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The $250,000 Mistake Most Retirees Never Know They Made

39m 39s

The $250,000 Mistake Most Retirees Never Know They Made

The episode emphasizes that retirement tax planning, specifically Roth conversions, RMDs, and the IRMAA cliff, is the highest-return activity for retirees, yet it's rarely explained well. The host reframes traditional IRAs as partly owned by the IRS, calling the deferred taxes a "tax bomb" that grows over time. The core strategy is to choose when the IRS collects taxes, using the eight-year window between retirement and RMD start—when income is lowest—to convert traditional IRA funds to Roth at favorable rates like 12%. This window is a "structural gift" from the tax code, and unused bracket capacity is "use it or lose it." The odds of future tax rate increases, driven by national debt and scheduled bracket sunsets, make pre-paying now a wise hedge. Mechanics are straightforward: call your custodian, consolidate accounts, avoid withholding taxes from the conversion, and plan for the tax bill. A detailed example shows a couple with $50,000 income and $18,600 taxable income after deductions can convert $82,000 annually, filling the 12% bracket, moving $656,000 over eight years at 12% tax, saving $100,000-$155,000 in lifetime taxes. The host stresses that doing nothing is a costly default, and being an active decision-maker in tax timing is crucial for long-term wealth preservation.

Transcription

6107 Words, 34515 Characters

English
The retirees who do this well don't have better portfolios than retirees who don't. They have a better practice. The same way that some people have a journaling practice or a meditation practice, they have a tax practice. And man does it compound over 30 years into hundreds of thousands of dollars of difference. This is the part the financial industry has done a terrible job of selling. The annual tax practice is the highest ROI work a retiree can do. Hello friends, this is Tyler Gardner welcoming you to another episode of your money guide on the side. Where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing. So let's get started and get you one step closer to where you need to be. Quick note before we dive in, August pre-order incentive for my book Real Wealth is now live and this one is my favorite so far. Pre-order this month, tell me you did at TylerGardner.com/book and I will send you a draft chapter of a new book that I'm already working on and no, not even my editor at Norton has seen this writing yet. This sneak peak is yours to keep delivered to your inbox in early September. Pre-order today and you're locked in for every monthly incentive through December 1. TylerGardner.com/book now let's get into it. Several years ago I sat down with a very nice retired couple. Let's call them Jim and Linda because every example couple in personal finance is named Jim and Linda. Now, they came to me convinced they had done everything right. They had saved aggressively, they had maxed every tax-deferred bucket the IRS had ever invented and by the time they walked into the meeting they had about 3.5 million in a traditional IRA, 180,000 in a Roth and a paid off house. Jim was 71, Linda was 69. They both looked at me with the kind of com of financial satisfaction that comes from doing 35 years of correct things in a row. Now one of the first questions I asked them is have you done any Roth conversions? They had not. We did a quick calculation on a notepad. I told them as gently as I could that they had just spent the last six years, the years between Jim's retirement at 65 and the RMD started 73, sitting on top of the single greatest tax arbitrage available to retirees in the modern US tax code and they hadn't quite taken advantage of it. The conservative estimate of the missed opportunity, just in undone Roth conversions during those six years, somewhere between 180,000 and 250,000 dollars in life time federal taxes that were now going to be paid for absolutely no good reason except that nobody had ever taught them how to do Roth conversions. Linda looked at Jim, Jim looked at me, the room got a little quiet. I've come to part three of the accumulation series and it is by my count the most expensive episode you will listen to all year. Not because it costs you anything, as always this is all free, but because the cost of not understanding what's in it compounded over the rest of your life is actually staggering. Today we're going to address three topics that very few people I know explain properly and simply. Roth conversions, RMDs and the Irma cliff. So sit back, you might want to bring a pen, maybe a glass of wine and I'll do my best to simplify what needs to be simplified. Part one. Why your traditional IRA is a beautiful thing for both you and the IRS. I want to start by reframing how you think about your traditional IRA because the standard framing is kind of wrong and the wrong framing leads to the wrong decisions for 30 straight years. The standard framing and I've been very guilty of this goes like this. Ooh, my traditional IRA is worth 1.2 million dollars. Therefore I have 1.2 million dollars. I am a person with 1.2 million dollars in retirement savings. And this is, I'm sorry to report not quite true. But you actually have if your traditional IRA holds 1.2 million is depending on your future tax brackets somewhere between 720,000 and 960,000 in spendable money. The rest belongs to the federal government. They just haven't asked for it yet. You're holding it for them. You are in fact a slightly fancy escrow account on behalf of the US Treasury and the Treasury will eventually send someone over to collect. You might have heard others refer to this as the "Rapt Tax Bomb" and I think it's the single most useful mental model for understanding traditional IRAs. Every dollar in there is going to be taxed at your ordinary income rate the moment it comes out. Not your cap gains rate, not some special retirement rate. Your full, regular, no discount, no coupon, ordinary income rate. Whatever the tax brackets look like in the year you withdraw, that's the rate. And unfortunately we don't have control over what those rates might look like in the future. This matters because most retirees look at their traditional IRA balance and they feel rich and they are. Just not quite as rich as the screen suggests. The screen is showing you the gross. The IRS is collecting the difference between the gross and the net and the longer you wait, the bigger that difference tends to get because the money keeps growing which means the tax bomb keeps growing along with it. Here's the practical implication. The objective of retirement from a tax planning standpoint is not to avoid paying taxes on the traditional IRA. That's impossible. The IRS will get it share. The objective is to choose when the IRS gets its share and at what tax rate. Thinking back to last week's episode, remember we want always to fill out the 10 and 12% brackets to the dollar if we can to take advantage of lower rates when we can. So when looking at the traditional IRA, heading into retirement, you have basically three options. One, pay tax now voluntarily at today's known rates while you're in control of your income. This is called a Roth conversion. Option two, pay the tax later involuntarily at whatever rates exist when the IRS demands it. This is what happens if you do nothing. Eventually, at 73 or 75 depending on when you were born, the RMD start and the bill becomes mandatory. In 3, you die and you let your kids pay it at their respective tax rates on an accelerated timetable. This is usually the worst option for most families for reasons we'll get into later. So the whole game becomes option one versus option two. Which one is cheapest for you, your spouse, and your heir is collectively given the realistic range of future tax environments. And almost nobody asks the question this way. Most retirees default to option two, do nothing let RMDs handle it because option two requires no additional action and humans are biased towards whichever option requires no additional action. The IRS, I should note, is delighted by said bias as this bias or indecision or inaction, if you will, results in roughly 1.4 trillion of the federal tax base. Not be the bias. Be the active decision. I've said it before and I'll say it endlessly. Whether you do or don't take advantage of Roth conversions, you always want to be in control of the things you can control in finance and investing. And when and how the federal government collects taxes is one of the things you actually can control. This episode is brought to you by Gelt. Most of you listening probably already work with someone for taxes. But if you're a solopreneur, a real estate investor, or a high net worth individual who CPA has gone completely radio silence since April, this is for you. A great CPA gets in touch with you. They call in July asking if you've thought about something, they don't wait until next March just to react. The moves that actually reduce your tax burden happen right now. TTE elections, S Corp timing, K1 cleanup, and prior year retirement contributions. Gelt is built around exceptional tax professionals focused on your strategies and your relationship powered by cutting edge technology that handles the rest, designed for those who demand talent and welcome innovation, and know the difference between ordinary and extraordinary everywhere. Gelt is taking on new clients this quarter, including an extension rescue program for anyone who filed an extension and needs a deadline safe handoff. And for new clients, they will help model your prior year retirement contribution opportunities and help you fund what's still on the table before October 15th. Visit joingelt.com/tyler to get started. That's joingelt.com/tyler. This episode is brought to you by FASIT. If you know who Frank the Tank is and your idea of a nice little Saturday involves heading to Home Depot, this is for you. Because I see you, Gen X, and I want to make sure you're ready for retirement. And if you're currently looking for a financial planner, there are three things a percentage-based financial advisor is hoping you never think about. Number one, it is not necessarily harder to manage more money. Yet these advisors will often charge you more just because you have more. Same asset allocation plan, same phone calls asking how the kids are doing, and yet the fee continues to grow. Number two, and the line they feed you, the "we do better when you do better," it sounds great until you realize that the fastest way for them to do better might be to put you in riskier assets than you wanted or needed. Your risk tolerance and their incentive structure need to be properly aligned. And number three, notice how they never tell you the fee in dollars, only the percentage. Because once it's not in dollars anymore, it doesn't feel like dollars anymore. FASSE IT WORKS DIFFERENTLY. One flat annual membership fee based on the services you need. No percentages, no commissions, just a dedicated team of CFP professionals who help you figure out what you want your money to say about your life. Head to facet.com/tyler to book your intro call, and you'll still have time to make it to bedbath and beyond. I'm not a member of FASSE IT, I have an incentive to endorse FASSE IT as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity and FASSE it based on this endorsement. FASSE IT is an SEC registered investment advisor, all opinions are my own, and not a guarantee of a similar outcome. Part 2. What a Roth conversion actually is. A Roth conversion is mechanically very simple. You take some amount of money, let's say $40,000 out of your traditional IRA, and you put it into your Roth IRA. The IRS treats this as a taxable distribution, UO ordinary income tax on the $40,000 in the year you convert it. The money now lives in your Roth, where it will never be taxed again, ever by anyone. That's the entire transaction. Pay the tax now, never pay again. And on the surface, this might look like a wash. Why would I voluntarily pay tax today, on money I don't have to pay tax on until later? Well, the answer is the entire reason this episode exists, and it has three parts. Reason 1. Years between when you retire and when RMD start are almost without exception, the lowest tax rate years of your entire adult life may be minus your 20s, and so sorry we might have missed that window. Your earned income has dropped to zero. You might not be collecting Social Security yet, or you're collecting only a portion of it. Your taxable investment income is whatever you've structured it to be. You are for a beautiful window of roughly 8 years, in the lowest tax bracket you have ever inhabited as an adult, and will ever inhabit again. These are the cheap years, the conversion window, and once they're gone, they're gone. RMD start Social Security ramps to full benefit, and you're pushed back into higher brackets for the rest of your life. The 8 year window between retirement, roughly 65, and RMD age, roughly 73, is a structural gift from the tax code that exists for exactly one reason to be exploited. Reason 2. The odds of tax rates going up? It's not zero. I want to be careful here because I have no political agenda and predicting tax policy is fraught, but the structural facts are these. The US federal debt is at historic highs. Social security and Medicare do face significant funding pressure over the next 20 years. The current bracket structure, the one we got from the 2017 Tax Act, is scheduled to sunset, after which rates revert to the pre-2017 levels, which were noticeably higher. Even if Congress extends the current brackets again, the long term trajectory of federal tax rates, over a 35 year retirement, is usually up, not down. A Roth conversion in this environment is essentially the financial equivalent of locking in today's mortgage rate when you think rates are going to rise. You're pre-paying at a rate you can see for an obligation you'll have to pay at a future rate that you can't see. Reason 3 is the one very few people talk about, but we did in the last episode, the bracket fill effect. If you're already going to be in the 12% bracket this year because of other income, you have a fixed amount of unused capacity in that bracket. The difference between your taxable income and the top of the bracket, and that's roughly $100,000 for a couple in 2026, that unused capacity is, in a sense, worthless unless you use it. IRS does not let you carry forward your 12% bracket capacity into the next year, use it, or lose it. A Roth conversion is the most efficient way to use it. You convert exactly enough traditional dollars into Roth dollars to fill the 12% bracket to the top. You pay 12% on those converted dollars, a rate you might never see again, and you move them permanently out of this wrapped tax bomb and into the never taxed again Roth. The combined effect of these three reasons is staggering. A couple converting 40,000 to 60,000 a year during the eight-year window between retirement and RMDs can move $320,000 to $480,000 of traditional IRA money into a Roth at an average tax rate of 12%, where it will never be taxed again. The same money sitting in the traditional IRA until forced out by RMDs and tapped during a 22% or 24% bracket year would have been taxed potentially at double the rate. That's a lifetime tax savings of $35,000 to $60,000 for the work of filling out one form per year, genuinely the highest hourly rate available to retirees in the legal tax planning universe. Part 3. How to actually execute a Roth conversion. The five things you've got to know. I included this following action list because my guess is you've already heard, "Hey, you should take advantage of Roth conversions." My guess is you haven't heard as frequently how to actually do them and the steps you need to take. But good news. The actual mechanics are simpler than the financial industry makes them sound, and surprise that's because as always complexity sells and they'd like to charge you 1% of your assets to do this stuff for you. And rant for now. Step 1. Call your custodian directly. If your IRA is at fidelity, Vanguard or Schwab, log in and search Roth conversion. There's literally a button. The custodian moves the money internally from your traditional IRA to your Roth IRA. No IRS form, no third party done in one to three business days. Step 2. If it were me, I would have both accounts in the same custodian first. If your traditional IRA is at Vanguard and your Roth is at Schwab, you'll be coordinating a cross institution transfer that could take weeks. But if it's same roof, it's the same week. So for me, I would consolidate before I started converting. And I would consolidate before I retired in the first place. Step 3. Again, this is not advice, but you really should look into this. Do not have taxes withheld from the conversion. This is the single biggest mechanical mistake I see many people make. Any dollar withheld goes to the IRS and never makes it into the Roth. So if you can, pay the tax separately out of your taxable account or savings so you can keep the full conversion amount inside the Roth. Why is this so important? Because remember, there are annual limits throughout your life to Roth contributions, but there are not annual limits to Roth conversions. So you want to fund that baby with every additional dollar you can. Step 4. The tax bill arrives in April, plan for it. The custodian will then issue a 1099R at your end. You report the conversion as ordinary income on your own return. Marriage conversions may require a quarterly estimated payment to avoid an underpayment penalty. Your CPA will or should flag this just don't be surprised. Step 5. Each conversion starts its own five-year clock. You generally can't withdraw the converted amount without penalty for five years. Even if you're over 59 and a half. So track each conversion year separately and it's usually in our best interest to start early and do this annually to create a type of ladder system. That's the playbook. One button, one tax bill, one five-year clock per conversion. The conversion takes three minutes. The strategy which bracket to fill, how much to convert, what year, that's where the effort comes in. Step 4. The math of bracket filling made all too visible. Bear with me because I want to do an actual numerical example with you this week because abstract talk about brackets and conversions is the kind of thing that washes over people. So let me show you what this looks like in real numbers. We've got a couple, married filing jointly, both 66 years old, retired, sources of income for the year are as follows. Combined social security, roughly $48,000 of which roughly 85% is taxable at the federal level. Pension or other taxable income? Zero. Interest from cash positions, let's say it's $4,000 a year in a money market fund. Capital gains realize from the brokerage account, let's say it's $6,000 in short-term gains, which would be taxed as ordinary income. Their total taxable income before any conversion is just over $50,000. After the standard deduction for a couple over 65, which in 2026 is about $32,200, including the additional age-related deduction, their taxable income net of the deduction comes down to around $18,600. The top of the 12% bracket for married filing jointly in 2026 is $100,800, which means this couple has $82,200 of unused capacity in the 12% bracket. Tax rate-wise, it is the cheapest empty space they will ever have access to again in their lives. If they do nothing, the capacity goes unused. They pay zero in federal tax this year, which feels wonderful in a way that crash-dieting feels wonderful for about 90 minutes, and they have moved exactly zero out of their wrapped tax bomb. Now, if instead they execute a Roth conversion of $82,000, moving 82 from the traditional IRA to the Roth, they'd pay roughly 10,000 in federal taxes this year, about 12% on the conversion. They are now $82,000 lighter in the traditional IRA and $82,000 heavier in the Roth, and that 82,000 will never be taxed again for the rest of their lives or their heir's lives. Now, if they do this for eight years from age 65 to 73, the conversion window we just talked about, they will have moved $656,000 out of the traditional IRA at an average tax rate of 12%, paid roughly 80,000 in conversion taxes total, and saved themselves and their heir's somewhere in the neighborhood of $100,000 to $155,000 in additional taxes they would have otherwise paid at higher bracket rates later. Net result, pay $80,000 of taxes now, buy back $100,000 to $155,000 of tax savings over the next 30 years. This is, I want to emphasize, completely legal, documented in the US tax code requires no creative accounting and is endorsed by basically every fee-only financial planner in the country. It is the most boring correct retirement move available and so few people do it because so few people have had it explained to them in a way that makes the numbers visible. So now you've seen the numbers and now they're all too visible. This episode is brought to you by Thrive Market. Here's something you might already know about me. I genuinely love to cook. It might be my favorite creative act of the day, but I'm also a raging introvert and the grocery store is where creativity goes to die. The parking lot, jockeying, the cart traffic. The fluorescent lighting calibrated to make every human look like they need immediate medical attention. It's psychological warfare with a loyalty card. The usual answer would be delivery, but I live in rural Vermont where delivery is a thing that happens to other people. And we've tried some meal prep services, but the quality of ingredients just wasn't what I want going into my body or my cooking. Thrive Market solved the entire equation. It's an online membership grocery, $5 a month and they've already restricted over 1,000 ingredients. I'm not standing in my kitchen, googling whether some unpronounceable additive is fine. The vetting is done before I ever click, add to cart. Member pricing runs up to 30% off with free delivery on qualifying orders and most members make their membership cost back in their first two orders. Mine paid for itself in peace and quiet alone. So if you're ready to build your ultimate summer cart, join Thrive Market with my link Thrive Market dot com slash Tyler for $20 off your first three orders plus a free gift. That's a Thrive Market dot com slash Tyler. Part five. The RMD trap and the single most underappreciated date on a retiree's calendar. Okay. Now we get to the part that explains why all of this matters as much as it does. RMD stands for required minimum distribution. It is the IRS's mechanism for ensuring that the wrapped tax bomb eventually detonates whether you want it to or not. Starting at age 73 for those born before 1960 and starting in 2033, age 75 for those born after January 1, 1960, thanks to a series of laws called Secure and Secure 2.0 because Congress seems to be a little unoriginal with naming things. You are legally required to withdraw a minimum amount from your traditional IRAs every year. Calculated based on your account balance and your remaining life expectancy as estimated by an IRS table that does not as far as I can tell care whether you eat your vegetables. The first year RMD for a 73 year old based on the current IRS uniform a lifetime table is approximately 3.77% of your traditional IRA balance, which means if you have $2 million in your traditional IRA. Your first RMD is roughly $75,400. The next year that rate will go up slightly to about 3.92% and so on, climbing every year for the rest of your life. By age 85, the RMD percentage is around 6.25% and by 95, it's over 10%. The IRS doesn't just want their money back, they want it back at an accelerating pace. Now, what does this mean in practice? Well, this is why I call the conversion window the cheap years. The same couple from our earlier example, the ones with 2 million in their traditional IRA who didn't do conversions. At age 73, they must now withdraw $70,400 minimum and that's $75,400 lands on top of their social security and any other income pushing them squarely into the 22% federal bracket and possibly higher. That same $75,400 could have been converted 8 years earlier at 12%. The RMD doesn't just create a tax bill. It creates a tax bill at the worst possible rate because by definition, the RMD is on top of everything else you're already earning. It's the marginal dollar. It's the dollar at the top of your bracket. It's the most expensive dollar to withdraw. And there's a cruel additional feature here too. Once you start collecting RMDs, remember the size of the RMD is a function of the balance of the account. So, if you don't convert during the cheap years and your traditional IRA grows from 2 million to 2.8 by age 73, you might think that's fantastic, but your first RMD is no longer $75,400. It's $105,000. The bigger the balance gets, the bigger the RMD gets, the higher the bracket gets, the more tax you pay. The IRS designed the system this way. They're not trying to be nice. So that conversion window exists because Congress, in its rare moments of clarity, recognized that retirees needed a runway to move money strategically before RMDs force them into permanent high bracket territory. But the runway is finite. It closes on your 73rd or 75th birthday and the math of what you can save by using the runway versus ignoring it is, as we've already seen, six figure territory for any couple with meaningful traditional IRA assets. So if you remember one date from this entire episode, remember this one. The day you stop working is the day the conversion window opens. Your 73rd or 75th birthday is the day it closes. The years in between should not be spent idly. They are the most strategically active years of your entire financial life, even though they will look from the outside like the laziest. Part 6. Irma, the tax nobody calls a tax. This is the part of the episode where I introduce you to a fun thing called Irma that is technically not a tax, but is functionally one of the most punishing taxes in the entire US system, and almost no one outside of professional financial planners knows it even exists. Irma stands for Income Related Monthly Adjustment Amount. It is the surcharge that Medicare adds to your Part B and Part D premiums when your income exceeds certain thresholds. The Social Security Administration calculates Irma each year based on your tax return from two years prior. So your 2026 Irma is based on your 2024 income. The thresholds for a married couple filing jointly in 2026 are approximately up to 218,000 modified adjusted gross income standard Medicare premiums. From 218,000 to 274,000, you add about 80 bucks a month additional per person. From 274,000 to 342,000, about 200 a month additional per person, from 342,000 to 410,000, about 330 bucks a month per person, from 410 to 750, about $450 a month per person, and anything above 750,000 married filing joint, you add about $485 a month additional per person. Now again, these are per person surcharges. A couple with both spouses on Medicare can pay double. Both spouses in Irma Brackett Jump can mean that they are not in the same situation. in extra 5 to 10,000 in annual Medicare premiums. But here's the part that makes EERMA particularly cruel and also particularly important to understand. It is not like the marginal bracket system for our taxes. It's a cliff. A regular tax bracket is a gradient. If you earn $1 over the 12% bracket, that $1 is taxed to 22%. Everything below is still taxed to 12%. It's painful but proportional. EERMA is not a gradient. EERMA is a cliff. If your modified adjusted gross income is $274,000, your premium surcharge is about $80 a month per person. But if that gross income is $274,000 and $1,000, $1 over, your premium surcharge can now be $205 a month per person. That $1 of additional income just cost you roughly $3,000 in additional Medicare premiums for the year across both spouses. The marginal tax rate on that $1 is over 300,000%. That's just math. This is what is sometimes called the EERMA cliff and it is the most consequential reason to manage your income year by year in retirement. Because crossing a cliff by accident is fully avoidable and almost always devastating to your annual budget. So here's the strategic implication. When you're planning your Roth conversions or your withdrawal amounts each year, you do not just look at the federal tax brackets, you look at the EERMA brackets too. You convert up to but not over the EERMA cliff that applies to your situation. You manage your income every single year with one eye on bracket fills and the other on EERMA proximity. This is the kind of thing that requires actually running numbers and there are calculators online that let you model EERMA against your projected income. Use one, please, because the cost of crossing a cliff by accident is one of the easiest losses to prevent and one of the most painful to absorb. Now, I can already hear some of you writing in one quick and crucial edition that nobody who I know who talks about EERMA really mentions. Though your EERMA surcharge this year is based on your tax return from two years ago, there is a fix and it is form SSA 44. It lets you ask social security to recalculate your EERMA based on a qualifying life-changing event and those events include retirement, work reduction, marriage, divorce, death of spouse, or loss of pension or property income. The form is one page. The process takes about three months. The savings for a recently retired couple can run $5 to $10,000 a year. So please search form SSA 44 on SSA.gov and potentially save yourself from falling off the EERMA cliff. Part seven. This is a quick technical block because if I don't cover these, someone will email me and the email will be 100% correct. First, the ProRata rule. If you have traditional IRA money in multiple places, especially if you have non-deductible contributions mixed in with deductible ones, conversion gets a little tricky. You can't selectively convert just the deductible portion. The IRS treats all your traditional IRA dollars as one big pot and perorates the tax accordingly. Now, if you've never made non-deductible IRA contributions, this doesn't apply to you. It's much easier. But if you have, talk to a CPA before converting. There is a work around called the Backdoor Roth that's relevant here, but it's beyond the scope of this episode, talk to your CPA. Second, spousal Roth conversions. Each spouse converts their own IRA independently. There's no joint Roth conversion. So if one spouse has one and a half million in a traditional IRA and the other has 200,000, you can convert from either or both, but the conversion shows up on the joint tax return as a single combined income number that determines your bracket and your misstatus plan accordingly. Third, year of death conversions. If your spouse dies, first, I'm sorry. The surviving spouse files jointly for the year of death and then becomes a single filer the following year. Single filer brackets and Irma thresholds are dramatically lower than married filing jointly thresholds, roughly half, which means the survivor faces a tax increase the year after the death, even if their income hasn't changed at all. This is called the widow's penalty. And it is one of the strongest arguments for aggressive Roth conversions while both spouses are alive. Because once one of you is gone, the cheap bracket capacity drops by half overnight. And the conversions you didn't do at 12% married now have to come out at 22 or 24% single. The widow's penalty is the kind of thing nobody warns retirees about, and it can cost a surviving spouse easily, 30 to 50,000 a year in additional taxes for the rest of their life. Part eight, the annual practice revisited. I want to bring this all back to the original framing I used in parts one and two of this series because I think it matters. The withdrawal order changes every year. The conversion amount also changes every year. The bracket fill changes every year. The Irma proximity changes every year. The social security claiming decision, that's fixed, but everything else is an annual decision. What this means practically is that good retirement tax planning is not a static decision. It's an annual practice. Every December, I want you to sit down, or sit down with your CPA, or your fee-only fiduciary advisor, and I want you to look at the year about to close and the year about to open. I want you to forecast your income for the coming year. I want you to identify the bracket fills available. I want you to check the Irma thresholds, and I want you to execute the conversions that make sense for you. I want you to realize the capital gains that make sense for you. And then file the paperwork. The same way that some people have a journaling practice, or a meditation practice, they have a tax practice. Once a year, maybe twice, and man, does it compound over 30 years into hundreds of thousands of dollars of difference? The annual tax practice is the highest ROI work a retiree can do, and almost nobody packages it that way. They sell investment management. They sell financial planning. They sell estate documents. The annual tax practice, which is the most valuable hour of your year, is bundled into all of those services as an afterthought, if it's even there at all. So your job right now is to find someone who treats it as the main event, pay them what they're worth, or do it yourself with a calculator and a couple of free online tools, once a year, every year for 30 years. It's work, but it's work that will pay immense dividends forever. That's part three. Three big ideas, and if you take nothing else, take this. Your traditional IRA is a wrapped tax bomb. RMDs are the IRS forcing the tax bomb to detonate when they want, not when you necessarily want. Yerma is a cliff, not a gradient, and the annual tax practice is the highest ROI work you could do as a retiree, and almost nobody's doing it. Next week, part four of the art of decumulation, market downturns in retirement, sequence of returns risk, the guard rail framework, when to actually deviate from the plan, and how to tell the difference between weather and climate in your portfolio. If this was useful, and given that we just walked through the highest stakes math of your retirement together, I hope it was, please consider sharing it with someone in the conversion window who has not yet started converting. They will thank you, or they will be deeply annoyed at you for telling them they should have started five years ago. Either response means you got the message across. This is the decumulation series. Five parts were three deep with two to go, and as always, hope this gives you something to think about throughout the week ahead. (gentle music) Thanks for tuning in to your money guide on the side. If you enjoyed today's episode, be sure to visit my website at TylerGardiner.com for even more helpful resources and insights. And if you're interested in receiving some quick and actionable guidance each week, don't forget to sign up for my weekly newsletter where each Sunday, I share three actionable financial ideas to help you take control of your money and investments. You can find the sign up link on my website, TylerGardiner.com, or on any of my socials at socialcap official. Until next time, I'm TylerGardiner, your money guide on the side. And I truly hope this episode got you one step closer to where you need to be.

Podcast Summary

Key Points:

  1. Retirees who succeed financially often have a proactive tax practice, not better portfolios, which compounds into significant savings over decades.
  2. Traditional IRAs are not fully owned by the retiree; a portion belongs to the IRS as a "tax bomb," taxed at ordinary income rates upon withdrawal.
  3. Roth conversions allow retirees to pay taxes now at known, lower rates during the "conversion window" (roughly ages 65-73 before RMDs), avoiding higher future taxes.
  4. The gap between retirement and RMD start is the lowest tax bracket period of adult life, ideal for filling unused 12% bracket capacity with conversions.
  5. Tax rates are likely to rise due to federal debt, Social Security/Medicare pressure, and the 2017 Tax Act sunset, making pre-paying at current rates advantageous.
  6. Executing Roth conversions is simple
  7. A numerical example shows a couple could move $82,000 annually at 12% tax, saving $100,000-$155,000 over 30 years by converting $656,000 over eight years.
  8. The financial industry poorly sells this high-ROI practice, but it's legal, endorsed by fee-only planners, and requires minimal effort per year.

Summary:

The episode emphasizes that retirement tax planning, specifically Roth conversions, RMDs, and the IRMAA cliff, is the highest-return activity for retirees, yet it's rarely explained well. The host reframes traditional IRAs as partly owned by the IRS, calling the deferred taxes a "tax bomb" that grows over time. The core strategy is to choose when the IRS collects taxes, using the eight-year window between retirement and RMD start—when income is lowest—to convert traditional IRA funds to Roth at favorable rates like 12%.

" The odds of future tax rate increases, driven by national debt and scheduled bracket sunsets, make pre-paying now a wise hedge. Mechanics are straightforward: call your custodian, consolidate accounts, avoid withholding taxes from the conversion, and plan for the tax bill. A detailed example shows a couple with $50,000 income and $18,600 taxable income after deductions can convert $82,000 annually, filling the 12% bracket, moving $656,000 over eight years at 12% tax, saving $100,000-$155,000 in lifetime taxes.

The host stresses that doing nothing is a costly default, and being an active decision-maker in tax timing is crucial for long-term wealth preservation.

FAQs

A Roth conversion is when you move money from a traditional IRA to a Roth IRA, paying ordinary income tax on the amount converted in that year. Once in the Roth, the money grows tax-free and is never taxed again.

They allow retirees to pay taxes at lower rates during the gap between retirement and Required Minimum Distributions (RMDs), typically the lowest tax years of their adult lives. This can save tens of thousands of dollars over time by avoiding higher future tax rates.

It's the deferred tax liability on your traditional IRA balance. You don't truly own 100% of it; the government will tax every dollar withdrawn at your ordinary income rate, so the balance shown is the gross, not your net spendable amount.

Log into your custodian's platform (like Fidelity, Vanguard, or Schwab), search for 'Roth conversion,' and move funds from your traditional IRA to your Roth IRA. It's typically done in 1-3 business days with no IRS form needed.

No, it's best to pay the tax separately from a taxable account or savings. If taxes are withheld, those dollars go to the IRS and never enter the Roth, reducing the amount that grows tax-free.

RMDs start at age 73 or 75, depending on your birth year. They force you to withdraw from your traditional IRA, increasing your taxable income and potentially pushing you into higher tax brackets, so it's best to convert before then.

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