The Retirement and IRA Show

Chris’s Summary Jim and I are joined by Jacob as we tackle four listener questions on Investment Positioning , covering Quicken tools for tracking positions, funding a delay period Minimum Dignity Floor with a stable value fund, evaluating a too-good-to-be-true real estate return, and weighing a target date fund for long-term care reserves. Jim’s “Pithy” Summary Chris and I are joined by Jacob as we work through four listener emails, all circling back to how we think about Investment Positioning in retirement. (6:45) One listener wants to know what Quicken features another listener used to track positions. Jacob reads the original listener’s own description of using Quicken to set up investment positions, plus separate categories for essential and discretionary spending. (14:30) George wonders whether the stable value fund in his large 401(k) is principal protected enough to draw on. He and his wife are both 60 and plan to delay Social Security roughly 10 years, and he’s weighing this fund as the source to bridge that gap. Jacob and I dig into rate reset timing, liquidity restrictions, and mandatory withholding before landing on an answer. (46:45) A listener asks whether a real estate offer promising 18 to 30 percent annual returns is worth pursuing. Chris lays out the single clearest test I’ve heard for spotting too-good-to-be-true returns. (1:09:30) Georgette raises the question of parking her long-term care dollars in a 2040 target date fund. Jacob walks through how we tier the L in our SEAL Reserve by age instead of relying on one fund’s glide path, and I get into the real difference between a “to” fund and a “through” fund, including the story of a deputy sheriff who learned that difference the hard way. The post Investment Positioning Questions: EDU #2635 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefits and earnings records, financing a home purchase, and using a fixed indexed annuity (FIA) for discretionary spending. (11:15) A listener asks why a Social Security estimate lists a $3,944 survivor benefit rather than the projected $5,101 age-70 benefit and which amount would actually be paid. (21:45) The guys consider whether adding previously omitted stock option income to a 2017 earnings record could result in higher Social Security benefits and back pay. (31:30) Jim and Chris weigh using a 60-day IRA or Roth IRA rollover to finance a home purchase before selling the current home against a HELOC or mortgage. (55:15) Another listener asks for their thoughts on using a fixed indexed annuity (FIA) with an income rider to support discretionary spending and how it compares with their simpler annuity strategies. The post Social Security, Social Security, Home Purchase, Fun Spending: Q&A #2635 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion on the Fun Number, this time as a dialogue episode built around one listener’s hesitation around spending retirement savings and how growth and legacy positioning and establishing his SEAL Reserve helped him work through it. We revisit the seesaw framework for undeployed assets, clarify how the SEAL Reserve consolidated the old reserve positions, and explain why the Fun Vision is never set in stone and can and should be revisited. Jim’s “Pithy” Summary Chris and I are picking the Fun Number conversation back up in dialogue form this week, working through a long email from a listener whose growth and legacy positioning helped him get more comfortable with spending retirement savings after years of struggling to spend the money he worked his whole life to save. I have spent twenty-seven years questioning the safe withdrawal rate approach, and this listener took what we teach and reshaped it around his own need for peace of mind. He admitted flat out that spending money is difficult for him, and I don’t think that makes him an anomaly. Honestly, that’s the norm for most people entering retirement. I compare it to growing lettuce in my own garden, nursing it from seed, only to cut it down and eat it. You still do it, but there is a pull to let it keep growing. That is why we built the Minimum Dignity Floor first: the older you gets an explicit promise that food, housing, and healthcare are covered no matter what, so the younger you can give yourself permission to spend on fun. This listener wanted more comfort than that alone gave him. So we walk through where that extra comfort came from for him. The post Spending Retirement Savings: EDU #2634 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on spousal Social Security timing, a listener PSA on the super catch-up contribution rule, early withdrawals from a Roth 457(b) plan, Minimum Dignity Floor coverage using SPIAs, QLACs as a hedge against potential Social Security cuts, and a couple’s retirement strategy. (10:00) — A listener asks whether a wife nearing full retirement age can claim her own smaller Social Security benefit now, then switch to a spousal benefit once her husband files at his full retirement age. (18:15) — A listener PSA offers clarification on a previous Q&A episode’s super catch-up contribution rule discussion. (22:15) — Jim and Chris are asked how early withdrawals of growth from a Roth 457(b) plan are taxed for someone who won’t yet be 59 and a half, since 457(b) plans avoid the 10% early withdrawal penalty but may not meet the usual requirements for tax-free Roth distributions. (32:30) — George asks for guidance on using a dual life single premium immediate annuity (SPIA) to help a retired couple with minimal Social Security and no pension cover their Minimum Dignity Floor. (45:00) — A listener asks several questions about how qualified longevity annuity contracts (QLACs) work and whether the current contribution limit could offset a potential future cut to Social Security benefits. (1:00:30) — The guys review a retirement drawdown plan involving brokerage assets, Roth conversions, and an inheritance, and are asked whether the overall strategy holds up. The post Social Security, Early Withdrawals, SPIAs, QLACs, Retirement Strategy: Q&A #2634 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined again by Dr. Philip Snyder as we continue looking at narrowing the gap between healthspan and lifespan and extending your go-go years. We discuss a listener-submitted article on health-adjusted life expectancy, which argues for concentrating retirement spending in the first decade of retirement rather than following a static, Monte Carlo-based safe withdrawal rate. Dr. Snyder updates his coronary artery calcium scoring correction, introduces the CCTA angiogram for non-calcified plaque, and outlines the four components of exercise, cardio, strength, balance, and flexibility, for maintaining function as we age. Jim’s “Pithy” Summary Chris and I welcome back Dr. Philip Snyder to pick up right where we left off, because folks, this whole thing, all of it, is about extending your go-go years, and I’ll admit this episode gave me some homework of my own. Dr. Snyder corrects something he got wrong last time on coronary artery calcium scoring, breaks down a newer angiogram option for catching the sneaky non-calcified plaque a clean CAC score can miss, and even mentions a blood test called PLAC2 for folks who can’t do the angiogram. A listener sent in a short article about spending more in your first decade of retirement instead of hoarding it for some rainy day that never comes, and it is basically what I have been calling the Fun Number for years. You spend your whole life saving, and then you’re too scared to spend it. My dad used to warn me about the Debbie Downers in his retirement community, folks with plenty of money left but no health left to enjoy it. Nobody wants to be that person, and nobody wants to be the wealthiest person in the graveyard either. Dr. Snyder walks through the four pieces of exercise you need as you get older, cardio, strength, balance, and flexibility, and Chris and I both admit we need a grease gun just to get moving some mornings. We get into tai chi, stretching, why I still cannot make myself do it consistently, and why one-third of people who break a hip never fully bounce back. Show Notes: “The First Decade Retirement Plan” article The post Extending Your Go-Go Years: EDU #2633 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on the Social Security Fairness Act, an IRMAA question involving deferred compensation, Roth conversions before and after key age milestones, Roth contributions for high-income catch-up savers, and how TEFRA affects an inherited annuity. (9:45) — A listener disagrees with the show’s characterization of the Social Security Fairness Act as unfair, explaining that after paying into both a government pension and Social Security for 40 quarters, she believes receiving both without penalty is fair for her situation. (27:45) — The guys field a question from a retiree who retired in 2025 and will receive deferred compensation payments through 2029 that push his income over the IRMAA threshold. He wonders whether he can file an SSA-44 in 2029 to eliminate the IRMAA surcharges. (37:00) — Jim and Chris are asked to revisit a recent discussion on moving money from Traditional to Roth accounts instead of taking distributions, with a listener wanting more detail on the implications of doing so before age 59 and a half and after RMD age. (48:30) — George asks for the pluses and minuses of continuing Roth 401(k)/403(b) contributions later in life compared with investing in a taxable brokerage account, including how a 50-year-old might decide between the two and whether those aged 61-63 should use the Roth option for super catch-up contributions. (1:03:30) — A listener has several questions about TEFRA, including what it stands for, when it was enacted, and how it affects distributions from an inherited annuity listing Pre-TEFRA and Post-TEFRA cost basis. The post Social Security, IRMAA, Roth Conversions, Roth Contributions, TEFRA: Q&A #2633 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Jacob Vonloh as we continue our discussion on investment positioning, wrapping up asset placement for emergency, aging, and long-term care reserves and the fun spending that flows from your Fun Number, across the Go-Go and Slow-Go/No-Go phases. Jacob also outlines the guaranteed inheritance set-aside and closes with the growth and legacy position, the leftover dollars not assigned elsewhere. Jim’s “Pithy” Summary Chris and I are joined by Jacob Vonloh as we pick back up right where we left off last week on investment positioning, finishing up the fun spending and SEAL Reserve pieces we didn’t get to. I keep coming back to this: retirement is the mirror opposite of the accumulation years, and when your whole portfolio looks like one big pot, a down market makes it feel like everything’s going down — and that fear is what stops people from spending on fun. That’s exactly why we don’t look at it that way. Jacob walks through how we tier the SEAL Reserve by age, and how fun spending gets laddered and benchmarked differently depending on how soon you’ll need it — all made possible by looking at each position on its own instead of one blended portfolio, which is the whole idea behind what I coined the See Through Portfolio. It’s also why you can’t compare your protected short-term Go-Go dollars to your long-term positions and think something’s wrong — that’s an apples-to-oranges comparison from the start. There’s a real cost to saving your whole life just to sit there and watch the money grow instead of enjoying it — don’t become what my dad used to call a Debbie Downer. Before we wrap, we also touch on two more positions that won’t apply to everybody. If you’ve got a specific bequest you want locked in today, there’s a guaranteed inheritance set-aside for that. And if you end up with dollars left over once everything else is funded, we get into what to do with what we call the growth and legacy position. The post Investment Positioning Part 2: EDU #2632 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security spousal benefits, a listener PSA on HSA tax strategies and treasuries, and inherited IRA RMD rules for minor beneficiaries. (9:00) A listener asks about qualifying for spousal benefits after a lengthy separation, since both spouses are now retired but remain legally married. (28:15) The guys share a listener PSA on tax strategies involving harvesting HSA-eligible expenses, including Medicare B and D premiums, as a tax-free funding source, and on laddering treasury bills through Fidelity or Schwab instead of TreasuryDirect. (40:15) George follows up on inherited IRA rules for minor child beneficiaries, asking whether an eligible designated beneficiary can elect the 10-year rule instead of taking the stretch, which requires RMDs. The post Spousal Benefits, HSA Tax Strategies PSA, Inherited IRAs: Q&A #2632 appeared first on The Retirement and IRA Show.

If you’d like to skip past Jim, Chris, and Jacob’s opening chat about Jacob relocating to Iowa, Jim’s hiking plans, weather, office dog Apollo, and generational pop culture gaps, skip ahead to (10:00). Chris’s Summary Jim and I continue our discussion on the Fun Number, joined this time by Jacob as we turn to investment positioning of those pieces. Jacob walks through tracking positions without professional software, using individual fund assignments, spreadsheets, and a two-credit-card approach, plus the liquidity account and fall tax planning. We then cover delay period and post-delay Minimum Dignity Floor investment options, moving from full principal protection in the near term to a lesser degree of it further out. Jim’s “Pithy” Summary Chris and I pick back up on the Fun Number series, this time bringing Jacob on to tackle investment positioning, the piece everybody asks about once they’ve done the math from the first two episodes. Jacob spent years helping me build this from scratch, back when we tracked everything by hand before we ever had access to professional-grade tracking software, and he shares some of the tools do-it-yourselfers can use to keep track of their own toy box of positions without that kind of software. We also dig into the liquidity account, the piece that quietly connects your positions to your actual spending. Jacob’s two-credit-card idea for separating Minimum Dignity Floor from fun spending ties directly into it, and I explain why we do our tax planning once a year, in the fall, rather than guessing all year long. There’s a reason we’d rather convert to a Roth than take a straight withdrawal when refilling that account, and it comes down to what happens if your plans change. Once Jacob turns to investment options for the delay period and post-delay portions of your essential spending needs, we get into how the degree of principal protection shifts depending on how far out that money is needed, from fully protected in the near term to something with a little more market exposure further down the road. This is the heart of what I call the See-Through Portfolio, the whole reason we break things out this way instead of running one big portfolio, and there’s a real difference in how we treat money a couple of years away versus a decade out. The post Investment Positioning Explained: EDU #2631 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefits after the GPO repeal, estate planning for minor children, and annuity safety. (10:00) A listener asks whether the repeal of GPO permits the survivor in a mixed Social Security and non-covered pension couple to keep both Social Security benefits rather than only the higher benefit, and where this rule appears in the POMS. (37:00) The guys review whether a revocable living trust should remain the contingent beneficiary of retirement accounts while the couple’s children are minors, despite the potential for higher taxes, and what alternatives or overlooked issues may apply. (1:16:15) Jim and Chris address whether someone considering a $500,000 single premium immediate annuity (SPIA) should split the purchase between two insurers to reduce insolvency and state guaranty association risk. The post Social Security, Estate Planning, Annuity Safety: Q&A #2631 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion on the Fun Number, this time tackling what comes out first and how we plan for covering retirement income gaps. We look at funding both the delay period and post-delay period, including how a SPIA quote helps determine how much to set aside today to close a future gap. We also address aging and long-term care, and the smaller, less common carve-out for a guaranteed inheritance tied to a special needs dependent. Jim’s “Pithy” Summary Chris and I pick up the Fun Number conversation right where we left off, and this time we’re finally cracking open the toy box to show you what has to come out before anything gets set aside for fun. I still say it best with the seesaw: younger you on one side, older you on the other, and every dollar you carve out first is a promise you’re making across that fulcrum. We walk through the delay period, those years before your Social Security or pension is fully turned on, and why we don’t discount those dollars down the way you might expect. Then Chris shifts to the post-delay period, pulling a real annuity quote to price out a future income gap and translating that future need into a present-day number using our See Through Portfolio thinking, so you can actually see which assets are spoken for and which ones aren’t. We talk through how to close retirement income gaps step by step, and I even work in my usual gripe about the crystal ball nobody’s built yet. From there we get into the harder, more emotional carve-outs, the ones tied to aging, long-term care, and in some cases a guaranteed inheritance, before circling back to what’s actually left over for you to enjoy. There’s a reason people tend to want to spend now rather than reserve for later, and we talk about why that instinct is so hard to fight. Next week Jacob joins us to talk through how we actually invest each of these positions, so consider this the setup for that conversation. The post Covering Retirement Income Gaps: EDU #2630 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefit strategies, a Roth 401(k) catch-up rule loophole, HSA reimbursement for Medicare premiums, pension options including a lump sum rollover, and trust titling versus individual beneficiaries. (13:00) — George asks whether his brother can claim his own Social Security benefit at 62 and switch to the higher survivor benefit at full retirement age. (22:45) — A listener asks whether starting a new job in 2026 could exempt him from the new mandatory Roth 401(k) catch-up rule. (28:45) — The guys field a question about using HSA funds to reimburse Medicare Part A premiums paid for a spouse before age 65. (40:00) — Jim and Chris review a listener’s decision to take a pension lump sum and roll it into an IRA over the annuity options. (1:13:00) — Georgette asks which accounts should be retitled into her trust versus left as individual beneficiary designations. The post Social Security, Roth 401k, HSA Reimbursement, Pension Options, Trust Planning: Q&A #2630 appeared first on The Retirement and IRA Show.

Chris’s Summary “Jim and I begin a multi-part discussion on the Fun Number, a retirement budgeting concept for how much someone can spend on what they want rather than what they need once other obligations are covered. Jim traces how the idea originated from a client hesitant to follow through with his retirement dreams despite having more than enough saved to do so. In response, a single undifferentiated portfolio evolved over time into separately identified reserve positions. Jim’s “Pithy” Summary Chris and I are kicking off a series on the Fun Number, the concept, along with the Minimum Dignity Floor, that I’ve built my whole approach to retirement budgeting on. This first episode lays the groundwork for a multi-part discussion, since arriving at that number means first identifying everything else that needs to be sorted out first. To get into where the idea actually came from, I tell the story of a client who had more than enough saved but still couldn’t bring himself to buy the camper trailer he’d been dreaming about for years. Watching that play out taught me something I just couldn’t shake: money sitting inside one big portfolio, all lumped together, is money many don’t feel safe spending, no matter what the math says. That realization led me to start pulling pieces out of a portfolio. It started with handwritten notes and a three-bucket approach that never quite solved the problem. I kept pulling pieces out, the way a kid digs through a toy box, separating out what’s needed for security and reserves so what’s left becomes visible and spendable, for whatever someone wants to do with it. That thinking eventually grew into what’s now called the See Through Portfolio. The post Retirement Budgeting – The Fun Number: EDU #2629 appeared first on The Retirement and IRA Show.

Jim and Chris discuss the new PROMISE Act’s potential impact on Social Security before covering listener emails on pension RMD timing, interest taxation versus capital gains indexing, and portfolio strategy around Social Security survivor benefits and multi-account allocation. (5:30) — Chris discusses the new PROMISE Act and how it may impact Social Security. (17:15) — George asks how long he can delay pension distributions without violating RMD rules, given his 73rd birthday falls in February 2027. (29:45) — A listener asks whether interest income should be inflation-indexed the same way some propose indexing capital gains for wealthier taxpayers. (43:00) — The guys field a two-part question on how a surviving spouse’s Social Security loss factors into MDF portfolio and annuity design, and how to allocate a portfolio strategy across different account types. The post Social Security, Pension RMDs, Interest Taxation, Portfolio Strategy: Q&A #2629 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I dig into two beneficiary disputes as part of what we’re calling a “potpourri” EDU show: the 1930s Goodman Triangle life insurance gift tax dispute and a recent Montana Supreme Court ruling on an uncashed cashier’s check. We also discuss a bipartisan proposal to raise the home sale capital gains exclusion and a separate proposal to index capital gains for inflation more broadly. Jim’s “Pithy” Summary Chris and I dig into a variety of topics, starting with a court fight that traces back nearly a hundred years, something folks in the industry call the Goodman Triangle. Picture three people tied to one policy: an owner, an insured, and a separate beneficiary. Mrs. Goodman took out five life insurance policies on her husband, moved them into a revocable trust, and thought she was fine, until he died and the IRS said she’d made a taxable gift. She fought it and the court’s decision on the case still gets cited whenever a policy or an annuity has three different people sitting in those three roles. From there we get into a couple of proposals sitting in Congress right now. One would finally raise the exclusion on gains from selling your primary home, something that hasn’t budged since the late nineties even as home prices have doubled and tripled around the country. The House and Senate versions land in slightly different places, but both would roughly double the current numbers and index them for inflation going forward. The other proposal is a longer shot, backed by senators who don’t have much bipartisan goodwill behind them, and it would apply an inflation multiplier to stocks, real estate, and other capital assets so you’d only owe tax on the growth that’s actually real. We close with one of our beneficiary disputes out of the Montana Supreme Court: a husband pulls eighty thousand dollars out as a cashier’s check made out to himself, hides it in the house, and dies without a will. His wife cashes it, his son sues, and the ruling comes down to whether a gift was ever actually completed. The post A Potpourri of Beneficiary Disputes and Tax Laws: EDU #2628 appeared first on The Retirement and IRA Show.

Jim and Chris welcome back returning guest Dr. Phillip Snider for a Q&A episode that plays a little differently than usual. Listener emails open a broader discussion of healthspan and lifespan, (including how wealth, genetics, and lifestyle factors shape longevity), retirement planning for longevity, and Dr. Snider’s recommendation for additional tests to help assess your health risks. (5:15) — George cautions that median longevity statistics are heavily influenced by wealth, genetics, and individual behavior, and shares CDC data showing life expectancy rises significantly once someone reaches age 65. (29:45) — A listener asks Dr. Snider to discuss the value of the cardiac calcium score in assessing longevity. She also asks about the science behind statins, including their effect on plaque stability and a possible link to reduced dementia risk. Show Notes: Dr. Snider’s list of recommended tests: CAC test (coronary artery calcium,) or heart scan – a noninvasive, low-dose CT scan that measures calcified plaque in your arteries to predict future heart attack risk. hsCRP (high-sensitivity C-reactive protein) – measures inflammation in the body related to cardiovascular disease risk. IL-6 (Interleukin-6) – elevated levels are associated with multiple conditions including cardiovascular disease, diabetes (insulin resistance), cancer, and autoimmune disorders.  The sample has to be frozen before sending to the lab for processing, so it may need to be collected at a hospital lab or free-standing lab facility rather than at a doctor’s office. MPO (Myeloperoxidase) – measures an enzyme found in white blood cells (neutrophils and macrophages). It is a key biomarker of inflammation and oxidative stress. In the bloodstream, high MPO levels indicate that immune cells are actively attacking vessel walls, making it a powerful predictor of cardiovascular disease and plaque instability. Lp-PLA2 (lipoprotein-associated phospholipase A2) – measures a specialized inflammatory enzyme highly concentrated in unstable, rupture-prone fatty plaques within your arteries. Unlike general inflammatory markers (like hs-CRP), Lp-PLA2 is specifically localized to inflammation of blood vessels. The post Healthspan and Retirement Planning for Longevity with Dr. Snider: Q&A #2628 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I review a reader-submitted article on funding essential expenses in retirement, examining how one engineer split his portfolio into what we would call the Minimum Dignity Floor and Fun Number, using Social Security and a TIPS ladder. We compare that approach to our own income-based framework, discuss mortality credits from income annuities, and address reader emails about how long an essentials-only spending floor should realistically last. Jim’s “Pithy” Summary Chris and I get into a short piece a listener sent us, written by an engineer who approached retirement spending in a very engineer style way: building a model, gathering the data, and running the numbers. But he initially still came up short on peace of mind and ended up splitting his retirement into two portfolios, leaning on Social Security and a TIPS ladder for funding essential expenses, and landing on a lot of ground Chris and I have been covering for twenty-five years, even though he’s never heard of the show. I’ve got some thoughts on that TIPS ladder approach, particularly around mortality credits and what happens when you’re the one holding all the longevity risk yourself instead of pooling it. It ties into what I call the See Through Portfolio, our approach to positioning assets so you can actually see what each dollar is doing for you rather than treating everything as one big undifferentiated pile. I also bring back my seesaw, the younger you on one side, the older you on the other, to work through what happens with whatever’s left once the essentials are covered. We close out on a couple of relevant reader emails, including one from someone who put together twenty-five years of essential spending coverage on his own. Chris and I do some math on what that actually means for him, and I end up talking about fish schooling and birds flocking, because nature figured some of this out a long time before we did. Show Notes: Humble Dollar Article The post Funding Essential Expenses in Retirement: EDU #2627 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security spousal benefit calculations, variable annuities in a 403(b), converting Inherited IRAs, and the Social Security child-in-care provision’s effect on spousal benefits. (10:00) — A listener asks Chris to explain why his additional high-earning years increased his own benefit so little, due to Social Security’s bend point formula, and how that translated into only a small spousal benefit adjustment for his wife. He also asks whether Social Security stops recalculating a worker’s PIA once they reach age 70. (28:00) — Georgette asks why her 403(b) funds are classified as variable annuities rather than mutual funds, and whether they function like other variable annuities sold on the open market. (54:30) — The guys field a question about a non-spouse inherited IRA, where the account holder wants to know whether the required RMD must be taken before completing a separate Roth conversion. (1:05:15) — Jim and Chris address whether the child-in-care provision removes the early-claiming reduction to a wife’s spousal benefit, in a case where she claims at 62 and her husband, the higher earner, waits until 65. The post Social Security, 403b Variable Annuities, Converting Inherited IRAs: Q&A #2627 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion on annuity insurer failures and state guarantee fund protections before turning to jointly owned annuities, examining how they differ from other jointly titled assets. We cover credited versus uncredited interest, mortality table calculations for annuitized contracts, and how a jointly owned annuity’s death benefit passes to named beneficiaries rather than the surviving owner. Contract language varies by insurer on how the surviving joint owner is treated relative to named beneficiaries. Jim’s “Pithy” Summary Chris and I pick up where we left off last week and close out our take on that NBC article about a woman whose annuity insurer ran into serious financial trouble. I get into the timing behind a related lawsuit, why I think the agent involved should have caught the warning signs, and why the insurance company itself deserves plenty of blame too. We also break down how state guarantee funds actually work once an insurer goes under, the difference between credited and uncredited interest, and what changes once you’ve annuitized and the fund has to figure out your payments using its own mortality tables. Then we shift into jointly owned annuities, and this is the part worth paying close attention to. Most people assume a joint annuity behaves like any other jointly titled asset, where the survivor automatically ends up owning the whole thing. However, that is not always how it works. I walk through language from two different insurance contracts we have dealt with over the years, and the two companies handle a joint owner’s death in completely different ways. If you have an older jointly owned annuity with someone other than your spouse listed as primary beneficiary, this is worth looking into now, because what actually happens at the first owner’s death might not be what you expect. The post What to Know About Jointly Owned Annuities: EDU #2626 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security benefits for a disabled adult child, SPIA timing and funding, longevity assumptions, and QLAC planning. (15:15) A listener asks why Social Security appears to be paying a disabled adult child benefit and child-in-care spousal benefit as a combined 50% of the worker’s PIA rather than 50% each, and how they might address the issue. (32:45) The guys discuss whether to buy a SPIA now or wait until age 70, along with the pros and cons of purchasing one with pre-tax, Roth, or brokerage assets. They also address where a DIY investor may be able to purchase a SPIA. (1:11:00) Jim and Chris respond to a listener considering whether expected AI-driven longevity advances should factor into the timing of a future SPIA purchase. (1:19:15) A listener asks about using a QLAC to help accelerate Roth conversions and whether a special needs trust for a disabled adult child could avoid a large lump-sum tax hit if both parents pass early. The post Social Security, SPIA, SPIA Timing, QLAC: Q&A #2626 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I examine an Annuity Collapse involving PHL Variable Insurance Company, a $99,000 annuity, private equity ownership, state guarantee funds, and the limits of what the article explains. We separate fixed annuities, variable annuities, general accounts, separate accounts, insurer insolvency risk, market risk, and rating history, while noting why the missing annuity details matter. Jim’s “Pithy” Summary Chris and I dig into Annuity Collapse coverage that had a lot of listeners understandably worked up, but also left out some details that matter. The headline says a woman paid $99,000 to generate retirement income for life and then the insurance company collapsed. That gets attention. It should. But before everyone runs around saying annuities are terrible and insurance companies should all be burned at the stake, we have to slow down and ask what she actually owned, because the article never clearly says whether this was fixed, variable, in payout, deferred, in the general account, or in a separate account. That distinction matters. If this was a variable annuity held in separate accounts, those assets may not be part of the insurance company’s bankruptcy estate, though market losses and access problems may still be real issues while the company is in rehabilitation or liquidation. If it was a fixed annuity or money sitting in the general account, state guarantee funds can matter, but they are not FDIC insurance, and they do not move in a few days. They can take a really long time, and the limits vary by state and product type. The larger issue is not that this woman did something wrong. I do not fault her. I fault the agent, the regulators, and the private equity games that Tom Gober has been warning about for years. PHL had weak ratings for a long time, and if it begins with a B, I think it is bad. We also talk about using AI to research insurer ratings, downgrades, ownership history, and state guarantee protections, especially before using an annuity for a lifetime income stream connected to a Minimum Dignity Floor. Link to the article: https://www.nbcnews.com/news/us-news/paid-insurance-company-99000-generate-retirement-income-life-collapsed-rcna331934 The post Annuity Collapse: EDU #2625 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on delayed Social Security credits, annuity provider ratings, DIA versus QLAC income planning, and fixed indexed annuity (FIA) recommendations. (10:30) A listener shares a long delay in receiving additional Delayed Retirement Credits on their Social Security benefit and asks whether there are any further steps to take or whether patience is the best option. (26:00) Another listener passes along Kiplinger reader survey results on annuity providers and asks whether the information may be useful in a broader discussion about choosing an insurance company. (45:00) The guys are asked when a deferred income annuity (DIA) might be better than a qualified longevity annuity contract (QLAC) inside an IRA, especially given the potential RMD and tax advantages of a QLAC. (1:15:45) Jim and Chris respond to a listener nearing retirement who was advised to move TSP G Fund money into a fixed indexed annuity (FIA) and wants to understand whether that is better than keeping the funds in the TSP and using a withdrawal strategy. The post Social Security, Annuities, Income, Annuities: Q&A #2625 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion on Forced Annuitization in a highly appreciated non-qualified variable annuity owned by a 90-year-old listener’s mother. We examine LIFO taxation, IRD, IRMAA, period certain annuitization, beneficiary options, IOVAs, and the difference between a codified annuitization approach and the less certain non-qualified stretch. The distinction between a noun annuity and a verb annuity does a lot of work here. Jim’s “Pithy” Summary Chris and I pick back up with a listener’s situation involving Forced Annuitization, a 90-year-old mother, and a non-qualified variable annuity with a tremendous amount of gain. This is not the insurance company being nefarious. These contracts have annuitization dates, and in an older contract, age 95 may once have seemed far away. Now it is an iceberg. The first question is still simple: what does mom want to do? From there, the insurance company’s actual annuitization options matter, preferably in writing, because every policy is unique. We get into the black-and-white choices and the gray area. A life with period certain option may spread payments beyond the forced annuitization point if the insurer allows it. If death occurs before annuitization, a non-spouse beneficiary generally faces two cleaner choices: annuitize within one year based on actuarially sound life expectancy, or use the five-year rule. Then we look at investment-only variable annuities, where the insurance company may provide the annuity wrapper, the assets remain in separate accounts, and one company Jim contacted allows new contracts up to age 95 with forced annuitization pushed out to age 121. The gray area is the non-qualified stretch. Jim explains why he has softened, but not flipped, on it. The SECURE Act changed Section 401, not Section 72(s), and that matters. Still, the comfort level depends on PLRs, insurance company practice, and how much uncertainty someone is willing to tolerate. One path is the verb annuity: give up access and control in exchange for a lifetime stream of income. The other keeps the noun annuity alive, with more flexibility, but less certainty. Same problem, very different wrappers. The post Forced Annuitization: EDU #2624 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security earnings limits, and two emails relating to using annuities for LTC planning. (13:00) — A listener asks whether income from selling NSO stock counts as earned income for Social Security, potentially triggering the earnings limit before full retirement age. (21:00) — George asks about using a 1035 exchange to move variable annuities with guaranteed living benefits into a product offering long-term care benefits, and wants help weighing the tradeoffs of this approach. (49:45) — The guys help a listener think through annuity planning to fund future long-term care costs for in-laws, including whether to use one joint annuity or two individual annuities and where to find SPIA quotes. The post Social Security, Annuities for LTC Planning: Q&A #2624 appeared first on The Retirement and IRA Show.

Chris’s Summary: Jim and I continue our discussion on annuity basics before turning to a listener’s email centered on forced annuitization, a maturity date built into every annuity contract requiring annuitization or full distribution by a set age. A listener’s mother faces this deadline at 95 with a variable annuity that grew over 10x, creating a substantial IRD (Income in Respect of a Decedent) tax burden. We consider options including period-certain annuitization, adding a younger co-annuitant, a 1035 exchange, and charitable strategies. Jim’s “Pithy” Summary: Chris and I are picking back up where we left off last week on the basics of annuities, and we take a hard look at the licensing mess on both sides of the industry: insurance agents selling products tied to indexes they’re not licensed to discuss, and investment advisors selling annuities through wholesalers without ever getting an insurance license. We also get into why AI is becoming the great equalizer for consumers, and how a 2005 class action lawsuit built on a complete misunderstanding of annuity maturity dates sets up the real conversation. That real conversation is a listener’s email about forced annuitization. His mother bought a variable annuity in 2002 with money she didn’t need to cover her Minimum Dignity Floor and invested it aggressively. Set it and forget it. Now, decades later, a deadline is closing in, and what looked like a smart, tax-deferred decision has turned into a significant IRD problem with no clean exit. The listener has been chipping away at it, but the math isn’t cooperating. There are options, some involving the existing contract, some involving moving it entirely, and at least one that surprised even me when I dug back through my notes. None of them are perfect, but the worst move may be the one he’s already making. We’ll get into all of it. The post Understanding Forced Annuitization: EDU #2623 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on whether Social Security should be compared to an annuity, Rule of 55 distribution rules, using period-certain annuities during the delay period, QLAC timing and taxes, and using a SPIA for Minimum Dignity Floor coverage. (5:20) The guys address a listener’s objection to describing Social Security as an annuity and whether that comparison is accurate. (32:00) A listener seeks clarification on Rule of 55 distributions after receiving conflicting information about whether plan-specific rules matter. (38:45) Georgette asks whether a 10-year period before her mortgage is paid off can be treated like a delay period and covered with a period-certain annuity. (51:30) Jim and Chris answer a question about whether QLACs can be purchased for a spouse from an IRA, how QLAC timing can be structured, and how payments are taxed. (1:13:45) George wonders whether relying on excess RMDs or purchasing a qualified second-and-survivor SPIA from IRA funds is a better way to support long-term MDF coverage. The post Social Security, Rule of 55, QLAC Timing, SPIAs: Q&A #2623 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I tackle annuity basics to start off another National Annuity Awareness Month. We cover what annuities are as insurance contracts, the four parties to a contract, the accumulation and distribution phases, and the key differences among the major annuity types. We also touch on tax deferral rules, LIFO treatment, and the historical and industry context behind why annuities remain so widely misunderstood. Jim’s “Pithy” Summary  Chris and I use National Annuity Awareness Month to get back to annuity basics. I have a book in my office, Lee Welling Squier’s Old Age Dependency in the United States, written in 1912, before Social Security existed, that begins by asking why people don’t use annuities to help provide against want in old age. That question stuck with me because I was taught early in this industry that annuities were horrible, while pensions were wonderful. But, if a pension was one leg of the old three-legged stool, and the 401(k) helped pull that leg out, then maybe we ought to at least understand the product that can mimic some of that pension-like income for retirees who need it. Not love it. Not hate it. Just understand it. So, we start with the basics: what you are buying, who is making the promise, who controls the contract, whose life the payment is based on, how the accumulation phase works, and when/if the thing you own turns into a stream of income all matter. The word “annuity” covers a lot of very different vehicles. Some are plain and straightforward. Some are complex, with riders, caps, participation rates, and spreads. Some may be useful in the right circumstances. Others may be costly, confusing, or misapplied. And if you do not understand which type of annuity you are looking at, it is easy to use the wrong one in the wrong place. The post Annuity Basics: EDU #2622 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor and ex-spouse benefits, using annuity income to satisfy RMDs, and annuity laddering strategies for both SPIAs and DIAs and MYGAs. (6:30) George writes in about a cousin who turns 62 in November 2026 and whose ex-spouse recently passed away — he wants to know what survivor and ex-spouse Social Security claiming options may be available. (19:45) A listener asks whether annuity income payments from a qualified annuity can be used to satisfy the RMD requirement on a separate IRA, potentially eliminating the need to take distributions from the IRA altogether. 43:15) The guys hear from a long-term buy-and-hold investor at the start of his transition from accumulation to decumulation who is drawn to the idea of purchasing SPIAs or DIAs in multiple chunks rather than a single lump sum and is curious about tradeoffs as well as how to apply a dollar-cost averaging mindset to annuity income. (1:01:00) Jim and Chris take a question from a listener about 2.5 years from retirement who is considering laddering MYGAs through his 401(k) and wants to know whether the yield advantage of A-rated carriers is worth the added risk compared to sticking with A+ or higher, and whether CD laddering might be a simpler alternative. The post Social Security, Annuity RMDs, Annuity Laddering: Q&A #2622 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss income annuities in retirement as a lead-in to National Annuity Awareness Month, using a Fidelity Viewpoints article to frame the discussion. We walk through the article’s points on essential expenses, paycheck-like income, and management simplicity later in retirement. We also distinguish traditional income annuities from more complex annuity products and address liquidity, inflation protection, insurance company risk, and death-benefit trade-offs. Jim’s “Pithy” Summary Chris and I use a Fidelity Viewpoints article on income annuities in retirement to get an early start on National Annuity Awareness Month. The article points out that an income annuity may help when Social Security and pensions do not fully cover essential expenses, may provide some peace of mind around income that lasts for life, and may make retirement easier to manage later on. Those are not new ideas around here! Those essential expenses the article discusses is what we refer to as the Minimum Dignity Floor: food, utilities, transportation, housing, and healthcare. If Social Security and pensions do not fully cover those expenses, a simple income annuity may be worth understanding because if the basics are projected to outlast the income already in place, the question deserves more than a knee-jerk yes or no. We also spend time on what happens when the paycheck stops. People can have plenty of money and still miss the safety of income showing up on schedule. That is where the bottomless cup of coffee idea comes back in, and why spending during the Go-Go years can feel different when the basics are covered. Chris also gets into the simplicity point: aging, confidence, fraud risk, and why the older you, or a surviving spouse, may not want every decision tied to a portfolio. We also get into the article’s trade-offs, including loss of liquidity, lack of inflation protection, insurance company credit risk, and what happens if someone dies earlier than expected. Show Notes: Fidelity Article – “How to feel financially secure in retirement” The post Income Annuities in Retirement: EDU #2621 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security spousal benefits, portfolio withdrawal strategy for early retirement, HSA and Medicare premiums, the 4% rule, Roth self-employed 401(k)s, Roth conversions, and retirement trusts. (10:45) A listener asks whether her husband claiming Social Security on his own record before she files at 70, including as early as 62, would reduce his eventual spousal benefit, and in what circumstances an earlier filing might make sense for them. (20:45) She also asks how to structure her portfolio to cover a seven-year income gap before Social Security begins and fund a potential home purchase at retirement. (46:15) George and Georgette want to know which Medicare-related costs – IRMAA surcharges, Part D, and supplemental insurance – qualify for HSA reimbursement, and whether they can apply HSA funds retroactively to prior-year premiums. (54:30) The guys address the idea that money reimbursed from an HSA isn’t restricted to medical use, so saving receipts over the years can turn an HSA into a source of tax-free cash for virtually any expense. (1:01:15) A listener compares the 4% rule to Newton’s laws of motion – foundational but not the final word – and describing how he’s combining that framework with their retirement income approach for his own long-range planning. (1:08:30) Jim and Chris share a listener’s PSA that Fidelity began offering a Roth self-employed 401(k) in 2025, in response to a question from a recent episode. (1:11:30) One listener pushes back on the idea that Roth conversions only make sense at a lower tax bracket, walking through a math example to show that tax-free compounding can make converting at the same — or even a higher — bracket financially worthwhile. (1:17:45) George has structured his IRA with a testamentary trust for a financially irresponsible adult child and asks whether a “retirement trust”, could allow the trust to receive IRA assets without the compressed tax rates that typically apply to trusts. The post Social Security, Withdrawal Strategy, HSAs, 4% Rule, Roths, Retirement Trust: Q&A #2621 appeared first on The Retirement and IRA Show.

Chris’s Summary: Jim and I discuss a listener’s strategy for funding the delay period in this dialog show. A 59-year-old chemical engineer shares his plan to transition from 100% equities by purchasing TIPS only when his portfolio reaches new market highs. We cover his Social Security claiming strategy, concerns about CPI-based inflation adjustments relative to Minimum Dignity Floor expenses, and the potential role of a QLAC for late-in-life secure income. Jim’s “Pithy” Summary: Chris and I dig into a listener’s email in this dialog show, examining the retirement strategy of a self-described Vanguardian and chemical engineer who is three years out from retirement. His approach is built around what he calls “pedal to the metal” accumulation – 100% equities for his working years – and now he is figuring out how to transition his assets to a decumulation model. The centerpiece of his plan is a TIPS ladder covering his eight-year delay period, funded by selling from his all-stock portfolio only when it reaches a new market high. Most of his rungs are already purchased, and the approach has worked – the market has been kind. But Chris and I both flag the same concern: it works until it doesn’t. If markets go sideways or drop and stay there, he could find himself heading straight into sequence of returns risk without the rungs he needs, still waiting on new highs that may not come. Beyond those mechanics, we get into some of the things he may be underweighting. The five expense categories that anchor his retirement spending — food, utilities, transportation, housing, and health care — tend to rise faster than headline CPI, which is what TIPS are tied to. His year-over-year projections are clean and consistent, but real-world spending in those categories is variable, not a steady march. We also touch on his Social Security claiming plan and his note that he still needs to fine-tune his Fun Number once that funding is complete. The episode wraps with his mention of QLACs for late-in-life secure income – something Chris and I agree can make sense, and buying sooner rather than later may give more income dollar for dollar given how deferral and mortality credits compound inside these contracts. The post Delay Period Funding Strategy: EDU #2620 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on the SSA-44 and IRMAA process for a couple approaching Medicare, Social Security survivor benefit strategy, tax diversification for young investors, HSA vs. IRA prioritization and spending strategy during the delay period, and inherited IRA RMD rules for non-eligible beneficiaries. (15:30) A listener approaching Medicare asks how the SSA-44 process applies when one spouse is retiring while the other continues to work, and whether their planned Roth conversions could complicate the IRMAA appeal filing. (33:15) Georgette wonders whether she can start her own Social Security at 67, switch to a lower survivor benefit if her husband passes, and then return to her own larger benefit at 70. (41:00) The guys hear from a parent helping his adult children decide whether to convert their traditional IRAs to Roth IRAs or preserve a mix of account types for tax diversification in retirement. (57:45) Jim and Chris address two questions: (1) whether HSA contributions should be prioritized over IRA contributions for retirement savings, and (2) how to bridge a cash flow gap when brokerage funds run out during the delay period without undermining ongoing Roth conversions. (1:26:15) A listener asks whether a non-eligible beneficiary who inherits a traditional IRA before the decedent’s required beginning date must still take RMDs, given that the decedent had already taken one RMD in the year they turned 73. The post IRMAA, Social Security, Tax Diversification, Delay Period, Inherited IRA: Q&A #2620 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Dr. Phillip Snider, in what we hope is his first appearance of many, as we discuss what a healthy retirement requires. In this episode we discuss health span versus life span, or how long a person stays vibrant and independent versus how long they simply live. Grounded in the idea that a retirement plan is not only about how long money lasts but how long someone is healthy enough to enjoy it. Jim’s “Pithy” Summary Chris and I are joined by Dr. Phillip Snider as we dig into what a healthy retirement actually means. We say it all the time on this show – we’re not getting younger, stronger, or healthier – but most retirement plans are built around all your retirement years being the same. Maybe only five, eight, or ten of them will be your go-go year where you can truly enjoy spending. That is exactly why we wanted a physician in this conversation who, for the record, genuinely geeks out on retirement. Dr. Snyder puts some real numbers around how long the average person stays vibrant and independent and how those numbers compare to average lifespan. That gap has direct implications for how you think about your Fun Number and when to spend it. He also gets into specific, measurable indicators that can give you a clearer picture of where you personally stand. Right now, no tool exists that can do for the go-go window what long-term care software already does for future care costs. That question comes up directly in this conversation and Dr. Snyder has a view on what variables such a tool would actually need, and what could be coming on that front. Show Notes: CalcVita Biological Age Calculator The post Enjoying a Healthy Retirement: EDU #2619 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on IRMAA appeals, Social Security survivor benefits, a Venn Diagram PSA, Roth IRA spousal rollover and the five-year rule, and Rollover IRA protections. (8:15) A listener asks whether their parents should appeal an IRMAA surcharge—triggered by a one-time annuity payout—on the basis of loss of pension income. (17:15) George asks how a serious health diagnosis may affect his Social Security strategy, including whether his wife should claim on her own record now and delay survivor benefits until he would have reached age 70. (35:30) A listener shares a Venn Diagram PSA 38:15) The guys hear from someone who used spousal rights to roll his late wife’s Roth 401k into his own Roth IRA, and wants to know whether doing so reset the five-year clock on her previously qualified funds. (54:00) Jim and Chris address whether the ERISA protections of 401k and 403b plans are reason enough to avoid rolling them into IRAs, and whether an umbrella insurance could offer additional Rollover IRA protections. The post IRMAA, Social Security, Roth 5-Year Rule, Rollover IRA Protections: Q&A #2619 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss the Safe Withdrawal Rate as a projection tool before retirement, but not as the distribution tool we would use for many retirees. We address Bill Bengen’s research, the 1968 retiree scenario, Monte Carlo planning, and why a worst-case floor can limit early retirement spending on fun. We also contrast accumulation planning with distribution planning and explain how the See Through Portfolio helps separate different retirement spending needs. Jim’s “Pithy” Summary Chris and I discuss why we think Bill Bengen’s research has real value, while still believing the Safe Withdrawal Rate is the wrong tool once the rubber meets the road in retirement. His work helped advisors move away from unrealistic withdrawal rates, and it can be useful for people still in the accumulation phase who are trying to see if they are on track. But once someone reaches retirement, especially with only so many Go-Go years ahead, I think the tool has to change. The part I don’t like is when the industry takes a worst-case historical number and turns it into the anchor for everyone. Chris and I talk about Bengen’s own comments, Monte Carlo probability statistics, and why software can make this kind of planning look cleaner than it really is. That may work for some people, especially if the goal is to leave the biggest portfolio possible, but that is not the same as helping someone spend with more clarity while they still have the health, desire, and ability to do so. That is where our process separates the money allocated for needs, reserves, and later-life planning from the money available for fun. Minimum Dignity Floor, SEAL Reserve, and the Fun Number help frame those dollars differently instead of treating retirement as one big portfolio with one smooth withdrawal path. You are not getting younger, stronger, or healthier, and most people’s retirement goals don’t include being the wealthiest person in the graveyard. The post Is The Safe Withdrawal Rate Useful? EDU #2618 appeared first on The Retirement and IRA Show.

Jim and Chris discuss emails on Social Security survivor benefit strategies, IRMAA exceptions, Roth conversion timing during market downturns, and the implications of naming IRA beneficiaries directly versus routing assets through a trust. (8:15) A listener whose husband plans to delay Social Security to 70 while she claims early at 62 asks whether she can still receive the maximum survivor benefit if he passes away before reaching 70. (19:30) The guys field a question about whether the SSA-44 reduced work exception to IRMAA applies when the reduction in earned income is far too small to bring MAGI below the applicable tier. (31:00) Jim and Chris address whether it makes sense to front-load Roth conversions during a market downturn so that subsequent recovery gains are captured tax-free. (1:06:00) George wants to better understand the mechanics a trustee must navigate when distributing IRA assets to trust beneficiaries, compared to simply naming beneficiaries directly on the account. The post Social Security, IRMAA, Roth Conversions, IRA Beneficiaries: Q&A #2618 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion of the New York Times article titled “You Saved and Saved for Retirement. Now You Need a Plan to Cash Out,” focusing on Retirement Spending Phases as the article moves into go-go, slow-go, and no-go years. We walk through how the article is using that framework and how it compares with how we approach retirement planning, particularly in how different types of spending behave and how that ties to Social Security, pensions, and simple annuities. Jim’s “Pithy” Summary Chris and I pick back up with the New York Times article from last week and this time we focus on Retirement Spending Phases and how that go-go, slow-go, no-go framework is being used. I’m not saying the concept is wrong. I’m saying if you apply it across everything, you’re going to miss the point. Because not all expenses behave the same way. Your Minimum Dignity Floor is there no matter what. Your Fun Number is what actually changes depending on how you’re living your life. If you don’t separate those, you can end up making decisions that don’t reflect reality. That’s really the issue we keep coming back to as we walk through this and react to how the article is presenting it. And that’s where this starts to matter. Because once you’re thinking about what has to be covered versus what can change, you’re dealing with different kinds of decisions. That’s where Social Security, pensions, and annuities come into the conversation. Not as a blanket solution, but as part of figuring out how different pieces of a plan are supposed to work depending on the job they’re trying to do. And it’s why you can’t just treat everything the same and expect the outcome to make sense over time, especially as those phases play out differently across different types of spending. The post Retirement Spending Phases: EDU #2617 appeared first on The Retirement and IRA Show.

Chris is joined by Jake Turner, while Jim is traveling, to discuss listener emails on Social Security spousal benefits, wash sales across brokerage and IRA accounts, estimated tax payments for Roth conversions, and tax withholding strategies in retirement. (6:45) A listener asks when an ex-spouse can claim a spousal Social Security benefit and if retroactive benefits are available. (19:20) The guys address if a surviving spouse automatically receives the higher benefit upon their spouse’s death, and why the family maximum benefit is affecting a couple who are each collecting their own individual benefit. (30:00) A listener wonders how wash sales are tracked across different account types, and if buying back only half the funds results in only half of the sold funds qualifying as a wash sale. (42:31) Chris and Jake help determine if a Roth conversion requires quarterly estimated tax payments throughout the year or just a single year-end payment. (55:00) George wants to know if skipping tax withholdings on a pension and part-time job is acceptable when prior over-withholding is expected to cover the year’s tax bill. The post Social Security, Wash Sales, Taxes: Q&A #2617 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss retirement spending plans through the lens of a New York Times article titled “You Saved and Saved for Retirement. Now You Need a Plan to Cash Out,” reviewing its key arguments about decumulation and where we agree, question, or hold no opinion. We cover why the Minimum Dignity Floor rarely fails in projections, why the 4% rule may be an outdated framework for structuring retirement withdrawals, how individual inflation rates for specific expense categories can produce more accurate projections than a single blended rate, and why underspending on fun during the go-go years may pose a greater risk than outliving assets for many listeners. Jim’s “Pithy” Summary Chris and I dig into a New York Times article — “You Saved and Saved for Retirement. Now You Need a Plan to Cash Out” — and use it as a jumping-off point to talk about what spending in retirement actually looks like in practice versus what the industry has been selling people for decades. Here’s what struck me most: the 4% rule was created in 1994 with rudimentary spreadsheets, and the recommended safe withdrawal rate swings from 2.8 to 4.7 depending on who you ask and what year it is. That’s supposed to be your anchor? Are you watching TVs that look like the ones from 30 years ago? Talking on the same phones? My beeper evolved into a smartphone with more computing power than the Apollo mission, and yet most of the industry is still essentially creating retirement spending plans with a beeper. What the Fun Number framework helps clarify is that you don’t need a universal withdrawal percentage. You need to isolate your actual expenses, inflate each one at the rate that reflects how that spending actually grows — not some blended average — and then see clearly what’s left for fun. The article also makes the point that fearful retirees may scrimp during their go-go years when they could afford to spend — and that’s something my dad reinforced in his own way. He’d watch people in his retirement community who had money but couldn’t bring themselves to spend it on fun, and he called them Debbie Downers. For many people listening to this podcast, that’s the real risk — not outliving your assets but failing to spend on fun while you still can. The post Retirement Spending Plans: EDU #2616 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security benefits for a family with a disabled adult child, survivor benefits, ERISA vs. non-ERISA 403(b) protections, a listener PSA on Monte Carlo simulations, special needs trusts, and how a revocable living trust handles a primary home transfer. (5:00) A listener asks whether her husband’s early Social Security filing while still working would suspend her child-in-care benefits, and whether his benefit would be recalculated to his Full Retirement Age amount once the earnings limit no longer applies. (20:20) George wonders whether survivor benefits for his wife would be based on his age-70 amount or her Full Retirement Age amount. (25:15) Jim and Chris take a question about the differences between ERISA and non-ERISA 403(b) protections, and whether state IRA protections offer comparable coverage. (39:45) The guys share a listener PSA pointing them to a recent Retirement Answer Man episode on Monte Carlo simulations. (44:00) Georgette enquires which assets belong in a special needs trust and how to structure it tax-efficiently. (54:45) A listener asks how a primary home transfers to children through a revocable living trust and what the selling process looks like. The post Social Security, ERISA, Trusts: Q&A #2616 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Jake as we discuss tax rules and mistakes through two tax-focused PSAs before moving into listener emails. Jake covers a denied non-cash charitable deduction due to an incomplete Form 8283 and missing contemporaneous documentation, then walks through how estimated tax payments and safe harbor rules are calculated from prior-year tax liability. We then address listener emails on establishing home basis after a spouse’s death, how the senior deduction is reduced for married couples, and comparing IRA versus Roth withdrawal strategies. Jim’s “Pithy” Summary Chris and I are joined by Jake as we spend some time on two tax-focused PSAs from Jake before getting into listener emails. Jake walks through a tax court case where a non-cash charitable donation was denied because Form 8283 wasn’t completed correctly and the required documentation wasn’t done at the time—even though the donation itself was valid. This highlights how strict tax rules and mistakes around them can cost you. He also breaks down estimated tax payments—those quarterly amounts that show up on your return after you’ve already paid what you owed—and how they’re calculated off the prior year to get you into the safe harbor. We then get into a situation involving a home purchased in the early 1970s, no improvements over the years, a spouse passing in a community property state, and now the question of what the basis actually is and how to determine it years later without anything documented at the time, which is more common than you’d think. There’s also a question on the senior deduction where the reduction ends up applying to each spouse, which changes the expected result. Finally, we look at two different withdrawal approaches using traditional IRA and Roth accounts over the next few years, and how those choices shift balances and taxes depending on how the income is sourced and what you’re actually trying to accomplish with it. The post Tax Rules and Mistakes: EDU #2615 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security claiming strategies, financial education electives for a college student, a listener PSA on podcast word counts, inheritance planning, and SEP IRA conversions. (11:15) A listener planning to delay Social Security to 70 asks whether proposed benefit caps should change that strategy. He also asks Chris for financial education course recommendations for his son at CSU. (35:45) The guys address a question from someone who discovered SSA shows zero earnings on their work record for a year they actually worked, following an overpayment dispute, and whether submitting a W-2 can correct the record and trigger retroactive back pay. (43:45) Jim and Chris share a PSA on podcast word counts, with a speaker-by-speaker breakdown to crown the King and Prince of Word Count. (49:30) A listener wants to create four separate Roth IRA accounts, each with one of their four adult children named as beneficiary, with the idea that any lifetime gifts to that child come out of their future inherited share. They ask whether this approach is more complicated than it needs to be. (1:09:30) George asks whether the money his son placed in a traditional SEP IRA can be converted to Roth, and how the IRS would treat it. The post Social Security, Inheritance Strategy, SEP IRA Conversions: Q&A#2615 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I share retirement lessons learned from a listener’s account of his mother. Her husband’s survivor pension elections, combined with Social Security, left her a unicorn — secure income covering all expenses — yet she died regretting trips never taken despite a $9 million portfolio. The episode also covers why joint account ownership with adult children can create legal exposure, and the importance of funding a living trust while you are still healthy. Jim’s “Pithy” Summary Chris and I walk through three retirement lessons learned from a listener whose mother passed at nearly 100 years old — what she did right, what she regretted, and what almost worked but she ran out of time. Lesson 1: Her husband elected survivor options on his pensions, and combined with Social Security, she had a steady stream of lifetime income long after he was gone. He thought ahead and protected her. Lesson 2: That income, combined with a modest lifestyle, allowed her to amass millions and become what we call a unicorn — guaranteed income that covered every expense, discretionary and otherwise. But she died with regrets, not because she ran out of money but because she could never bring herself to spend it. Her son urged her repeatedly to spend more on fun, but she was a child of the Depression, and that created a mindset that no amount of counseling could change until it was too late. Her husband, who died at 66 was “the other guy” — he probably expected to live at least into his 80s — so did not get to enjoy the money either. These are exactly the kinds of situations the Fun Number was built for. Lesson 3: She did do a great deal right with her estate — POA designations in place and proper beneficiary designations so no assets were subject to probate. She even had a living trust in the works – but she ran out of time to fund it, and that distinction — between having a living trust and actually funding it — is a surprisingly common mistake people make when they set one up. The post Retirement Lessons Learned: EDU #2614 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security claiming strategies, IRMAA income adjustments, a listener PSA on the Roth five-year rule, conduit trusts for minor IRA beneficiaries and I-Bond tax reporting, and an inherited IRA passing through a trust. (10:30) George asks about the Social Security “January Rule” and whether claiming in December 2027 or January 2028 would capture the most delayed retirement credits after reaching full retirement age in May 2027. (21:00) A listener who retired early and has been performing Roth conversions asks whether he can also file an SSA-44 based on his wife’s upcoming reduction in work income, even though his conversions have been elevating their household MAGI. (31:00) The guys review a listener PSA clarifying that the fifth year of the Roth five-year rule must be completed entirely—not merely begun—before the holding period is satisfied. (39:45) Jim and Chris take a two-part question on how conduit trusts handle IRA distributions inherited by minor children, and whether the annual interest-reporting election used for EE bonds can also apply to I-Bonds. (1:06:00) A listener whose father-in-law named a trust as the IRA beneficiary — rather than the daughters directly — is getting conflicting advice on whether the IRA funds must be taken immediately or if they can spread the distributions — and the taxes — over five years. The post Social Security, 5-year Rule, Conduit Trusts, Inherited IRAs: Q&A #2614 appeared first on The Retirement and IRA Show.

If you would like to skip over the guys’ banter this week about Jim’s experience going to a Cincinnati Reds game, you can go to (7:00). Chris’s Summary Jim and I are joined by Jacob as we revisit buffered ETF mechanics in light of recent market volatility and explain why 100% and 20% buffers can still show interim losses. We also cover how renewals work, why resets are not taxable events in brokerage accounts, where these products may fit in retirement positioning, and a listener email comparing them with bonds and fixed indexed annuities. Jim’s “Pithy” Summary Chris and I are joined by Jacob as we go back into buffered ETF mechanics during a stretch where people are actually seeing movement in these products and questioning what they own. When markets pull back, even modestly, the expectation is that protection means no decline at all. Jacob walks through why that is not how these function in real time, and why a 100% buffered ETF can still show a small loss while a 20% buffered ETF can show more, even when the market decline remains within the stated buffer range. The distinction comes down to how these are priced day to day versus how the protection applies over the defined outcome period. We also clarify how renewals work, what happens when values reset higher or lower, and how that process functions within a brokerage account. The discussion also covers how these may fit within portfolio positioning depending on how the dollars are being used. Jacob outlines how full principal protection may be used for nearer-term spending needs, including the Minimum Dignity Floor, while partial buffers may apply to longer time horizons where some level of downside can be accepted in exchange for additional upside potential. A listener email introduces the idea of using these as ballast, along with a comparison to bonds and fixed indexed annuities, including differences in liquidity, tax treatment, fee transparency, and how returns are delivered. The post Buffered ETF Mechanics: EDU #2613 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security timing, whether you can “leave” your Social Security benefit to a spouse who doesn’t independently qualify, having a spendthrift trust purchase an annuity, and using a revocable living trust to manage aging parents’ complex financial affairs. (13:15) A listener born in November asks what their Social Security benefit would be if they begin claiming now, before full retirement age, while still earning $100,000, and when the earnings penalty would lift. (25:15) Jim and Chris field a question on whether you can “leave” your Social Security benefit to a spouse who does not independently qualify for Social Security. (34:00) George asks how to structure his estate so that one child receives an inheritance in installments over 20 years rather than as a lump sum, and whether a trust purchasing an annuity could accomplish that goal. (1:11:30) The guys hear from a listener who explains how being added as co-trustee on his aging parents’ revocable living trust resolved the recurring problem of financial institutions refusing to honor their power of attorney. The post Social Security, Spendthrift Trust, Living Trust: Q&A #2613 appeared first on The Retirement and IRA Show.

Note: In this episode some information regarding the 5-year rule was misstated – one must get through the fifth, not just be in the fifth year. Jim and Chris clarify on the April 4, 2026 Q&A #2614 episode. If you would like to skip over Jim and Chris’s banter on the weather, that manages to touch on Colorado water rights (an issue many east of the Mississippi probably find baffling), then you can start listening at (11:45). Chris’s Summary Jim and I continue our look through the Ed Slott IRA quiz, covering IRA recharacterization rules, how a surviving spouse may use a deceased spouse’s five year period following a spousal rollover, which IRA funds can roll into an employer plan, and the timing trap that can unravel the strategy of using an employer plan to separate after-tax basis from pre-tax funds. Jim’s “Pithy” Summary Chris and I are continuing our run through the Ed Slott IRA quiz — the questions Ed sends out after his twice-yearly training sessions to make sure advisors know not just the right answer but the reasoning behind it. That reasoning is where most people get tripped up, and this episode has several good examples of exactly that. We start with IRA recharacterization rules — the deadline, what has to happen at the custodian level, how attributable gains or losses factor into the math, and a conversion planning tool that Congress took away in the 2018 Tax Cuts and Jobs Act. It was a strategy that made conversion timing far more forgiving than it is today, and the fact that it is gone still stings. From there we get into the Roth IRA five-year rules — specifically a spousal rollover scenario with a twist that most people, including Chris, do not see coming. The answer turns on a benefit the tax code extends to surviving spouses that is easy to overlook if you are not specifically looking for it. We wrap up with which IRA funds can actually be rolled into an employer plan and why that distinction matters if you are sitting on after-tax basis inside a traditional IRA. There is a clean strategy for separating it, but there is also a timing mistake that catches people who think they have successfully pulled it off — when they have not. More people fall into that trap than you would expect, and the consequences are not trivial. The post Ed Slott IRA Quiz Continued: EDU #2612 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails, opening with listener PSAs on Medicare Advantage HSA reimbursement eligibility, then moving into questions on Social Security beneficiary rules and finishing their look at conduit trusts for IRAs. (7:00) A listener asks whether Social Security benefits can be passed on to a significant other. (28:00) The guys continue from last week with a listener’s multi-part question on whether a conduit trust should be structured to distribute RMDs before allowing any additional withdrawals — as a strategy for controlling how beneficiaries access inherited IRA funds. The listener also asks what else could trigger a large tax bill in that setup, and whether a conduit trust provides creditor protection. (1:15:30) George asks for the follow-up promised at the end of a recent episode — specifically, the better approach for having a trust inherit an IRA when you’re concerned about an heir mismanaging the funds. The post HSA Reimbursement, Social Security, Conduit Trusts: Q&A #2612 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss the Ed Slott quiz questions from his November advisor training, opening with the widow/widower tax penalty and required beginning dates for IRA required minimum distributions before moving into inherited IRA rules — year of death RMDs with multiple beneficiaries and the deadline for satisfying them, spousal rollover options, and spousal RMD timing. Jim’s “Pithy” Summary Chris and I dig into the Ed Slott quiz from my November advisor training — 20 questions, open book, and I scored 100 this time. We have been doing this for years and it is not just a matter of asking the question, giving the answer and moving on. We get into the rabbit holes, explain the nuances, and use it as a chance for everybody listening to test their own knowledge. We open with the widow/widower tax penalty and required beginning dates for IRA required minimum distributions — and the widow/widower question has nothing to do with IRAs but everything to do with retirement planning. The younger a spouse passes away the more intense the penalty, and the longer both of you live together the less it bites. From there we get deep into inherited IRA rules, which make up the bulk of the episode. How year of death RMDs work when there are multiple beneficiaries, and what the deadline is for satisfying them — there is a question in here that Ed Slott himself argued both sides of for years because the IRS never gave guidance until July 2024. We close on spousal rollover options and RMD timing rules that only apply to surviving spouses. A spouse has choices that no other beneficiary has, and the decision of which way to go can look very different depending on the ages involved. Chris makes the point well — whenever a spouse dies, hit the pause button before you do anything. The post Ed Slott Quiz – Widow(er) Tax Penalty and Inherited IRA Rules: EDU #2611 appeared first on The Retirement and IRA Show.

Chris is joined by Jake Turner to discuss listener emails on tax filing for mega backdoor Roth contributions, use of HSA funds, I Bonds redemption timing, lowering RMD pressure, and Roth conversions. (6:30) George asks whether leaving a 1099-R off a return after after-tax 401(k) money was immediately converted to Roth means an amended return is needed or whether the IRS will simply follow up. (12:15) A listener asks whether HSA funds can be used pre-tax to pay fully self-funded health insurance premiums. (17:30) The guys are asked how to evaluate redeeming high fixed-rate I Bonds over several years versus waiting until maturity and risking a large one-year tax bill and IRMAA hit. (30:45) Chris and Jake hear from a widowed listener looking for ways to reduce future RMDs and IRMAA without using Roth conversions or QCDs. (47:45) Another listener asks whether doing very large Roth conversions over a few years could make more sense than staying within lower tax brackets over a longer period. The post Tax Filing, HSAs, I Bonds, RMDs, Roth Conversions: Q&A #2611 appeared first on The Retirement and IRA Show.

Chris’s Summary With Jim at the T3 conference in New Orleans, I am joined by Jake Turner to cover how to factor a defined benefit pension into retirement planning, using the situation of a 45-year-old law enforcement officer with a non-covered pension as the backdrop. We walk through evaluating his savings rate against the 15–20% rule of thumb, the lump sum equivalent value of his pension income, why the presence or absence of a COLA matters significantly, and how pension income fits into covering essential expenses over a long retirement. Jim’s “Pithy” Summary While I’m at the T3 conference in New Orleans, Chris and Jake use a listener’s situation to dig into retirement planning with a defined benefit pension. The listener is a 45-year-old law enforcement officer who has been contributing to his pension since day one but only started building outside accounts five years ago. He wants to know where he actually stands — and the answer is more nuanced than a simple savings rate comparison can capture. A big part of that nuance is whether the pension is a non-covered one, meaning it replaces Social Security rather than sitting alongside it. That single distinction changes how you benchmark the savings rate entirely, and it’s the kind of thing that gets glossed over when people just throw out rules of thumb without knowing what’s underneath them. Chris and Jake also get into how pension income fits against the Minimum Dignity Floor — and why a pension that looks rock solid at retirement can tell a very different story decades later if there’s no cost-of-living adjustment attached to it. There’s also a conversation worth hearing about lump sum options — what they’re actually worth, how to think about comparing them to the lifetime income stream, and why the big number isn’t always the better answer. If you have a defined benefit pension and you’ve been wondering how it fits into the bigger retirement picture, or whether you’re ahead or behind where you should be, this episode covers the framework for thinking it through. The post Retirement Planning With a Defined Benefit Pension: EDU #2610 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on PSAs regarding IRMAA reimbursements, RMD in-kind transfers, and naming a conduit trust as a retirement account beneficiary. (8:15) A listener shares a PSA that an IRMAA reimbursement was applied as a credit balance drawn down over several months rather than a lump sum. (17:00) The guys discuss a listener PSA on SSA-44 filing: when income is underestimated and IRMAA is owed, Medicare reconciles the difference the following November or December with no penalties or interest assessed. (33:45) George asks whether an RMD can be satisfied through an in-kind transfer of mutual funds to a brokerage account, and whether only a portion needs to be sold to cover the tax bill. (46:00) Jim and Chris take up a listener question about naming a conduit trust as a contingent beneficiary for retirement accounts, kicking off Part 1 of a broader discussion on see-through and conduit trusts — what each structure is, how they differ, and what happens when an IRA names a trust as its beneficiary. They begin exploring the tax implications and planning considerations involved, noting that these arrangements can create both benefits and unintended complications depending on how they’re set up. The conversation will continue on the next week’s Q&A episode, where they’ll complete this listener’s question and address additional questions received on the topic. The post IRMAA, RMDs, Conduit Trust: Q&A #2610 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue our discussion on 99 Retirement Tips from Fisher Investments, picking up where we left off last week. We cover involving children in financial decisions, the liquidity trade-off of paying off a mortgage early, renting before buying in a new retirement location, lifetime gifts as part of the fun budget, and watching for financial predators including a disputed suggestion that low advisor fees may be a warning sign. Jim’s “Pithy” Summary Chris and I are back where we left off, working through Fisher Investments’ 99 Retirement Tips, and there’s still plenty to dig into. Tip 23 makes the case for involving your children in your financial decisions — and the reasons go deeper than most people think about. Tip 26 gets into mortgage payoff, and while we partially agree with what Fisher says about it — paying it down doesn’t change your net worth. But it does change your liquidity, and that distinction is worth considering. Tip 32 is one I feel personally right now: if you’re relocating in retirement, rent first. Never move anywhere with a vacation mindset. I’m doing it in Ohio as we speak, and I’d tell anyone thinking about a move to do the same. Tip 74 recommends lifetime gifting — and the way we handle it, that spending belongs in your Fun Number budget. There’s no written rule you have to wait until you’re gone to help the people you care about. And tip 86 covers financial predators, which is largely solid — but there’s one line in there that made my blood boil when I read it. The implication is that an advisor charging lower fees might be a warning sign. I have never seen any consumer advocate say that. The 99 retirement tips review of this particular point raises a question worth sitting with: who exactly benefits from that framing? The post Fisher’s 99 Retirement Tips, Part 2: EDU #2609 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefits, IRMAA relief and the SSA-44 process, the Social Security earnings test, disclaiming inheritances that are brokerage accounts, and Roth conversion rules for retirees. (6:00) A listener asks whether his wife’s early Social Security claim at 62 would reduce the survivor benefit she’d receive upon his death. (14:00) George asks several questions stemming from a successful SSA-44 IRMAA relief request, including whether a retroactive refund is due, whether Step 3 covers the following year, and whether a separate filing is needed for his own income reduction. (27:30) Jim and Chris respond to a listener who clarifies that benefits withheld under the Social Security earnings test are deferred, not lost, and are returned as a higher benefit at full retirement age. (31:00) Georgette asks when it makes sense to disclaim an inherited brokerage account and whether passing the assets directly to their children is the right move. (40:45) The guys are asked about the rules and tax implications of converting brokerage account funds to a Roth IRA, including whether having no earned income in retirement disqualifies someone from doing The post Social Security, IRMAA, Disclaiming Inheritances, Roth Conversions: Q&A #2609 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I review Fisher Investments’ 99 Retirement Tips and begin working through the list, covering only a handful in this episode. We discuss estate planning basics such as having a will, the importance of reviewing estate documents, and considering living wills and trusts, with emphasis on incapacity planning. We then examine longevity statistics, why life expectancy at birth is often misapplied, and how that connects to retirement income decisions, including Fisher’s warning on annuities. Jim’s “Pithy” Summary Chris and I start digging into Fisher Investments’ 99 Retirement Tips and, true to form, we only make it through a few because I may have wandered down a rabbit hole or two. The estate planning stuff is straightforward—have a will, review it, don’t ignore the documents that matter if you’re alive but not fully capable. Death is easy administratively. Incapacity is where things get messy, and that’s where families struggle. And that’s where better planning matters most. Then we get into longevity. If you’re going to say people might live longer than they think, you better use the right numbers. Not the “life expectancy at birth” headline stat. If a couple makes it to 65, the odds shift. That matters. That changes the runway. That changes how you think about income. It also changes how long that portfolio has to work, and how long decisions have to hold up. And from there we run into the annuity warning. We’re not pro-annuity and we’re not anti-annuity. Many deserve criticism, but if longevity risk is real—and it can be—then you should evaluate lifetime income options on their merits. Social Security is guaranteed lifetime income. Income annuities are too, so they should belong in the conversation. Whether you use them depends on the situation, but you can’t talk about taking longevity seriously and then issue a blanket warning against annuities. The post Fisher’s 99 Retirement Tips: EDU # 2608 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Jake Turner to discuss listener emails in this special tax related episode covering Roth conversions after RMD age, balancing Roth versus Traditional IRA contributions, HSA versus Roth contributions, IRA reporting questions, filing deceased tax returns, and a listener PSA on tax planning software. (11:30) A listener asks whether converting to a Roth makes sense at age 75 while currently in the 12% bracket and taking RMDs, and whether recent tax law changes create a strategy opportunity. (20:20) George wonders whether his 30-something children should continue using Roth contributions exclusively or begin balancing with Traditional IRA contributions as their wages increase, and asks what percentage split between Traditional and Roth accounts looks reasonable in retirement. (48:45) The guys discuss whether covering medical expenses from an HSA and contributing to a Roth IRA, or leaving the HSA intact and paying medical bills out of pocket will result in greater retirement spending flexibility. (57:00) Jim, Chris, and Jake address whether a spouse who retired during the year is considered covered by a workplace plan, how to answer prior nondeductible IRA contribution questions, and whether Form 8606 is required after making and converting a small IRA contribution in the same year. (1:10:30) George asks how to handle the direct deposit of a refund on a deceased final 1040, including whether to use the estate bank account with an EIN or the decedent’s existing account, and whether a paper check remains an option. (1:15:30) A listener PSA introduces Catalyst Tax Insights, a free tool to run “what if” scenarios and estimate taxes owed without using full tax software. The post Tax Special – Conversions, Contributions, HSAs, Tax Returns, Tax Software PSA: Q&A #2608 appeared first on The Retirement and IRA Show.

If you would rather not listen to the guys’ banter about Jacob’s upcoming move to Iowa, Jim’s garden planning, and a listener correction about the word “imbibe” you can skip ahead to (33:30). Chris’s Summary Jim and I are joined by Jacob Vonloh as we discuss using Buffered ETFs prompted by a Morningstar article titled “Buffer ETFs Are Not for Everyone.” We explain how defined outcome ETFs use options to provide an explicit amount of loss protection over a given period while limiting potential gains, and we outline why these products are generally suboptimal for long-term investors. We then connect this to investment positioning, focusing on risk capacity, distribution planning, and why dollars assigned to delay-period Minimum Dignity Floor and Go-Go spending may require a degree of principal protection. Jim’s “Pithy” Summary Chris and I are joined by Jacob Vonloh as we take a listener-submitted Morningstar article—“Buffer ETFs are not for Everyone”—and use it to kick off what is going to be a series on principal protection. Morningstar does a very good job in this article laying out what it likes about buffered products, and it also makes some excellent points on where these types of products would fit and where they don’t fit. They’re not for everybody, but they could be of interest in certain cases, in a certain application, and we’re going to share how we use them. What I want to do in this series is broaden the conversation. Buffered ETFs are just one type of principal protected product. There are multiple tools in that category, and we’re going to walk through where they fit into distribution planning. As you transition from accumulation into what I call the Venn diagram phase, and ultimately into distribution, you have to stop thinking of your portfolio as one big portfolio and start thinking in terms of smaller portfolios—investment positions—based on assigned spending. Dollars earmarked for a legacy position can be invested aggressively. Dollars earmarked for immediate spending—like the Go-Go reserve or the reserve for your MDF—need a degree of principal protection. This ties directly into the Secure Retirement Income Process and the See Through Portfolio and how we navigate asset positioning in retirement.   Show Notes: Morningstar Buffered ETFs article The post Using Buffered ETFs: EDU #2607 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Medicare Part B decisions for retirees abroad, Social Security survivor benefit surprises, inherited Roth IRA distribution rules, and balancing Treasuries versus annuities when “safety” is more emotional than mathematical. (6:45) A listener asks about situations where it might make sense to skip Medicare Part B, including retirees living abroad with strong foreign coverage and people who move to the U.S. later in life and must pay for Parts A and B. (33:30) George asks why some widows and widowers don’t end up receiving the full benefit their spouse was receiving, even when the surviving spouse’s payment increases after the death. (52:30) The guys respond to a question about whether an inherited Roth IRA requires annual distributions when the original owner was old enough to have RMDs, or whether the beneficiary can wait until year 10. (1:11:00) Jim and Chris revisit the annuities versus Treasuries discussion through the lens of fear and peace of mind, including why someone might emotionally trust Treasuries more than insurer guarantees even if the math favors SPIAs. The post Medicare, Social Security, Inherited Roth, Annuities: Q&A #2607 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Steve Sansone as we revisit Cash Balance Plans and respond to listener follow-up emails. (8:30) A CPA asks whether cash balance plans could be a fit for farmers with high income near retirement driven by deferred grain and equipment sales. (18:30) A listener with two controlled-group businesses asks how a cash balance plan works with divergent profit cycles, whether it can support succession planning, and whether it makes sense if ownership works until death. (36:45) A financial advisor asks for real-world details on costs, duplication/administration, duration, interest crediting rate risk, investment management, participant inclusion decisions, partner exits, lifetime maximums, and terminate/restart mechanics. Jim’s “Pithy” Summary Chris and I are joined by Steve Sansone as we dig back into cash balance plans, but this time we’re doing it by letting listener questions drive the conversation. We take three listener emails that each come at this from a different angle: one from a CPA working with farmers facing lumpy income near retirement, one from a family dealing with two controlled-group businesses that don’t behave the same way financially, and one from an advisor who’s basically saying, “Convince me this isn’t just theoretical.” Chris and I talk with Steve about what makes these plans work and what makes them a headache—cash flow consistency, the “permanence” expectation, why manufacturers with lots of employees can be a tough fit, and how quickly the math changes when you have to fund meaningful benefits for staff. We also get into the stuff people don’t always hear in the sales pitch: what “interest crediting” really means, where the risk lives if returns don’t cooperate, and why newer market-rate designs change the conversation compared to older fixed-rate versions. And we cover the messy real-life questions: what happens when partners leave, what it looks like to terminate and restart a plan, and why you can’t treat this like an investment strategy with a neat five-to-ten-year horizon. It’s a tax and retirement-acceleration tool with rules, tradeoffs, and guardrails—and Steve does a solid job laying out when it’s worth the complexity and when it’s just not. The post Cash Balance Plans Part 2: EDU #2606 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on IRMAA appeals using Form SSA-44, avoiding the 10% early withdrawal penalty, and whether a 403(b) distribution can be rolled into an IRA. Jim also manages to turn a discussion on Superbowl food to a conversation on retirement planning for the Go-Go phase of life (with a few other stops in between). So, if you typically skip the banter you may want to tune in around (10:10) for that discussion. (16:30) George shares his experience repeatedly filing Form SSA-44 to correct IRMAA determinations and explains how Social Security processed and applied his updated income information. (35:00) A listener asks whether a qualified annuity can be used instead of a 72(t) series of substantially equal periodic payments to avoid the 10% early withdrawal penalty. (1:04:45) The guys discuss whether 403(b) distributions can be completed as 60-day rollovers into Traditional and Roth IRAs, and whether a custodian could refuse to accept the rollover. The post IRMAA, Early Withdrawal Penalty, 403b Distributions: Q&A #2606 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss spending anxiety in retirement using a Washington Post article written by a personal finance columnist describing her fear of spending after her husband retires. We look at why the shift from saving to spending can feel destabilizing even when pensions and Social Security are in place, and why fear can persist despite adequate planning. We also address the difference between spending income and spending savings, and how that distinction often affects behavior once retirement begins. Jim’s “Pithy” Summary Chris and I use a Washington Post article as a jumping-off point to talk about the moment retirement stops being theoretical and the fear around spending often shows up. The part that stuck with me in this situation is that nothing went wrong. One spouse retires. The other is still working. Pensions are there. Social Security is there. The house is paid off. And the fear shows up anyway. That’s what made me save the article in the first place. She writes about personal finance for a living, and she’s still cutting small expenses, feeling better for five minutes, and then right back to worrying. I’ve said it before, and I’ll say it again—I don’t expect to be immune to that when it’s my turn. What keeps coming up for me is how differently people react to where the money comes from. Most people are comfortable spending a pension check or a Social Security deposit. It’s like a bottomless cup of coffee—you don’t think about the last sip because another one’s coming. But savings? That’s different. Even when the math works, even when the plan says you’re fine, drawing from something you’ve built for decades feels heavier. That’s where the spending anxiety shows up. Spending slows down. Decisions get second-guessed. Things get pushed out a year at a time. Not because people can’t afford them, but because the shift from saving to spending is uncomfortable. Show Notes: Article: My husband just retired. I’m scared of running out of money. The post Retirement Spending Anxiety: EDU #2605 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security timing for HSA contributions, investing in a SPIA vs buffered ETFs, and using SEPP 72(t) income to manage ACA credits. (7:00) A listener describes delaying a Social Security filing to avoid Medicare Part A backdating that would have reduced prior-year HSA contributions, while still receiving full retroactive benefits. (28:00) Georgette asks what to do with money originally set aside for a condo purchase, weighing ETFs against buying a single premium immediate annuity (SPIA), given an existing fixed indexed annuity (FIA), and pension income that cover living expenses. (55:45) The guys address whether a SPIA purchased inside a rollover IRA can be used to satisfy SEPP 72(t) rules while keeping income low enough to preserve max ACA credits. The post Social Security, SPIAs, SEPP 72(t): Q&A #2605 appeared first on The Retirement and IRA Show.

If you’d like to skip over the guys chatting about cold weather and football you can to (8:15). Chris’s Summary Jim and I are joined by Jacob as we continue our discussion on asset positioning and explain how we approach managing investment assets within a distribution portfolio. We outline why dollars are assigned based on purpose and timing and how asset positioning functions as a form of asset-liability matching. The episode addresses cash versus cash-like roles, outcome periods, and how specific tools are evaluated within a broader distribution-focused framework. Jim’s “Pithy” Summary Chris and I are joined by Jacob as we dig further into how we think about handling portfolios once people are in retirement, specifically through the lens of asset positioning. This episode is built around clarifying how dollars get assigned jobs based on when they’ll be needed and why that sequencing drives the structure of a distribution portfolio. We spend time breaking down the difference between cash and cash-like holdings and why that distinction matters when money is earmarked for different time horizons. A big part of the discussion centers on outcome periods, how certain tools behave between start and finish, and why mark-to-market pricing during that window can be misleading if you don’t understand what the holding is meant to do. Jacob walks through concrete examples that show how interim movement can look unsettling even when the structure is functioning exactly as designed. We also get into why disclosure language sounds the way it does across virtually every type of holding, including ones most people are comfortable calling cash. The point isn’t semantics — it’s understanding the gap between legal language and functional role inside a portfolio. Everything ties back to structure, timing, and purpose. This is about how distribution portfolios actually operate in retirement, and why evaluating them with the wrong expectations creates confusion that doesn’t need to be there. The post Asset Positioning for Retirees: EDU #2604 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security survivor benefits and the earnings test, share a listener PSA on Social Security timing and IRMAA, then cover ERISA protections for retirement rollovers and a PSA from Greg on lifetime unlimited long-term care policies. (9:45) Georgette asks whether she must still take her husband’s required minimum distributions if he passes during his RMD year and how Social Security survivor benefits work, including whether she should claim a widow’s benefit or wait to take her own. (50:45) A listener asks how the Social Security earnings test applies when someone retires before full retirement age and applies midyear, and how to avoid missing a month of income due to the timing of benefit payments. (55:00) The guys share a PSA about applying for Social Security and receiving benefits within days, which caused an unexpected IRMAA impact. (1:00:35) Jim and Chris discuss whether rolling Roth and pre-tax 401(k) assets into IRAs results in losing ERISA protections, or if separate rollover IRAs are needed to preserve those protections. (1:15:15) Greg, from our office, shares a PSA clarifying that some lifetime unlimited long-term care policies still exist. The post Social Security, ERISA, LTC: Q&A #2604 appeared first on The Retirement and IRA Show.

If you want to miss all the fun banter about Jim’s Singo (song bingo) night and his trip to Kentucky and Amish country you can skip ahead to (16:00). Chris’s Summary Jim and I are joined by Jacob Vonloh as we discuss investing for retirees, using a listener email as the starting point for a broader conversation about how investment advice and asset management work in practice. We explain why investing changes once people move from accumulation into distribution, including differences in risk tolerance, liquidity needs, and volatility. Jacob outlines how investment tools are evaluated based on time horizon and downside exposure rather than labels. We also discuss planning for aging and long-term care costs, including liquidity needs, inflation considerations, and the SEAL (Savings for Emergencies, Aging, and Long-Term Care) reserve framework. Jim’s “Pithy” Summary Chris and I are joined by Jacob Vonloh as we start a new series of conversations inspired by listener emails, and we use those questions as a jumping-off point to talk about what really changes when you’re investing in retirement. A lot of DIY investors successfully built wealth with an accumulation mindset and then try to carry that same approach into retirement, where it doesn’t work. The problem is that accumulation investing and retirement investing are not the same thing, and pretending they are is where people get themselves into trouble. Once withdrawals begin, volatility feels different, timing matters more, and the emotional impact of market swings gets amplified in ways people don’t expect. We spend time pulling apart how the investment advice industry presents itself, how fee structures are typically layered in, and why we’re very intentional about separating retirement planning from asset management. Jacob walks through how we evaluate investments based on when the money might be needed and how much downside someone can realistically tolerate. Buffered ETFs come up in that context, not as a recommendation, but as a clean example of how downside protection and upside caps reshape risk. The point isn’t the product — it’s that comparing retirement-stage tools to a fully unbuffered equity index without adjusting for risk is fundamentally misleading. From there, we connect investing back to real planning issues retirees face, especially aging and long-term care. We talk about why insurance isn’t always available or sufficient, how covering one spouse can still protect a household, and why the financially hardest stretch is often when both spouses are alive and care costs begin to show up. That leads into how we think about liquidity, inflation, and time horizon working together inside what we call the SEAL reserve. This isn’t about chasing returns — it’s about structuring money so it can actually support people through retirement without forcing panic decisions at the worst possible time. The post Investing for Retirees: EDU #2603 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security survivor benefits and divorce rules, a listener PSA on spousal benefits, HSA contribution limits, and whether annuities make sense versus Treasury bonds. (8:45) A listener asks whether someone who is newly widowed can claim survivor Social Security now, keep working part time, and later switch to their own benefit, and also asks whether you still offer a “coffee and second opinion” or an a la carte Social Security review. (23:00) The guys field a question from someone with two ex-spouses asking if it’s possible to combine their own Social Security with part of either (or both) ex-spouses’ benefits. (33:30) George shares a PSA on how filing for Social Security online triggered a spousal-benefit eligibility notice for their spouse, and how the follow-up phone appointment worked without needing an in-person visit or marriage certificate. (45:15) Jim and Chris answer a question about 2026 HSA contribution limits for two spouses on an ACA family plan who each opened their own HSA and want to avoid overfunding. (54:45) One writer asks why they should consider annuities given fees and insurer risk when they can buy 20-year Treasury bonds, and adds a quick note about simplifying word choice from a prior email discussion. The post Social Security, HSA, and Annuities: Q&A #2603 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I continue last week’s EDU discussion on Roth IRA mistakes from an Investopedia article. We cover direct versus 60-day rollovers, the one-per-365-day IRA-to-IRA limit, and the 401(k) 20% withholding rule with the RMD and NUA exceptions. We revisit backdoor Roth mechanics and the pro rata rule, then shift to beneficiary designation forms and why naming an estate creates probate and creditor issues. We close with inherited Roth withdrawal timing under SECURE Act rules and the 10-year window. Jim’s “Pithy” Summary Chris and I pick up where last week’s EDU episode left off, using the Investopedia Roth mistakes article as a launching point to correct what they compress or misstate. The rollover section is where people get hurt, because they describe the old IRA rule like it was “once per calendar year,” and it wasn’t. It’s a 365-day framework, and the one-per-365-day limit still matters when you do the “show me the money” version of a rollover. I also keep pushing back on indirect rollovers from a 401(k), because the 20% withholding isn’t optional. There are narrow exceptions—but those aren’t general flexibility, they’re specific rules people routinely misunderstand. The other item that’s far more important than its position on the list is beneficiary designation forms. These accounts pass by beneficiary form first, not your will, which can create probate delays, attorney fees, and creditor complications for the people left to sort it out. Chris adds the practical version of the same mistake: circumstances change, paperwork doesn’t. Old beneficiaries stay on file, and the form controls the outcome even when it creates an awkward situation. We also get into inherited Roth timing under the SECURE framework—who qualifies as an eligible designated beneficiary, what the 10-year window actually requires, and why Roths don’t fit the required beginning date logic the way traditional accounts do. That difference matters when you’re thinking about flexibility for heirs and how long the account can sit untouched. If the real goal is the zero in the 2-1-0 Tax Ordering Number, the logic behind leaving a Roth can look very different than what you’d conclude from a short listicle about Roth IRA mistakes. Show Notes: Article – 11 Mistakes to Avoid With Your Roth IRA The post Roth IRA Mistakes, Part 2: EDU #2602 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Jake to discuss listener questions on SSA-44 and IRMAA surcharges, inherited IRA spousal rollover rules, long-term care insurance benefit caps, and ACA tax credits. (4:45) George asks whether an unexpected W-2 stock option payout in 2025 could support filing SSA-44 to reduce 2027 IRMAA surcharges, especially if he stops consulting income afterward. (12:00) A listener asks whether SSA-44 can be used retroactively to request a refund of 2025 IRMAA surcharges after a job loss pushed MAGI below the threshold. (18:15) Georgette asks whether she can take withdrawals from her deceased spouse’s inherited IRA without penalty and still later move the remaining balance into her own IRA. (28:00) The guys address why long-term care insurance policies often have a lifetime benefit cap and whether benefits can run out during an extended care event. (46:45) Chris and Jake cover whether long-term capital gains count toward the modified adjusted gross income used for ACA tax credits and can affect eligibility. The post IRMAA, Inherited IRA, LTC, ACA Tax Credits: Q&A #2602 appeared first on The Retirement and IRA Show.

If you want to skip over some weather banter you can go to (14:15). Chris’s Summary Jim and I review Roth IRA mistakes and walk through key rules on earned income eligibility, income limits, spousal contributions, excess contributions, and qualified distributions. We use an Investopedia article as a framework, clarify how MAGI impacts Roth eligibility, explain the October 15 correction deadline, and break down the two-prong test for tax-free Roth earnings withdrawals, including how the five-year rule is measured across tax years. Jim’s “Pithy” Summary Chris and I kick off the first EDU show of 2026 by taking an Investopedia piece called “11 Mistakes to Avoid with Your Roth IRA” and using it as our launchpad. We’re not reading the article to you—we’re breaking down what they got right, what they explained too loosely, and what they left out that changes the meaning. We start with the basics that still trip people up: you need earned income to contribute, and a lot of income that feels “earned” (like dividends, interest, rental income, or IRA distributions) doesn’t count. Then we pivot to the opposite problem: earning too much and accidentally making an ineligible Roth contribution because your MAGI crossed the line, often after a late bonus or surprise taxable payout. We get into a category of mistakes that can create problems with the IRS: excess contributions. We walk through how easy it is to overfund a Roth when you have multiple accounts, and why the correction rules matter more than most people realize. We talk about the October 15 deadline, how the custodian won’t stop you, and why “removing the excess” isn’t always the same as removing what you deposited. We also get into the weird but real quirk where, if you miss the correction deadline, you may only need to remove the excess contribution itself, not the growth tied to it. We also dig into the qualified distribution rules for Roth earnings, because this is where the five-year rule gets misunderstood. The Roth has to be five tax years old, and you need a qualifying condition—59½ is one, but it’s not the only one. That’s where the article oversimplifies, and where people make avoidable mistakes when taking earnings out too early.   Show Notes: Article – 11 Mistakes to Avoid With Your Roth IRA The post Roth IRA Mistakes, Part 1: EDU #2601 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security claiming strategies, deemed military wages, and survivor benefits timing, a PSA from Jim and Chris on their New Year’s resolution, and QLAC use for inherited IRAs. (11:00) A listener asks whether a spouse who will be collecting spousal benefits should ever delay claiming past full retirement age and also asks for retirement drawdown calculator recommendations. (24:30) George asks how veterans can verify that deemed military wages were credited correctly to their Social Security earnings record. (36:00) The guys address whether a surviving spouse can keep both Social Security checks after a spouse dies after being given conflicting answers from the Social Security Administration. (45:00) Jim and Chris share a PSA on their New Year’s resolution relating to estate planning. (1:02:45) A listener asks whether an inherited IRA can be used to purchase a QLAC with payments starting at age 84. The post Social Security, Deemed Military Wages, Estate Planning, QLACs: Q&A #2601 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I review new MYGA variations and examine how insurers and product developers are marketing hybrid annuity designs using MYGA language. We walk through four examples from an April 2025 article—“Lockdown,” “Minimum Accumulation Guarantee,” “Extra Extra,” and the “End-of-Term Equity Kicker”—and explain why these products, despite being labeled as MYGAs, rely on index-linked features and do not behave like traditional MYGAs. Jim’s “Pithy” Summary Chris and I spend this episode talking through an article from earlier this year that highlights where the annuity industry seems to be headed. While not all good or all bad it centers on something I don’t think needed fixing in the first place. A MYGA is simple. It’s predictable. It’s easy for people to understand. It looks a lot like a CD (minus the FDIC protection, of course) issued by an insurance company, with a guaranteed rate for a defined period of time. That simplicity is exactly why we use MYGAs in our retirement plans for principal protection to cover near-term spending, including the delay period Minimum Dignity Floor and early Go-Go spending. What the article describes are four designs that are being positioned under the MYGA label, even though they introduce index-linked elements that change how the product behaves. The names alone tell you this is marketing at work. “Lockdown,” “Minimum Accumulation Guarantee,” “Extra Extra,” and the “End-of-Term Equity Kicker” are all attempts to add features that sound appealing while keeping the comfort of the MYGA name. In reality, these designs are borrowing from the fixed indexed annuity world and layering those ideas onto something that was not originally intended to work that way. But I’m not at all surprised that the insurance industry couldn’t leave well enough alone and took something simple and practical and complicated it with these new MYGA variations. The post New MYGA Variations: EDU #2553 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security filing timing and online claiming language, a listener PSA on IRMAA and the online SSA-44, ACA income planning before Medicare, an IRA to HSA transfer, and annuity income needs. (6:45) The guys address how to word an online Social Security application so the first check is paid for a specific month when claiming at age 70, and whether applying 2–3 months before the 70th birthday is the right approach. (14:00) A listener shares a PSA on filing SSA-44 online after retirement, including how IRMAA recalculations reflected estimated future-year income and how the resulting tier was communicated in the approval letter. (25:00) Jim and Chris discuss whether it makes sense, from a planner’s perspective, to stop working and manage income in a way that keeps health insurance affordable until Medicare eligibility. (38:45) George asks about doing the once-in-a-lifetime tax-free IRA-to-HSA transfer, how the HSA testing period works, and whether it’s worth doing before starting Medicare to reduce future RMDs. (49:00) A listener asks whether annuity income is still useful for covering a minimum dignity floor gap when assets are high and spending needs are modest, and how to think about guaranteed income given planned retirement timing and gifting goals. The post Social Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Steve Sansone as we discuss cash balance plans and explain how they function as hybrid defined benefit plans that present as account-based arrangements. We cover who these plans are designed for, including high-income business owners and professional groups, how age and employee demographics affect feasibility, and why allowable contribution levels can far exceed defined contribution limits. We also outline nondiscrimination rules and how they are applied, employer commitment requirements, and other general setup considerations. Jim’s “Pithy” Summary Chris and I are joined by Steve Sansone as we take a deeper dive into cash balance plans and why they show up in very specific situations, not as a one-size-fits-all solution. Steve explains how these plans sit in the defined benefit world but look like a defined contribution account, which is where a lot of confusion starts. We spend time on who they’re actually built for, why high-income professionals tend to be the ones asking about them, and why the contribution numbers can look startling if you haven’t seen the mechanics before. We also talk through the tradeoffs, because these plans are not free money and they are not magic. Steve walks through how demographics drive everything, why age gaps between owners and employees matter, and how employer contributions to staff are part of the deal. We discuss why, in the wrong situation, these plans can pour fuel on the fire of a future tax problem, and why, in the right situation, they can make sense when paired with intentional planning during the retirement tax planning window before required minimum distributions begin. We frame that discussion around the same planning lens we use elsewhere on the show, including how the 2-1-0 Tax Ordering Number concept helps evaluate whether the front-end tax benefit is worth the back-end complexity. The post Cash Balance Plans Explained: EDU #2552 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails on Social Security spousal eligibility and claiming coordination, a listener PSA on Social Security proof of marriage requirements, RMD planning while still working, money market earnings in brokerage accounts, and using QLACs for long-term care planning. (16:15) Georgette asks whether the repeal of WEP and GPO affects her eligibility for a spousal benefit if her ex-husband worked for the federal government and she did not pay into Social Security. (26:45) A listener asks how Social Security works when one spouse lacks enough work credits for their own benefit and only qualifies for a spousal benefit, including whether both spouses must claim at full retirement age to access that benefit. (42:00) The guys address a PSA on why Social Security may already have proof of marriage on file for one spouse due to a name change but still requires documentation from the other spouse when benefits are claimed. (49:30) Jim and Chris discuss whether maximizing pre-tax retirement contributions and rolling a SEP IRA into a 403(b) can reduce or eliminate RMDs under the still-working exception. (1:06:45) A listener questions the statement that Money Market earnings are minimal, pointing to current yields in a fund they hold. (1:12:00) The guys respond to feedback on whether a QLAC could be an effective way to address long-term care planning when self-funding alone does not feel sufficient. The post Social Security, RMDs, Money Market Earnings, QLACs: Q&A #2551 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I are joined by Jake Turner as we cover the Math Act and a set of shorter EDU topics Jim has been collecting. We start with an SSA-44 update, including listener and client feedback on submitting the IRMAA redetermination form online through an SSA.gov account. Jake explains how IRS “math error” notices work today, why they’re often vague, and what the new law requires for clearer explanations and response deadlines. Jim then walks through the Automatic IRA Act’s proposals, including an annuity-style “protected lifetime income solution” requirement over certain balances, and we close with a quick way to sanity-check MYGA rates using AnnuityRateWatch’s yield curve. Jim’s “Pithy” Summary Chris and I are joined by Jake Turner as we bounce from Social Security admin housekeeping to Washington trying, yet again, to make the IRS act like it’s talking to actual humans—starting with the Math Act. If you’ve ever opened one of those IRS letters that basically says “you owe us money” without showing you how they got there, you already know why this matters. Jake lays out what those notices are really doing behind the scenes, why clients forward them to preparers in a panic, and what the new requirements are supposed to force the IRS to include so you can actually understand what they’re alleging and what happens if you don’t respond. Then we pivot into the Automatic IRA Act, and I’ll be honest: I’m less interested in the political theater than I am in what it signals. There’s the small-business auto-enrollment concept—opt-out, no match requirement, and all that—and then there’s the part that made me laugh out loud when I saw who was cheering it on. Once you cross a certain 401(k) balance, the proposal would require employers to offer a “protected lifetime income solution,” which is just a polite way of saying “annuities are trying to get a bigger seat at the 401(k) table.” That opens up all the practical questions: what counts, who defines it, and how this intersects with the slow drift of defined contribution plans trying to behave a little more like pensions. The post Math Act and Automatic IRA Act: EDU #2551 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener emails starting with PSAs about IRMAA and Social Security spousal benefit applications, then questions on IRMAA, QLAC-related RMD rules, and a Roth conversion involving a fixed indexed annuity (FIA). (9:30) Georgette shares a PSA explaining that she successfully filed Form SSA-44 preemptively—before receiving an IRMAA determination letter. (21:15) A listener offers a PSA describing issues with an online Social Security spousal benefit application that was denied after being submitted separately from the working spouse’s application. (29:45) The guys discuss how the Social Security Administration determines IRMAA when a tax return is delayed due to combat-zone service and whether a significant drop in income qualifies for Form SSA-44 relief. (38:45) Jim and Chris address whether overestimating income on Form SSA-44 results in a refund, how survivor benefits are affected if claimed early, and whether post-retirement employer coverage is treated as active employee benefits for Medicare Part B and IRMAA purposes. (50:45) George asks whether payments in excess of the RMD from a QLAC can be applied toward RMDs for other IRAs, or only toward the non-annuitized portion of the same IRA. (1:00:20) A listener asks how the pro rata rule applies to a Roth conversion when assets include a fixed indexed annuity (FIA) with a guaranteed lifetime withdrawal benefit. The post IRMAA, Social Security, QLACs, Roth Conversions: Q&A #2550 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss secure income as we review a Yahoo Finance article for middle-class retirees. We use it to highlight longevity considerations and the differences between guaranteed income approaches and traditional safe withdrawal rate or Monte Carlo methods. We also cover where spending-segmented planning and hybrid long-term-care annuities might fit in. Jim’s “Pithy” Summary Chris and I discuss an article titled “How Middle-Class Retirees Can Make Their Money Last 25 Years or Longer” to get into the parts of retirement planning that actually matter when you may be retired for far longer than the industry tends to model. The article leaves out the realities of aging, the changing ability to manage complex finances, and the specific expenses that follow you for life, which lets me lay out why the Minimum Dignity Floor needs to be treated differently from everything else rather than blended into one big withdrawal strategy that assumes stability where none exists. I talk through why I push back so hard on traditional safe withdrawal rate thinking, especially the notion that retirees should simply trim spending whenever markets dip. I know you’ve probably heard me say it before – that approach ignores the reality many retirees face by not addressing what people cannot reduce and overstating what they can. It also glosses over how income behaves differently depending on its source, why some streams ratchet upward while others swing unpredictably, and how risk pooling creates stability that a portfolio alone cannot. The gaps in the article also give room to dig into long-term care, including why certain tax-driven situations make hybrid LTC annuities funded by non-qualified contracts worth considering. And underlying all of this is the point that the goal is not to react to markets for decades on end—it is to build a structure that supports the life you want to live. That is where secure income becomes essential. Show Notes: Yahoo Finance Article The post The Importance of Secure Income for Retirement: EDU #2550 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security family maximum and suspending benefits, a listener PSA on IRMAA premiums, a listener PSA on Medicare premiums, a listener PSA on Social Security claiming strategies, Roth contribution rules, and Roth conversion disadvantages. (4:30) George asks how the combined family maximum benefit works when two retirement records are combined to increase the family limit for auxiliary benefits paid to a spouse and two minor children. (16:00) A listener asks what additional factors should be considered when suspending a Social Security benefit at full retirement age and restarting at 70 after previously claiming early. (30:15) The guys share a PSA in which a listener states that IRMAA is a premium rather than a tax because Medicare enrollment is optional. (37:45) Georgette shares her objections to Chris describing the base Medicare premium as “free” and explains why she feels that is misleading. (44:30) A listener offers a couple of PSAs, first sharing their thoughts on Nokbox, then sharing an article on a Social Security claiming strategy they believe could help people concerned about sequence of returns. (51:00) The guys answer a question about how a 529-to-Roth IRA transfer affects the annual Roth contribution limit when part of the rollover is gains. (56:30) Jim and Chris address what disadvantages exist when choosing a Roth conversion instead of a non-RMD IRA withdrawal when both would be taxable. Show Notes: NokBox Social Security | Readjust your claiming strategy | Fidelity The post Social Security, IRMAA, Medicare, Roth Contribution Rules, Roth Conversions: Q&A #2549 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I review the QLAC 1098-Q and walk through how this form reports premiums, fair market value, and contract status. We compare it to Form 5498, outline how the fair market value and excess annuity payments can be used under Secure Act 2 Section 205 with other IRAs, explore the age-85 and surviving-spouse reporting rules, and touch on listener PSAs about using QLACs as part of a broader self-funded long-term care approach. Jim’s “Pithy” Summary Chris and I use the QLAC 1098-Q as a way to show how the IRS keeps tabs on your QLAC and why that little form matters more than people think. I talk about it as the “kissing cousin” of Form 5498, walk through how box 3 tracks cumulative premiums against the current $210,000 lifetime limit, and explain how the fair market value and projected income give the IRS what it needs while also giving you the data to run the Section 205 strategy after Secure Act 2. Then I get into the strange rule that says the company only has to send 1098-Qs until age 85 or death for the original owner, contrast that with the different rule for a surviving spouse, and spell out why it could be a real problem if the insurer stops providing a usable fair market value once income has been turned on. We kick around how that interacts with the prohibition on DIY fair market value calculations, the inability to get a QLAC quote after age 85, and why advisors and clients are going to care which companies keep sending this information even when they technically don’t have to. On top of that, I read listener emails about using QLACs alongside self-funding long-term care and push back on the idea that you only insure things you are “sure” you’ll need. The post The QLAC 1098-Q: EDU #2549 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on IRMAA brackets and several QLAC topics including RMD interaction, suitability, payout values, and purchase timing. (19:30) A listener wonders if their lower 2024 income will automatically reduce their 2026 IRMAA even though it doesn’t qualify for an SS-44, or if they must contact the SSA. (25:15) George asks whether going above certain income thresholds in 2025 could keep IRMAA lower in 2027 because of inflation adjustments. (34:30) The guys weigh whether QLAC income, once it begins, can offset RMDs on other IRA holdings. (54:00) Georgette wants to know who is a good candidate for a QLAC, how it is purchased, and which features to consider. (1:05:00) A listener seeks guidance on determining early- and late-start payout values for a QLAC and whether those values are fixed or variable. (1:10:15) Jim and Chris consider whether buying a QLAC earlier leads to higher payments at the same deferral age and what factors affect purchase timing. The post IRMAA Brackets and QLACs: Q&A #2548 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I discuss QLAC use cases in the context of retirement income planning and how the Treasury Department designed these annuities to function. We walk through when someone might consider using one, how the absence of cash value affects planning decisions, differences among providers on turning income on early, the impact of mortality credits on later-life payouts, and how QLACs can help stabilize the post-delay period for people focused on long-term secure income. Jim’s “Pithy” Summary Chris and I take a deeper dive into QLACs by taking what we talked about last week and looking closer at where these things might fit into a retirement plan. The Treasury Department set QLACs up with no cash value, which locks them straight into that verb-annuity world we often talk about. That design wasn’t about selling a new product—it came out of watching people’s IRAs get hammered in 2008 and realizing some retirees needed secure income for the older version of themselves. Like so much in retirement planning I see these products as part of the negotiation between the younger you and the older you. The younger you has to decide how much certainty you want in the years when your body and your mind aren’t running at full speed. I talk about that all the time: we are degrading, and it doesn’t take much—like me tripping on a hike—to be reminded of it. A QLAC is one way to make life easier for the older you by guaranteeing income that covers the Minimum Dignity Floor when you may not want to be making complex decisions. Some insurers let you turn income on earlier, some don’t, and those differences matter. Chris brings in sample quotes, and when you see what mortality credits can do in your 80s, you understand why people might actually consider using one. Not everyone needs a QLAC. A lot of you value flexibility and liquidity, and that’s exactly what you give up when you commit to something with no cash value. What I point out here is how easily the conversation around these annuities drifts into investment comparisons when that’s not what they’re built on. QLACs are insurance products, tied to longevity and mortality credits, and that’s the context they belong in. Understanding them inside that framework—what they can do, what they can’t, and how their structure differs from account-based assets—is the real goal of this discussion. The post QLAC Use Cases and Planning: EDU #2548 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security spousal benefits, IRMAA’s classification, concerns about buffer-style funds, the growing push toward private investments, and moving from mutual funds to ETFs. (22:30) A listener presents a hypothetical asking whether the repeal of WEP/GPO could allow Georgette to receive a spousal benefit based on her ex-husband’s Federal Employee record. (28:30) Jim and Chris review a listener’s question about when his spouse can file for her spousal Social Security benefit after he submitted his own application. (37:30) The guys address a listener’s challenge to the explanation that IRMAA is an insurance premium rather than a tax. (43:45) George asks about a recent AQR paper evaluating the effectiveness of buffer funds. (1:01:45) A listener wonders whether the growing push toward private investments—such as private equity and private debt—means they should consider using them. (1:10:45) Jim and Chris review a listener’s question on whether long-held mutual funds can be moved into ETFs without triggering large capital gains. The post Social Security, IRMAA, ETFs, Private Investments: Q&A #2547 appeared first on The Retirement and IRA Show.

If you would prefer to miss Jim’s update on his broken-down truck and recent travels you can skip ahead to (12:45). Chris’s Summary Jim and I walk through QLAC rules and explain how qualified longevity annuity contracts fit into our Secure Retirement Income Process for people who want reliable income later in life. We look at how the Treasury Department designed QLACs after the 2008 market correction, how they work inside IRAs and employer plans, why mortality credits matter, and what Secure 2.0 changed for RMDs. Jim’s “Pithy” Summary Chris can’t hide his reaction when QLACs come up and one listener wondering why brings about today’s conversation. A QLAC is simply a very specific deferred income annuity the Treasury Department carved out after the 2008 market mess—its purpose was to let people secure future lifetime income inside IRAs and employer plans without RMD rules getting in the way. I make the case that none of this is about chasing returns. It’s about recognizing that longevity insurance is a different tool entirely, one built around mortality credits and the power of deferring income to a later phase of life. We talk through how those credits work, how payout structures change when you share them or hold more back for beneficiaries, and why people get whipsawed by the industry: asset managers who never want assets to leave their books, and commission-driven annuity salespeople who try to turn everything into a product pitch. A listener’s email raises a real-world concern—how to make sure the later years’ Minimum Dignity Floor is supported when a portfolio has had its ups and downs. QLACs come into the discussion as one answer to that problem, and I lay out who this kind of deferred lifetime income tends to help and the situations where people might consider using it inside their IRA. The post QLAC Rules and Uses: EDU #2547 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security claiming timing with a listener PSA on application details, Social Security earnings rules at FRA, estate planning organization systems, and restrictions for annuity payments. (15:30) Georgette shares a PSA about the Social Security application process and asks whether applying for benefits to start the month she turns 70 ensures she receives all delayed credits. (30:00) A listener asks how the earnings test applies in the months before full retirement age, what the 2026 limits are, and whether six months of retroactive benefits can be claimed at FRA without triggering the income test. (43:15) The guys share a listener’s PSA on preparing the non-planner spouse, concerns about health-care constraints, and using an organizational system so a trusted friend can help without sharing passwords in advance. (1:04:30) Jim and Chris discuss an annuity owner’s difficulty getting IRA annuity payments direct-deposited when the receiving account is titled in a Trust and ask how to address name–titled account mismatches. The post Social Security,Estate Planning PSA, Annuity Payments: Q&A #2546 appeared first on The Retirement and IRA Show.

Chris’s Summary With Jim away this week, I review the 2026 Social Security changes from the recently released SSA Fact Sheet covering the 2.8% COLA, the new taxable maximum, quarters-of-coverage earnings, and earnings test limits. I also walk through projected Medicare Part B premiums and the deductible, explain the hold harmless provision, and outline 2026 IRMAA brackets for joint and single filers, including how compressed brackets affect survivors. Jim’s “Pithy” Summary With me out in the Utah mountains chasing elk, Chris takes the mic solo to dig into the updated Social Security Administration Fact Sheet—and he brings plenty of insight to go with it! He explains how the 2.8% COLA will show up in January payments, what the new taxable maximum means for workers, and how the earnings test still trips up retirees earning wages before full retirement age. He even touches on the grace-year rule, breaking it down in the clear, detailed way only Chris can. He also reviews projected Medicare changes, walking through the expected $206.50 Part B premium, the $288 deductible, and the timing behind the official release delays. From there, he unpacks the hold harmless provision—who qualifies, who doesn’t, and why IRMAA can still sting even with protections in place. Finally, Chris connects it all to real-world planning, outlining the 2026 IRMAA brackets and showing how compressed thresholds hit surviving spouses hardest. He ties these updates back to our 2-1-0 Tax Ordering Number philosophy, showing how tax strategy, IRMAA, and retirement income all intersect. The post 2026 Social Security Changes: EDU #2546 appeared first on The Retirement and IRA Show.

With Jim is away at a conference, Chris is joined by Jake to discuss listener questions on Social Security survivor benefits, and Roth conversion strategies. (6:30) A listener asks how a widow can maximize her Social Security benefit when her late husband had not yet claimed his. (14:15) George seeks guidance on figuring out if he and his wife need to do Roth conversions, and, if so, how much. (40:00) The guys address a listener considering redirecting new Roth contributions to instead pay taxes on larger Roth conversions in a higher tax bracket for the next five years. The post Social Security and Roth Conversion Strategies: Q&A #2545 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I explore retirement preparedness through a listener’s experience navigating a sudden medical diagnosis, relocation for care, and the challenges of bringing an uninvolved spouse up to speed. His reflections on estate planning, account access, and survivorship highlight how fragile assumptions can be—especially around health and timelines. The story reinforces our emphasis on planning that remains clear and functional even as circumstances change unexpectedly. Jim’s “Pithy” Summary Chris and I share one of the most personal emails we’ve ever received—written by a listener who now finds himself in a situation he never thought he’d face. He had a clear plan, a vision of his Go-Go years, and the confidence that he’d have time to enjoy them. Then life changed. A misdiagnosis. A serious illness. A move across state lines to be closer to proper care. And through it all, a deep reflection on what he hadn’t prepared for—and what he’s now urging others to think about. This isn’t just a medical story. It’s about the ripple effects of life-changing events. There are a lot of questions to consider beyond what medical services are available before retiring somewhere. What happens when the spouse who never handled the finances suddenly has to run the show? What if they don’t know the passwords, the process, the plan? How do you prepare someone to make decisions they have little interest in and never expected to deal with? And that’s what today’s conversation is really about—retirement preparedness in the real world. Not the kind built around ideal assumptions, but the kind that survives when those assumptions fall apart. We talk about the importance of simplicity, the vulnerability of aging, and why our Secure Retirement Income Process is designed to keep things clear, steady, and understandable—especially for the people left behind. The post Retirement Preparedness and Planning Lessons: EDU #2545 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security COLA timing, spousal claiming strategy, IRMAA tax treatment, Roth IRA rollovers from 529 plans, and a listener PSA on deferred annuity RMD rules. (8:00) Georgette asks whether her initial Social Security benefit—approved in September for a December start—will reflect the January COLA increase. (15:30) A listener with similar PIAs and ages to their spouse asks whether it makes sense for one to claim early and the other to delay until 70. (30:30) George shares his realization that the IRMAA surcharge appears to be included in the SSA-1099’s taxable benefit amount, and calls it out in a PSA. (50:30) The guys respond to George’s question about whether a $5,000 rollover from a 529 to a Roth IRA will be treated entirely as contributions for tax-free early withdrawal. (1:08:00) Jim and Chris address Peter’s PSA about calculating RMDs when comparing DIAs and FIAs with GLWBs for a future income stream starting at age 75. The post Social Security, IRMAA Taxation, 529 Rollover, Deferred Annuities: Q&A #2544 appeared first on The Retirement and IRA Show.

If you would like to skip Jim and Chris discussing Jim’s travel plans and the guys’ frustration with low-cost airline pricing, you can skip ahead to (10:30). Chris’s Summary Jim and I continue our discussion on Social Security claiming strategies, revisiting the debate between Professors Derek Tharp and Laurence Kotlikoff. We explore how academic disagreements overlook the practical realities of retirement, emphasizing that Social Security is a resource, not a contest. We examine listener experiences, psychological factors, and portfolio interactions, highlighting how claiming decisions should reflect individual comfort, income structure, and long-term needs—not just mathematical optimization. Jim’s “Pithy” Summary Chris and I wrap up our walk through of Professor Kotlikoff’s response to Derek Tharp’s Social Security article—two academics with brilliant résumés and completely opposite opinions on claiming strategies. One says claim early. The other says delay to 70. But both, in my opinion, miss the bus when it comes to what actually matters to retirees: peace of mind. We read two listener emails that bring the conversation back to reality. One listener puts it simply: “delaying Social Security is longevity insurance”. The second shares two real stories: a friend who claimed at 63, had a serious health event at 68, and passed away at 72, and a father who claimed at 62 but lived to 95. Same choice, very different outcomes. That’s why I say retirement is just a seesaw between the younger you and the older you—and you don’t know which one’s going to show up. We also dig into some of the risks that get thrown around to justify early claiming—like sequence of return risk or loss of spending flexibility—and explain why they don’t hold much water if your retirement plan is structured the right way. The delay period isn’t something to be afraid of. It has an end date. You can plan for it. For us, there’s no single right answer. The correct claiming strategy is whatever works for the person. But too many people focus on how to die with the most, instead of asking what their Social Security has to do for them. Show Notes Derek Tharp article Laurence Kotlikoff article The post Social Security Claiming Strategies, Part 2: EDU #2544 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on how Medicare enrollment affects HSA contributions, Social Security survivor benefits and IRMAA adjustments, financial advisor fee disclosures, and the Thrift Savings Plan (TSP) as a tool in retirement planning. (10:00) A listener asks whether enrolling in Medicare in December with coverage starting in January limits HSA contributions due to the six-month retroactive rule. (31:00) The guys address how a December birthdate affects delayed retirement credits and whether a surviving spouse would receive the full 8% annual increase. (39:00) George wants to know if he can use SSA Form 44 to reduce his IRMAA premium calculation after retiring and lowering his income. (47:00) Jim and Chris respond to a question about financial advisor fee disclosures. (59:15) A listener asks for Jim and Chris’ thoughts on the Thrift Savings Plan, particularly use of the G Fund. The post HSA Contributions, Social Security, Fee Disclosures, TSPs: Q&A #2543 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I examine a recent Social Security claiming strategies debate prompted by articles from Derek Tharp and Laurence Kotlikoff. The episode highlights how opposing valuation frameworks—economic modeling versus purpose-driven income planning—can lead to drastically different conclusions. We explain why assigning Social Security a clear job, such as covering your Minimum Dignity Floor, provides a more reliable foundation for deciding when to claim. Jim’s “Pithy” Summary Chris and I walk through the disagreement between Professor Tharp and Professor Kotlikoff on Social Security claiming strategies. These are incredibly smart guys, and I respect what they’ve accomplished—but I think they’ve both missed the boat. They’re focusing on who’s right from an academic standpoint instead of what actually matters to real people: how Social Security fits into a retirement plan. I go back to the woman I bought strawberries for—the one who thanked me and told me she lives on just Social Security. That moment changed my life. It’s why I became a retirement planner. Retirement is a seesaw between the younger you and the older you. And you have to make an explicit promise that the older you will be okay. I’ve never liked making that promise with volatile assets. For core expenses—food, utilities, transportation, housing, and health care—you need income that lasts as long as you do. So no, I don’t think everyone should delay to 70. And I don’t think everyone should claim early. It depends on what Social Security needs to do in your plan. If you don’t need it, fine. But if you do, and you claim early just because “you might die,” what happens if you don’t? That older you could have had 76% more—and they’re the one who’ll feel the difference.   Show Notes: Tharp Article Kotlikoff Article The post Social Security Claiming Strategies, Part 1: EDU #2543 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on spousal Roth IRA eligibility, backdoor Roth contributions using a solo 401k, Social Security timing, post-tax contributions to an IRA and 401k , and an HSA strategy coordinating withdrawals with Roth conversions. (9:30) George asks whether he can contribute to a spousal Roth IRA after his retirement if his wife continues working and their income meets eligibility thresholds. (20:00) A listener wonders if switching from a SEP IRA to a solo 401k would allow him to make backdoor Roth contributions and improve tax deductions. (31:45) The guys address a listener’s plan to claim Social Security at 62 despite having sufficient pension income and IRA savings. (1:01:30) Jim and Chris respond to a question about making post-tax contributions to a traditional IRA and whether post-tax 401k contributions converted to a Roth 401k right away ever create basis. (1:05:45) A listener considers paying medical expenses from his HSA instead of IRA withdrawals to allow more room for Roth conversions without increasing taxes. The post Spousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542 appeared first on The Retirement and IRA Show.

To skip over Jim and Chris chatting about the government shutdown delaying Social Security and Medicare announcements, and Jim’s upcoming travel plans—including concerns about flight delays and his upcoming elk hunt in Utah you can skip ahead to (8:15). Chris’s Summary Jim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth conversions and employer plan transfers. We explain the differences between direct and indirect rollovers, how constructive receipt is determined, and when a spousal rollover might cause unexpected tax penalties. We also outline when 60-day rollovers can still be useful, especially with maturing MYGAs, and share practical tips to avoid triggering unexpected distributions. Jim’s “Pithy” Summary Chris and I cover IRA rollover mistakes—especially the ones that crop up with 60‑day rollovers. We’re talking the kind of errors that can cost you taxes, penalties, and your sanity. This all started with some emails about the 60‑day rollover strategy for Roth conversions, but it quickly turned into a full‑blown EDU on how rollovers go sideways—fast. We explain the difference between a direct and indirect rollover (hint: if you’re frolicking in dollar bills on your living room floor, it’s indirect), why you can’t do more than one IRA‑to‑IRA rollover per 365 days, and how the IRS finally shut down the old rollover shuffle thanks to the poor guy in the Bobrow case—who won one fight and lost the big one in the same ruling. Then we take it further. Surviving spouses? You’ve got options. But if you’re under 59½ and roll inherited IRA money into your own account too soon, you just triggered the 10% penalty. Only a spouse can do that kind of rollover, by the way. Chris and I get into a whole scenario with a dead husband, a widow, and a girlfriend who didn’t get the memo on common‑law marriage. No joke. And if you’re sitting on a MYGA in an IRA, you better pay attention when that thing matures. Insurance companies love to auto‑renew on day 31, and we explain how a 60‑day rollover can give you breathing room—if you haven’t already used your one for the year. Our go‑to move with IRA‑based MYGAs? You guessed it: the 60‑day rollover. Just don’t mess it up or you’ll blow your chance at penalty‑free flexibility—and that includes protecting your Minimum Dignity Floor. The post IRA Rollover Mistakes and Exceptions: EDU #2542 appeared first on The Retirement and IRA Show.

Jim and Chris discuss a listener PSA on estimating early retirement benefits, followed by questions on Social Security benefit calculations and reductions, HSA held annuities, and IRA annuity pro rata rule application. (14:45) George shares a PSA explaining how to input future earnings on the SSA site to better estimate early retirement benefits. (25:15) A listener asks whether their benefit is funded by the Social Security trust fund and how to estimate their benefit if the trust fund becomes depleted. (37:30) The guys respond to a question about a survivor benefit reduction due to a government pension and whether this reflects an error based on the GPO elimination. (42:00) Jim and Chris weigh-in on the pros and cons of HSA held annuities to generate secure income. (55:00) A listener wants to know how the pro rata rule applies when holding both an annuity inside an IRA and in a separate Roth IRA. The post Social Security, HSA Held Annuities, IRA Annuities: Q&A #2541 appeared first on The Retirement and IRA Show.

Chris’s Summary: Jim and I are joined by Rear Admiral Brian Luther to discuss veterans benefits and military retirement planning. We explore how Navy Mutual supports service members, examine the survivor benefit plan, and talk about the role of annuities in managing longevity risk. Rear Admiral Luther also shares insights on TRICARE, VA health care, and the importance of financial literacy throughout a military career. Jim’s “Pithy” Summary: Chris (“Cowboy”) and I (“Bugs”) are thrilled to welcome Rear Admiral Brian Luther—better known on this episode as “Lex”—to discuss veterans benefits, military retirement planning, and the mission of Navy Mutual. Lex brings an incredible background to the conversation: he served as a naval aviator, commanded the George H.W. Bush on its maiden deployment, and ultimately became the budget officer of the entire U.S. Navy. Now, as CEO of Navy Mutual, he’s focused on protecting military families and promoting financial literacy—something that became personal to him after being sold a lousy product early in his career. That bad experience stuck with him, and it shows in how Navy Mutual approaches everything. This episode covers a lot. We talk about how Navy Mutual came to be, the long-standing military tradition behind it, and how it provides life insurance and annuities without the exclusions and fees often found in commercial products. Lex gives a clear rundown of the Survivor Benefit Plan (SBP), how remarriage impacts SBP eligibility, and why spousal protection is so important. He also introduces their “RETIRE” acronym—risk, education, taxes, investment, retirement, and estate planning—and how those areas guide service members through their financial journey. We explore how military retirees can use VA health care and how that fits—or doesn’t—with Medicare, TRICARE, and travel needs. Lex explains how Navy Mutual separates education from sales, offers no-commission policy reviews, and discloses actual embedded interest rates in their annuities—something almost no one else does. He also shares how annuities can be used as a risk-transfer tool to manage longevity and support retirement dignity, especially when paired with secure income sources like pensions and Social Security. The post Military Retirement Planning: EDU #2541 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security spousal benefits, a listener PSA on IRMAA repayment silence, IRMAA reduction eligibility and planning considerations, and a PSA on how 60-day rollover Roth conversions affect year-end RMD calculations. (7:45) A listener points out a possible error from a recent episode and looks for clarification whether delaying benefits past full retirement age increases spousal benefits. (19:15) George shares a PSA about his ongoing wait for clarity regarding IRMAA repayment adjustments from 2021 and 2022. (28:30) Jim and Chris respond to a listener wondering whether their limited consulting income and work stoppage qualify for IRMAA relief, and what documentation would be needed. The listener also seeks feedback on using a late-year Roth conversion to create a flexible cash flow account for future planning. (1:01:00) The guys share a PSA-ish “question” on the nuanced issue around year-end Roth conversions and RMD calculations—specifically, whether funds moved via a 60-day rollover for conversion purposes need to be added back into the December 31 IRA balance when determining required minimum distributions. The post Social Security, Roth Conversions, RMD Calculations: Q&A #2540 appeared first on The Retirement and IRA Show.

Chris’s Summary Jim and I return for an EDU dialogue episode focused on a listener’s delay period strategy. His plan includes laddered CDs, equity ETFs, delayed Social Security, and Roth conversions. We use his plan to discuss bracket drift, spending liquidity, and how rising markets can complicate a fixed glidepath. We also cover the tax planning window, crossover risk, and why even strong plans need regular adjustments—especially when they rely on assumptions that may not hold up year to year. Jim’s “Pithy” Summary Chris and I are back with an EDU dialogue show, and this one is a deep dive inspired by a listener who shared what he calls a simple delay period strategy. Honestly, I like a lot of it. He’s got a plan. He’s doing Roth conversions, delaying Social Security—all good stuff. He’s even laddered out CDs to fund his Minimum Dignity Floor and his Go-Go fun. That’s great—until you read the line that made me pause: “when the markets rise.” Not “if the markets rise.” And what if they don’t rise? What if your equity side’s down and your CDs aren’t enough? Now you’re spending from equities when you didn’t want to. Suddenly, the conversion you were planning that year? You can’t do it as planned without jumping to a higher bracket.  So, do you cut back on spending or on your planned conversion? That’s how these things fall apart. He’s got structure, he’s got glidepaths, he’s even adjusting the ladder year by year. But don’t assume growth will keep bailing you out. If you do and markets stall, your whole glidepath strategy starts to crack. And as Jacob and I just talked about at lunch—Go-Go money is tough. You don’t know if someone’s going to call and ask for money for a dream vacation or a home remodel and we’ve got to build with that in mind. We also explain why I call it spending liquidity. Liquidity isn’t enough. You need cash you can actually spend without penalties, volatility, or surprise taxes. That’s what makes this kind of planning work. The post Delay Period Strategy: EDU #2540 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on Social Security disability, dependent benefits for an adult child, a 60-day rollover nuance, inherited IRA RMD rules, and a deferred income annuity strategy. (15:00) George asks whether his brother, who is on SSDI and will transition to retirement benefits at 67, can suspend and restart his benefit to grow it until age 70. (27:30) The guys address how the family maximum affects benefits when one child ages out, whether a disabled adult child’s status remains unchanged, and what impact spousal and survivor benefits may have on future payments. (43:15) Jim and Chris review a listener’s experience with a 60-day rollover where an RMD calculation excluded funds rolled back after year-end. (58:00) A listener asks how RMDs are determined when his aunt inherits an IRA that had previously been inherited under pre-SECURE rules. (1:14:00) Georgette considers purchasing a deferred income annuity in her IRA to cover future RMDs and guaranteed income needs and wonders if her strategy has flaws. The post Social Security, 60-Day Rollover, Inherited IRA, and Deferred Income Annuity: Q&A #2539 appeared first on The Retirement and IRA Show.

This week, with Jim away at a conference, Chris is joined by Jake for an EDU episode that takes the shape of a Q&A, focusing on tax planning strategies. The guys cover a series of emails that highlight how different tax rules and opportunities intersect with retirement planning, income management, and financial decisions. (10:30), the first question explores how the new OBBB changes—particularly the $40,000 SALT deduction and $6,000 senior deduction—are affecting Roth conversion strategies. Chris and Jake break down who might benefit from larger conversions, who may want to scale back, and how the extension of lower tax brackets plays into long-term planning. (26:45), a listener with high health care costs asks what qualifies for deduction, how the 7.5% AGI threshold works, and whether items like chiropractor visits and insurance premiums count. The guys walk through the rules, the limits, and which expenses can make a difference. (39:00), the third question looks at the backdoor Roth. A “long-lost” 401(k) rolled into an IRA raises concerns about the pro rata rule and whether it threatens the clean execution of annual conversions. The guys explain how to handle the rollover and keep the strategy on track. (49:45), tax-loss harvesting and the wash sale rule take center stage. The listener wants to know how dividend reinvestments across different accounts might complicate reporting and whether timing strategies can keep things clean. Chris and Jake lay out how the rule works and what to watch for. (1:02:45), a self-employed listener asks if funding a solo 401(k) before converting to Roth could save self-employment tax. The guys explain the mechanics, the limits on employer contributions, and the modest but real savings this tactic may offer. The post Tax Planning Strategies: EDU #2539 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on IRMAA reductions and Roth-conversion effects, widow filing status and IRMAA, in-kind stock Roth conversions and RMD transfers, annuity RMD interactions, and 60-day rollover mail timing. (7:45) George asks whether an approved SSA Form 44 that reduced 2025 IRMAA will also govern next year, how a large 2026 Roth conversion will be trued up and affect future IRMAA brackets, and whether that conversion will cause higher IRMAA in multiple subsequent years. (18:45) A listener wonders if a recently widowed spouse’s IRMAA in 2026 will reflect single status or remain based on the 2024 joint tax return. (24:45) The guys ask whether in-kind stock Roth conversions change the stock’s tax basis inside a Roth and whether an in-kind RMD transfer to a brokerage establishes a stepped-up basis. (49:45) Jim and Chris consider a hypothetical where an IRA annuity’s annual payout might be less than the RMD and what happens if the RMD exceeds the annuity payment. (1:02:15) One listener argues that claiming a mailed check took longer than 60 days to arrive is implausible because USPS optical scans and Informed Delivery images could let the IRS verify delivery dates. The post IRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538 appeared first on The Retirement and IRA Show.