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  • Bogleheads® Live with Sean Mullaney: Episode 40

Bogleheads® Live with Sean Mullaney: Episode 40

Post on: March 14, 2023 by Jon Luskin

The John C. Bogle Center for Financial Literacy is pleased to sponsor the 40th episode of Bogleheads Live with Sean Mullaney.

In this podcast Sean- FI Tax Guy - discusses how the new tax law, SECURE 2.0, impacts those targeting early retirement.

Sean Mullaney

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Transcript

 Jon Luskin: Bogleheads Live® is our ongoing Twitter Space series where the do-it-yourself investor community asks their questions to financial experts live on Twitter. You can ask your questions by joining us for the next Twitter Space. Get the dates and times for the next Bogleheads® Live by following the John C. Bogle Center for Financial Literacy on Twitter. That's @bogleheads.

For those that can't make the live events, episodes are recorded and turned into a podcast.

And our next live Twitter Space is going to be this Thursday at 12:00 PM Pacific, 3:00 PM Eastern. Go to twitter.com/bogleheads to join us for the live conversation asking Derek Tharp your questions about retirement planning and the problems with it.

 And now onto the 40th episode of Bogleheads® Live. 

Thank you for joining us for the 40th Bogleheads® Live, where the do-it-yourself investor community asks their questions to financial experts live. My name is Jon Luskin, and I'm your host.

Today's topic is the recent tax law - Secure Act 2.0 - and what it means for those targeting early retirement: the FIRE community or financial independence retire early. For today, tax pro Sean Mullaney, AKA FI Tax Guy, answers your questions.

Let's start by talking about the Bogleheads®, a community of investors who believe in keeping it simple, following a small number of tried-and-true investing principles. This episode of Bogleheads® Live, as with all episodes, is brought to you by the John C. Bogle Center for Financial Literacy, a 501(c)(3) nonprofit organization dedicated to helping people make better financial decisions. Visit boglecenter.net to find valuable information and to make a tax-deductible donation. Or you can jump straight to boglecenter.net/donate

Before we get started on today's show, some announcements. For our next Bogleheads® Live, we'll be discussing retirement planning and the problem with it. Returning for that conversation will be Derek Tharp, a previous guest on Bogleheads® Live. Derek joined us for the 24th episode where we discussed spending in retirement and how it changes over time. For our next conversation with Derek, we'll talk more about the challenges when doing retirement planning, and what you can do about it. That'll be Thursday, March 16th at 12:00 PM Pacific, 3:00 PM Eastern. If you're doing retirement planning, you'll want to check that out. You can see the full list of future guests at bogleheads.org/blog/bogleheads-live

Also, thank you to everyone who has checked out the podcast version of this show so far. We've now hit over 100,000 downloads. I'm certainly honored and humbled that so many folks have checked this show out. 

The most downloaded episode has over 5,000 downloads, and that's the interview with JL Collins, author of the FIRE favorite, “The Simple Path to Wealth.” That's Episode #19 if you want to give that a listen.

Before we get started on today's show, a disclaimer. This is for informational and entertainment purposes only and should not be relied upon as a basis for investment, tax, or other financial planning decisions. 

Sean, thank you for joining us once again for Bogleheads® Live. On December 23rd, 2022, Congress passed Secure Act 2.0. You wrote a bit about it, and actually did a video as well about what that means for the FIRE community with an emphasis on two main takeaways. Why don't you start us with what those two main takeaways are? 

For those who aren't tax planning nerds, I will link to a clip from Episode #11 in the show notes, where we discuss the strategy that Sean is going to touch on in his answer right now, deducting taxes during your working years by making traditional contributions only to pay those taxes back at lower rates in retirement when making Roth conversions.

Sean Mullaney: I think there are two things in terms of the FIRE community to be very aware of. One is a very good development and that is this: they have extended the time at which one is required to take required minimum distributions [RMDs].

Those who were born from 1951 to 1959, they under Secure 2.0 do not need to take RMDs until age 73. It used to be age 72. So that's one more year that maybe you could do some more tax-advantaged Roth conversions without having to worry about RMDs. That's a little bit of good news. Nothing paradigm shifting.

 But for those of us who were born after December 31st, 1959, the required beginning date in terms of RMDs is now age 75. So that gives you three more years where you could do Roth conversions before you have any required minimum distributions. And so that makes the classic FIRE [Financial Independence Retire Early] tax planning that much more desirable, right?

The classic FIRE tax planning is arbitrage between our working years and our non-working years. If we can get to an early retirement, the idea is many in the FIRE movement get to a place where they're working and they're in their highest income years and they're contemplating the early retirement.

So the classic planning has been: deduct, deduct, deduct. Load up that traditional 401(k). We just want those deductions. And that's great because we get a tax benefit today. We get the tax deduction.

But we are creating a beast. We are creating a deferred account in our 401(k), and one day we're going to have to pay the piper, but we have hope. So, the idea is, well, yes, I'm feeding the beast. I'm creating these tax-deferred accounts, and eventually people are going to have to pay tax on this whether it's me or my heirs. But I'm going to get to early retirement, and what that means is I'm going to have years of artificially low taxable income.

Because I'm not going to be working and I'm not going to be on RMDs yet, and I'm mostly not going to be collecting Social Security. So, when you start my tax return every year, all it's going to have is a little interest income, a little dividend income. By the way, the low yield world we live in has helped this planning. So low yield on interest and dividends, so just a little bit of income there. And maybe some capital gains as I withdraw assets from my taxable accounts to fund my living style. But that's not going to be that bad. I look artificially low in terms of my taxable income.

And then I do Roth conversions to take advantage of things like the standard deduction, 10% bracket, 12% bracket, for some even the 22% bracket could work. Maybe even more. Depends on your particular facts and circumstances, but particularly that 10% and 12% is very juicy. 

But there is this limit of, eventually I have to take RMDs. So eventually that party ends where I can do these low-cost Roth conversions. Well, the Secure 2.0 says the party just got three more years. So that's very powerful. 

 So, Secure 2.0 helps the traditional, classical FIRE tax planning where we deduct while we're working. We do Roth conversions in early retirement before taking RMDs. We have three more years of runway to bail out the old traditional retirement accounts into Roth.

Here's the second thing that I think folks in the FIRE movement should keep in mind when it comes to Secure 2.0. There are a lot of folks in the FIRE movement who just love the Roth concept. And by the way, there's a lot to like there. Tax-free growth is an easy sell. 

What I'm a little worried about is maybe too much of a good thing is a problem. So, what Secure 2.0 does is it says, well at work you have a 401(k), you get an employer match. That has been - until Secure 2.0 - required to be a traditional deductible contribution. There's been no Roth option there. 

Well, now Secure 2.0 says to employers, if you want to, you can offer a Roth employer contribution. So, in theory, you could have members of the FIRE movement who say, all right, I'm going to do Roth IRA at home, Roth 401(k) contribution on my employee contributions, and then Roth employer contribution. You can do now all Roth. That was never possible before Secure 2.0. in terms of if the employer was giving you a contribution, it had to be a traditional tax-deferred contribution. 

All right, well let's play that out though. Let's get to early retirement and everything we have is we have small savings account, we have some taxable brokerage assets, and then we have all these Roth accounts, and that's it. No traditional deductible accounts. Oh, and our health insurance and our early retirement is going to be an Affordable Care Act plan. Because we don't have the employer coverage. We're not working anymore. 

Well, what about those premium tax credits that reduce our premiums? Those go through the tax code and here's the rub. In order to qualify for a premium tax credit, one has to have a certain amount of modified adjusted gross income. If they don't, well guess what happens? They don't qualify for these premium tax credits, so they have two options. 

They can either go on Medicaid or in California it's Medi-Cal. A lot of folks don't want to do that for a variety of reasons. From an end-user experience, in terms of doctors and healthcare providers, and that's a whole other Bogleheads® Live episode. So, a lot of people don't want to do that.

Or they could still do an ACA plan to my knowledge. But they would qualify for zero tax subsidy. So, they'd be paying full freight, which could be tens of thousands of dollars. 

So, I'll give you an example, if you look at the state of California. If you're a family of four right now, in order to get an ACA premium tax subsidy, you've got to have modified adjusted gross income of almost $40,000 in the year 2023.

Well, if your assets are literally all Roth accounts and you have a half million or a million in taxable brokerage accounts, that might be very difficult to achieve. Especially at the half million in taxable brokerage accounts. And even if you could do it one year, you probably couldn't do it the next year. Something like tax gain harvesting.

So there're going to be people in the FIRE movement who are going to need these traditional deductible retirement accounts so that they can trip some Roth conversion income every year so they can get to that level. It depends on the state. Some states it's 100% of federal poverty level, or 138% of federal poverty level. Some states it's 150% of federal poverty level. 

You're going to want to have some of that income in early retirement, or at least the ability to toggle it on, to have that activity to say, okay, I'm going to push my modified adjusted gross income just above what the IRS is saying in terms of premium tax credit qualifications so I don't get on Medicaid.

I call this the “Rothification” trap. If everything we have in early retirement is Roth, that's probably not a good answer. There are other reasons we want to avoid that. Standard deduction. Maybe we do qualified charitable distributions – QCD - for our charitable giving in our seventies and eighties.

So, we don't want every last dollar in Roth. And I worry that Secure 2.0 is sort of setting the “Rothification” trap for some in the FIRE movement. 

Jon Luskin: So, it sounds like with Secure 2.0, we've got an even stronger case for making traditional contributions than we had before, because now we've got a longer window to make those Roth conversions.

And the other thing we want to be thinking about with Secure 2.0 is that now we've got even more opportunities to get money into tax-advantaged accounts via Roth dollars growing tax-free. But we might not necessarily want to do that because that might mean giving up some of those ACA premium tax credits, meaning we might be paying a lot for healthcare in early retirement.

Sean Mullaney: Jon, I think you've got it. Really good. 

Jon Luskin: And if nothing else, we can certainly expect future tax law changes. That's virtually guaranteed. 

Sean, let's talk a little bit more about the “Rothification” trap. Username “jarjarM” from the Bogleheads® Forums writes: “For Section 604 Roth matching, is it beneficial for high income earners?”

Given all the points you've already shared about what that could mean for ACA subsidies any thoughts to share with “jarjarM”?

Sean Mullaney: I generally don't advocate for that for those who are members of the FIRE movement. Why do I say that? I say that because in the FIRE movement, we have a reasonable expectation that if we can retire at age 50, at age 55, something like that, generally speaking we can have a decade or two decades of artificially low taxable income where we can reverse out the traditional deductible contributions into Roths through affirmative Roth conversions and pay a marginal tax rate on that that is lower than the marginal tax rate at which we deducted previous contributions while we were working. 

To reduce total lifetime tax, we have to look at our entire lifespan and what does our tax picture look like. And for those in the FIRE movement, if done properly, we're probably going to be at our highest marginal tax rates while we're working, too. That's where we want to throw the deductions.

And then we're going to have this span between end-of-work and the beginning of RMDs where we're hopeful to be in a very low marginal tax bracket. So that's where we want to throw the income in, i.e., the Roth conversions.

Jon Luskin: Said a little bit differently, it's a question of do I want to pay taxes now or do I want to pay taxes later? Because you've got to pay them at some point. If you're in your peak earning years, you're in a high tax rate, so you don't want to pay taxes now. And you do that by making those traditional contributions.

So although Secure Act 2.0 gives us more opportunities to pay taxes now, we might not necessarily want to do that. We may want to pay those taxes later when we're in a lower tax rate in retirement. 

We've got another question also from “jarjarM” that asks about a new feature in Secure Act 2.0 that allows you to move some money from a Roth IRA to a 529. This user from the Bogleheads® Forums writes: “What are some potential benefits with the new 529 to Roth allowance? What are some of the pitfalls?”

Jon Luskin: A 529 is a tax-advantaged investing account for college. Qualifying distributions for higher education expenses are made tax-free.

Sean Mullaney: There is this issue about overfunded 529s and people worry about stranded money in the 529 because if you take the money out of the 529 for anything other than college, you pay - generally speaking - ordinary income tax plus the 10% penalty on the earnings. The growth, not the basis. But that's still not a great outcome. Who wants to pay a 10% penalty? 

Now, the traditional solution when we have overfunded 529s is to change the beneficiary. So, we find a younger sibling, we find a grandchild, that sort of thing. But some people are only children. Maybe the younger sibling isn't going to college. Maybe there are no grandchildren in the picture yet, right?

So, what they did was they said, "well, you know what we're going to do, we're going to address some of those concerns by allowing a bailout of 529 money into the beneficiary’s Roth IRA." 

And the idea is that it's still in a tax-advantaged account, this can't just be taken out of the 529 to go to Vegas. It's now doing something else that's productive, which is building up the beneficiary's retirement accounts, which is helpful to the beneficiary and to society as a whole because now that beneficiary has retirement savings.

I look at this a couple ways. One is this is a bailout tool to the extent folks have money in 529s, particularly if you have a junior in college now and the 529 is overfunded. Or, you have a daughter who graduated two years ago and there's still money stranded in that 529. This is a really good development. 

 It always is helpful for us to have tools in our toolbox when we're thinking about bailing out otherwise overfunded 529s. That is a really good thing.

Now, I will say I prefer the move where we change the beneficiary. Because that doesn't have the limits that this new 529 to Roth IRA rollover has. There's a 15-year limit, a 5-year limit, an annual limit based on the Roth IRA contribution. But, the nice thing about changing the beneficiary is we don't have any limits on that. We don't have to worry about the balance. How old is the 529? We can just do that. Okay, fine. 

Where I've seen some attention that this thing has received that I think is unwarranted is this idea that we're going to use this new provision to do some wealth planning. So, folks are saying, "well, that's $35,000 I can get to a Roth IRA. Isn't that necessarily a good thing?" 

Well, you’ve got to remember: this doesn't change the limits that we can get to a Roth IRA every year. That is still the $6,500 today for those under age 50. It's going to go up by inflation.

If they had said this is $35,000 in addition to that, well then, okay. Then let's start doing some affirmative planning. But they didn't say that. They just said, "well, if you do this 529 to Roth thing, that replaces the beneficiary’s annual contribution."

And some folks are saying, "well, this could seed the beneficiary’s Roth IRA - you get the $35,000 in there and then you wait four or five decades, you have returns that are consistent with historic norms for the stock market. And voila, you have a million dollars in a Roth IRA. Isn't this incredible? Isn't what Congress did just amazing?" 

Well, you have to step back and you have to say, why wasn't that possible before Secure 2.0? And the answer is it's absolutely possible before Secure 2.0. If mom and dad want to do something like that, they have a checkbook, right? Mom and dad can use their checkbook and "Hey Junior, you're in college and you worked as a lifeguard. You made $5,000 this summer. Great, we'll just write a check to your Roth IRA." Nothing in this 529 to Secure 2.0 thing changes that one iota.

But people say, "well, what about that million-dollar growth?" Well, that all came from the Roth IRA rules that are in place today. It didn't come from this new 529 to Roth rollover. 

So I look at it as it's a great bailout tool and we're happy to have in the toolbox. But because it does not increase Roth IRA contribution limits, I just don't see it as this great planning tool. 

The other thing I've seen is, oh, maybe you should do this 529 for your adult children today. You have a 30-year-old son or daughter. They work wherever they work. They're out of college. You could start one of these 529s for them and then in their forties or fifties do this rollover. 

And I come back to a couple things. One, I worry that that's not a good 529 because the 529 has to be the primary benefit of the higher education expenses of that person. The 30-year-old has no higher education expenses. So, I worry about qualification.

But for putting that to the side, you don't need to do this maneuver. You can fund your 30-something, 40-something, 50-something child's Roth IRA at any time with your own checkbook. Now, they have to have earned income and those sorts of things.

But, long story short: really good bailout tool, worthwhile in terms of considering for stranded amounts in 529s. But I don't view it as a good affirmative planning tool that we want to plan into.

Jon Luskin: Sean, I think you said all of that really well. Effectively, this just helps folks who want to get some money to a Roth IRA and have money left over in a 529. It's just a little bit of a tool for those in a little bit of a cash crunch, not a magical financial planning or tax planning opportunity. 

Let's jump to another question we got from the Bogleheads® Forums. This one is from username “Wannaretireearly” who writes: "For someone wanting to retire in five years at age 50 and needs 10 years of expenses before hitting age 60, what are a few ideas for setting up a taxable portfolio? Anything new or special based on the new tax laws? For example, Roth conversions are one established strategy. MYGAs seem to be popping up as another new strategy."

Sean Mullaney: I'll say just a couple things. One, obviously taxable assets play a role, especially in early retirement. They can help bridge the gap between leaving work and starting to collect Social Security and having RMDs. And, if one can live off taxable assets as opposed to traditional retirement accounts, they have more runway to do the Roth conversion planning. 

And I do think, look, I'm not a huge sequence of returns risk person. Meaning, there's this risk that I retire and then a month later the stock market goes down 40%. Oh, woe is me. Stock markets tend to rebound, right? No guarantees. There is at least some merit depending on one's particular circumstances to consider starting early retirement with a cash balance and spending that down first.

What that does is it allows the other investments in the portfolio to keep growing and it reduces any capital gains when you early retired. Which can be very helpful. Having that six-month cushion, year cushion in cash, and that's the first thing you spend down, that can be productive.

And then the last thing is, and I have a blog on my FI Tax Guy blog on this, oftentimes the best assets to spend down in early retirement first are the taxable assets, not the traditional retirement accounts or Roth retirement accounts. Not even the HSA.

And that can have several advantages. One of them is actually a creditor protection reason. One of the nice things about traditional IRAs, 401(k)s, Roth IRAs, is to varying degrees - and this depends a lot on state law but not exclusively on state law, there's some federal law here too - the traditional IRA, 401(k), and Roth IRA generally speaking enjoy varying degrees of a combination of bankruptcy and non-bankruptcy creditor protection. But your taxable brokerage account, generally speaking, is not going to enjoy much, if any, federal or state asset creditor protection. 

If we spend down the taxable brokerage accounts and those get depleted because that's where all our spending's coming from, and then separately we're just letting those traditional and/or Roth IRAs grow, maybe we're doing Roth conversions, but together those things are growing in sum total. We're not actually consuming a penny of those. What we're doing is we're diminishing those assets that are not creditor protected and growing, hopefully the stock market, the bond market is growing. These things that won't happen every year, but many years, we're going to grow those assets that enjoy creditor protection. So, we're making our balance sheet in early retirement more desirable from a creditor protection perspective. 

Jon Luskin: Related to that is that at least one nice benefit of Secure Act 2.0 is that where RMDs weren't required before on Roth IRAs, they were originally on Roth 401(k)s. But now Secure Act 2.0, there aren't RMDs on Roth 401(k)s. And to your point, Sean, that's really great because those 401(k)s, they have better creditor protections than you're going to get in an IRA.

At least that's the case in California. It does vary state by state. But for those California folks, all else being equal, there are creditor protection benefits to leaving money in your 401(k), not rolling it to an IRA. And now, with the new Secure Act 2.0 law, you don't have to roll your Roth 401(k) in your Roth IRA to avoid those RMDs. So that is certainly a nice feature of the new tax law change.

Sean, this question is from username “Scrooge McDuck” from the Bogleheads® Forums who writes, "I was wondering whether early retirees in their thirties who want to stay above their state's Medicaid income threshold should focus on Roth conversions or tax gain harvesting?"

So we certainly talked about this topic, but I don't think we answered this specific question. Sean, what's your take on Scrooge McDuck’s question? 

Sean Mullaney: This question applies, frankly, beyond one's thirties. Roth conversions versus tax gain harvesting. Tax gain harvesting generally allows zero income (federal). Oftentimes there's going to be a small state tax, but 0% long-term capital gains rate. You basically get to reset basis.

My general impression on this question is this. I tend to be biased towards the Roth conversion instead of the tax gain harvesting. And it has nothing to do with premium tax credit.

For premium tax credit qualification, if that's your concern, either one works because they both create MAGI. They both create modified adjusted gross income. So, they’re neutral if that's the only consideration. 

What I like to think about is this: this is a person with taxable brokerage accounts with built-in gains and a traditional retirement account - IRA, 401(k) whatever it is. Here's the thing though: someone in human history is going to pay the tax on the traditional IRA. It's either going to be you, your spouse, or your heirs. 10-year rule, right? Either you are going to pay the tax on that traditional IRA or your spouse is or your children or other heirs are just based on the rules. Somebody's paying that ordinary income tax. 

With the taxable brokerage account with the built-in gain, here's the thing: one's own death means that generally speaking, no one may pay that tax.

Recall that at one's death, if you have assets in a taxable brokerage, generally speaking, they are stepped up to the fair market value on the date of the death for tax basis purposes. So that capital gain can go away because of your own death.

The latent tax inside the traditional IRA is not excused by anybody's death, and in fact can be accelerated because of somebody's death. If everything else was equal, I'm biased in a general sense towards the Roth conversion over the tax gain harvesting. 

That said, I'm going to give you a use case where I would prefer the tax gain harvesting over the Roth conversion. And it's this: the retiree has three mutual funds that they really want to own, and their traditional IRA right now has those three mutual funds in the proportion that the retiree wants. Okay. So, they're invested just like the retiree would like. And then separately, the taxable brokerage account has maybe three individual stocks that this person bought 20 or 30 years ago, or even 10 years ago, 5 years ago when their investment preferences, their outlook on personal finance was just different. 

I think JL Collins refers to these as the cats and dogs. So, in the taxable brokerage we have cats and dogs. Their preferences on life have changed. And so now this person would rather not hold those cats and dogs. I would rather do tax gain harvesting in that case because they can tax gain harvest and then redeploy into the desired mutual funds. I'd rather have the investment tail wag the tax tail there, as opposed to focusing on, oh, well this Roth conversion, somebody's got to pay the tax on that.

Jon Luskin: Sean, I'm going to agree with you a hundred percent. Tax gain harvesting to get your portfolio right. I like to say "investments first, taxes second."

Sean, I'm curious, what about those without heirs, if they're just going to leave all their money to charity? Any considerations then? 

Sean Mullaney: So, Jon, I'm happy to say the HSA is non-taxable when you leave it to your spouse. It becomes their HSA. But if you leave it to any individual who's not your spouse, unfortunately the HSA is fully taxable the year of your death to them. So that's a hidden HSA death tax that no one's talking about. So, if you're otherwise charitably inclined and you've got $50,000 in HSA and you have other assets, maybe you should leave the HSA to your charity because they don't pay tax. So, that's a good asset to leave to the charity and then leave your loved ones taxable accounts because they get set up basis. Roth accounts. 

 I think the HSA is one of those things you want to think about leaving to a charity if your spouse is already deceased or if you're single. 

Jon Luskin: That is a phenomenal consideration: HSA is a good asset to leave to charity. Thanks for sharing that.

That's all the time we have for today. Thank you to Sean for joining us today, and thank you to everyone who joined us for today's Bogleheads® Live.

For our next Bogleheads® Live, we'll be discussing retirement planning and the problem with it. Returning for that conversation will be Derek Tharp, a previous guest on Bogleheads® Live.

Derek joined us for Episode #24 where we discussed spending in retirement and how it changes over time. For our next conversation with Derek, we'll talk more about the challenges when doing retirement planning and what you can do about it. That'll be Thursday, March 16th at 12:00 AM Pacific, 3:00 PM Eastern. If you're doing retirement planning, you'll want to check that out.

Until then, you can access a wealth of information for do-it-yourself investors at the John C. Bogle Center for Financial Literacy at boglecenter.net and bogleheads.orgBogleheads® WikiBogleheads® Twitter, the Bogleheads® YouTube channel, the Bogleheads® On Investing podcast with host Rick Ferri, Bogleheads® FacebookBogleheads® Reddit, the John C. Bogle Center for Financial Literacy on LinkedIn and local and virtual chapters.

For our podcast listeners, if you could please take a moment to subscribe and to rate the podcast on Apple, Spotify, or wherever you get your podcasts.

And finally, a thank you: thank you to Barry Barnitz for his work on the show. And thanks to Nathan Garza and Kevin for editing the podcast. And a final ‘thank you’ to Jeremy Zuke for transcribing the podcast episodes. I couldn't do it without everyone's help.

Finally, I'd love your feedback. If you have a comment or guest suggestion, tag your host @JonLuskin on Twitter. 

Thank you again, everyone. I look forward to seeing you all again next time. Until then, have a great one.

About the author 

Jon Luskin

Board member of the John C. Bogle Center for Financial Literacy


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