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Andi Last
Saving into Roth instead of traditional accounts to bring down required minimum distributions in retirement and whether retiring early is in the cards. That's today on youn Money, you, wealth podcast number 579. Brian in New York and Todd and Margot in Utah each have over $3 million in their pre tax accounts. What should their Roth conversion strategies look like? And can Todd retire this year? But first up, should Captain Morgan go Roth to avoid RMDs? And can he retire in a couple of years? Should Chloe Jopine contribute to Roth instead of traditional if his income will always remain the same? Finally, Kyle and Katie have high incomes and need a spitball on how they can avoid future RMDs. You think Roth conversions might be in their future? We'll find out. Let us know what you think of today's episode. Hop onto our YouTube channel to watch us and to join in the conversation in the comments. I'm executive producer Andi Last, and here are the hosts of youf Money, you, Wealth, Joe Anderson, cfp and Big Al Clopine, cpa.
Joe Anderson
Let's kick it off with Captain Morgan.
Big Al Clopine
You like Captain Morgan?
Joe Anderson
No.
Big Al Clopine
You're not a rum guy? No, I am. I like Captain Morgan.
Joe Anderson
Captain Morgan. No, sir.
Big Al Clopine
Especially the Spice rum. I like that.
Joe Anderson
Yeah. What? Wasn't there like a slogan for Captain Morgan?
Big Al Clopine
Yeah, I mean he.
Joe Anderson
The pirate.
Big Al Clopine
The pirate chair. Well, I don't know what the slogan was, but he put his, his, his leg in the barrel.
Andi Last
Yeah, that's what I spice on, apparently is the current slogan.
Big Al Clopine
Bison. Okay, cool.
Andi Last
There was also live like a Captain and better than gold.
Big Al Clopine
Okay, okay. So now we're in the mood. Captain Morgan. I can sort of. We can sort of place.
Joe Anderson
So what is it like Captain and Coke. So. Or you just go straight Captain?
Big Al Clopine
No, I, I like.
Joe Anderson
Or you put it in a Lego.
Big Al Clopine
My ties or all this, all this Hawaiian drinks, little fruity thing.
Joe Anderson
Pina coladas. They're Roman pina coladas.
Big Al Clopine
Oh, yeah. Okay.
Joe Anderson
All right. So my drink of choice is Captain Morgan and Sprite.
Big Al Clopine
Well, that's another way to go.
Joe Anderson
Yeah. Captain Sprite. I don't know. That doesn't sound. I'm 48, single, have two kids, 10 and 12. I have a monthly expense of $8,500 and I make $240,000 a year. I currently have 1.9 million across all my investment accounts. In my pre tax accounts, I have $600,000, adding $23,000 plus $200,000 in the employer match. Have a Roth IRA and Megatron. This guy's got to Be a long term listener.
Big Al Clopine
I think so.
Joe Anderson
$270,000. Add $24,000 mega backdoor and a $7,000 backdoor IRA annually. Taxable brokerage, million bucks. Adding $15,000 annually. HSA 40,000 max family 529 plan $20,000, adding $3,600 annually. I expect to get $35,000 in my Social Security at age 65. So here's my question. Should I continue pre tax 401 or change to Roth 401 in order to reduce future RMDs?
Big Al Clopine
Yes.
Joe Anderson
Captain Morgan. Captain Morgan, he's 48 years old, right?
Big Al Clopine
He's already thinking about RMDs about something
Joe Anderson
30 years from now.
Big Al Clopine
Well, that's called preplanning.
Andi Last
He's apparently been listening to this show for a while for multiple reasons. Not only does he know the Megatron, but he also knows starting early gets you the best results.
Joe Anderson
So then he's like, also is retiring at 51, reasonable and still be able to fully fund college tuition. I'm thinking of moving some 401 pre tax to an IRA to withdraw from and pay for tuition to avoid that 10% penalty. Please poke as many holes as you want.
Big Al Clopine
All right, Captain, well, let's start with this first question.
Joe Anderson
So his salary is $240,000 as a single taxpayer. 240, 24% tax bracket. But he's.
Big Al Clopine
Well, top of the 24 is 200,000. That's a single. No, no, no, that would be single top of the 24.
Joe Anderson
24. Okay, how about 22 is 200 for married, correct?
Big Al Clopine
That's right. That's right. So Joe, if you think about it that way, his 401k, if it's pre tax, that's about 20,000. 23, 24, whatever. I don't know what his interest in dividends are, but let's just say million dollars, 2%, $20,000. So I think those two cancel each other out roughly. And then you got the itemized deduction, which is $13,000, $14,000. So I think he's in the 32% bracket. Um, so I think I'd stick with the pre tax. Me personally, but you may have a different opinion.
Joe Anderson
Yeah, let's see. The top of the 24 is $200,000.
Big Al Clopine
Yeah, $202,000 to be exact.
Joe Anderson
So taxable income. Yeah, 38 years old.
Big Al Clopine
So taxable income is somewhere around 225, something like that. That's with the pre tax. So I think I'd stick with pre tax.
Joe Anderson
Yep, I agree 100% 32. Yeah, that's too high. Go pre tax. He's 48 years old. He wants to retire at 51.
Big Al Clopine
Yeah, so that's, that's a, that's a little tricky. So I ran that amount. So, so 1.9 million is the starting point. Three years, 6% rate of return. He's adding about 90,000 a year, which is great. Right now. If you're listening and want to do this yourself, you can pick any rate of return. I like, 6% just because it's a little bit more on the conservative side. I'd rather be conservative than aggressive. But Anyway, Joe, that two and a half million is what he ends up with in three years. And spending of 102 becomes, with inflation, about 111. That's about a 4.4% distribution rate at 51.
Joe Anderson
That doesn't have enough non qualified to even come close to retiring.
Big Al Clopine
Yeah, well, right.
Joe Anderson
And so got a million dollars. So I suppose what, you drain your, your Million dollars from 51 to 60?
Big Al Clopine
Yeah.
Joe Anderson
He wants to spend 100,000. A million dollars. So he's got enough. Well, I suppose he's got enough there. If he wants to spend $100,000 over nine years, it's 900,000.
Big Al Clopine
Yeah. A million there, there's enough there. But I think at that age I'd probably rather see a 3% distribution rate, which would put him at about 75,000, which means to cover the gap, he'd need about 40,000 of income from somewhere.
Joe Anderson
And he still has to fund college.
Big Al Clopine
Right. And that's just to get by for himself, not fund college. So it's pretty tight, I think now I ran it at 55 just to see. Cause that would be. You know, it's funny how just a few years makes a big difference. So then with these same assumptions, he would end up at 3.6 million and his spending would be 125k. That's a 3.5% distribution rate. At 55. It's still kind of on the border, but that, that is more reasonable, I would say. Okay, still, Still, I'm not sure how he pays for college.
Joe Anderson
Then where does the kids want to go?
Big Al Clopine
Yeah, well, right.
Joe Anderson
I mean, it could be pretty cheap or it could be quite expensive.
Big Al Clopine
It sure can. We know that. That's. That's the smartest thing you've said all day.
Joe Anderson
My God, as soon as I came out of my mouth, it was like, you are an idiot.
Big Al Clopine
So. So I would say if it were me, I would, I would try to work to at least 55 yeah, I like that.
Joe Anderson
55. I would continue to go pre tax. You're in the 32% tax bracket. You, you do have a lot of money in a non qualified account, the brokerage account. You're adding 15,000 to that.
Big Al Clopine
Yeah.
Joe Anderson
So you're doing a phenomenal job from a savings perspective. But.
Big Al Clopine
Right.
Joe Anderson
You know, when you want to spend $100,000 a year and put a couple kids for school, you need a lot of capital to do so.
Big Al Clopine
Yeah. And realistically, a lot of people work until their kids are out of college or when they know they can fund the college and still be okay. Right. Maybe that's another way to say it.
Andi Last
Yeah.
Joe Anderson
But let me. If I think about this, you know, this is just back of the envelope. He's got a bridge. So at 51, it's too rich. At 55, I think he's close with funding college because of the Social Security bridge. He wants to spend 100. He thinks he's going to get $35,000 there, so his distribution is going to go down. So it's close.
Big Al Clopine
It's close.
Joe Anderson
Of course, you got to run, you know, you've got to run these numbers on an ongoing basis because who knows what's going to happen over the next 12 months, let alone the next 12 years.
Big Al Clopine
But, you know, I mean, he could retire at 51 if he got some kind of part time work, in my view. But sometimes just knowing that Joe makes a difference to where you can handle work. Knowing that you could qu an alternative. Right.
Joe Anderson
Yeah. Giving up a $250,000 paycheck is tough.
Big Al Clopine
Yeah. When you're single and have two kids and you want to put them through college.
Joe Anderson
Yeah, yeah. The kids are 10 and 12.
Big Al Clopine
Right.
Joe Anderson
If they were a little bit older and you're a little bit closer to college, where you kind of have a handle on what that expense is.
Big Al Clopine
Correct.
Joe Anderson
But there's a lot of unknowns. And giving up that paycheck at 51, that's. I don't know, 51 is really young to retire. I don't know. What would, what would you do, Captain Morgan?
Big Al Clopine
Well, you would have to have something else to fill your time. I can tell you that from experience.
Joe Anderson
Oh, God. I met with a client that's always been a little bit of a nervous Nelly. He retired pretty early. I was like, how's your stress level now that you're retired? He's just as stressed just because he's like, well, I need to fill my time.
Big Al Clopine
Yeah. Right.
Joe Anderson
You know, it's like, well, before it Was like, I work, but now I'm working on this. And you know, so yeah, retirement you have. There's a lot of planning that we rarely talk about that has nothing to do with the dollars and cents.
Big Al Clopine
You know, it's funny when we do talk about it, Joe, it's, it's. And I'm serious when I say this, which, which is I think that what you're doing, what you want to be doing or should be doing or to fill your time, that's as important as the financial part. You know, we, we've seen all kinds. People getting depressed after retirement because their job was everything. Their social circle, their purpose in life and all that.
Joe Anderson
Yeah. Then you just say, oh man, my parents died at this age. What time is it? You know, clock is ticking on me.
Big Al Clopine
No, I, I get it. And as you know, I tried to retire myself at 47.
Joe Anderson
Yeah. That worked out well for you.
Big Al Clopine
So good.
Andi Last
Hey, if you're brand new to youo money, you, wealth, welcome. This is a great week to find us. The DIY Retirement guide is our special offer right now. But it' only available until sometime this Friday, May 1st. This is 40 plus pages of the same practical do it yourself retirement planning information that normally only lives inside our retirement classes and one on one client meetings. How to draw from the right accounts in the right order to keep your tax bill low. How to protect yourself from inflation, market swings and sequence of returns risk. And a quick retirement calculation worksheet is on page 44 so you can find out right now whether you're actually on track or just hoping for the best. We only make the DIY Retirement Guide available a few times a year and the special offer changes sometime this Friday, May 1st. Click or tap the link in the episode description and claim your copy of the DIY Retirement Guide right now.
Joe Anderson
All right, let's go to Chlo
Big Al Clopine
Chlo Jopine. I think that's a play on our names.
Joe Anderson
Look at that. Clo Jopine.
Andi Last
That's got to be one of the most creative names somebody has come up with to be on this show.
Joe Anderson
Cloth. All right. YMYW. I'm a 39 year old freelance musician. Well, send us some tunes.
Big Al Clopine
Yeah, Go clow.
Joe Anderson
Yeah, Love to hear what you got. My drink of choice is whatever shows up on stage for free.
Andi Last
Spoken like a true musician.
Big Al Clopine
You know, that's a good way to think about it. Maybe. Yep.
Joe Anderson
I drive a 994 runner with an indestructible 4.7 liter engine. I'm in a situation where my income will essentially Never raise. As I age roughly $70,000 annually, occasionally up to $90,000. And I'm looking for a three bucket spitball to help escape inflation. I'm debt free. Besides my mortgage at $250,000 and I DCA weekly into my Roth IRA which is $46,000 currently to max it out over the course of the year.
Big Al Clopine
Dollar cost average, by the way dca,
Joe Anderson
due to starting later in life, my Roth will continue contributions will likely barely make it to a million dollars by 65, putting my 4% withdrawal firmly in the 12% tax bracket if I went pre tax instead. As such, should I switch to traditional IRA contributions from here on out? I'm also considering Open a solo 401k traditional to put more cash away. In that case, would you prioritize one account over the other? Roth 401k or traditional solo? For my third bucket, I'm hoping to up my brokerage account equally. I could see myself doing $583 a month into the IRA, 7,000 divided by 12, 583 into the Solo and 583 into the brokerage beginning 1099. These are the only accounts available to me. Spitball away. Also, I still don't know how to calculate self employment tax on on top of federal income tax. Thanks. Okay, couple of tidbits here.
Big Al Clopine
So what do you got?
Joe Anderson
Let's see. Clo Jopine, he's got $70,000 that he makes and occasionally up to $90,000. He's a single guy. Freelance or single gal? I don't know what Chloe Joe Pine is a boy or girl? 39, hard to say. I would open up a Solo 401K and with the Solo 401K, you can do Roth and or pre tax.
Big Al Clopine
Right now you are, you are limited to 25% of your your income. Right.
Joe Anderson
Not in a solo 401k.
Big Al Clopine
Oh, I'm thinking a sepi. You are? I stand corrected. You're right.
Joe Anderson
Yeah. So a solo 401k is a 401k plan for people that are self employed. So for this individual, I would definitely open up a solo 401k to give you more flexibility of how much money that you can actually put into the overall account. When I go Roth or pre tax. Let's see. Well, it depends. How much money does he currently have is saved up?
Big Al Clopine
He's got $46,000 right now.
Joe Anderson
It's $46,000 and he's saving.
Big Al Clopine
It's all in a Roth.
Joe Anderson
It's all in a Roth.
Big Al Clopine
Yep. So we Sort of have a clean slate. So this is kind of a good one. So how would you do it?
Joe Anderson
Single at $90,000. 70,000 to $90,000. So he's in the 22% tax bracket plus self employment tax.
Big Al Clopine
Right.
Joe Anderson
I would probably try to defer as much income as I possibly can.
Big Al Clopine
For the tax break.
Joe Anderson
For the tax break. Plus that's also going to save him self employment tax. So his effective rate is probably a little bit better. Right. You're the cpa.
Big Al Clopine
It doesn't, it doesn't change the self employment tax because that's how you calculate your, your earned income. But I do agree with you. I think at this point I love getting some in a Roth, but there's
Joe Anderson
no, if I had $40,000 of, so I'm playing gigs and I make $70,000. Okay, all right. Of cash, 1099 employment income and I put $30,000 away in a solo 401k.
Big Al Clopine
Okay.
Joe Anderson
All right. So that equals $40,000 plus my item or my standard deduction of another, call it 15 if I'm single. So my taxable income at that point would be what, 25, 30, 35,000.
Big Al Clopine
It'd be low. Yep.
Joe Anderson
So my self employment tax is based on gross or my tax. How is self employment tax calculated?
Big Al Clopine
Yeah, so self employment tax, Joe, is based upon your bottom line profit in your business. Okay. And so think of it like as a, like salary. So when you put money like an employee side, that's just like a payroll deduction. It's not a, not a deduction to anybody. So that's not a deduction per se. However, if your company makes a match, then that's a deduction. So that does reduce self employment tax.
Joe Anderson
But if I'm just a sole prop, it doesn't matter. The sole prop is the business. And then that's going to determine how to calculate this. How maybe I ask you this, how would this musician reduce his open self employment tax?
Big Al Clopine
The main way you reduce self employment tax is to have more deductions in the business. Not, not in general, but in the business. So, so in other words, buying new musical instruments, mileage. Right. Anything you can think of that you know, maybe you go to conferences with other musicians, I don't know. But those are expenses that you could then put against the gross income from the, from the business.
Joe Anderson
Okay. And if I set up a solo 401k and match myself on the employer side.
Big Al Clopine
Yeah.
Joe Anderson
Would that work?
Big Al Clopine
Yeah, because that would be a pre tax match and it would be. Let me think how that works. That's a deduction. You know what, I don't think that's a deduction though for the self employment because that's earned income. I think it's. I could be. It's been a while since I've done this, but I think it may just be a deduction against taxable income, not self employment tax.
Joe Anderson
Got it.
Big Al Clopine
Because if it was a deduction for self employment tax, it'd be a circular calculation. Right. Because you'd get the calculation and then you figure out then it would have to go back into the self employment income, which changes the Social Security. Yeah. So I'm pretty sure it's outside of the self employment calculation. That's a frustrating thing for being self employed. A lot of times you can have a pretty low taxable income, but it's harder to get rid of your self employment tax because that's based upon your earned income and your earned income is based upon your bottom line profit and your business with which that number determines how much you could put into solo 401k and or Roth IRA or regular IRA.
Joe Anderson
Got it. So it's based on earned income, non taxable.
Big Al Clopine
Yeah, yep. Earned income for your business.
Joe Anderson
Yeah, yeah, yeah, yeah. All right. Yeah. So I would open up the Solo 401K. You have the flexibility to do Roth or pre tax. I think right now I would still do pre tax because of the 22% tax bracket. If he's going to do 583, I don't know why. I think I would all put it into the 401k plan versus building up his brokerage at this point.
Big Al Clopine
Yeah, 22% bracket is a decent bracket that you might want a tax deduction. I think I agree with that because
Joe Anderson
he's going to be in the 12% tax bracket. Given the math that he did. He says I'm going to have $1 million. I'm going to draw my 4% at $40,000. I'll be in the 12%. But you also want to do some other math here given what you're thinking, because you still want to have some diversification because you could be in the 0% tax bracket in retirement, but if I'm in the 22. So this is an interesting case because. Let's go. I'll go post tax and put it all into the roth and pay 22% today, but then when I'm retired I'll be in the zero percent. There's got to be a. There's a combination here.
Big Al Clopine
I agree.
Joe Anderson
I think it's a little Bit of both. But you would want to forecast what both of those would look like. And I think he's already done that to some degree because he's looking at, well, if I'm saving X, I'm going to have million dollars. So find out how much that you should save pre tax, where you can pull out, let's call it $20,000 a year because that would be tax free given if we had the same current standard deduction for a single taxpayer given a little bit of inflation.
Big Al Clopine
Now, when I looked at this, I think starting at $46,000 and 26 years to retirement, if he retires at 65. Did I do that right? 55. Yeah, 65 at a 6% rate of return, adding $21,000 a year, that's a million and a half. That's actually a pretty decent number. So it just goes to show you can have very little at 40 and still end up in a great spot as long as you're disciplined and keep funding it. But with that, $60,000 would be a 4% distribution rate plus Social Security, whatever that would be. So that would, he'd replace his income almost. Yeah. Right. And it would be 22% bracket as we know it today. Right. So anyway, I don't mind some diversification, but I do like the idea of some tax deduction in the pre tax. I think one of his ideas is split it a third. A third, A third. I, I guess without doing any more advanced planning, that's probably a good place to start. Jim?
Joe Anderson
Yeah. How? Yeah, I guess that's one way to look at it. I think if, if I look at this, if I would want to put cat. I don't know how that math worked out, but let's say if I want to pull out $20,000 from an IRA and pay tax on it, and then I want all my other income to be tax free or capital gains.
Big Al Clopine
Right.
Joe Anderson
So that means I need to accumulate at least $500,000 by the time I'm 65. And so if his math says it's a million, then yeah, split the baby. But I think your math says it's $1,500,000. So I don't know. A third, A third, A third is probably the right number.
Big Al Clopine
Yeah, I'm good with that. And adjust as you go.
Joe Anderson
Yep.
Big Al Clopine
What you don't want to do is end up with too much in a deferred. And then. Because then more, your Social Security is going to be taxable.
Joe Anderson
Yeah. Right.
Big Al Clopine
In the future.
Joe Anderson
Yep. Because if he plans this. Right. 100 of his income could be tax free, including a Social Security. Yeah.
Big Al Clopine
Or close to it, right?
Joe Anderson
Yeah.
Big Al Clopine
Yep. Chloe Joe Pine. That's still. Yeah, it's a good one. So, so it could be, let's see, Ann Allerson. If you do your last name and split it with my first name, I
Andi Last
can see why they went with Chloe Jopine. Flow's a little better.
Big Al Clopine
A little better. Yep.
Joe Anderson
We got Brian in New York. He goes, hey guys, thanks for performing a spitball on my situation. I'm a 53 year old and I'm considering retiring at 56. Right now I have three and a half million dollars in a tax deferred account, $2.3 million in a brokerage account, $600,000 in a Roth IRA, all invested in the S&P 500 index fund. I'm entitled to $120,000 a year pension which will cover all of my living expenses. Well, damn, Brian, you're sitting in a pretty good spot.
Big Al Clopine
I would say.
Joe Anderson
My calm, my concern is my traditional 403 account is growing faster than I can convert to a roth in the 24% tax bracket when I retire. My question is, is there an amount I should just do a large conversion when I retire and pay like 35% tax for a couple years to bring that 403 traditional account balance down to where the growth in the pre tax matches the future yearly conversion rate in the 24% individual tax bracket. Haven't heard you guys talk about this issue before. For people with large pre tax retirement accounts. My employer does not offer a Roth. All right, Brian, I would like to know what your assumptions are in regards to growth rate. So he's in the s and P500. What is he running like a 10% growth rate within the overall account?
Big Al Clopine
Could be.
Joe Anderson
You want to convert when the market's down so you're 100% all in the market. So when the market's down 20%, I'm totally fine with you converting a lot larger number than the 24% tax bracket. Then all of that future growth is going to grow tax free. There's no secret science here because you can't determine what a straight line rate of return is in the overall markets because you can have an average rate of return. But your math is going to be screwed, screwed up once you're. You put it into practice in real life because it's like, wow, my account's up 20% and I can't keep up with the growth of my account to get a lot of this out without blowing me up, you know, later in life. I think you take it year by year, you convert to the bracket that's appropriate for you. But then I think you can take advantage of other instances if markets, you know, going to decline.
Big Al Clopine
Ditto. All right, you killed it. Because I don't think you want to convert in these higher brackets just as a, as a matter of course. But the market does dip. It does. Correct. Those are the years where you do large conversions maybe into the 37%. You know, you got a lot of money in non qualified that you can pay taxes with. So that, that. And let me give you an example. It's, it's a ridiculous example, but at least you'll understand the math. So you convert a hundred thousand dollars, you're in a high tax bracket, let's just say 37%, Joe. So your tax is 37,000 in between the time you convert because the market's low and it does a full recovery and now it's worth 200,000. Not going to happen. I just want to do the math. Right. So in essence, you got 200,000 into a Roth, but only paid taxes on 100. That 37% tax is now more like 18%. Yeah, cut in half. Right. So that's why you want to think about doing your large ones at the time of a correction. By correction, I mean something that goes down 10% or 20, 20.
Joe Anderson
I think that the larger the correction, the more conversion.
Big Al Clopine
You got that right. Because. And the thing is, the market may not recover in the time you pay the tax, but it will and you'll be glad you did it.
Joe Anderson
Yes, but this is where it takes discipline and this is where it takes help in guidance. Because normally when markets drop 10, 20, 30%, people freeze. They don't want to do anything. There's no strategy. They're like, oh my gosh, should I sell? Should I go into cash? The last thing people are doing is converting dollars into a Roth IRA and paying taxes on those dollars when their account balance just dropped 25%. But if you understand how markets work, is that you would much rather have their recovery. If you don't believe the market will ever recover and it will go to zero, well then no, you don't want to do it because. Because we're not gonna have any cash anyway.
Big Al Clopine
Yeah, you would never convert. Cause what's the point?
Joe Anderson
What's the point? But if you believe that markets do come back and they recover, all of the recovery of the market, it might take two, three, four, five years or longer, but that recovery will now be in a tax free environment versus getting that recovery in a tax deferred environment. So you will definitely save significantly more taxes over the long term if you think about it that way.
Big Al Clopine
Yeah. 100%. Cool.
Joe Anderson
All right, Good question. Like that one?
Big Al Clopine
Yep.
Joe Anderson
Okay, let's go to Todd and Margo from Utah.
Big Al Clopine
Okay.
Andi Last
You know that reference, right?
Joe Anderson
I do not.
Andi Last
Christmas vacation. They were the yuppie couple. Why is the carpet wet, Todd?
Big Al Clopine
Yeah, you're right.
Joe Anderson
Oh, wow. That's with Elaine.
Big Al Clopine
Elaine, yes. Yeah, from Seinfeld.
Joe Anderson
Todd and Margot Love.
Andi Last
I figured you'd get that one right off the bat.
Joe Anderson
Nah, I didn't forget Todd. Margot. Todd's 54, Margo's 53. We both like a good old fashioned hers without a Hers without the sweet. Has to have the right cherry. All right, now we got two 14 year old cockapoos and a recent empty nest.
Big Al Clopine
Okay.
Joe Anderson
Margot retired in 2024 and Todd wants to retire in 2026. We split time between a home in the valley and a home in the mountains for a change of altitude and a change of attitude. Todd drives a 2025 Hyundai Palisade and Margot drives a 2020 Infiniti QX50. Our mountain rides are 2002 Silverado in Todd or that's for Todd in a 2016 Jeep Wrangler for Margot. Here's our situation. Primary and vacation homes are paid in full. We got three rental properties with a million dollar total equity and $1,500 a month in cash flow. We have an $800,000 in a defined contribution plan with a 10 year annual payout, a dcp plan, $2,300,000 in 401s, $500,000 in Roths, $150,000 in HSA. $1.1 million in a taxable brokerage account. Two boys in college, five hundred and twenty nine balances covered their undergrad. Margo plans to take Social Security at 67, Todd at 70. Combined annual benefit of $105,000. Goal is $200,000 pre tax spending in retirement. Can Todd retire his plan and give Margo the lifestyle she craves or should he stay on the grind a bit longer? What would be right for a Roth conversion strategy given our situation? Thanks, ymyw. We love your show. Todd and Margo.
Big Al Clopine
All right.
Joe Anderson
They've done a really good job of saving close to $5 million of liquid assets at 54 and 53.
Big Al Clopine
Amazing. Yep.
Joe Anderson
He wants to retire in 2026. So that's this year.
Big Al Clopine
That's this year, Yep. But I Think you got to, got to look at it. What's it look like right now?
Joe Anderson
All right, so he is the. As long as he's 55.
Big Al Clopine
Yeah, I do think that's. He should retire when he's 55, or at least in the year he becomes 55, which is probably 20, 26.
Joe Anderson
Yep.
Big Al Clopine
Yeah. So, Joe, I guess the way I look at it is deferred compensation plan is an asset. Yes. But it's going to be paid out over 10 years. So I actually subtracted that out of the assets to get a cash flow for the next 10 years. That leaves 3.9 million in assets.
Joe Anderson
What is the. $80,000 is going to get paid on in 10 years. So I wonder what the, the, the, the discount rate is. What?
Big Al Clopine
Well, we have, we have no idea. I just took straight line 800. 800,000. 10 years, 80,000 a year. It's going to be different year to year, of course, but anyway, so we got 200,000 of, of spend that they would like. Subtract 80,000, subtract 18,000. That's the rental income. Net rental income shortfalls. 100,000. That's a 2.6% distribution rate on 3.9 million. Yeah, I'm okay with that. And, and that will run out in 10 years, but then Social Security will kick in pretty quickly thereafter. So. Yeah, I think this looks fine.
Joe Anderson
Yeah, I think so, too. No debt. They can kind of vary their. They're spending 200. That's healthy.
Big Al Clopine
It is healthy. But the assets. And the deferred comp plan is pretty helpful.
Joe Anderson
Yeah. I mean, they've done a phenomenal job of saving, I mean, that much cash. Liquid assets with no debt.
Big Al Clopine
Yeah.
Joe Anderson
At that age is pretty remarkable.
Big Al Clopine
And they're empty nesters, so they don't, you know.
Joe Anderson
Yeah.
Big Al Clopine
They got colleges covered. Yeah, I like it.
Joe Anderson
Yeah, I do, too. So, yes, Todd can retire his plan to give Margo the lifestyle she craves. How do you crave a lifestyle?
Andi Last
It's got dry carpets.
Big Al Clopine
How do you crave a lifestyle?
Joe Anderson
I just crave a lifestyle.
Big Al Clopine
I do. Which includes travel.
Joe Anderson
And you crave it.
Big Al Clopine
Oh, yeah.
Joe Anderson
All right, sounds good.
Big Al Clopine
What do you think about the. What's the right Roth conversion strategy?
Joe Anderson
I think once he retires this year, they got the DCP plan that's going to give him $80,000 a year. They have $1,100,000 in taxable brokerage that they can use to supplement their income. They're going to be in the 12% tax bracket. I would convert $100,000 a year or a little bit more to get them to the top of the 22. And I would do that for a few years and I would just want to keep my taxable brokerage account in check. I wouldn't want to deplete it. But over the next, I don't know, I would at least do a three, four year conversion strategy of at least $100,000.
Big Al Clopine
Yeah, I think that makes sense to me too. And I think, yeah, you wait till 20, 27, Joe, because then he'll have no other income then. Yeah, you could probably, you could probably convert 100 to 120, 130. You know, you have to run the numbers but in that range to get to the top of the 22% bracket. And just like with, with our last listener question, if there is a dip in the market, a correction, you could convert a little bit more in that year because you got a lot of money in tax deferred. It'd be nice to get a little bit more out than a hundred thousand a year.
Joe Anderson
But still, I mean, you could get a good chunk, 7, $800,000 out. You could RMD is not going to then kill you. It's not going to pop them into a higher tax bracket. You can maintain that 22% tax bracket for a while and have, you know, maybe a million and a half sitting in Roth IRAs.
Big Al Clopine
Yeah, maybe if the market dips even 5%, you go to the top of the 24 that year. I don't know different ways to think about it.
Joe Anderson
Yeah, and that's why I think this is an ongoing thing that you guys need to be thinking about. It's not set it and forget it, you know, at his retirement date.
Big Al Clopine
Correct.
Joe Anderson
But yeah, really good shape. Love the savings, love the strategy, love the question, love the names.
Andi Last
Todd and Margo's retirement math likely works. They've got two paid off homes and zero debt. But if you've been on social media lately, you may have seen the opposite advice that equity sitting in a paid off home is dead and you should mortgage it out and invest it. Joe and Big Al tackle that idea head on along with a bunch more of the Internet's worst retirement strategies. This week on youn Money, you, Wealth tv. As soon as you've finished watching or listening to this podcast, click or tap the link in the episode description to watch YMYW TV and to grab that DIY retirement guide. When you're requesting that guide. See that how did you hear about US Dropdown? Do me a favor and choose podcast. Then do your friends a favor and tell them to get their own copy before the special offer changes. Sometime this Friday, May 1st.
Joe Anderson
Help me avoid a potential R D nightmare. Hi Andy, Joe, Big Al. I'm Kyle, a 40 year old physician working for a state federal university hospital system in the Midwest. My wife Katie, age 38, is a private practice attorney. We file taxes separately and plan to work full time until at least age 50. In between ages of 50 and 60 would like the option to go part time or retire early. Our long time spending Target is around $200,000 a year. My income is $500,000. Total university is $350,000 plus the BA is $150,000. Katie's is $150,000. My contributions all invest in broad diversified low cost index funds. University self directed pension, mandatory 8% pre tax dollar for dollar match of the contribution. I also max my $457,000 and the 403 with the 5% match. We do backdoor Roth IRAs, HSA and we put $80,000 a year into a brokerage account. Katie's contribution, she makes 401 minimal match in a Roth IRA. Former employer, 457 is $50,000. Assets me self directed pension $300,000. $457,000 is $160,000. 403, $190. Former employer 403185 Roth IRA 110 brokerage account $270,000. HSA 30 primary home is $500,000 with a $360,000 mortgage. Rental property, $250,000 value, $125,000 mortgage, currently not cash flowing. Katie's got $200,000 in a Roth in about, let's call it $75,000 in 401ks. So total liquid assets for these individuals is what? One, one and a half?
Big Al Clopine
Yeah, one and a half, that's right.
Joe Anderson
Okay, one and a half million of liquid assets. That's tied between 403bs, 457 plans, Roth IRAs and a brokerage account. They also have a three unit rental property, $700,000 value, $400,000 mortgage, 10 years left, positive cash flow, we have no debt. Besides these mortgages, my main question, Given the high annual pre tax contributions and the possibility of significant RMDs later in life, should I begin shifting some of these contributions to a roth? All right, so 40 years old, 38 years old, they make $750,000 of total income. This is what, this is my just gut reaction. Yeah.
Big Al Clopine
What do you got.
Joe Anderson
He's got a 403B, 457 and he's got a mandatory pension. Self directed pension.
Big Al Clopine
Sure.
Joe Anderson
I would do pre tax in the 403B and then. Or, or in the 457 and then I would do a Roth 403B if he has that option, which I think he does, and then the mandatory pension and then I would have Katie do the Roth. So you would have two Roths going into pre tax. That's what I would do. Like it at 40 and 38 years old for sure. I got a ton of plans. What's interesting about state employees, teachers, things like that, they had the 403B and the 457 and a pension. Yeah. So the print, the pension's pre tax. That's going to come out as ordinary income. But if you have 403 and a 457, you can, you have two full retirement plans there. So fully take advantage of one pre tax and then take the advantage of the other one.
Big Al Clopine
Wrong. Yeah. And Joe, when I do little calculations here, I just want to see could he retire at 55 just because he said between 50 and 60. So I just picked a number, got about one and a half million to start.
Joe Anderson
He's going to have plenty, right?
Big Al Clopine
It's a little closer than you think. Okay, yeah, yeah. Start a million and a half, 6% rate of return, maybe that's low. But 15 year, I think he's adding about 150,000. When you add up all these various categories, including the match, which then gets him to 7.1 million, which theoretically he could do anything. Right. But his spending at 200,000 now and 15 years with inflation is 312,000. And that's about a 4.4% distribution rate at 55.
Joe Anderson
But he's going to have cash flow on all this real estate. Help me.
Big Al Clopine
Well, and he didn't say how much, so I didn't add that. But I think if he retires at 55, he might need to do a little bit of part time work just to bridge the gap. But it's so far out and there's so many assumptions, it's hard to know.
Joe Anderson
Well, he's saving $150,000 a year and he's got $1,500,000 liquid at 40 and 38,000.
Big Al Clopine
Yeah, yeah, yeah. It's just though, it's just a relationship though between what you've got and what you're spending that we look at.
Joe Anderson
Yeah, of course. But the real estate is a variable that I believe will give cash flow.
Big Al Clopine
And chances are if you're saving for 15 years, you could have it more in stocks and maybe earn 7% or even 8. I just go conservative just to try to see.
Joe Anderson
Yeah, they're in a really good spot. I like the diversification. They're putting $80,000 a year into a brokerage account. They're fully funding their 401ks, the 403s, the, the 457s, the pension plans. They're saving more than 120.
Big Al Clopine
Al, I estimated 150, but.
Joe Anderson
150.
Big Al Clopine
Yeah, maybe, you know, it's just with those assumptions that I picked, so it's, it's hard to know. Okay.
Joe Anderson
But yeah, I think they're in a really good spot. 50 is going to be a little bit, could be a little bit tight, But I think 55 for sure is.
Big Al Clopine
And line 60 is great. 55 is probably fine. But I come up a little short with my conservative assumptions. I'll put it that way.
Joe Anderson
Okay.
Big Al Clopine
Yeah.
Andi Last
On page two, they actually ask if they should file separately or jointly.
Joe Anderson
I don't know why they're filing separately because he's a doc. That wouldn't have anything to do with it. I would file joint.
Big Al Clopine
Well, I don't know because he's not in a community property state. So I don't know how to answer that question without running it both ways. You have your CPA running both ways and he could tell you, or she can tell you.
Joe Anderson
What's the assumption to.
Big Al Clopine
Well, in a sense. Well, if you're in a non community property state, which most are, then I mean, community property we're familiar with, half of my income is hers, half of her income is mine. And you end up with two mirror returns with higher tax rates. Right. That's what we face. But in other places, then his income is his, hers is hers. They might be in brackets that are low enough that maybe she could do all Roth in a low bracket and do conversions and he would do all pre tax.
Joe Anderson
But that's your state. Is that state and federal?
Big Al Clopine
Yeah, yeah. In other words, whatever, whatever the state is, the feds follow for, for taxation. So I, I guess I'm not sure because in like in California community property state, which is where I live, you have two mirrored returns because half of everyone's income is each other. So it's two returns that look identical almost unless you have separate property before the marriage. And when it's two mirror returns, you're going to pay more tax. It's it's like the, the married tax brackets cut in half, but with, with a little extra tax on top of that, it. It doesn't quite work out as good. And I, I think the IRS doesn't really want you to file separately to get a tax advantage. So that's why they like lower standard deduction, you know, lower phase outs. Yeah. Cool.
Joe Anderson
All right.
Big Al Clopine
Oh, we wanted to know Roth versus Continued.
Joe Anderson
I didn't know we had that page on that.
Big Al Clopine
Yeah, there is. Yeah.
Joe Anderson
Aaron printed this out with double sided.
Big Al Clopine
Yeah. Makes it tricky.
Joe Anderson
Sided is tricky.
Big Al Clopine
Yeah. I don't like double sided.
Joe Anderson
It's terrible.
Big Al Clopine
Not when we're trying to read it on air.
Joe Anderson
Secondly. Okay, how should I think about this? I think we're on track for part time or fully retired. Between 50 and 60, right?
Big Al Clopine
Yeah. Yeah, we agree with that.
Joe Anderson
Separate or joint? We don't know. I think both have pros and cons, depending on what state you actually reside in.
Big Al Clopine
Yeah. You just have to have your accountant run the analysis and you can change year by year so you're not locked in.
Joe Anderson
Early retirement years 50 to 60 as an opportunity for Roth conversions. How much each year? Thank you. I'd love to hear how you'd approach Roth versus pre tax optimization for high income dual professional household with early retirement goals.
Big Al Clopine
Well, you already answered that.
Joe Anderson
I answered that. But conversions. How much do you want to do? How much does he have in non qualified? Again? Well, enough to pitch the gap.
Big Al Clopine
No, it's too early to say because It's. They have 270 right now.
Andi Last
270.
Joe Anderson
But he's saving $80,000 a year for the next 15 years.
Big Al Clopine
Yeah. So it'll be a big number himself
Joe Anderson
and I don't know. I would do conversions. No, no larger than 22% tax bracket today. Whatever that equivalent is in 15 years.
Big Al Clopine
I might do 20, 24. But the real answer is, who knows? Calculate when you get there because tax rates will probably be totally different. Yes.
Joe Anderson
Cool. Great. Hey, thanks for the questions this week. We gotta run. We'll be back next week to answer more of your lovely questions. Great job, Andy.
Andi Last
Thank you. Great job to you both.
Big Al Clopine
And you too. You killed it this week.
Joe Anderson
Oh, man, I'm tired. We're going strong.
Big Al Clopine
It didn't show. I'm just like ball of energy.
Joe Anderson
Yeah. Thanks, Aaron. Appreciate you staying up. We'll see you next time. Show Scotty money.
Andi Last
Well, next week on ymyw. When can Martha stop working full time and foster puppies instead? How can Bandit and Chilli and Kevin and Winnie retire this year. Make sure you're following us in your favorite podcast app so you don't miss a thing. Better yet, subscribe and watch Ymyw on Spotify or YouTube. And spoiler alert, coming soon, you'll have the option to listen or watch Ymyw in Apple podcasts as well. If you're fluent enough in YMYW speak that you know what the Megatron is, you probably have questions of your own that go a lot deeper than a spitball can reach. You know a spitball isn't the full picture. The full picture is what you get when you sit down with one of the experienced professionals on Joe and Big Al's team at Pure Financial Advisors for a free financial assessment. They'll look at everything your tax strategy, your investment mix, your income plan, your risk tolerance, and how you can weather inflation and market swings without losing sleep. It doesn't cost anything, it obligates you to nothing, and you'll walk away with a lot more clarity than you can get from any spitball. Probably a lot quicker, too. Pure has locations across the country from California to Tennessee, but Zoom works just fine. If you aren't near one, or if you'd rather just take that, call in your jammies, click or tap the free financial assessment link in the episode description or call 888-994-6257 and get on the calendar now. Pure Financial Advisors is a registered investment advisor. This show does not intend to provide personalized investment advice through this podcast and does not represent that the securities or services discussed are suitable for any investor. As rules and regulations change, podcast content may become outdated. Investors are advised not to rely on any information contained in the podcast in the process of making a full and informed investment decision.
Your Money, Your Wealth – Episode 579
Date: April 28, 2026
Hosts: Joe Anderson, CFP® & Big Al Clopine, CPA
Executive Producer: Andi Last
This episode answers listener questions about advanced retirement planning for high-net-worth individuals: tackling the challenges of large pre-tax retirement accounts, choices between Roth and traditional contributions, how to avoid future Required Minimum Distribution (RMD) "nightmares," and optimal Roth conversion strategies for those with $3M+ in tax-deferred money. The hosts blend sharp financial spitball analysis with their trademark humor, covering scenarios from early retirement dreams to multi-million-dollar “Roth conversion problems.”
“Yep, I agree 100%. 32%—yeah, that’s too high. Go pre-tax.” – Joe (04:58)
“A few years makes a big difference… 55, it’s still kind of on the border, but that’s more reasonable.” – Big Al (06:30)
"There's a lot of planning we rarely talk about that has nothing to do with dollars and cents." – Joe (09:43)
“I would probably try to defer as much income as I possibly can… for the tax break.” – Joe (15:19)
“The main way you reduce self-employment tax is to have more deductions in the business.” – Big Al (17:09)
“You convert when the market's down… You can take advantage of down years to convert more at the same tax bracket.” – Joe (24:15)
“If you convert a lot in a down market, the recovery happens tax-free. That’s where you make a killing.” – Big Al (25:11)
“That’s a 2.6% distribution rate … I’m okay with that.” – Big Al (30:44)
“I would at least do a three, four year conversion strategy of at least $100,000.” – Joe (32:52)
“Fully take advantage of one pre-tax, and take advantage of the other one Roth.” – Joe (38:25)
“Retirement… has a lot to do with what you want to be doing to fill your time. That’s as important as the financial part.” – Big Al (09:58)
"If you convert a lot in a down market, the recovery happens tax-free. That’s where you make a killing.” – Big Al (25:11)
“If you have 403b and a 457, fully take advantage of one pre-tax, and take advantage of the other one Roth.” – Joe (38:25)
“My drink of choice is whatever shows up on stage for free.” – Chlo Jopine (12:00) “How do you crave a lifestyle?” – Joe (31:56)
The episode is conversational, practical, and laced with the hosts’ signature humor and straight talk. Listeners are encouraged to run their own scenarios, regularly update their numbers, and focus as much on preparing emotionally for retirement as they do financially.
Whether you’re aiming for early retirement, worried about your pre-tax balance, trying to beat RMDs with Roth conversions, or maximizing your plan contributions as a high-income saver, this episode delivers actionable, nuanced advice. The hosts favor evidence-based, tax-bracket-aware recommendations, stress the importance of adaptability and ongoing planning, and remind listeners to enjoy the process – both financially and personally.