The Retirement and IRA Show

Chris’s Summary:Jim and I take a step back in this Dialogue EDU episode to explore how we design retirement plans for again. We talk through common misunderstandings around projections, explain how our See Through Portfolio helps people navigate retirement with more confidence, and clarify how simplicity is built into the process. Jim’s “Pithy” Summary: Chris and I use this EDU episode to have a dialogue on some of the feedback we’ve received about our planning approach. A few listener emails spark a broader discussion about how people interpret our process, where confusion creeps in, and how we intentionally design retirement plans for aging—plans that simplify as clients get older rather than becoming more complex. It’s not about right or wrong but how a retirement plan holds up when real-world questions come into play. Along the way, I dig into why every projection is technically wrong (but why that doesn’t mean you shouldn’t do one!), how we use the law of large numbers to find planning value, and why the first few years of retirement are the hardest. I rant a bit about outdated bond assumptions, explain how our forward-looking returns are built, and revisit my old fog and boat analogies (yes, again). We talk about how retirement should get easier over time, how to protect your future self from cognitive decline, and why someday—even for all you hardcore DIYers—it might be worth hiring a firm like ours, as long as they’re not charging AUM fees. I even manage to tie it all together with a story about firewood. You’ve been warned! The post Retirement Plans for Aging: EDU #2519 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Jake and Paul to discuss tax-related listener questions on IRA contributions from self-employment income, special needs trusts, year-of-death Roth conversions, Cost Basis, and IRMAA. (9:00) George asks how QBI and self-employed health insurance deductions affect how much he can contribute to a traditional IRA.(20:00) Jim, Chris, Jake, and Paul respond to a question about whether creating multiple special needs trusts can multiply the $5,000 federal tax deduction.(28:00) The guys weigh in on a year-of-death strategy involving large Roth conversions and other planning considerations for a surviving spouse.(49:45) A listener wants to know how Form 8606 helps during retirement and when its tracking of after-tax basis becomes useful.(57:00) George asks what documentation the IRS will accept to establish a 2001 cost basis for inherited land now worth significantly more.(1:07:45) The team evaluates whether Roth conversions make sense for a retiree already in the third IRMAA tier. The post IRA Contributions, Special Needs Trusts, Roth Conversions, and Cost Basis: Q&A #2518 appeared first on The Retirement and IRA Show.

Chris’s Summary:Jim and I are joined once again by Jacob for the third and final part of our series on transition period strategy. This time, we focus on the practical side of asset positioning: how near-retirees can begin structuring spending reserves without overreacting to short-term volatility. We use an example case study to explain how to segment early retirement needs into time-based chunks, identify dollars that require principal protection, and distinguish between your Minimum Dignity Floor and Fun Number spending. Jim’s “Pithy” Summary:Chris, Jacob, and I finish up our series on positioning assets during what we call the Venn diagram years or transition period. That’s that murky overlap between accumulation and decumulation, where you’re not retired yet, but you’re gearing up to live off your savings. This week, we dig into a listener’s question—he’s five years out from retirement and feeling nervous about market drops. He doesn’t know when or how to start making changes. So, we build a hypothetical case to show what this might actually look like on paper. I walk through how to start allocating dollars across time without trying to do everything at once (because that’s how people freeze up or make bad calls). Jacob jumps in to explain why we don’t just ladder investments, we build what we call a liquidity timeline—an approach that gives you structure and flexibility. I dig into recency bias, the emotional hang-ups that stop people from spending even when they can—and should. We talk through which dollars need principal protection, which don’t, and why timing matters. And then I get into buffered strategies, laterals, the illusion of statement dollars, and, of course, my ongoing beef with growth-focused asset managers who don’t understand the first thing about distribution planning. The post Transition Period Strategy Part 3 – A Case Study: EDU #2518 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to Social Security spousal benefits, IRMAA relief, suspending Social Security for tax planning, and QCD timing with RMDs. (3:00) A listener enquires whether her 85-year-old mother, who recently remarried, must remain on her ex-spouse’s record for one year before switching to spousal benefits on her new husband’s record.(12:15) The guys address what happens if you file form SSA-44 for IRMAA relief but end up in a higher income tier than estimated.(23:30) George asks to revisit a previous question about if suspending Social Security could allow for more Roth conversions and tax savings.(34:30) Jim and Chris respond to a listener who challenges whether QCDs must be taken before RMDs. Show Notes: QCD Timing Article by Lord Abbet The post Social Security Benefits, IRMAA, and QCD Timing: Q&A #2517 appeared first on The Retirement and IRA Show.

Chris’s Summary:Jim and I are again joined by Jacob as we continue exploring transition period strategy—the years just before retirement when you’re not yet withdrawing but want to prepare. We cover how near-retirees can manage emotional reactions to volatility while positioning assets to support early retirement spending. For those using our Minimum Dignity Floor and Fun Number approach, we walk through how to identify which dollars need protection and where a degree of principal protection fits. Jim’s “Pithy” Summary: Chris, Jacob, and I pick up where we left off last week—diving even deeper into what we call the “Venn diagram” years. That’s the messy overlap between accumulating assets and using them, when you’re still working but close enough to retirement that your portfolio better start shaping up for showtime. This is where a solid transition period strategy can make all the difference. We dig into the emotional side of repositioning, including why I think “locking in a loss” is more of a mental roadblock than a financial catastrophe, and why trying to time your way back to some magical high-water mark is a recipe for regret. I take a bit of a detour into prospect theory, sequence of return risk, and what I jokingly call the 11th Commandment (spoiler: it’s not “thou shalt not sell unless at an all-time high”). Chris breaks down how DIYers can map out future spending in those first critical retirement years, Jacob walks through investment timelines and buffered strategies, and I try not to spill coffee on my laptop mid-rant. Show Notes: As promised here is the photo of the foot space on Jim’s flight. According to our helpful listener, the space shown in the red box between the aisle and middle seats belongs to the middle seat passenger. This is because the middle seat loses space to the window seat due to the fuselage curve, and regains it on the aisle side. The aisle seat has slightly less space overall but can extend into the aisle if needed. The post Transition Period Strategy Part 2 – Positioning and Repositioning: EDU #2517 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to tax planning at full retirement age, the minus-one method for RMDs, inherited Roth RMDs, and early Social Security. (9:10) A listener jokes about the state trivia and offers a suggestion for Chris’s benefit.(11:10) Another listener shares a PSA about delays in online Social Security applications and recommends visiting a local office.(20:15) Georgette asks whether delaying her husband’s Social Security filing would be beneficial for Roth conversions.(39:30) Jim and Chris address whether the minus-one method for RMDs was paused during the IRS’s waiver period.(59:20) The guys answer if inherited Roth IRAs are ever subject to RMDs other than the 10-year deadline.(1:14:15) George questions whether there are ever good reasons to take Social Security early. Show Notes: the Slott Report The post Tax Planning, Minus-One Method, Inherited Roth RMDs, and Early Social Security: Q&A #2516 appeared first on The Retirement and IRA Show.

Chris’s Summary: Jim and I are joined by Jake and Jacob to discuss listener emails related to asset positioning for retirement and the transition period leading up to it. We break down how we think about asset allocation across account types, what a liquidity account is and why we use it, and how we handle year-end tax planning. It’s all part of how and why our Secure Retirement Income Process focuses on spending needs, not just portfolio performance. Jim’s “Pithy” Summary:Chris and I are joined this week by Jake and Jacob for the first in what will likely be a multi-part series—because if you’ve listened to us long enough, you know we don’t exactly breeze through these things. This all started with two listener emails that were clearly related: one asked how to position assets across different types of accounts—Roth, IRA, brokerage, and so on—while the other came from someone in what we call the “transition period,” not quite accumulating anymore but not yet distributing either. We figured it was a perfect opportunity to dig in. So, we walk through our approach to asset management, why we don’t believe in being dogmatic with account assignments, and how we use the Fun Number and Minimum Dignity Floor as anchors when planning for retirement spending—and why trying to map out every distribution years in advance is a fool’s errand. Instead, we focus on creating a flexible structure that can adapt as life throws curveballs. I share why I’m a fan of the liquidity account concept, Jake dives into how we handle tactical tax planning each fall, and Jacob brings his Jello-themed wisdom to the world of asset positioning. Chris keeps us on track (mostly), but yes, there’s a brief derailment involving a questionable turn of phrase on my part—and now Jake and Jacob have recorded evidence of me offering them raises. The post Transition Period Strategy Part 1 – Asset Positioning: EDU #2516 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to Social Security, origins of the RMD age, the tax planning window, and RMDs from Inherited Roth IRAs. (11:00) Georgette asks how to qualify for child-in-care survivor benefits if her ex-husband, who has been missing for seven years, is legally declared deceased. (23:00) A listener wonders when to file for her Social Security benefit to ensure no reduction in the first payment. (32:00) The guys share a listener’s PSA about why the IRS originally chose age 70½ as the starting point for RMDs. (46:30) A listener questions whether the tax planning window should actually end at age 63 due to potential IRMAA impacts. (59:45) George is puzzled by an Ed Slott newsletter discussing RMDs from Inherited Roth IRAs. The post Social Security, RMD age, Tax Planning, and Inherited Roth IRAs: Q&A #2515 appeared first on The Retirement and IRA Show.

Chris’s Summary:Jim and I are joined again by Jacob as we discuss listener emails about “unicorn” status—our term for retirees whose Minimum Dignity Floor and Fun Number are both covered by secure income. We clarify what qualifies as secure income and explore whether a very low withdrawal rate from a conservative portfolio might serve as a substitute. We also touch on when rental income might count and how longevity risk influences planning. Jim’s “Pithy” Summary:This week’s EDU is a dialog episode—where we take listener emails and use them as a jumping-off point to talk through the philosophy behind our approach. Chris and I are joined again by Jacob for a discussion on what it really means to be a “unicorn,” our nickname for retirees whose Minimum Dignity Floor and Fun Number are fully covered by secure income sources. We get into why secure income isn’t just about predictability, but also about risk pooling, inflation, and longevity. One listener asks whether having an ultra-low withdrawal rate from a conservative portfolio might be good enough—and we talk through that with real-world examples, including a client case Jacob and I worked on. I also go off on a bit of a tangent (as I do) about SPIAs, mortality credits, and why I’m setting up a donor-advised fund that’ll stick around long after I’m gone. If you’ve ever wondered whether it’s worth striving for unicorn status—or how to think through portfolio-based income—this is one of those conversations that gets to the heart of how and why we plan the way we do. Plus, you get to hear me throw a few curveballs at Chris and Jacob, which is always fun. The post Defining Unicorn Status in Retirement: EDU #2515 appeared first on The Retirement and IRA Show.

This week’s is a bit of a non-traditional Q&A episode where Jim and Chris address two listener questions on Social Security but then move into Public Service Announcement mode. For the first PSA they discuss a listener email about a potential state-level Roth conversion tax saving strategy. Then, to wrap up the episode, Jim shares a continuation of the payday loan saga from last week. Jim and Chris are also joined by Jacob Vonloh from the office (who you have heard Jim mention many times), who shares a scam he recently encountered himself. (13:00) George asks about child-in-care and spousal benefits tied to a disability claim and whether benefits increase if the higher earner delays until age 70. (28:15) A listener wonders whether it might make sense to claim Social Security now rather than delay to age 70, given the additional spousal benefit that would be triggered. (40:45) A listener PSA highlights how state-level exemptions may influence Roth conversion strategies. (49:00) Jim provides a follow-up PSA about his recent payday loan fraud experience.   Show Notes According to Norton you can help protect yourself by requesting your annual consumer reports and security freezes with the agencies below: Teletrack: https://www.corelogic.com/support/credco-consumer-assistance/x FactorTrust: www.transunion.com/client-support/factortrust-consumer-inquiry Microbilt/PRBC: www.microbilt.com/us/consumer-affairs Clarity Services: https://consumers.clarityservices.com/securityFreeze The post Social Security, Roth Conversion Tax Strategy, and Identity Theft PSA: Q&A #2514 appeared first on The Retirement and IRA Show.