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How Much Is Your Happiness Worth?


Chapters

0:0 Intro
2:12 Finding a good CPA
7:20 Magnificent 7 RSUs
12:44 Time horizons and tax planning
15:55 Monetary benefits vs. lifestyle enjoyment
23:3 Maxing Roth conversions for estate planning

Transcript

Welcome back to Ask the Compound. This week I'm joined by Corporal, Lieutenant, what was your rank Bill? Captain. Captain. Yes sir. Filling in for Duncan who is driving a German sedan on the Autobahn right now I think. In honor of Duncan I was looking for my goofiest hat and I think this fits the bill.

I like it. Thanks. Today's show is sponsored by Rocket Money. I was playing around with Rocket Money today. It's a pretty cool app. It's really easy to link up your bank accounts and your credit cards through Plaid. And then you go through and you see all of your different subscriptions.

Lucky me, I did not find one subscription that I doubled up on so I'm doing okay there. But they also have this little tab that says, "Hey, let us negotiate a lower bill for you." Everyone here knows that I'm good at negotiating with my cable company every year. I'm undefeated.

But they said, "Let us take a look at your cable bill or your phone bill with AT&T or your internet bill and we will try to lower the rate for you." And it says I have an 85% hit rate, which is pretty cool. But just seeing all of your different-- it shows you recurring.

This is a monthly basis. This is a quarterly. This is an annual. It's a really cool little budgeting tool just to help understand where your money is going. Because I think a lot of people frankly just don't know. Maybe they don't want to know, but I think it's very helpful.

Willful ignorance. That's what I would plead. So rocketmoney.com/atc to sign up. Again, that's rocketmoney.com/atc. It's really, really easy. It's a cool little tool you can use right on your phone. Big fan. Yeah. All right. Bill Sweet stepping in today. So we have a lot of text questions. We've got other stuff.

We get 75 Roth questions a week. So people really like the Roth. Keep them coming. Floyd. I dig it. They let me out of my cage. Yeah, if we get 10. I want to say thanks to, as always, the people who are here on YouTube for the live show.

Amen. It feels like we have the same people here every week. You can always count on them being there. And they were here before I even signed in. I know they're there. They're talking to each other. They're asking us questions. They're making us jokes. I want to say I appreciate all of you in the live chat as usual.

John, let's do question number one. Let's do it. All right. Samuel. Oh, I'll take this one. OK. Samuel. Good name, right, Bill? It's perfect for a firstborn. Tweeting to me, "Any advice on how to find a good CPA, particularly for personal or small business taxes when hiring one versus doing it myself would be a good idea." We've talked about this one a little bit on the personal side of things.

We've never done it from a small business angle. Before we get into the question, John, do a chart on for me. This is from Bloomberg. Monthly U.S. small business applications, or business applications, has just skyrocketed since the pandemic. And after falling, it continued to stay in a pretty good range, and it's way, way above the pre-pandemic trend.

So I think this is one of my favorite unintended outcomes of the craziness of the pandemic is just an explosion in entrepreneurship. But if you do have your side hustle or side business or start going out on your own, there's a lot more to think about. So I guess technically, I have a small business between my blog and books and podcasts, that sort of stuff.

It's true. So when my tax stuff started getting more complex, I came to you for help. So how much more complicated is a small business than personal when thinking through this tax stuff? How much more important is it to have a professional there to help you? Yeah, this is a great question, Ben, and a common one.

And Ben, to me, it's very similar to a question we've got commonly on the advice side, which is, when should I hire an advisor versus run my own portfolio? What I would argue is, like financial advice, taxes is very niche. It ends up being a relationship business. And again, similar to financial advice, that the value comes in the advice about what you should do, how to plan.

And that conversation, thinking intuitively and viscerally with a professional about how to plan for the future, the tax preparation is the commodity, just like for us, a portfolio is a commodity. So I would start with, take a look at TaxSlayer, Tax Act, IRS free file if your AGI is less than 70K.

But the threshold for when you should start looking for a professional, in my opinion, Ben, is when you want advice. When it stops being a commodity, you just don't want to get the work done, but you want to talk through, should I do this, should I do that? That, to me, is where the bar is.

And probably for taxes more than anything, we have a pretty educated audience here. But I think a lot of it in taxes is, there's stuff in the tax code that you don't even know exists. Like, you can get this break here, or you can actually write this off, or there's probably a lot of stuff out there that most people don't even realize exists because it is so complicated, our tax code.

Yeah, and it gets more complicated every year, unfortunately. But yes, how you treat a home office deduction, a lot of those decisions on corporate structure going into a small business, that is the type of thing I would strongly recommend speaking to a CPA or experienced professional. So, the next question coming from Sam, Samuel, was how do I find one?

So, John, can you pull up that chart that I put together? I would say three big buckets. The number one place, and it's the same thing with financial advice, how do you find a professional, a CPA? I would look for a referral. Talk to a friend. If you happen to be starting a small business, something that you have someone else who is a mentor, somebody that you look up to who runs a similar operation, I would talk to them.

Hey, how did you get started? Who did you talk to? Who's your CPA? Those to me are totally legitimate questions, and it's a fantastic way to grow a business from my point of view, which is to get good referrals because you end up replicating your clients over time if you know how to ask that.

So, I'd start with asking for a referral from somebody that you trust or look up to in the business. The second thing I would think about is specialties or niches. There are CPAs that focus on real estate partnerships. There are CPAs that focus on getting depreciation right. One of my favorite interactions I have each year, Ben, is with a client who happens to be a dentist, and he interacts with a CPA business that all they do is dentist.

That's it. So, I really like that specifically for tax because I think, again, the advice is what you're going to be paying for, and you are going to pay more, by the way, versus tax later. So, depending on your business, yeah, CPA for dentist, CPA for lemonade stand, whatever it is, find your niche.

I like that one. Yep, seek that. And then, finally, the third bullet point was just business organization. If you strike out on one or two, go to a local chamber of commerce, go to a local rotary, because I think that one-on-one, that face-to-face, you can get an idea of people's reputation.

I think, unfortunately, tax is not something that's translated well online, outside of very niche stuff and tax Twitter. Mostly, you're going to want to find somebody local that you can sit down and talk to. Before I used you, I relied heavily on my father, who was a former CFO in the same vein as you, and his thing that keeps him busy during tax season in retirement is he goes and does people's taxes at goodwill.

They actually do it for free. Yeah. Right? And I think they use the IRS free filing software. That's for people who have very little complexity, but there are services like that that you could look for as well. Yeah, and I give Ed Carlson a lot of props, because it's a great way for him to use his skills, right, and donate what he has most right now, which is time, right, to help people out.

So, I give him a lot of credit. You raised an excellent son, Ed. Great work. He made me do my first tax return when I was like 15 years old with my first job. On the kitchen table with a pencil, did you have to erase when you made a mistake?

I mean, I probably had three boxes I had to fill out, because I had a job, and that's it. I bet they don't do that. But when should I start that for my son? Do you think age seven, is that appropriate, the next couple of months? What do we think?

Yeah, put him to work. I've got my first one, 1987, my very first tax return. Maybe I'll bring it to the next show. You still have it? Yeah, I do. I do. I worked really hard on that, Ben. All right. Let's do another one. Great. Question two. I work for a Magnificent Seven company.

Ben, on titles, why are we Magnificent Seven? Where did this come from? We just keep moving the goalposts for the biggest companies. It's getting crazy. It's a new name every six months. But Robert says, I've accumulated RSUs quarterly for the past four years, and each of those carries its own cost basis.

It's about 30% of Robert's investable assets, almost $300,000, which is not to brag. I'm in my mid-30s. I have a pretty high risk tolerance. But what is a good rule of thumb for single stock exposure? What's a tax-efficient way to rebalance into index funds? I am considering selling them as there's more to vest.

There isn't much capital gain. But what do I do with my existing stocks? Should I sell my highest cost basis first? Do I care if it's mixed between short- and long-term gains? What are my options from Robert? And Robert's going to show up several times here on this show.

That's right. Yeah, double question. Yeah, yeah, yeah. So it always kind of boggles my mind how many 20- and 30-somethings we have running into on this show who work for a tech company, who have very high salaries, and have some really good RSUs and are doing very well for themselves, obviously.

Worked hard for it. Yeah, and probably have high-stress, high-work jobs, and probably are highly educated. So the first one is he obviously knows I have way too much single stock exposure. I need to get this down. So kudos to you for admitting that and understanding that. Some people don't ever get there.

We have plenty of clients who come to us in similar situations. For a lot of them, it could be way more than 30%. We've had people with 90, 95% of their wealth in, like, one stock, and they know, like, "Listen, I made a lot of money on this. Now I need to diversify." Yeah, and one of my talking points for Robert here, it's not just the stock exposure, but not only is 30% of your net worth tied to the company that you work for, so is your income.

So if something happens to that company, you're in pain in a lot of different kinds of pain. So how does this work between--because for some of these, you have to pay the taxes up front to vest the stocks, and then he has to pay after. How does this actually work?

Yeah, so relative to other types of equity-based compensation, Ben, RSUs, Restricted Stock Units, are extremely simple. Ben, the concept is each year you get paid based on a vesting number of shares, but instead of getting paid in cash, you're getting paid in company stock. That's it. And what they do is they play a little bit of game and chip in that they say, "Look, we're going to declare that you have a $50,000 RSU grant, but those shares aren't going to vest for five years." And so you see the stock price, you do the math, this is how much it's worth.

But in reality, you can't do anything with that stock until it vests, and that's the most important date when we talk about RSUs. Which has got to be such a psychological toll because, you know, like I'm worth this much based on the stock price, and then you see it fluctuating and it goes up and you feel better, and it goes down and you feel worse.

Yeah. Right, that rollercoaster, living that with your income. I guess the concept is you want people pulling in the same direction, right? You want a profitable enterprise, and so if people are thinking as owners, that's the concept. But yeah, I would agree. It's a bit of a game because ultimately the minute that you get that stock, there's really no tax benefit at that moment.

It's exactly as if they handed you exactly that same amount of net worth in cash, and it gets taxed that same way too. So step one for me, Robert, would be the minute that your next tranche vests, just sell it immediately. You already have 30% of your net worth in the stock in a company that you work for too.

There's no reason to take on additional single stock exposure. And if there's no tax benefit like there is with ISOs, like there is with ENSOs, just liquidate the shares going forward. That's step one for me. So as they come in, it's like reverse dollar-cost averaging. You're slowly selling them off as they vest.

That's great because your cost basis is equal to your market value on the date of vest. So that's step one. In terms of percentage spend, not sure how you feel about this, but yeah, I get really queasy when we get up to 50%, and Robert's more than halfway there of his total net worth.

I prefer for my clients to keep the total single stock exposure to 10%. I get kind of uncomfortable when we get north of 20. So, Robert, you're in the danger zone in my opinion. And, Ben, you've written a lot about financial history. General Motors, Enron, SVB, Lehman, General Electric we were talking about with a client today.

These are companies that were the largest, most stable, most growing companies that you could possibly imagine in their day, and they declined net worth, some of them to zero, right? And so many people in these individual positions that work at a company probably get a little overconfident, like, "Hey, I know this business.

I understand it," and that is tough for people who are in the situation of-- Precisely. --the business goes down, maybe your income falls, you lose your job, and your retirement is gone because the stock got wiped out. Yeah, you don't want to get into that situation. Amen. So our friend and colleague, Mr.

Joel Fishman from Bend, Oregon, likes to use a regret minimization framework. I would sit down and do the exercise, Robert. What happens if that stock goes to zero? What moves looking backward would you wish you would have made, right? You want to be a company man. You want to help invest in your stock.

You're going to continue to get RSUs. Do you need to have that much exposure? And I would just rip off the highest-cost basis, the lowest capital gains stock that's long-term, and do that more or less as soon as you can. In working for one of these magnificent seven companies, it's Google or Amazon or Microsoft or whoever, the stock price is probably up quite a bit.

So you've probably already done pretty well in these, so the time to diversify after you've made some money, it's probably pretty decent timing. I'm not going to say these companies are going to fall off a cliff, but you've probably done okay in these. A millionaire in mid-30s, yeah. When you've won the game, it's time to stop playing.

And again, you're going to continue to receive RSU grants, so there's no reason to hold that percentage. He sounds like he's thinking about this thing the right way, which is that's a good first step. Very good. All right, let's do a Roth one. Maxed out my contributions to my Roth 401(k) IRA every year for almost a decade, with my 401(k) match being the only traditional I have.

Always weird to me that they have a Roth 401(k), but then the traditional has to be the match. You've explained it to me, I still don't get it. Bill Sweet recommends Roth until the 32% tax bracket. I do. This person has been paying attention. But how does your time horizon affect the decision?

I'm in the mid-30s now, and 35% tax bracket. I don't plan on touching it until I run through my taxable account first, when I eventually retire. Does the 30-plus years of tax-free compounding growth trump the high tax rate, even if I am in a lower tax bracket later? Again, we've got someone in their 30s here who is thinking way ahead.

They're already thinking about retirement withdrawal strategies. They're in the tax bracket thoughts. This is a good question. Does age or time horizon ever affect your rule of thumb on the tax rate? Yes, I think it does. And, Robert, good to be with you again. The answer, of course, is it depends.

But for me, Ben, 35% is right around the place where I would favor a traditional contribution over a Roth as a general rule of thumb. We do happen to have a lot of details about Robert, but we're not in a place where we can give him specific financial advice.

But in my opinion, Ben, most folks in our practice that I observe, they kind of slow down and they stop working, usually in their 60s. And usually when RMDs, when Social Security kicks in, let's say 70, 73, sometime in that time frame, most taxpayers settle in around the 22, maybe 24% tax brackets.

And 35%, where Robert is now, relative to where he's probably going to be, that's a full 12% higher today than it is in the future, right? And so, Robert, if you plan to delay Social Security, you're going to have a few years at 0%, 10%, 12% to fill up those lower tax brackets.

22% bracket in today's dollars runs all the way up to $198,000 for a married couple. P combined, the primary thing I think that a lot of taxpayers don't accumulate for or think about when they're considering this is that tax brackets are also adjusted for inflation, Ben. And that's a key point, that if I can do up to $200,000 of Roth conversions today at 22%, if we have a 4% inflation rate over the next 30 years, that number is going to be up to 1.1 million, right?

So yes, we need to account for compounding. I guess I didn't realize that. So does that mean they've been tracking the actual inflation rate, so they've been going up pretty high in the last couple of years? Yeah, so it's tied to CPI-U, just like a lot of other indices.

There are some discussions to switch that to chain CPU, like Social Security did. But in my mind, right around 35%, that's when it stops making sense. And even a great study I'm going to reference later showed that even when you dial up the tax rates, like we think might happen in 2026, people are probably going to revert to pay about 3% more.

That's not what moves the needle. What moves the needle is these big shifts from '35 to '22. I think '35 is too high to recommend a Roth, and so I'd stick to traditional as a general rule today. Okay, that makes sense. The last point for Robert, state taxes might move the needle, particularly if you're in a high-tax state now.

Yeah, if he's a Magnificent Seven company, he might be in California. Yeah, or California, and you plan to move to Nevada, let's say. You plan to move to Washington state, no state income tax. Traditional makes all the more sense, right? Because you're not going to pay that state income tax in addition to higher federal tax.

So get out of San Francisco and move to Seattle. Yeah, assuming that anything's left there that's not nailed down in San Francisco, I would agree. Okay, all right, let's do the next one. So I just turned 27, and I make $260,000 at a job that started less than a year ago.

That's a lot of money, Ben, at 27. It is. It was a grind to get there, but the job itself is very stressful. I dread going to work in the morning, but I deal with it for the money, and I save an investment majority, so I don't have to do this forever.

For context, I have about $400,000 in investments right now. Recently an opportunity came up that's much more interesting and pays well, but not as much as my current job. It's around $150,000. At this is the intersection of what I do for work and my actual interest, so it could be a tap dance to work situation, but can I stomach a $100,000 income drop in the vanishing years of compounding?

Should I continue to grind it out and pack cash away or let myself go down the more interesting road? From Gavin. Ben, have you ever tap danced to work? Only Warren Buffett does that, I thought. I think so. Buffett and Munder. I have a lot of thoughts on this.

You're going to have to let me cook here for a minute. Oh, let's do it. This is one of my favorite questions I've gotten because I think most career advice is useless because I think your career path and trajectory is governed so much by luck and timing and personality and politics and skills in your network that it's basically impossible to say, "My career went this way, so if you just follow my lead, you'll do the exact same thing," because I look back at so many forks in the road for my career, if I would have done this, and how it changed, and the jobs that I did get and the jobs that I didn't get.

But this question totally hits on a trade-off that you-- do you want to earn a lot of money or do you want to work in the job that you love? That's a difficult decision. So the way I see it, especially in your 20s-- and again, this person is very blessed to make that much money in their 20s-- there's three types of jobs.

So there's learning jobs. Some jobs are just more about learning than earning, like learning what industries or jobs you want to work in, the people you do or don't want to work with, the types of companies you want to work with, and some people just need experience and on-the-job training.

Then I think there's earning jobs. A lot of my friends going out of college, the sole reason they picked a specific company was because of the salary. They took the best offer they could get, the best signing bonus, whatever. You might have to put in more hours and more stress, and a lot of these people did, but setting a baseline early in your career for future negotiations with different companies I think is something to think about.

You earn a lot of money at first and you set that baseline high, but in the future when you're negotiating salary, you already have that high starting. Then I think the third one is the dream job, which is perfect industry, perfect company, people you want to work with. I think 99% of people in their 20s probably never get the dream job right away.

If you do, you're lucky. Obviously, the ideal scenario is I want a job that I'm going to learn a lot, I'm going to earn a lot, and I'm going to be my dream job. My 20s were the learning route. I worked for a company that didn't pay much right out of school, mostly out of necessity because I had no idea what the hell I wanted to do, and that was part of it.

I was learning on the job, but I think that job springboarded my career because I learned so much about the investment business from my boss that I still use today, stuff about investment policy and asset allocation and making good decisions. So I think it was totally worth it for me.

I had a friend who went into investment banking who worked 80, 90 hours a week. His first year he had three days off all year, but he kind of loved it, and he used that to go into a different-- So I mean a lot of that is about your personality.

So I can totally sympathize with the reluctance to give up a big salary because you're always going to be anchoring to that level, and the psychological toll of losses sting twice as bad as gains feel good. If you get rid of that salary-- I could say right now you could pay me five times as much, and I wouldn't leave because I love working with you and working with all the stuff I get to do at Ritholtz and the creative projects.

The feeling is mutual then. Yeah. So I love that job, and you couldn't pay me enough to work somewhere else because you just wouldn't have the freedom and work with the same people, but I think it's easier for me to say I wouldn't take this mythical higher number versus saying I have a higher number, now I'm going to go lower to take that.

So you've heard of this Harvard study before. I think it was performed in the '90s. They asked a bunch of students and faculty, "Would you rather have a yearly income of $50,000 but everyone else makes $25,000 on average, or would you rather have $100,000 and everyone else earns $200,000 on average, keeping prices and cost of living constant?" And it was interesting.

The results were right down the middle. It was half people said, "I would rather make more relatively and less absolutely," and half people said, "I would rather make more absolutely and less relatively." And it's totally a psychological how-you-think-about-things kind of-- So I think life is full of tradeoffs. I'm a huge principles guy, personally.

I would have a hard time working in a soul-sucking job that's high-stress. I just don't have that type-A personality of I'm going to do this job, it stinks, but I'm making a lot of money and I'm packing it away. So I think it's hard to put a dollar figure on the tap-dance-to-work situation.

Here's the questions I would ask yourself. Because there really is-- There's no right answer here, right? I think you have to ask yourself-- Like you said, half of that Harvard study would do this and the other half wouldn't. Yeah, so I think it's personality. Do you really think your long-term financial situation is going to be markedly worse by taking this job?

We're dealing with a 27-year-old that saved $400,000. Yeah, they're already in a pretty darn good place. If you compound that over 30 years, you're already in a very good spot. How much do you really hate your current role? I think how much better would other areas of your life be if you didn't have this stress?

And what other perks might you get from this job? Like remote work, ability to benefit, some of these other things you can't quantify in a salary number. And then I think you have to think through is this opportunity ever going to come knocking again? Could you put it off for two or three years and if you wanted to pack away 70% of your income for a couple years to really make yourself good?

Or the inverse. Could you go back to this hellish investment job? If you had to, right. The question really boils down to how much is your happiness on the job worth? Which, again, you cannot answer, but I think this is-- I would have a very difficult time answering this if I was put in this scenario.

I'd like to say I'd go with my dream job, tap dance to work situation, but it would be hard to let go of that salary. A story that this makes me think of, my favorite author, Ben, is Kurt Vonnegut, and there's a great story with him and Joseph Heller, the author of Catch-22, and they're walking at a beach party in the Hamptons, and there's some hedge fund guy, and he's got all the cars on the beach, and he's got the models, and there's the shrimp and the cocktails, all this stuff in the '60s.

And Heller looks at Vonnegut and says, "I've got one thing this guy doesn't have." And Vonnegut says, "What's that?" And Heller says, "Enough." Yeah, I love that. Big Slaughterhouse-Five guy here. Oh, great, great. Classic story. So, Gavin, I'd go. I'd go, man. That would be my answer. Here's one of the things.

I talk to a lot of friends and family members who just hate their bosses or hate the people they work with or hate their job. With people outside of the industry, I rarely talk about my job because I actually enjoy it. I like what I do. I like the people I work with.

We have fun together. My wife is always saying, like, "Stop talking about your job to other people and saying that you like it," because they don't, obviously. So I don't know how you can put a price on having a job that you love going to just because of how much time you spend working in your life.

True, true. And especially if you can find that dream job in your 20s, I do agree that I don't know how often that comes around where you have that opportunity. Yep. Gavin, money's not all that's in life. Trade some money for time. True. All right. Last question. All right.

65, recently retired. When my employer started offering a Roth 401(k), I switched my contributions to the Roth. See, everyone's listening to Bill. But most of my career retirement savings went into traditional 401(k) before. As I look at what I will be getting in retirement, I'm realizing that I'll be in the 24% bracket forever.

That's pretty close to your estimate earlier. Delayed Social Security, RMDs from the TSP, and a nice federal pension. They all add up. I'm keeping Federal Employee Health Benefit instead of Medicare, so I don't need to worry about higher Medicare bills because of IRMAA. What's that? Yep, IRMA. IRMA. It's a Medicare adjustment for higher income folks.

You pay more for Medicare in your 60s. Getting assets into the Roth will protect them from possible future tax increases. Some of my account will go to my heirs, so the Roth might be a better wrapper for that asset for them. Given all that, should I just move my money out of the traditional account into the Roth now?

For example, do the minimum Roth conversion that keeps my income within the 24% bracket each year? My total is all in the Roth. What am I missing? So they're essentially wanting to transfer as many of those traditional assets to Roth now, so they'd be paying the taxes, obviously. Right.

Is it still called the backdoor Roth if you do it this way? No, that's a conversion. Okay, just a Roth conversion. Yeah, that's a front door or ceiling or roof. So this is a little bit of the opposite of the other one about the time horizon. Well, I guess it is because they're looking for their heirs, but is this overkill?

Is this too much, or do you think this makes sense? No, I think David's got all the checkboxes, right? So like he said, Ben, he mentioned an IRMA. He mentioned delaying Social Security. He's got a pension coming. He's got a TSP, a Thrift Savings Plan, which we've talked about on this show.

It's a 401(k) for government workers. My man, David, did everything right, and now he's thinking, "Gee, I'm probably going to pass these assets on to my kids, to the next generation. What is the most efficient way to do it?" And I think it comes down to, Ben, do you want to maximize your net worth now, or do you want to maximize your after-tax spending or your kids' or grandchildren's after-tax spending?

Ed McWorry, Ben, at Santa Clara University, wrote the best paper on this in 2021. It's called "When and For Whom Roth Conversions Are Most Beneficial," and the quote that I want to share with the listeners, "A Roth conversion will always pay off if the time span is long enough." The problem is, on a long enough timeline, according to Tyler Durden, we're all dead, right?

But David's thinking beyond his life, and I think that's really cool. The curveball, I think, that Congress threw us, the Value Secure Act in 2020, is now your time span for inherited IRAs, including Roths, is 10 years after your death. But to me, that's still long enough for somebody who's 65, probably has another 25, 30-year life expectancy, tack on another 10 years after that.

We're talking about 40 years. John, can we pull up my final chart here of the day? This is from the Ed McCrory paper from Santa Clara. It just measures very quickly Roth conversion or surplus, and for folks listening to my podcast, I've adjusted the ages to 65. The break-even point for most taxpayers at a 22% bracket is somewhere between age 80 and 84, depending on the situation.

Can we take the chart off for a sec, John? So you still have some time, then? I think we have some time. And keep in mind, again, that you've got 10 years after your mortality, right? So if we've got a life expectancy in late 80s, if David's already hit 65, his life expectancy is probably in the 90s.

We're really looking at a 35-year horizon here. So how much will those heirs appreciate? So let's say he does it just-- I'm going to do it just for the money I'm leaving to my heirs. If he just does those Roth conversions for them, how much will they appreciate getting a Roth as opposed to traditional money?

I mean, it solves all the tax problems, right? Because if you end up getting a Roth on the back end, tax-free, you're not writing a check to the IRS. You're not doing any tax withholdings. You don't have to mess around with your own IRMA, assuming you're somebody 65. I think it's the thing to do if you're looking at a 35- or 40-year time horizon.

David, I give you all the credit to doing it. The key point I wanted to emphasize, though, Ben, is I wouldn't go beyond--I said this before-- I wouldn't go up to the 32% tax bracket. I would draw a line at 24, because after that, it stops making sense. I don't know what the dollar amount is we're looking at, but assuming that we have income from our TSP, from our Social Security, from our government pension, we just don't want to go too far, right?

We don't want to be paying at 37%. So I think it's a multi-year process, but David's got the right idea, and I don't mind getting started here today. Kudos to the audience today. These are all great questions. I think this also--but I think this also proves-- all these questions prove-- you can study all this stuff you want and know everything, and it's still hard to make decisions at some point, right?

Because I've done this right, I've done this right, I've done this right, I know this, I understand what this means, but still, now, what do I do? And I think that's always the challenge with financial decisions is, even if you do everything right, it's still difficult psychologically to realize, like, "What if I go left and what if I go right?" Because it's rarely black and white for these things.

Yep, and it goes back to the first listener's question from Robert, which I believe--or Samuel, "When do I look for a CPA?" When you want to sit down and talk about advice. And I would not be afraid to ask a professional, "What should I do?" At the end of the conversation, going back to Joey Fishman, regret minimization, what am I going to regret more, looking back?

Am I going to regret more not doing enough Roth or paying the tax? And that probably would give you the answer. Perfect. Okay. We only have a million more tax questions in the doc, so they'll be back again, of course. Keep them coming. Thank you for filling in for Duncan.

I'm very excited for Duncan to come back. There's a part of my heart that's missing right now. Yes, we all miss him. Come back from Germany. Thank you to John for handling everything behind the scenes, as usual, all the charts. God bless you, John, Nicole, big shouts. Remember, our email here, askthecompoundshow@gmail.com.

Leave us a comment. Thanks again to everyone in the live chat. Leave us a comment on YouTube. Always ask some questions there. What do you call it? Rate, review, subscribe, all that good stuff. See you next time.