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 R

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 Peri

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.

div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 gap-3 standard-markdown"> Chris’s Summary Jim and I are joined by Dr. Philip Snyder, 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. Philip Snyder 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 personall

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 SummaryJim 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” SummaryChris 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. <

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 <a href="https://www.theretirementandirashow.com/podcast/retirement-

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 SummaryJim 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” SummaryChris 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 SummaryJim 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. *]:pointer-events-auto scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id="request-WEB:7fee8561-5255-457c-96c3-0b60a2943aec-14" data-testid="conversation-turn-30" data-scroll-anchor="true" data-turn="assistant"> Jim’s “Pithy” SummaryChris 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 t

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 <span

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 SummaryJim 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” SummaryChris 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 SummaryJim 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” SummaryChris 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:</str

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 SummaryJim 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” SummaryChris 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 SummaryJim 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” SummaryChris 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 SummaryJim 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 SummaryJim 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” SummaryChris 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

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 SummaryJim 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” SummaryChris 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

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 SummaryJim 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” SummaryChris 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 SummaryJim 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” SummaryChris 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 SummaryJim 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” SummaryChris 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 SummaryJim 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” SummaryChris 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.