the blow by moving some of your stock allocation to a more conservative stock allocation as well. Well, and I agree with you that the answer to 72T is going to play a big role in this because to your point, Joe, the drawback of 72T and the reason why I'm biased towards taxable brokerage, if you can do it from that, is because of the fact that there is a mandatory annual withdrawal. And whenever you're in a situation where you lack flexibility, you have to curtail your investments and you have to invest a little bit more conservatively because you lack that flexibility.

17:49You know, versus just a hypothetically, if your strategy was entirely to pay for your cost of living through a combination of lower paying work plus withdrawals from the taxable brokerage account, but you could adjust on an annual basis. Maybe there are some years that you make more than you did the previous year. There are some years where maybe there's a year where you decide that you want to spend that time in Bali, where the cost of living is a heck of a lot cheaper. And so you're going to have this dynamism both in your compensation income and also potentially in your expenses. right? There's going to be annual fluctuation there as there is for most people.

18:40And so with a taxable brokerage strategy, you have the freedom and the flexibility to modulate accordingly. And with a 72T strategy, you have to take at least some, whatever portion that is, what that number will be is based on a huge variety of factors. Whatever that number is, you're going to have to take it out every year. And because that is a must and that is a non-negotiable, regardless of what is happening in your life, you do have to invest more conservatively because you don't want to be drawing down from a 2008 scenario. The cool thing is, and this is what people don't know about 72T, is I can make that number fairly small.

19:19Right, right. That 72T doesn't have to be as huge as people think. I said 72T on a$2 million IRA, oh my God, that's going to be just a monster amount of money. And I don't need to take all that money out. Well, you don't have to. That's the cool thing here. So yeah, if we have more of a trickle from the faucet than this huge 72T, I'm all in favor of that. I think a good asset allocation example are foundations, charitable foundations. They are required, the ones that don't do any active work, the ones that are set up for the purpose of making distributions to other charities, they are required to distribute 5 % per year.

20:01And because of that 5 % distribution mandate, they have to invest accordingly. That's the model that comes to mind when I think about the 72T mandate. Yeah. You'll automatically create kind of a two-tier system inside of your traditional retirement accounts. You'll have some sliver of money that's made to continue to fund that I need it now machine. And then the rest of it goes to the far end of your timeline. This is the money that you're letting grow. So it's funny because you'll have your most aggressive money and your most conservative money in traditional retirement accounts. But to get this done, you have to segregate the piece that's 72T money.

20:45It makes it much easier on your dashboard to know which part is the part I'm taking money from because I literally have to have a different IRA for the 72T money than the one that I'm not 72Ting. So dashboard-wise, it's not that hard to grok. But in your head, you're like, I got my most conservative and my most aggressive money in the same what? Same tax treatment? Yes. Slade, I hope that gives you some insight and some next steps. And again, congrats on everything that you've built. I'm excited for this chapter ahead. We're going to take a moment to hear from the sponsors who make this show a reality.

21:27And when we return, we're going to hear from David, who's wondering which account to use first for college costs, 529 or 457B. We're also going to hear from Graham, who has some thoughts on bonds that actually relates to the question that we He just answered from Slade. Kevin Harlan here. Tonight, the NBA on Prime Crew has another thrilling NBA doubleheader. It tips off with an Eastern Conference showdown as Tyrese Maxey and the Philadelphia 76ers head to Madison Square Garden to take on Jalen Brunson and the New York Knicks. Then it's Western Conference action. SGA and the defending champion Oklahoma City Thunder visit Anthony Edwards and the Minnesota Timberwolves.

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25:45Welcome back Our next question comes from David. Hey, Paula and Joe. This is David down in Georgia. I have a senior in high school, and I have a question regarding which of our accounts to draw from first with his educational spending. Currently have about$60 ,000 in a 529 plan. Additionally, my wife is an educator, and we have about$200 ,000 in a 457B plan from a former employer. So theoretically, we have access to that money. My question is, should we draw down on the 457B plan first and pay the little bit of taxes on those? is that would be a taxable event and grow the 529 so that that money could be passed on to our child's progeny.

26:36Should he have some? Or should we draw off of the 529 plan first and avoid touching the 457B as long as possible? In theory, we have enough money in our other accounts based off of the great advice we've gotten from you and others in the community to where we don't necessarily need our 457B money for the purpose of retirement. But again, always nice to have options. Thanks. David, thank you so much for the call. What a great place to be in, Paula, when we have this account from a previous employer that we've done well enough saving that we don't need it. So it can be flexible money for education if we want it to be.

27:21Right. I'm actually going to answer this the opposite way of the way that I answered Slade's question. And the reason is, is I feel like the damage that it creates and the messiness that it creates when you tackle the 457 before the 529 plan outweighs any opportunity benefit that I see. So the first thing that I would do is spend the 529 plan. That's what the money's there for. That's what you saved it for. See how much of that you go through. The cool news is, is you know you have a backup in that 457 money that you don't need. So the college fund is the college fund. Spend the college fund. I'll tell you what really bothers me, Paula, is if they go with the 457 money first, you Besides the wonkiness of trying to get money out of what is traditionally known as a retirement account to spend for college, having 529 money left over afterwards, yeah, okay, I can turn into Roth money if I don't spend it, but I don't see a reason to do that.

28:33If we empty out the account, the goal's over, done, goodbye, don't have to worry about 529 at all anymore. Okay, I'm going to take the opposite argument, but I'm curious to hear your reasoning. 457 money, once you've left the job, you can withdraw it at any time. So why wouldn't you? They've got this bucket of money in the 457 that they don't need for retirement. I'm going to take that statement at face value. I'm going to trust that they've run the numbers and they know that they don't need this bucket of money for retirement. so why not take it and let the 529 become essentially part of the legacy that they pass on to their grandkids you know like a family educational trust type of a thing why wouldn't you do that with the 457 and with the 457 the cool thing is is that you can put just your son as the beneficiary okay done and we have no tax bill at the end of it like he will have if he takes it out during his lifetime.

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29:33I have no reason to touch the 457 money versus the 529. The 529 is built for college. Use it for college. Get it done with. The cool news is this. This, I guess, is the heart of it then, which is 457 money is so flexible and you can leave it in your name and you can use it for life changes. I mean, things happen. My uncle just died. The last year and a half of his life, he needed a bunch more care. I mean, I'm at the stage of life where I know a lot of old people, right? The generation ahead of me is going through those final years. And there are so many expenses that we don't know about. And so if you get to that point in life, and you know you still don't need the money, your kids are still at an age, your son is still at an age where he'll appreciate the fact that you can give it to him during your lifetime.

30:32I've had some family members that we've been lucky enough that have done that with us. And it's cool to give money to people when they're alive. But without David going into more about his personal funds and how close he might be, sure, he might be fine and he's going to be okay. But if the what ifs in life and life changes enough that he's not okay, and I already King Lear'd that money away to my kid. This is your second King Lear reference on this show in the last month. You're welcome. But if I've already done that. Spoiler alert. Spoiler alert on King Lear. King Lear. I hate to spoil Shakespeare for those of you, but did not get taken care of.

31:23It doesn't end well for King Lear. Yeah. But if I give that money away and then I end up needing it later, I mean, I could do the same thing with the 529, but why do I have the 529 still sitting around? Then I got the same rando problem, but it's even more rando because that was college money. Okay. So why is your college fund still sitting there? Well, because I decided to use this excess retirement money that I had because I don't need it anymore. Now, I do love the idea, David, of the 529 being a legacy like education trust. I think that is really cool. In fact, I don't even know, Paula, that we needed this ability to change it over to the Roth IRA.

32:11I can make a lot of arguments about there was already enough flexibility built in, but whatever. I'm not the government. My job is just to help you figure out the way things are now. So I do love that ability to do that. And if there's money left over, then you can still do that. But you can also do it with a 457. And the cool thing is with that beneficiary option on that account, you can do it very easily. If you pass away, you can do it during your lifetime. If you stuff. And the cool thing about the 457 is I have a lot more options for investing it than I do in a 529. Like 529 plans have some cool options, but they're generally limited because of the fact that people are looking at one specific goal.

33:02So I can get a little more creative around the 450s. I just think there's a lot more reason to keep the 457 than there is to keep the 529. I do appreciate that the 457 has more flexibility and also that your costs in retirement, we kind of touched on this with Slade's question, but your costs over the span of your life are highly dynamic. and sometimes bills pop up, particularly around medical care, long-term care, activities of daily living. Bills will often pop up in your final years that you might not have anticipated because your care needs can be so much greater. And I think that is just stepping back from this question and going to a big picture, like philosophical stance on retirement planning.

33:56I think the greatest threat to any retirement plan and the greatest challenge of good retirement planning, planning for those final years. So I do appreciate that if he can fund his retirement out of these various other accounts and keep the 457 as a, in case of emergency, break glass account, with the idea that that account will then pass on to his son if he ends up not needing it. Okay, I definitely appreciate the retirement planning flexibility in that. That being said, when it comes to legacy planning, I think one of the fundamental key questions is, does he want this 529 money? Does he want to pass something down to his grandchild rather than his child?

34:51Does he want it to make sure, essentially, that there's money that's set aside for that grandchild? because if it's 529 money, he knows it's going to be spent on educational purposes or is likely to be spent on educational purposes. Once his son is done with education, that would go to a grandchild versus if his son inherits the 457 money, his son could spend it on whatever. So essentially, I'm being a little bit wordy now, but essentially the question is, how strongly does he want to create a family educational trust and name a grandchild rather than a child as the beneficiary. And he can't literally name a grandchild right now because that grandchild doesn't exist yet.

35:34And you can't name a beneficiary who does not yet exist. So this would be an indirect way to do that. Which brings up the question, the son is a senior in high school. Maybe there is a grandchild. I'm going to never know that. But if there isn't a grandchild yet, And let's say there never is one. If there's a grandchild now, and that is the goal, then certainly Paula, I'm in. I'm in. That's great. Because my goal is to give something to my grandchild. Yeah, we can take care of your kids situation with the 457 money. We got the 529, which is designed for this legacy education thing. Yeah. Okay.

36:19Now I'm using the account the way it was designed. And you know what's cool about this? This is what's really cool about this, David, is that I don't know there's a wrong answer to your question. I truly don't think there is a wrong answer. And I think that Paul and I have explored both sides of the argument. And you probably know based on what you just heard us go through, which way you're thinking about more. the good news here is I don't think there's a ton of pressure on you to get this one 100 % right and that's the cool thing about having that 457 in place yeah is that I think you can go either way and you're going to be okay that said I'm probably right I actually I do agree with that so many of the arguments that I've put forth have been for the sake of playing devil's advocate in order to work through the problem.

37:18But given my predisposition to be extremely worried about end-of-life care, I do like the idea of the 457 being the in-case-of-emergency-break-glass fund for end-of-life care purposes. Because sometimes you get to retirement and realize, you know, the travel in your 60s, discretionary. Take it or leave it. Depending on how strongly you want that, for many people, that might be take it or leave it. Right. This is Paula. I mean, let's give a real world example of somebody that you and I know and your Afford Anything audience has met in a previous episode, our friend Paul Merriman. Paul Merriman has said, and Paul's an older, incredibly dynamic dude, Paul has said in years when the market goes down, he then just explores the Pacific Northwest where he lives because then he doesn't spend as much money.

38:14He still gets to see some cool stuff. And in years when the stock market does really well, back when he was a little younger, he and his spouse, they would then travel the world during those years. So to your point specifically, using a specific, we've seen this work for somebody in action. But the thing that Paul doesn't know about is medical care. And he can't say, well, if the stock market does really good, I'm going to use great medical care. Right. And if the stock market does poorly, I'm going to be rationing my prescriptions. We call it micro dosing.

38:57Oh, this just got dark. That is just horrible. But to your point, there's a big difference. And you know, in the world of financial planning, what you're looking for are periods of your life when there's huge amounts of volatility. There's huge amounts of volatility right out of college or right out of high school because the future is very uncertain. Your income streams are very uncertain. And you haven't yet established a spending pattern for yourself. So a lot could go off the rails. And then you get more established. You get more set in your ways. You're able to develop some planning. And then you go through these years when things are not that volatile.

39:36When you have a job change, things get volatile again. If you decide to turn a significant other into a spouse, things get volatile again. If you have a pet who needs a lot of veterinary care and you don't have pet insurance, things get very volatile again. Well, then anytime a family member, including a pet, happens, things get volatile. So you look for these periods of volatility and how am I going to plan for those? And one period of volatility we know for certain is end-of-life care. You can just look at all of the statistics around the healthcare industry and who most of the care goes to and where most of the dollars go.

40:16And it's people that are within five years of the end of their life. That's when the vast majority, where the vast majority of money is spent. And so that's the period where in financial planning, I'm almost like, I don't know. I don't know. I mean, we all hope that we go quickly, right? There's another spoiler alert, not just the King Lear one. Spoiler alert. None of us get out of here live. I don't know if it's too soon. Death and taxes. To give that away. But David, great question, great thought exercise, and I loved working through it. What a depressing answer we gave him. Well, we're all going to die.

40:59you've got a lot of bills to pay and it culminates in death there's your answer david here's some fodder for the therapist right welcome to the little miss sunshine podcast on that note happy holidays well on on that note should we listen to some ads oh yeah is that what we do next i think that's the best part all right well Well, David, thank you so much for the question. I hope we gave you some food for thought and some insight. Next, we are going to ignore our impending mortality by listening to some words from our sponsors.

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44:16Welcome back. Our final real comment today, not a question but a comment, but a final fodder for discussion comes from Graham. Hi Paula, this is Graham. I loved your recent episode about Brandon's question on holding bonds in his taxable account. You made a great point that since it's his only liquid account for the next 20 years, keeping bonds there makes sense for convenience. But here's the rub. In order for Brandon to diversify and add more bonds, he'll have to sell those beautifully appreciated stocks, and Uncle Sam will be waiting with a costly capital gains bill in hand. Here's a sneaky workaround if he's also got a pre-tax retirement account.

44:58Brandon can sell equities inside the pre-tax account and use that money to buy bonds. Boom, instant diversification, zero capital gains, and bonds are now tucked safely where they won't throw off taxable dividends every year. Fast forward to the next recession. Stocks drop, bonds rise, and Brandon wants to cash out some bonds. But wait, you say? They're locked behind the age 59 and a half gate. No problem. We'll use the asset swap escape hatch. Let's say Brandon wants to withdraw$5 ,000 worth of bonds. Step 1. Brandon's going to sell$5 ,000 worth of equities in his taxable brokerage account and withdraw the cash.

45:40Step 2. In his pre-tax account, Brandon's going to sell$5 ,000 worth of bonds and use the proceeds to buy$5 ,000 of equities. Voila! He's effectively sold bonds and withdrawn$5 ,000, but his overall stock allocation across accounts hasn't budged. Even better, the IRS has no idea a financial magic trick has just happened. The same deal is true with dividends. When bonds in the pre-tax account spit out$1 ,000 in income, he buys$1 ,000 worth of stocks there, sells$1 ,000 of stocks in taxable brokerage, and withdraws it, creating tax-efficient income without disturbing the asset allocation. So Brandon can diversify, rebalance, and pull cash, all while dodging capital gains and dividend taxes.

46:34Hopefully this helps Brandon and others in the same situation. Thanks again for the awesome show, Paul and Jo. Graham, thank you for the comment. Thank you for laying out the asset swap strategy. I love the strategy. It works under the following set of assumptions. You mentioned if there's a recession and there's a scenario in which stocks fall and bonds rise, which often but not always happens, and there have been times when equities and bonds have not been inversely correlated, But if there is a situation in which during a recession, stocks fall, bonds rise, and you want to rebalance your portfolio by virtue of selling out of some of that bond allocation and into buying more equities in a recessionary context, then yes, absolutely.

47:26Well, it can also work for in Slade's situation. And so if Slade is trying to sell and doesn't want to hold bonds in his after-tax portfolio, he'd rather hold them in the pre-tax portfolio. He's going to have to make a few moves instead of making just one, right? You're not just selling and you can't set up just the automatic sale every month, which a lot of retirees prefer to do. You can't do that. So it's a little more time intensive, but you certainly get the workaround that you're looking for. And the beauty, Graham, of the strategy that you laid out is that a person pays long-term capital gains on the equities, the sale of those equities.

48:02And that means that you're getting a much better tax treatment than paying at the income tax level for dividends. So it does overall reduce your tax bill. So we like it, a seal of approval. So the question becomes, if we like it, why haven't we, Paula, talked about doing this in the past? And I can't speak for you, but I can certainly speak for me, almost like the difficulty that we just had with the whole 72T discussion for Slade earlier today and how we get into some really advanced planning. What I found during my financial planning years is this, people will try to do the things that Graham said and behaviorally, it becomes frustrating.

48:51It becomes time intensive. And I I can hear Graham. I can hear you yelling at your device. It's not that time intensive. It isn't if you get it. But if you're somebody who's talking to a wider audience, what I often found was the wrong people would try to implement Graham's strategy. They're hanging out for dear life when it comes to all these concepts. They hear about this. Oh, my God, I can save a bunch of taxes. This is the hidden thing I've been looking for. And then four months later, you're disenchanted. You're frustrated. You have no idea the hell that you created for yourself by having to set these things up on your calendar to do them all the time.

49:28And so you end up doing nothing, which is the most frustrating thing for me, because I think the whole goal, Paula, of the show is to help people do more, not to do less. And so I love this strategy. I think it's a great strategy. I do think that it's going to be something you're going to have to continually cultivate unless now, Graham, if you're just using it once a year for rebalance, then what's this extra step? It's no big deal. You know, then I think your strategy is no big deal. If I'm trying to take a monthly income stream, like Slade's talking about, yeah, I'm doing it swapping every month.

50:10Does it work? Yes. Is it a nightmare? A hundred percent because 12 months a year, I'm digging in, deciding what to sell in my pre-tax and then what to sell in my after-tax. And I'll tell you the other thing that ends up happening is that instead of just selling the obvious thing, this is when the market timing starts coming in, Paula, which is, oh, I have this position. It's quote, doing real good, right? And I don't want to touch it this month, even though my plan, it says to touch it, I'm just going to let my winter run a little bit, or I'm just going to deviate this one time. And you begin creating messes for yourself, which is another reason I like automation.

50:54Unless I give my brain a chance to mess it up, the better off I'm also going to be. I hope Graham, though, you hear that correctly. I don't dislike it. I think it's fantastic. And I think it solves the tax issue that a lot of people face. And specifically, Slade, this is a strategy that might work for you, depending on your ability to be able to do this on a recurring basis. Yeah. I think the reason that my brain immediately locked in on fast forward to the next recession is because that, to your point, Joe, the effort burden of doing it once annually during a recession. Okay, cool. Not so bad.

51:46Assuming it's a recession in which stocks and bonds move inversely to one another, which doesn't always happen. But assuming that that's how a given recession unfolds and you're doing this once a year, cool. But it certainly can become onerous if this is how you're paying yourself monthly, if you're relying on it for a monthly payout that covers your costs of daily living. Yeah. And I think about, even as we were talking about this, okay, so how do I mitigate all those risks? If I set out once a year, a systematic approach of how I'm going to do this. So the only thing I need to do is a few more keystrokes and I'm not going to think about it every month.

52:30I'm just going to do a few more keystrokes that could take this potential hassle and make it fairly, fairly quick and easy as well. But you definitely have to think around the system. What's my system going to be doing this versus every month? How am I magically evading the tax police? I will also say, and Joe and I are both coming from the perspective of we hear the questions that we get from a wider audience and we hear how those questions change depending on what's happening in the broader market. And of course, your individual behavior patterns will vary. but listening to a mass aggregate audience, no matter how many times we say time in the market is more important than time in the market, we say that till we're blue in the face.

53:22And yet, every time something happens, we get calls from people saying, this time it's different. We heard it during the pandemic. We heard it this past April, April of 2025, when there was that very brief, but pretty extreme market dip, we hear it over and over and over. And so we know from hearing the types of questions that we receive every time the market goes down, that it is hard for many people to stay on track, stay on plan when the reality of a diminished portfolio hits. When you log into that Vanguard account and you see the numbers and they are much smaller numbers than what you're used to seeing, there is an emotional gut response.

54:14So much of what we do and what we talk about is to help people protect themselves from the downsides of that. Which often are behavioral. It's a reason why people efficiently pay off debt. You're going to win because of the behavior change, not because of the interest rate. Mathematically, it's a bad move. Behaviorally, it's a fantastic move. You're referring to the debt snowball? Yeah. Yeah, behaviorally, it's a wonderful move. That win that you experience when you pay off that smallest one. It was also the number one reason I think that people, when I was a financial planner, hired me. Just the fact that we were going to check in four times a year and they were going to be physically in my office twice a year.

54:59Was this accountability pattern that behaviorally worked? You know, you'll see all day online. Don't hire somebody. You can do this yourself. I mean, I'm not going to go back through that diatribe. But I think the number one reason was because behaviorally, if I've got a check-in, if there's somebody holding me accountable, I'm going to do it. I talked about before, I'm planning for this race, this race in our community in Texarkana, half marathon to benefit our walking trails in town. We have a meeting every month. My job is to help with publicity. I will tell you more gets done in the area of publicity the three days before that meeting than happens the 27 other days.

55:39So behaviorally, these check-ins, these things matter. They 100 % matter. Yeah. I take standup comedy classes every Wednesday night. You know, when I write most of my jokes, Wednesday afternoon. Exactly. Right. Yeah. It's the reason people cram for a test. Yeah, exactly. Because I know I'm going to class that night. I know I'm going to have to stand up in front of the class and do an act. And so every Wednesday evening, I am standing up doing an act that I have just written and have not practiced, but I got it written. But thank you, Graham, for contributing to the conversation. I love the asset swap strategy.

56:23Let's continue the conversation in the broader community, affordanything.com slash community. It's a great place to go to talk to like-minded people about all of these topics and more. Totally free. Affordanything.com slash community. Joe, we did it again. I can't believe it. Another one. In the history books. In the bag. Yes. All right. When you are not buying your seven-day, your Advent Christmas mug collection. If somebody would like to take that off my hands, by the way, just write me. I will send you some Christmas mugs because I have 30. No, I have seven. When you're not importing mugs from, where were you?

57:06I was floating down the Rhine River. Ah, nice. I've started in Cologne and ended in Basel and went through Strasbourg and a few small cities a long way. Just fantastic trip. Oh, beautiful, beautiful. Well, when you're back at home, where can people find you? Well, even if I'm not at home, which I'll be home off and on, but the show must go on and it does at Stacking Benjamins. We're at end of the year time, which every year we have a few traditions. Number one is we have our fantastic roundtable with Paula, Jesse Kramer and OG, Doug and I about what should we have learned from the events of 2025.

57:49The following Monday, we always have guests from the personal finance community. It's been people like David Bach, Jill Schlesinger, Gene Chatzky. This year, we have Joel and Matt from How to Money who are joining us. Yeah. And the reason we have Joel and Matt on is because we kicked their a** at a fundraising competition in November. So I just want to say that as well. We have a lot of fun on that episode, but we also get these wonderful guys take on what they think at the end of the year. Then we go into our year-end holiday, which we look back five years ago, Paula, and take our greatest hits from five years ago and play them every day during the week between Christmas and New Year's.

58:33So people get to hear these fantastic interviews from five years ago. And we're going to replay our number one hit from 2025, which our most listened to episode was with Alex Harmozy. and on Christmas Eve, we're going to replay our favorite yearly tradition, Doug and the Three Ghosts, which is this totally story that I came up with myself with no help about how Doug gets visited by these three ghosts in the course of one night and it changes his life. No inspiration from anywhere in particular. Do we have to spoiler alert this one? So lots of holiday festivities happening at Stacking Benjamins.

59:19That's great. Well, you can find all of that on the Stacking Benjamins podcast. Thank you all for being part of this community. If you enjoyed today's episode, please do three things. First, subscribe to the newsletter, affordanything.com slash newsletter. Second, open your favorite podcast playing app, hit the follow button so you don't miss any amazing upcoming episodes. And third, while you're there, please leave us up to a five-star review. F-I-I-R-E. Five stars for five letters and five days of the week. Thank you again for being an Afforder. I'm Paula Pant. I'm Joe Solcihai. And we'll meet you in the next episode.

From the publisher

#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K brokerage account and plan withdrawals to make the transition financially smooth.

David (21:50) - David has a high school senior and is deciding how to pay for college. Should he tap the $60K 529 plan now or the $200K 457(b) from his wife’s former employer to maximize tax efficiency and preserve future growth?

Graham (37:52) - Graham loved the episode on holding bonds in a taxable account, but he’s curious about a tax-efficient twist. Can an asset swap strategy let you rebalance and pull cash without triggering capital gains?

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