Episodes

3d ago

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 .

6d ago

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

Dec 13

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 .

Dec 10

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

Dec 6

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

Dec 3

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

Nov 29

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

Nov 26

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

Nov 22

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

Nov 19

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

Nov 15

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

Nov 12

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

Nov 8

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

Nov 5

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

Nov 1

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

Oct 29

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

Oct 25

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

Oct 22

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

Oct 18

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

Oct 15

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

Oct 11

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

Oct 8

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

Oct 4

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

Oct 1

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

Sep 27

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

Sep 24

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

Sep 20

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

Sep 17

If you would like to skip over Chris and Jim chatting about a recent Colorado hail storm and Jim’s garden while he’s in Ohio, please skip to the 7:45 mark. Article discussed in today’s show: https://www.kiplinger.com/retirement/retirement-planning/the-me-first-rule-of-retirement-spending Chris’s Summary I chat with Jim about a recent article regarding retirement planning and compare how the article approaches a number of concepts in a similar way to the way that we look at retirement planning here at the firm. Jim’s “Pithy Summary” Chris and I chat about a Kiplinger article that was sent over by a couple of our frequent podcast listeners to get our thoughts. I walk through some of the background on our unique approach to retirement planning including concepts like the Minimum Dignity Floor (MDF) and covering expenses with secure income rather than relying on a safe withdrawal style of approach. We weigh the seesaw between the younger you and the older you when it comes to spending in your youth versus saving in retirement. The post Discussing An Article On Retirement Planning: EDU #2538 appeared first on The Retirement and IRA Show .

Sep 13

Jim and Chris discuss a listener PSA on WEP treatment for foreign pensions, followed by questions on Social Security strategies, benefit calculators, account consolidation, and MYGA selection. (13:00) Georgette shares a PSA on how a lump-sum superannuation payout impacted WEP treatment under the POMs rule and led to a successful Social Security appeal. (21:45) George outlines his family’s situation and asks if claiming Social Security now is the best strategy to activate child-in-care and DAC benefits. (36:15) A listener asks which online calculator Chris previously recommended to determine the taxable portion of Social Security benefits. (38:45) The guys address a question about whether the SSA benefit estimates shown at FRA and age 70 include COLA adjustments. (43:30) Jim and Chris respond to a question about how different retirement plan components might be treated when considering account consolidation. (56:00) A listener asks what criteria to use in MYGA selection, including how to evaluate insurers and what the minimum AM Best rating should be. The post Social Security, Account Consolidation, and MYGA Selection: Q&A #2537 appeared first on The Retirement and IRA Show .

Sep 10

If you would like to skip over Chris and Jake chatting about Jake’s recent trip to Ireland you can go to 7:00. Chris’s Summary I am joined by Jake today, while Jim is traveling, to examine taxes in retirement. We look at why not all taxes belong in the Minimum Dignity Floor . We also consider the trade-offs between Roth conversions and IRMAA, and the role of a cash reserve during the delay period in protecting both essential and discretionary spending when markets move against you. Jim’s “Pithy” Summary While I’m traveling, Chris and Jake dig into taxes in retirement. The Minimum Dignity Floor comes up, and a lot of folks get part of this wrong. It’s about protecting the basics with secure income. Start dragging every tax expense into it and that’s when you end up purchasing annuities you don’t need. Roth conversions and IRMAA can trip people up too. Skip the conversions and you dodge the tax bill for now—but that just means bigger RMDs and bigger taxes later. Convert more today and you feel the hit right away, sometimes with IRMAA stacked on top. There’s no move that makes it painless, and with larger portfolios IRMAA simply becomes part of life. The delay period brings up that old 3% safe withdrawal. The problem is what it puts at risk when markets stumble. It’s not the basics that get cut first—it’s the Fun Number . That’s why Chris and Jake talk about keeping a moat. A pool of safe assets would give you the security and confidence to keep enjoying retirement even if the markets dip. The post Planning for Taxes in Retirement: EDU #2537 appeared first on The Retirement and IRA Show .

Sep 6

Jim and Chris discuss listener questions on surviving spouse Social Security benefits and Roth conversions, SSDI and pensions, the Social Security Fairness Act, managing large HSA reimbursements, and choosing between MYGAs and the TSP G Fund. (7:45) George asks whether Roth conversions count toward the earnings test when planning to claim his surviving spouse Social Security benefits. (26:30) A listener asks how SSDI interacts with pensions, how SSDI transitions to regular Social Security, and why SSDI can sometimes be higher. (35:00) The guys address a listener’s point that repealing WEP and GPO also benefits immigrants with foreign pensions, not just government employees. (44:45) Jim and Chris consider whether taking large HSA reimbursements could increase the risk of an IRS audit. (52:00) Georgette wonders whether to move fixed income from the TSP G Fund into MYGAs, including questions on protection limits and rate comparisons. The post Social Security, HSA Reimbursements, and MYGAs: Q&A #2536 appeared first on The Retirement and IRA Show .

Sep 3

Chris’s Summary Jim and I look at behavioral finance in retirement planning, noting that spending from secure income feels safer while drawing from assets feels like a loss. People resist balances going down after decades of saving, even though the money was built to be spent. We highlight how framing savings as deferred spending and covering the Minimum Dignity Floor with income addresses uncertainty, complexity, and the tendency for retirees to underspend. Jim’s “Pithy” Summary Chris and I dive into two listener-sent pieces — a Kiplinger’s article and a research report from Blanchett and Finke — and they line up perfectly with what we’ve been saying for years. Folks, this is behavioral finance! Retirees spend Social Security, pensions, and annuity checks with ease, but hesitate to touch their own savings. I call it the bottomless cup of coffee: when the pot keeps getting refilled, you drink. When it’s just a thermos, you guard it and leave joy on the table. We also get into how framing makes all the difference. Too many people see their IRA as wealth to preserve instead of deferred spending to use. That’s why Required Minimum Distributions suddenly feel like permission slips — people spend because they think they’ve been told they can. And while loss aversion is real, taxes push those same buttons too. This is why we push to cover the Minimum Dignity Floor with secure income. If food, utilities, transportation, housing, and healthcare are guaranteed, you take uncertainty and complexity off the table. That’s what gives you the confidence to pursue your Fun Number , knowing the basics are covered and you can spend without second-guessing every dollar. Show Notes: Blanchett and Finke Report The post Behavioral Finance in Retirement Planning: EDU #2536 appeared first on The Retirement and IRA Show .

Aug 30

Jim and Chris discuss listener questions on Social Security timing rules, retroactive benefits for an ex-spouse, investment strategy philosophy, fraternal benefit societies, and Roth conversions. (6:30) The guys address a listener’s question about whether applying for Social Security at 70 requires enrolling in Part B or if retroactive filing is an option without losing payments. (16:00) A listener asks why their 75-year-old father was denied six months of retroactive spousal benefits while a widowed friend who applied at the same time received them. (33:30) Jim and Chris respond to a listener who questions the “You won the game, why take the risk” from a previous episode and asks whether a high-equity portfolio still makes sense. (53:00) The guys respond to a listener’s email about fraternal benefit societies that operates outside guaranty associations. (1:12:00) Georgette asks whether converting to a Roth and then spending from it makes more sense than other withdrawal options. The post Social Security, Risk Philosophy, Fraternal Benefit Societies, Roth Conversions: Q&A #2535 appeared first on The Retirement and IRA Show .

Aug 27

If you are not in the mood for Jim and Chris’s delightful banter, you can skip ahead to (5:45). It should be noted that of all the episodes to start sharing that information, it’s the one in which Jim said “we didn’t even banter!”. But, from now on, right here before the guys’ summaries you can find the timestamp to jump ahead to if you want to get to the meat of the show. Chris’s Summary Jim and I continue working through Ed Slott’s advisor quiz. After introducing the mandatory Roth catch up rule last week, we now focus on how W-2 wage definitions determine who’s affected, which plan types are exempt, and how administrative delays impact implementation. We also clarify rules around QCDs from inherited IRAs and debunk common errors made by ChatGPT when interpreting the 60-day rollover rule and plan eligibility. Jim’s “Pithy” Summary Chris and I keep going with the Ed Slott quiz, diving deeper into how the mandatory Roth catch up rule will actually work when it takes effect. We go through how wages are defined for this purpose—specifically Box 3 of the W-2, not Box 1—and why that matters for who’s subject to the rule. That single detail creates big carve-outs for groups like self-employed individuals and many state or local government employees who don’t pay into Social Security. We also highlight how a plan’s design matters. If your employer doesn’t offer a Roth option and you’re over the wage limit, you won’t be allowed to make catch up contributions at all. And we explain how the one-year look-back works, including why a job change can give someone a temporary exemption. ChatGPT joins us again and gets several key questions wrong—like saying the rule applies to SIMPLE IRAs (it doesn’t), or insisting QCDs can’t come from inherited IRAs. Wrong again. If the beneficiary is over 70½, QCDs are allowed, and the IRS has even designated a code on the 1099-R for that exact scenario. Once it thought a little harder, Chat backed off and conceded. Smack talk retracted. We close with a scenario on the 60-day rollover rule—what happens if a distribution check shows up while you’re out of town for months. Chat claimed the clock starts when it hits your mailbox. But that’s not how it works. According to private letter rulings, the 60-day window starts when you actually receive the check. The post Roth Catch Ups and the 60-Day Rollover Rule: EDU #2535 appeared first on The Retirement and IRA Show .

Aug 23

Jim and Chris discuss listener questions on Social Security retroactive payments and delayed retirement credit timing, share a listener PSA on horse speed, and answer questions on fixed indexed annuity default credits, a living benefit rider with a proprietary index, and RMD rules for an inherited account. (15:45) A listener asks if the lack of a prior formal application affects eligibility for retroactive spousal benefits following the GPO repeal. (27:30) The guys address a question about how delayed retirement credits are calculated based on specific months and what to consider when not claiming exactly at full retirement age or 70. (37:45) Georgette shares a PSA on an earlier episode’s horse speed discussion. (44:00) A listener seeks clarification on how a fixed indexed annuity with withdrawal benefits might outperform a DIA, particularly how default credits and fees interact. (1:07:30) Jim and Chris respond to a listener who shares details about their nationwide annuity with a living benefit rider, its performance, fees, and expected income stream. (1:25:45) George asks whether RMD rules for an inherited account require a distribution in the year of his mother’s death, despite the Vanguard calculator indicating otherwise. The post Social Security, PSA, Annuities, RMD Rules: Q&A #2534 appeared first on The Retirement and IRA Show .

Aug 20

Chris’s Summary Jim and I review catch up contributions across IRAs and workplace plans using questions from the Ed Slott training quiz. We clarify the $1,000 IRA catch up (now indexed), explain the age 60–63 super catch up in 401(k)/403(b) plans, and outline the Roth mandate that will require high earners’ catch ups to go to the Roth side. I focus on what’s actually changing and where these rules create practical planning tradeoffs. Jim’s “Pithy” Summary Chris and I dig into the latest Ed Slott quiz, focusing heavily on catch up contributions and how Secure Act 2.0 continues to reshape the rules. We start by clarifying what’s true and false about the standard catch up, then dive into the new super catch up available between ages 60 and 63. I explain why I find this provision frustrating, since adding a few thousand dollars so late in the game hardly moves the needle compared to what earlier compounding could have achieved. And here’s the part that drives me nuts: Congress pats itself on the back for giving people in their 60s this special window, but where was that option decades earlier when it really mattered? If you let someone in their 30s or 40s make bigger contributions, you give compounding time to actually do its job. Instead, they created a rule that looks generous but, in practice, is mostly symbolic. From there, we tackle the Roth mandate for higher earners. If your wages exceed the threshold, your additional catch up dollars must go into the Roth side of the plan. That’s going to be a big surprise for many workers who are used to putting everything pre-tax, especially in higher-cost states where salaries above the threshold aren’t unusual. The upshot is that many workers in this situation will find their catch up contributions directed into a Roth account, which takes away the immediate deduction but allows those dollars to grow and be withdrawn tax-free later in retirement. The post Catch Up Contributions: EDU #2534 appeared first on The Retirement and IRA Show .

Aug 16

Jim and Chris discuss listener questions on Social Security spousal benefits, filing logistics and spousal eligibility with a disabled child, an inherited Roth IRA, and IRMAA concerns. (14:30) A listener asks why his spouse’s Social Security spousal benefit is less than half of his primary benefit amount. (21:45) George asks about the process and documentation needed when filing for Social Security benefits that will also increase payments for his spouse and disabled adult son, and about eligibility for a spousal benefit while delaying his own claim. (40:30) The guys review a ChatGPT summary of Inherited Roth rules and whether there are RMDs for a non-spouse beneficiary that inherited in 2023. (1:03:30) Jim and Chris address a question about an IRMAA increase caused by a lump-sum Social Security payment. The post Social Security, Inherited Roth, and IRMAA: Q&A #2533 appeared first on The Retirement and IRA Show .

Aug 13

Chris’s Summary Jim and I continue discussing funding discretionary spending in Robert Merton’s three bucket retirement income framework from last week’s article, focusing on how his flexible and aspirational spending categories compare with our philosophy. We explore why annuities are insurance products, where TIPS fit into income planning, and why funding Go-Go years demands liquidity and principal protection. The conversation also examines how Minimum Dignity Floor expenses differ from discretionary goals and why tying those goals to high-risk investments can be problematic. Jim’s “Pithy” Summary Chris and I pick up where we left off last week, taking a closer look at Robert Merton’s second and third retirement income “buckets” and how they’re presented in the article we’ve been dissecting. While I can see value in some of the thinking, I have a hard time with the notion that your passions and big adventures should be considered optional spending that you cut when markets turn. These Go-Go years don’t last forever, and I’m not about to tell someone to shelve an elk hunt, delay a trip to see family, or skip the project that brings them joy because of a short-term dip. That’s not my idea of funding discretionary spending. We also look at the tools Merton and the article highlight for flexible spending—TIPS, for example—and how those compare with keeping your discretionary funds liquid and principal-protected. On paper, some of these options sound flexible, but real life rarely plays out as neatly as a model suggests. If the market timing works against you, that “flexibility” can disappear fast. Then we’ll get into the aspirational spending—the so-called extras—and the suggestion to tie them to higher-risk assets. We share our thoughts on matching the right investments to the right spending, why emotional comfort matters in retirement planning, and how your Go-Go years deserve a funding approach that lets you enjoy them while you can. The post Funding Discretionary Spending: EDU #2533 appeared first on The Retirement and IRA Show .

Aug 9

Jim and Chris discuss listener questions on Social Security timing strategies, Roth conversions in an RMD year, annuity return calculations, account sourcing for SPIA purchases, and Rule of 55 withdrawal rules. (12:30) A listener asks whether his brother should delay claiming Social Security to age 70 for better longevity protection despite a narrow breakeven. (35:15) George asks if he can complete a Roth conversion before taking his first RMD and when a QCD would fit in that sequence. (58:15) Jim and Chris respond to a question on how to calculate the return on a lifetime income annuity. (1:11:15) The guys address which account—IRA, Roth, or brokerage—is best for funding a future SPIA purchase. (1:19:45) A listener asks if they can take penalty-free withdrawals from a previous 401(k) under the Rule of 55 while working elsewhere, and whether the rule would apply to both plans after leaving the current job. Show Notes: This is from the IRS final RMD regulations: (f) Determination of whether a distribution is a required minimum distribution —(1) Determination for calendar year of distribution. Except as provided in paragraphs (f)(2) and (3) of this section, if a minimum distribution is required for a calendar year, then the amounts distributed during that calendar year are treated as required minimum distributions under section 401(a)(9) to the extent that the total minimum distribution required under section 401(a)(9) for the calendar year has not been satisfied (and accordingly, those amounts are not eligible rollover distributions). For example, if an employee is required under section 401(a)(9) to receive a minimum distribution for a calendar year of $5,000 and the employee receives a total of $7,200 in that year, the first $5,000 distributed will be treated as the required minimum distribution and will not be an eligible rollover distribution, and the remaining $2,200 will be an eligible rollover distribution if it otherwise qualifies. If the total section 401(a)(9) required minimum distribution for a calendar year prior to the calendar year of the distribution is not distributed in that calendar year (for example, when the distribution for the calendar year in which the employee reaches the applicable age is made on April 1 of the following calendar year), then the amount that was required to be distributed, but not distributed, is added to the amount required to be distributed for the next calendar year in determining the portion of any distribution in the next calendar year that is a required minimum distribution (and, thus, is not an eligible rollover distribution). The post Social Security, Roth Conversions, Annuities, and Rule of 55: Q&A #2532 appeared first on The Retirement and IRA Show .

Aug 6

Chris’s Summary Jim and I review a recent article featuring Robert Merton’s views on retirement income versus savings, using it as a springboard to unpack income planning fundamentals and annuity projections. While we agree with many of Merton’s framing points—especially the focus on secure income—we also note several key areas where academic theory diverges from real-world retirement dynamics. Jim’s “Pithy” Summary Chris and I dig into an article summarizing Nobel Prize winner Robert Merton’s take on retirement income, and I must say—it gave us plenty to talk about! We agree with the premise: retirement is about income, not just a pot of savings. But as always, I’ve got thoughts. Merton’s framing—that income matters more than assets—misses how closely tied the two actually are. You can’t generate income without savings, so they’re not distant cousins—they’re spouses, hand in hand! We also explore his idea of guaranteed income and how it relates to our own Minimum Dignity Floor approach. His categories echo ours—he starts with guaranteed essentials like food, housing, and healthcare. Sound familiar? He even lists sources like Social Security, pensions, and annuities. But when he suggests a 3% inflation-adjusted annuity from a “highly rated insurer”? Well, good luck finding one. Those vanished after COVID. Today, most annuities with inflation protection are just fixed increases—and even those come at a steep cost. That leads us into a deep dive on how we handle inflation during the delay period. I explain why projecting future income shortfalls isn’t about guessing—it’s about monitoring trends and setting up flexible reserves. Chris walks through how we model that gap using actual quotes from insurance companies to estimate how much a future retiree might need. Do we recommend buying now? Nope. We wait. Because retirement plans need recalibration every few years— and they’re far more effective when you understand the math and monitor the risks over time. Show Notes: Article: Why Retirement Income is More Important than Retirement Savings The post Retirement Income Versus Savings: EDU #2532 appeared first on The Retirement and IRA Show .

Aug 2

Jim and Chris discuss Jim’s relocation experience to Ohio, a listener PSA on Medicare, questions about Social Security payment timing and divorce eligibility, Roth 401k withdrawals under the rule of 55, and close with an annuity comparison answer so long it practically qualifies as a mini EDU. (17:00) A listener PSA reminds others that Medicare Part A only covers hospital costs and that Parts B, C, and D must still be actively enrolled in. (24:30) A listener asks whether it’s normal for his Social Security payment date—initially based on spousal benefits—to remain the same after switching to his own record. (31:45) Georgette asks what Social Security benefits she might be eligible for after divorce, given she’s receiving Disability and will have been married 11 years. (39:15) Jim and Chris offer clarity on how the rule of 55 applies to Roth 401k withdrawals and confirm whether earnings would be taxable before age 59½. (55:30) George asks whether it’s better to use a fixed indexed annuity (FIA) with living benefits or a deferred income annuity (DIA); the guys break it down in an extended segment that might even earn you CPE credit. The post Ohio, Medicare, Social Security, Roth 401k, and Annuities: Q&A #2531 appeared first on The Retirement and IRA Show .

Jul 30

Chris’s Summary Jim and I are joined by Matt Kaufman, Senior Vice President and Head of ETFs at Calamos Investments, to discuss buffered ETFs vs stocks and cash, focusing on AQR’s recent critiques. We examine the flaws in AQR’s methodology, the broader history of buffered products, and why these tools can offer certainty in retirement planning. Matt explains how buffered ETFs differ from accumulation strategies and why they may suit specific roles in a distribution-focused portfolio. We also touch on annuity comparisons and institutional adoption by endowments. Jim’s “Pithy” Summary Chris and I welcome back Matt Kaufman from Calamos Investments to talk through the controversy around buffered ETFs. AQR recently published two articles criticizing these tools, and I had some questions—not just about their numbers, but about their motives. If you understand how we use buffered products, especially in retirement distribution, you’ll see why I don’t think these critiques hold up. We talk about the emotional side of retirement—how people freeze up when they’re supposed to start spending. My dad warned me about the Debbie Downers in his assisted living facility: folks who had money but waited too long and couldn’t spend it anymore. That’s why we look at buffered ETFs as a way to give retirees confidence, not as accumulation tools. When I saw AQR lumping these products together and treating them like they were all the same, it reminded me of the way Ken Fisher says “I hate annuities and so should you.” That kind of broad-stroke bashing doesn’t help anyone. Matt walks through the technical flaws in AQR’s analysis—especially how they mischaracterized equity exposure and ignored how buffered ETFs are actually used. We compare them to annuities, explain cap rates, and look at why institutions like the University of Connecticut are dropping hedge funds for these products. There’s more nuance here than some people want to admit, and it’s worth taking the time to understand how these work—especially if you’re in retirement and trying to protect the money you spent 40 years building. Show Notes: For those who would like to read the AQR articles discussed in this episode you can find them here: https://www.aqr.com/Insights/Perspectives/Rebuffed-A-Closer-Look-at-Options-Based-Strategies https://www.aqr.com/Insights/Perspectives/Buffer-Madness The post Buffered ETFs vs Stocks and Cash: EDU #2531 appeared first on The Retirement and IRA Show .

Jul 26

Chris is joined by Jake and Jacob to answer listener questions on Social Security, followed by a PSA about unexpected Social Security payment timing, then additional questions on transition planning, asset positioning across account types, weighing Roth conversions against the senior deduction, and planning around IRMAA. (6:15) George asks what percentage of taxes he should have withheld from his 2025 Social Security income if that is his only source of income. (22:45) A listener PSA describes how their spouse’s first Social Security payment arrived earlier than expected and shares a 40-day approval timeline. (29:45) Chris and the Jacobs respond to a question about transition planning focused on protecting principal before retirement and enabling Roth conversions by age 70. (53:45) A listener seeks guidance on how to position retirement assets across multiple account types when it’s not yet clear which accounts spending will come from. (1:02:45) The guys consider how a single filer should weigh the value of Roth conversions against maintaining low income to maximize the senior deduction before RMDs begin. (1:07:00) Georgette outlines her plan to limit Traditional IRA withdrawals to avoid IRMAA and asks whether it’s better to spend from the Roth or take higher withdrawals and accept IRMAA. The post Social Security, Transition Planning, Positioning, Roth Conversions, IRMAA: Q&A #2530 appeared first on The Retirement and IRA Show .

Jul 23

Chris’s Summary Jim and I explain living benefits on annuities, covering how guaranteed income riders work and why they can appeal to those hesitant to annuitize. We describe what we call noun annuities (pre-annuitization) and verb annuities (post-annuitization), then unpack how living benefit riders like guaranteed minimum withdrawal benefits provide income without giving up access to principal. We also discuss what we refer to as the “pretend account,” alongside actual account balances and the significance of guaranteed versus hypothetical projections. Jim’s “Pithy” Summary Chris and I finally deliver the long-promised show on annuity living benefits! After wrapping up Annuity Awareness Month, we realized this topic still needed its own deep dive—so here it is. I explain how living benefits evolved from death benefits to guaranteed accumulation and now to income riders that let you turn your noun annuity into a verb without actually doing so. Why? Because people hate the verb! They don’t want to give up their lump sum—they want to “keep a noun a noun,” as I say—and still get some income out of it. We also talk about the trickery behind what I call “pretend accounts”—those “mystical magical” numbers insurance companies use to calculate your guaranteed income while your real account shrinks from fees. I explain how the ten percent growth you’re promised isn’t on your actual money—it’s on that “pretend account.” And yes, your fees? Those are based on the “pretend account” too, not your real balance. It’s all sizzle, no steak for most people—unless you’re like me and you’re actually using the income. I share that I own one of these riders myself, but only because the guaranteed income benefit made sense for my Roth IRA. Bottom line: these products aren’t always terrible. If you know you want income and you understand what you’re paying for, some of these living benefit riders might actually make sense—even after you account for the outrageous fees. But the key is understanding what you’re buying and not falling for a hypothetical illustration that doesn’t tell you what you’re actually getting. The post Living Benefits on Annuities: EDU #2530 appeared first on The Retirement and IRA Show .

Jul 19

Chris and Jake address listener questions on Social Security, single premium immediate annuity (SPIA) taxation, IRMAA impacts from NQDC payments, and Roth conversions. (9:45) George asks whether the restricted application strategy for Social Security spousal benefits is still possible, and if so, whether birth year requirements apply, along with what changed after the 2015 law change. (22:15) The guys share a PSA about a listener’s experience with the Social Security application process, explaining how failure to submit a marriage certificate caused delays when applying for spousal benefits. (31:00) A listener asks whether untaxed tip income affects the amount of Social Security benefits a worker may receive in retirement. (36:00) Georgette asks whether SPIA payments purchased using Traditional IRA funds are considered taxable income for life. (45:15) A listener asks if ongoing NQDC payments will be included in MAGI calculations and impact IRMAA. (55:30) Chris and Jake discuss whether taxes owed from a Roth conversion can be paid when filing taxes the following year, or whether quarterly payments are required to avoid penalties. (1:09:15) A listener asks whether living in a state that exempts Social Security from state taxes should impact Roth conversion planning. The post Social Security, SPIA Taxation, IRMAA, Roth Conversions: Q&A #2529 appeared first on The Retirement and IRA Show .

Jul 12

Jim and Chris answer listener questions on Social Security filing and its effect on HSA eligibility, Social Security means testing, the timing of annuity purchases in IRAs, the Roth and Roth TSP 5-year rule. (7:30) Georgette asks whether the six-month Medicare Part A lookback is triggered by her husband’s Social Security application date or benefit eligibility date, and how that affects HSA contributions. (22:45) A listener worries about possible future Social Security means testing for those who are past full retirement age but not yet claiming. (36:30) George questions whether buying a Fixed Indexed Annuity inside an IRA is problematic if RMDs begin before maturity and whether turning on a living benefit might help him spend more. (56:00) Jim and Chris weight in on an office debate on the Roth conversion 5-year rule. (1:05:55) The guys clarify the Roth TSP 5-year rule and whether the clock resets when transferring to a new Roth IRA. The post Social Security, Annuities, Roth and Roth TSP 5-Year Rule: Q&A # 2528 appeared first on The Retirement and IRA Show .

Jul 9

Chris’s Summary I am joined by Jake and Paul to discuss OBBBA tax changes and retiree impacts from the Inflation Reduction Act. We cover changes to brackets, deductions, personal exemptions, and estate limits. Paul explains how new SALT caps, Social Security deductions, and ACA credit rollbacks affect planning opportunities for retirees, especially those near income phaseouts or considering Roth conversions and business deductions. Jim’s “Pithy” Summary Chris, Jake, and Paul talk through a range of retiree-focused updates, including several OBBBA tax changes and provisions from the Inflation Reduction Act. These aren’t just technical adjustments—they have real planning implications, especially for people navigating income limits, deductions, and benefits. They cover updates to itemized deductions, new limitations for higher earners, and what’s changing with the lower tax brackets and standard deduction. Paul walks through how these changes might help—or get phased out—depending on your situation. There’s also a new personal exemption for those over 65 that sounds straightforward but includes some cutoff points retirees need to know about. The Social Security deduction comes up too, and it’s not what most people think. Paul clears up who qualifies and how it works. They also talk about the rollback of enhanced ACA premium credits and how enrolling in Medicare affects HSA eligibility. Some of the rules people have counted on in the past won’t function the same going forward. They touch on other updates as well—charitable giving, estate and gift exemptions, even vehicle loan interest. Not all of it applies to everyone, but plenty of retirees could be caught off guard by the fine print. The post OBBBA Tax Changes Explained: EDU #2528 appeared first on The Retirement and IRA Show .

Jul 5

Jim and Chris answer listener questions on Social Security family maximum rules, spousal and disabled child benefits, defined benefit pension concerns, and 401k managed payout funds. (7:45) A listener is trying to understand how the Family Maximum Benefit might reduce the amounts paid to his spouse and disabled adult child once he claims his own retirement benefit. (16:45) Jim and Chris respond to a listener who has a disabled son and is planning to claim a spousal benefit based on his wife’s record. He asks how the family maximum could affect his son’s eligibility for SSDI and future Medicare access. (30:00) George asks for input on whether to take monthly payments or a lump sum from his pension weighing the potential risks if the company eventually transfers the pension to an insurance company. (49:00) The guys address a question about a “Managed Payout” fund offered in a 401(k) plan and whether this might be a good way to generate retirement cash flow compared to annuities. The post Social Security, Pension Buyouts, and Managed Payout Funds: Q&A #2527 appeared first on The Retirement and IRA Show .

Jul 2

Chris’s Summary: Jim and I examine broker vs advisor sold RILAs using real cap rate comparisons from 2024 to highlight how identical contracts can offer different outcomes. We explain how six-year outcome periods work, what locking in gains actually does, and when fees can reduce returns more than commissions. This episode is less about product bias and more about understanding the trade-offs between access, structure, and transparency in how these annuities are priced and delivered. Jim’s “Pithy” Summary: Chris and I return to RILAs because, well, June wasn’t enough! We had more to say—especially about the quirks of six-year outcome periods and how they affect investor expectations. A listener email pointed out that clients often get emotionally attached to growing RILA balances, forgetting that those numbers aren’t locked in until the full term ends. That’s especially true with longer terms like six years, where market swings can reverse paper gains. We explain how this can lead to misunderstandings about what’s really protected—and when. We also dig into the mechanics of locking in gains early. Some RILAs let you reset into a new term right away, while others force you into a cash-style holding account until the original term ends. That difference can make or break your returns. And if you’re thinking “buffered ETFs already do this,” you’re right—we talk about that too. But the real highlight today is the cap rate comparison between broker vs advisor sold RILAs. Same insurance company. Same date. Same indexes. And yet, in multiple examples, the commission-based version offered meaningfully better cap rates—even after accounting for advisor fees. In one case, the broker version had a 60% cap while the advisor version capped at 30%. So much for the narrative that fee-only automatically means better. It’s a great reminder that both commissions and fees are just compensation structures—and neither tells you whether a product is actually better for the client. The post Broker vs Advisor Sold RILAs: EDU #2527 appeared first on The Retirement and IRA Show .

Jun 28

Jim and Chris shares listener PSAs on IRMAA and Delayed Retirement Credits, and answer questions on Social Security Spousal Benefits, annuity use cases, and fixed indexed annuity payout concerns. (13:00) A listener shares a PSA about a positive Medicare and IRMAA reduction experience at a Central Florida SSA office. (19:00) Georgette follows up with a PSA confirming her husband received all delayed retirement credits despite a February 1 birthday. (26:45) George asks whether his wife will be automatically moved to a spousal Social Security benefit when he files, or if she needs to apply separately. (37:45) Jim and Chris provide clarification on what problems different types of annuities are designed to solve and when each might be used. (1:03:45) The guys address a listener’s concerns about a specific fixed indexed annuity, asking whether a MYGA or money market alternative would offer better long-term value. The post PSAs, Spousal Benefits, Annuity Use Cases, and FIAs: Q&A #2526 appeared first on The Retirement and IRA Show .

Jun 25

Chris’s Summary: Jim and I explore registered index-linked annuities and compare RILAs vs buffered ETFs across liquidity, taxation, and cap rate dynamics. We walk through how the insurance and investment structures differ, where principal protection varies, and how commission-based and advisory products compare from a fiduciary standpoint. I also explain the tax treatment of qualified versus non-qualified annuities and why IRD status matters when evaluating options for legacy planning. Jim’s “Pithy” Summary: Chris and I dig into RILAs—Registered Index-Linked Annuities—and boy, do these things get pushed hard. They’re the lovechild of fixed indexed annuities and variable annuities, designed to sit in the middle of the risk spectrum. I call them the insurance industry’s answer to buffered ETFs and structured notes. The appeal? Some downside protection, some upside potential, and growing popularity with both brokers and RIAs. But here’s the kicker: the same annuity from the same insurance company can have wildly different cap rates depending on whether it’s sold by a broker (commission-based) or an investment advisor (fee-based). I’ve seen broker-sold versions offer higher cap rates than advisory versions—even after paying a commission! That’s why I harp on this: if you’re considering one, you’ve got to compare both sides of the distribution channel. Otherwise, you might end up paying an advisor 1% a year and getting less upside than if you’d bought it through a broker. It also pays to compare RILAs vs buffered ETFs with regard to taxation, liquidity, and advisor compensation. These all factor into whether these products make sense. I’m not anti-RILA. They can be compelling—especially in IRAs where the tax downsides of non-qualified annuities don’t bite as hard. But outside retirement accounts, the tax treatment stinks: no step-up in basis, income taxation, IRD status—it’s a mess. So, if you’re going to lock up your money, know exactly what you’re giving up in liquidity and tax flexibility. And for heaven’s sake, check those cap rates side-by-side! The post RILAs vs Buffered ETFs: EDU #2526 appeared first on The Retirement and IRA Show .

Jun 21

Jim and Chris begin with three PSAs on Social Security experiences, then answer questions on fixed indexed annuities with market value adjustments, SPIA payout options for the Minimum Dignity Floor , and the tax aggregation rule for MYGAs. (11:30) In this PSA Georgette clarifies that her husband, born February 1, received January benefits at full age 70, with payments starting at the end of January. (19:45) A listener shares a PSA about their struggle recovering original documents from the SSA after submitting an IRMAA appeal and only getting help after contacting her senator. (24:15) The guys read a PSA from a listener whose Social Security application was approved, but his first payment was withheld due to how he reported earnings; he later filed an appeal and was paid. (36:00) George asks why the EDU episode on Fixed Indexed Annuities didn’t mention five-year FIAs with market value adjustments and no surrender fees, noting one issuer allows early access with interest rate risk. (54:00) Jim and Chris address when they may recommend SPIAs with life-only vs. return of premium options, discussing how payout levels vary based on longevity risk-sharing. (1:12:15) A listener asks whether a 1035 exchange into a different insurer’s MYGA can avoid the tax aggregation rule; Jim explains how proration works and why the trade-off might not be worth the hassle. The post Social Security PSAs, FIAs, SPIAs, and MYGAs: Q&A #2525 appeared first on The Retirement and IRA Show .

Jun 18

Chris’s Summary: Jim and I continue our focus for Annuity Awareness Month by explaining how fixed indexed annuities work and the regulatory nuances that distinguish them from other fixed products. We walk through their structure, common misconceptions, when they can be appropriate, and how to compare them to MYGAs and buffered ETFs. We also highlight the motivations behind annuity recommendations in the financial services industry and the risks of proprietary index products. Jim’s “Pithy” Summary: With Annuity Awareness Month continuing through June, Chris and I wade into the world of fixed indexed annuities—what they are, how they work, and why they’re not universally good or bad. I explain how they use options to generate index-like returns, how the “fee is baked in,” and how they compare to MYGAs and the buffered ETFs Wall Street has been offering over the past five or six years. If you’re locking up your money for five or ten years, you need to understand what you’re getting—and what the person recommending it is getting too. We also break down how advisory platform annuities are changing the landscape. Advisors who used to bash annuities now love them—because they can charge their AUM fee inside the annuity without holding an insurance license. But the one actually recommending the product and earning the commission? That’s the wholesaler, and they’re not a fiduciary. And while some moves might be justified, I’ve seen plenty that just don’t sit right. If someone’s trying to move you from one annuity to another, you’d better ask what you’re giving up—and what they’re getting in return. I also share what I found digging into one of those so-called “uncapped” proprietary indexes. I used ChatGPT’s deep research tools and spent a good 45 minutes pulling disclosures apart—and what I found didn’t impress me. These indexes often skim returns off the top and bury fees most agents can’t explain. If you’re being sold one of those, do some homework. We’ll get into RILAs next week—because yes, I ran out of time. The post Fixed Indexed Annuities: EDU #2525 appeared first on The Retirement and IRA Show .

Jun 14

Jim and Chris address questions on Social Security survivor benefits, unreimbursed HSA expenses, SPIA funding from multiple accounts, and Fixed Indexed Annuity details. (7:45) Georgette asks whether drawing her own reduced Social Security benefit at 62 will affect her ability to switch to her deceased husband’s full survivor benefit at age 67. (23:15) A listener follows up on an HSA discussion, asking whether reimbursing heirs with a shoebox of unreimbursed receipts is valid post-death, or if only unpaid bills qualify. (33:00) The guys address a question about funding a SPIA when assets are distributed across various accounts like IRAs, Roths, and brokerage accounts. (52:15) Jim and Chris respond to a listener who wants clarification on the features, surrender schedule, and commission of a fixed indexed annuity a friend recently purchased in his IRA. The post Social Security, HSA Rules, SPIA Funding, and FIA Details: Q&A #2524 appeared first on The Retirement and IRA Show .

Jun 11

Chris’s Summary: Jim and I discuss annuity types and features during Annuity Awareness Month, focusing on immediate vs. deferred annuities and fixed vs. variable structures. We cover how each type works, what they offer, and where caution is warranted. Jim’s “Pithy” Summary: Chris and I continue our Annuity Awareness Month series by diving into the foundational aspects of annuities—what they are, how they work, and what to watch out for when buying one. We explain the four primary annuity types and features—immediate, deferred, fixed, and variable—and share why understanding the difference between a noun and a verb matters in this world. When you annuitize, that’s the verb; you’re locked in, and there’s no getting out. That’s why we call deferred income annuities a big commitment—once you’re in, there’s no divorce clause! I share my concerns with the tax deferral hype, especially when annuities are held inside IRAs. Many folks mistakenly believe they’re gaining tax advantage, but in reality, they might just be compounding future tax headaches. We talk about how annuities can offer principal protection and guaranteed lifetime income—but not all annuities do both. And we dive into what happens if you die early or live long, covering things like period-certain options, cash refunds, and installment refunds. We also walk through the origin of single premium immediate annuities as a modern-day answer to tontines—yes, those ancient, now-outlawed mortality pools where surviving members collected increasingly larger checks. Mortality credits are still alive and well, just repackaged into today’s SPIAs. And if you’ve ever been pitched a variable annuity with enhanced death benefits or living benefits, we explain how those work, what they really cost, and why you need to read the fine print. From mortality and expense fees to revenue-sharing subaccounts, there’s a lot going on behind the scenes. The post Understanding Annuity Types and Features: EDU #2524 appeared first on The Retirement and IRA Show .

Jun 7

Jim and Chris answer questions on defined maturity bond ETFs, Social Security account linking and spousal offsets, 401k annuities vs IRA Annuities, and annuitization definitions. (14:30) Jacob joins the guys to explain how estimated net acquisition yield works for defined maturity bond ETFs, including how to interpret it and evaluate risk when holding through maturity. (38:30) A listener asks about sending a marriage certificate to Social Security for account linking and whether there’s any confirmation of linking on SSA.gov. (44:15) George wonders whether his wife will automatically receive a spousal benefit increase once he claims Social Security at age 70, and how to confirm PIA and eligibility. (52:30) Jim and Chris address a suggestion that annuities held inside 401k plans may be less tax efficient than IRA annuities because of RMD aggregation rules. (1:06:45) A listener asks why so few annuities are annuitized and whether turning on income from a DIA or SPIA counts as annuitization. The post Bond ETFs, Social Security, 401k Annuities, and Annuitization: Q&A #2523 appeared first on The Retirement and IRA Show .

Jun 4

Chris’s Summary: Jim and I kick off our annual Annuity Awareness Month series by explaining how using annuities in retirement planning can help manage longevity risk and provide guaranteed income. We cover when they’re worth considering, what they actually solve for, and how they might fit into a plan—if at all. We also explain why many people are skeptical of annuities and why, in many cases, that skepticism is justified. Jim’s “Pithy” Summary: Chris and I launch our annual series for National Annuity Awareness Month with a foundational discussion on annuities: what they are, why they exist, and how we use them—sparingly but strategically—in retirement planning. This episode lays out the key insurance roles of annuities: to protect against longevity risk and to provide principal guarantees. We explain the importance of matching secure income to the Minimum Dignity Floor , especially for clients who worry about running out of money or spending too little early in retirement. We also touch on the emotional and cognitive benefits of predictable income streams—what I call “bottomless cup of coffee” money. It helps people feel secure, simplifies decisions as we age, and eases the burden on a less-involved spouse. We explore the history of how annuities got such a bad rap—some of it deserved, especially when the industry prioritized commissions and free dinners over client outcomes. I also share how my own financial education at Boston University drilled anti-annuity rhetoric into my head, even while praising the “three-legged stool” of Social Security, pensions, and savings. It made no sense: the annuity was the obvious substitute for the lost pension leg. If you’re a regular listener, you already know we’re not annuity salespeople, and we certainly don’t hate them either. We see them as tools, and just like dogs, you match the tool to the task. You wouldn’t take a bichon duck hunting, and a Chesapeake Bay retriever doesn’t belong in a carry-on crate. Same principle with annuities. The post Annuities in Retirement Planning: EDU #2523 appeared first on The Retirement and IRA Show .

May 31

Jim and Chris answer listener questions on Social Security filing, a PSA on SSA’s online application process, the Roth 5-Year Rule, HSA strategy, and bond principal risk. (8:00) A listener asks whether Social Security’s claim that delayed retirement credits aren’t applied until the end of the following year is accurate, and whether anyone receives them without persistent follow-up. (29:15) The guys share a listener PSA with their experience applying for Social Security online and highlights the confusing communications around application status and approval timelines. (18:15) George asks how and when to apply for Social Security if they want benefits to begin at age 70 and their birthday falls on the first of the month. (35:45) Jim and Chris respond to a question about whether each Roth conversion has its own 5-year clock, even for someone over age 59½ with existing Roth IRAs. (42:15) Georgette wonders how the Roth 5-Year Rule applies to non-spouse beneficiaries and whether it transfers from the original account holder. (48:00) A listener shares their HSA strategy as a substitute for long-term care insurance, along with personal experience on how cafeteria plan deductions affected Social Security earnings. (56:00) The guys explain whether bondholders risk losing principal at maturity when interest rates rise significantly. The post Social Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522 appeared first on The Retirement and IRA Show .

May 28

Chris’s Summary: Jim, Jake, and I use this Dialogue EDU episode to explore how we approach flexible retirement spending. We respond to listener emails about DIY simplicity, budgeting for irregular expenses, and how we assign assets to spending needs. The conversation highlights why we prioritize adaptability over rigid withdrawal rules. Jim’s “Pithy” Summary: Chris, Jake, and I use this Dialogue EDU episode to explore what flexible retirement spending really looks like—beyond the spreadsheets and into the real-life tradeoffs people actually face. A few listener emails set the stage, from a DIYer aiming for simplicity to someone tackling unexpected home repairs, and another asking how we assign dollars to various spending needs across tax categories. We take those as a jumping-off point to talk about the importance of structure without rigidity, and why having a plan doesn’t mean you need to over-optimize every detail. I share thoughts on safe withdrawal rates (you can guess where I land!), why the best-laid plans always get tested, and how people get in trouble when they assume retirement is just a math problem. Jake weighs in on building plans that bend instead of break, and Chris brings it all back to how our See Through Portfolio and 2-1-0 Tax Ordering Number provide enough order to make decisions—without painting you into a corner. Along the way, I go on a bit of a tangent about why rules of thumb usually leave people stuck—especially if they’ve been good savers their whole life but have trouble flipping the switch to spending. We get into how why simple doesn’t always mean easy and how people can tie themselves in knots trying to make every move efficient. There’s a reason we keep coming back to flexibility: it’s the only way a plan actually holds up when life starts throwing curveballs! The post Flexible Retirement Spending: EDU #2522 appeared first on The Retirement and IRA Show .

May 24

Jim and Chris answer listener questions on Social Security timing, the Earnings Test, nondeductible IRA basis, and the Roth 5-Year Rule. (16:15) Georgette asks whether filing retroactively in December, with Social Security payments issued in January, ensures that all income—including the retroactive amount—will be reported on the following year’s tax return. (28:00) A listener working in a State job who is eligible for a Social Security widow benefit asks whether large pre-tax contributions to 403(b) and 457(b) plans would reduce his earnings under the Earnings Test. (42:30) The guys address whether IRA basis can be isolated from gains when converting a nondeductible IRA to a Roth. (1:02:15) Jim and Chris respond to a listener seeking clarification on the 5-Year Rule for Roth IRAs, including how it applies to earnings distributions by original owners and non-spouse beneficiaries. The post Social Security, IRA Basis, and Roth 5-Year Rule: Q&A #2521 appeared first on The Retirement and IRA Show .

May 21

Chris’s Summary: Jim and I are joined again this week by Kevin Sebesta from the Rock Retirement Club in this EDU episode. We explore what helps retirees start spending confidently— especially when markets are volatile or the saver mindset is hard to shake. Kevin shares how structure, support, and community all play a role, and why building confidence takes more than just having a solid financial plan. Jim’s “ Pithy” Summary: Chris and I bring Kevin Sebesta back this week for round two, and this time we’re talking about what it really takes to start spending confidently in retirement. Kevin’s been retired for over a decade and now coaches others through the emotional messiness of it all— because let’s face it, knowing you “ have enough” and actually feeling comfortable using it are two very different things. We dig into how savers struggle to flip the switch, how things like the Fun Number and Minimum Dignity Floor can give people the permission they need to enjoy their money, and why building in a simple cash reserve might just be the difference between “ Hey, let’s upgrade the cruise cabin” and “ Let’s sit in steerage because the market dipped 8%.” We talk about community, support, peer influence ( yes, even a little friendly shaming), and how watching other retirees live well can sometimes do more than a spreadsheet ever could. Kevin shares some great anecdotes— including what happens when frugality runs too deep— and I get into my usual rants about emotional risk, the real cost of inaction, and why deferring fun until your 80s is a plan only a masochist could love. Retirement planning isn’t just about having a secure strategy— it’s about creating a life worth funding! The post Spending Confidently in Retirement with Kevin Sebesta: EDU #2521 appeared first on The Retirement and IRA Show .

May 17

With Jim away at a conference, Chris is joined by Jake and Jacob to answer listener questions on child- in- care spousal benefits , the Earnings Test , HSA strategy, reconstructing cost basis , and Social Security timing concerns . ( 6: 00) A listener asks whether reaching full retirement age makes him ineligible for child- in- care spousal benefits, and what steps he can take to appeal the denial. ( 21: 30) George questions whether excess earnings prevent payment of family Social Security benefits when the worker’s own benefit is offset ( 34: 00) The guys address how inheritance and medical spending may influence HSA strategy and if it’s possible to overfund an HSA. ( 50: 00) “ Chris and the Jacobs” respond to a couple trying to reconstruct the cost basis of mutual funds purchased in the 1980s without access to their records. ( 1: 02: 15) Georgette wonders if divorce should be considered while deciding when a lower- earning spouse should claim Social Security, as well as whether pre- tax 401( k) contributions reduce reported earnings for benefit calculations. The post Social Security, HSA Strategy, and Cost Basis: Q&A #2520 appeared first on The Retirement and IRA Show .

May 14

Chris’s Summary: Jim and I welcome Kevin Sebesta from the Rock Retirement Club in this Dialogue EDU episode to explore the retirement mindset and why preparing for life after work goes beyond just the numbers. Kevin shares lessons from his own journey and the broader retirement community about identity, purpose, and what makes a fulfilling transition. Jim’s “ Pithy” Summary: Chris and I welcome Kevin Sebesta to this Dialogue EDU episode for a conversation that veers off the usual technical path and gets into something trickier— the retirement mindset. Kevin’s a retirement coach and longtime member of the Rock Retirement Club, and he joins us to talk about the emotional challenges of leaving work. Kevin shares lessons from his own early retirement and what he’s learned working with hundreds of other retirees—plus a few gems that made even me and Chris stop and think. We get into why so many savers have a hard time flipping the switch to spending, the tension between saving and spending, and how tools like the Fun Number can help reframe your mindset around using money for more than just security. The post Exploring the Retirement Mindset with Kevin Sebesta: EDU #2520 appeared first on The Retirement and IRA Show .

May 10

Jim and Chris respond to listener emails on Social Security record accuracy, IRMAA repayment options, naming a Trust as an IRA beneficiary, and the Roth 5-year Rule. (12:00) Georgette shares five important Social Security lessons from her family’s experience, prompting a PSA-style discussion on earnings record errors, divorce and remarriage rules, survivor benefit delays, and claiming strategies. (40:15) A listener offers a PSA about what happens if your IRMAA appeal lowers surcharges, but your income later exceeds expectations. ( 45: 15) Jim and Chris address a question about naming a T rust as IRA beneficiary, discussing both how to complete a beneficiary designation form and how custodians title I nherited IRAs when a T rust is involved. (1:04:30) The guys weigh in on whether a Roth conversion to create a new account two days before the owner’s death must meet the Roth 5-year rule for beneficiaries to access funds tax-free. The post Social Security, IRMAA, IRA Beneficiary, and the Roth 5-Year Rule: Q&A #2519 appeared first on The Retirement and IRA Show .

May 7

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 .

May 3

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 .

Apr 30

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 .

Apr 26

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 .

Apr 23

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 .

Apr 19

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 .

Apr 16

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 .

Apr 12

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 .

Apr 9

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 .

Apr 5

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 .

Apr 2

Chris’s Description Jim and I talk about how market downturns—like the one we’re seeing now—can cause people to second-guess their plans, even when they’re well prepared. We walk through how our Secure Retirement Income Process is designed to provide structure and clarity during volatile times, and explain how proper positioning can help you maintain perspective. Jim’s “Pithy” Description Chris and I are back this week with a timely conversation—because if you’ve looked at the headlines lately, you’d think the sky is falling. “Boomers in Trouble,” “Retirement Fears,” you name it. Meanwhile, the S&P is down about eight and a half percent from its recent high, and you’d think it was 2008 all over again. I get it. Even folks with millions in savings start to feel uneasy when their statements show a dip. Especially if you’re newly retired and that paycheck just stopped coming. So we took a step back and talked through why I built the Secure Retirement Income Process and the See Through Portfolio in the first place. It’s not about chasing returns—it’s about helping you see your money clearly. Which dollars are for next year? Which ones are for twenty years from now? That clarity matters. Especially when fear starts knocking. And yes, I go on a bit of a rant (a productive one!) about how headlines prey on emotions, how panic can sabotage your go-go years, and how, if you’re not careful, you’ll rob yourself of the very fun you saved all those years to enjoy. I even share a new addition to my own bucket list—a historical tour through Italy, inspired by my latest deep dive into Roman history. You think I’m putting that off because the market’s down eight percent? Not a chance! The post Weathering Market Downturns: EDU #2514 appeared first on The Retirement and IRA Show .

Mar 29

Jim and Chris discuss listener questions relating to spousal Social Security benefits, RMD tax withholding, IRA withdrawals, and 401(k) contribution limits. Jim also shares a PSA about a recent attempt at identity theft. (20:15) Jim shares a PSA about a fraudulent payday loan application attempted in his name and what he learned about credit freezes and loan monitoring. (30:15) George asks whether his wife will be subject to the earnings test if she retires mid-year and starts claiming Social Security benefits in the same year. (39:15) George asks whether tax withheld from his RMD can satisfy IRS requirements for avoiding quarterly estimated taxes. (47:30) A listener wonders whether taking cash from two small IRAs will result in capital gains taxes. (1:03:00) Jim and Chris weigh in on a question about the total 401(k) contribution limit for those over age 50. The post Identity Theft, Spousal Benefits, RMD Taxes, IRA Withdrawals, and 401(k) Contribution Limits: Q&A #2513 appeared first on The Retirement and IRA Show .

Mar 26

Chris’s Summary Jim and I continue our review of interesting and sometimes confusing retirement planning facts, mostly drawn from Jim’s recent Ed Slott conference. We focus on the two Roth five-year rules and how they apply to Roth IRAs versus Roth 401(k)s. I explain the key distinctions between tax-free earnings and penalty-free access. Jim goes further into how “seasoning” from a Roth 401(k) carries over to a Roth IRA. We also touch on pro rata distribution rules in Roth 401(k)s, the IRS’s strict interpretation of the age 55 exemption, and the unique planning window between 59½ and RMD age. Jim’s “Pithy” Summary Chris and I continue our “things that make you go hmm” EDU series with more head-scratchers, funny moments, and some planning tips you’ll definitely want to remember. I came back from the recent Ed Slott conference with a pile of notes, and we dig into the most confusing—and most commonly misunderstood—rules surrounding Roth accounts: the dreaded five-year rules. I walk through both of them, explain how they apply to Roth IRAs and Roth 401(k)s, and we talk about the critical difference between tax-free and penalty-free withdrawals. Then we hit what I think is the big “ah-ha!” moment—the idea of “seasoning” Roth 401(k) dollars. Whether you picture that as a cast iron skillet like Chris or a cracked pepper roast like me, the point is: once a Roth 401(k) is fully seasoned, it keeps its flavor—even after being moved into a Roth IRA. We also touch on a Roth 401(k) rule that surprises many people: how distributions are treated when they’re not qualified. Spoiler—it’s not like a Roth IRA! Plus, we go over a tax court case involving a guy who thought he was exempt from the 10% early withdrawal penalty and got hit with taxes, penalties, and interest anyway. It’s a cautionary tale, and the court’s response had us both shaking our heads. Finally, we wrap up with some strategic talk about what Ed calls the “donut hole,” which matches what we refer to in the office as the tax planning window—that sweet spot between age 59½ and your RMD age when there are no penalties, no withdrawal restrictions, and total flexibility in how you tap your retirement accounts. If you’re doing any kind of serious tax or retirement planning, understanding this window is critical. Oh—and yes, there are plenty of food metaphors in this one, because I was hungry the whole show. Hope you enjoy! The post Roth 5-Year Rules and the Tax Planning Window: EDU #2513 appeared first on The Retirement and IRA Show .

Mar 22

Jim and Chris discuss listener questions relating to Social Security strategies, spousal benefits, Roth conversions, and annuities. (8:15) George asks whether a widow who was widowed before age 60 has two Social Security claiming strategies available based on the FRA benefit of each spouse. (20:30) The guys address a question about how spousal benefits are calculated when one spouse took Social Security early and the other has a PERA pension. (29:30) Georgette wonders how she and her husband should approach Roth conversions given their $4 million in IRAs, her larger balance, and concerns about future RMDs and legacy planning. (1:03:30) Jim and Chris provide guidance on whether to use current or future spending when purchasing a SPIA to cover base expenses and how laddering might play a role. The post Social Security Benefits, Roth Conversions, and Annuities: Q&A #2512 appeared first on The Retirement and IRA Show .

Mar 19

Chris’s Summary: This week’s EDU show is a throwback to an old favorite—things that make you go “hmm.” Jim brought back a list of oddities from the latest Ed Slott training, covering everything from RMD rules the IRS only recently addressed to real-world court cases involving bankruptcy, lottery tickets, and IRA self-dealing gone wrong. Turns out, there are plenty of IRA mistakes you can make—some more ridiculous than others. Jim’s “Pithy” Summary: It’s another round of “things that make you go hmm,” straight from my latest trip to Ed Slott’s two-day training. These are the kinds of cases and quirks that catch my attention—some because they’re important, some because they’re just bizarre, and some because they make you wonder why no one’s brought them up before. Ever wonder what happens if your IRA balance drops so low that you can’t take your full required minimum distribution? Turns out, the IRS finally put something in writing—but it took them long enough to address it. Then there were some real-world case studies that left me shaking my head. One involved an all-or-nothing gamble with an IRA that didn’t go as planned. Another showed how trying to get too creative with IRA-owned real estate can backfire in a big way. And here’s one you probably haven’t thought about—doing an in-plan Roth conversion in your 401(k) might have unintended consequences that could close the door on a major tax strategy. We’ll also talk about a handy tool for checking state estate and inheritance taxes—because where you live (or where you move) could have a bigger impact than you think. Hope you enjoy the mix of useful, surprising, and “you’ve got to be kidding me” moments! The post Things That Make You Go Hmm – RMD Rules, IRA Mistakes, and Tax Court Surprises: EDU #2512 appeared first on The Retirement and IRA Show .

Mar 15

Jim and Chris answer listener questions on Social Security records, GPO, QCD timing, annuity costs, and excess IRA contributions. (10:30) Georgette asks about fixing gaps in her Social Security record. (19:30) The guys discuss how a listener’s spousal Social Security benefits work after the repeal of GPO. (28:30) George seeks clarification on the timing of QCDs and RMDs. (53:30) Jim and Chris answer a query about the administrative costs of annuities. (1:04:15) George faces challenges with excess IRA contributions and MAGI limits. The post Social Security records, GPO, QCD Timing, Annuity Costs, and Excess IRA Contributions: Q&A #2511 appeared first on The Retirement and IRA Show .

Mar 12

Chris’s Summary: Jim’s back from his conference and Jake joined the show again this week as we tackled the latest Ed Slott quiz. Unlike last time, Jim didn’t give us the book to reference—so Jake and I were going in cold. Jim also decided to test ChatGPT by giving it the entire quiz and the manual. With all that information, the AI was still imperfect. While seeing if we could outscore both the AI and each other, we covered Inherited IRA RMD rules, SECURE Act 2.0, self-certification for disability, Roth 401(k) rules, and spousal consent for IRA beneficiaries. Jim’s “Pithy” Summary: It’s time for another Ed Slott IRA quiz, and this time, I decided to put both AI and my co-hosts to the test. Before the show, I handed the entire quiz—along with the Ed Slott manual—to ChatGPT to see if it could finally outscore us mere humans. Turns out, even with all that information, AI still flunked five questions. So, while the robots might be getting smarter, they’ve still got a long way to go before they can challenge a real retirement planner. Chris and Jake joined me as we tackled some tricky questions on Inherited IRA RMDs, Roth 401(k) surprises, SECURE Act curveballs, and even some quirky beneficiary rules. To make things more interesting, I made sure they had no book, no notes—just their wits. And, of course, I had the pleasure of revealing exactly where the AI got it wrong (which, let’s be honest, was just as fun as answering the questions). Along the way, we covered why certain Inherited IRA RMD rules have changed, how Roth 401(k)s can still trip people up, and why SECURE Act provisions aren’t always as straightforward as they seem. Plus, we had some fun debating the bizarre quirks of beneficiary designations—because apparently, even the IRS likes to keep us guessing. Think you can outscore AI? Maybe even outscore Chris and Jake? Play along and see how you do! The post IRA Rules Quiz: EDU #2511 appeared first on The Retirement and IRA Show .

Mar 8

Jim and Chris are joined by Paul Neiffer, CPA to answer listener questions on qualified dividends, gifting strategies, Roth conversions, and trust taxation. (09:00) George wonders if frequent rebalancing in his taxable brokerage account is causing more of his dividends to be classified as unqualified. (21:30) A listener asks for guidance on which accounts to withdraw from when planning a large financial gift to an adult son. (37:15) The guys offer their perspective on doing Roth conversions early in retirement in order to reduce RMDs, and thus taxes, later in retirement. (59:30) Georgette seeks clarity on revocable trust taxation, IRA beneficiary designations for minors, and whether a trust should be named as the beneficiary of a Roth or brokerage account. The post Qualified Dividends, Gifting Strategies, Roth Conversions, and Trust Taxation: Q&A #2510 appeared first on The Retirement and IRA Show .

Mar 5

Chris’s Summary: Jim is at yet another industry conference, so Jake is stepping in to join me this week. We pick up where Jim and I left off last time, discussing misleading financial articles. This time, we take a critical look at an article from Moneywise that claims to lay out the “standard” order for withdrawing retirement funds—but seems more focused on promoting paid links than providing useful advice. We break down why a one-size-fits-all withdrawal strategy doesn’t work, how tax planning should drive these decisions, and why you should always approach articles like this with skepticism. Jim’s “Pithy” Summary (Even Though He’s Not in This One): Well, I wasn’t on this episode because—surprise, surprise—I was off at an industry conference (again!), this time hunting for the next great fintech tool to help our office and clients. I’m always looking for ways to improve the advice we give, the services we offer, and maybe—just maybe—find a tool that doesn’t require me to beg Chris to teach me how to use it! Meanwhile, Chris and Jake tackled yet another clickbait financial article, this time from Moneywise , which attempted to pass off a barely disguised ad as solid financial advice. Now, I haven’t listened to the episode yet, but I can already feel my blood pressure rising. Articles like this—pretending to provide helpful guidance while actually steering unsuspecting retirees toward whatever paid service they’re shilling that day—really get me going! From what I gather, Chris probably got straight to the point, and Jake—being the level-headed guy he is—kept things grounded with solid explanations. They covered why tax planning should drive your withdrawal strategy, how blindly following a set order can lead to higher taxes, and why taxable accounts might be more valuable later in retirement than these so-called experts admit. And I’m sure they took a few well-earned jabs at the deceptive ways financial content is being turned into a giant ad machine. I’ll be back next week, but in the meantime, Chris and Jake are more than capable of keeping things straight—though, let’s be honest, the episode is probably missing at least one good rant from me, plus a few mispronounced words, incorrect names, and deep rabbit holes that make Chris sigh in exasperation! The post Setting the Record Straight on Clickbait vs Reality: EDU #2510 appeared first on The Retirement and IRA Show .

Mar 1

Jim and Chris sit down to discuss listener questions relating to Social Security, 529 plans, Fun Vision, and Annuities. (Intro – 12:00) Chris provides a Social Security PSA. (19:00) A listener wonders whether her husbands Social Security benefits have been getting a COLA since his passing or if they’ve been frozen. (26:00) A listener wonders if missed payment history from the 1980’s can be corrected and included when calculating their Social Security benefit. (36:15) A listener asks about other alternative investment options for his 529 plans depending on the future of his daughters education needs. (50:45) A listener wonders what the difference is between Fun Vision and the Fun Number. (1:03:30) George looks for advice on taking his 401(k) as an annuity versus a SPIA down the line. The post Social Security, 529 Plans, Fun Vision, and Annuities: Q&A #2509 appeared first on The Retirement and IRA Show .

Feb 26

Chris’s Concise Summary: Jim and Chris examine a recent Suze Orman article on inherited IRA rules, identifying key errors that could mislead readers. They clarify the nuances of the 10-year rule, explain how the required beginning date determines whether annual RMDs are necessary and why Roth IRAs don’t have required minimum distributions. The guys also emphasize the importance of verifying financial information before making decisions. A note to listeners: Regular listeners know that Jim is always looking for ways to improve. The podcast is no exception, so some changes are coming in the EDU episode descriptions! In this space, between the usual basic summary (now called Chris’s Summary ) and the new, more detailed, Jim’s Summary, you’ll soon find links to related articles, documents, and other resources that Jim and Chris believe may be useful or interesting to listeners. Jim’s “Pithy” Summary : The guys take a critical look at a recent Suze Orman article discussing inherited IRA rule changes for 2025, identifying inaccuracies that could mislead readers navigating these complex rules. One key issue they highlight is the claim that all inherited IRAs, including Roth IRAs, require annual RMDs under the 10-year rule. Jim and Chris explain why this is incorrect and clarify that the rules depend on whether the original account owner had reached their required beginning date before passing away. They break down how the “at least as rapidly” (ALAR) rule applies to inherited accounts when RMDs were already in progress, ensuring listeners understand the distinctions that many articles fail to address. The conversation also dives into Roth IRAs, reinforcing that they do not have required minimum distributions during the original owner’s lifetime, which means beneficiaries are not required to take annual distributions. Instead, most non-spouse Roth IRA beneficiaries can allow the funds to grow tax-free and withdraw the full balance in the 10th year. Chris and Jim stress that financial publications often oversimplify these rules, leading to confusion and potential missteps for individuals managing inherited accounts. In addition to dissecting the article’s errors, the guys discuss broader issues with financial media, including the need for thorough fact-checking and the risks of relying on clickbait-style headlines for retirement planning guidance. They express concerns that many widely shared articles fail to provide the necessary nuance, which could result in readers making uninformed decisions. Beyond the technical discussion, Jim and Chris also touch on upcoming podcast plans, including a potential follow-up episode covering a “Moneywise” article that Jim believes may be misleading in its own way. With Jim’s upcoming travel, they discuss the logistics of recording, including the possibility of Jake stepping in for an episode to analyze the “Moneywise” piece. The post False Facts and Real Consequences: EDU #2509 appeared first on The Retirement and IRA Show .

Feb 22

While Jim is attending a conference, Chris is joined by Jake to discuss listener questions relating to Social Security benefits, RMD taxes, IRMAA, and taxability considerations for claiming Social Security. (5:00) Georgette asks whether her survivor benefit will be reduced since her husband passed away at age 71. (13:30) The guys address whether claiming early on a work record reduces a spousal benefit or if the child-in-care provision prevents the reduction. (22:15) An email comment corrects a hint given on a previous episode regarding NFL team names. (26:30) A listener questions whether Chris overlooked the Qualifying Widower status in a previous Q&A episode answer. (35:00) Chris and Jake respond to a listener asking whether taxes on a December RMD must be paid immediately or with the next estimated payment. (44:30) George, who pays IRMAA due to a large Roth conversion, wonders if there’s a way to avoid it without qualifying under the listed exceptions on the SSA-44 form. (53:45) A listener considers whether changes in Social Security taxation at the state and federal levels should influence their decision on when to start benefits. The post Social Security Benefits, RMD Taxes, IRMAA, and Social Security Taxation: Q&A #2508 appeared first on The Retirement and IRA Show .

Feb 19

Chris flies solo for this long promised, very special, EDU episode where he describes our retirement planning philosophy and approach in just 30 minutes. The post Our Retirement Planning Philosophy and Approach, Condensed Version: EDU #2508 appeared first on The Retirement and IRA Show .

Feb 15

Jim and Chris discuss listener questions relating to Social Security benefits, IRMAA, IRA distributions, Roth contributions, catch-up contributions, and inherited IRA RMDs. (6:30) George asks how inflation adjustments apply when a reduced Social Security benefit converts to a spousal benefit. (13:45) The guys address whether the end of non-qualified deferred compensation qualifies as a life-changing event for IRMAA purposes. (22:00) Jim and Chris discuss whether taking IRA distributions in a lump sum or spreading them out over time is the better approach for someone retiring at 63. (35:45) A listener explores the idea of making an intentional excess Roth contribution then reevaluating their options before the extended tax filing deadline. (54:45) The guys clarify the defined contribution limit and how catch-up contributions affect the total amount allowed. (58:00) Jim and Chris answer whether RMDs on a recently inherited IRA must begin in 2025 or if the clock starts in 2026. The post Social Security, IRMAA, IRA Distributions, Roth Contributions, Catch-up Contributions, and Inherited IRA RMDs: Q&A #2507 appeared first on The Retirement and IRA Show .

Feb 12

In this EDU episode Jim and Chris review and discuss an article sent in by a listener after their critique of the safe withdrawal rate approach to retirement. Some of the points made in the article should sound familiar to listeners… Nobel laureates William F. Sharpe and Robert C. Merton argue that traditional retirement withdrawal strategies, like the 4% rule, fail to adequately balance investment risk with income certainty. The laureates highlight the inefficiencies of relying on volatile investment portfolios to fund fixed expenses, proposing instead that retirees match investments to specific future expenditures through strategies like Sharpe’s “lock-box” method or Merton’s tiered income approach. Ultimately, they advocate for securing a base level of guaranteed income, embracing flexible spending, and recognizing that higher returns always come with higher risk. Show Notes: How do Nobel Laureates Approach Retirement ? The post A Smart Approach to Retirement: EDU #2507 appeared first on The Retirement and IRA Show .

Feb 8

Jim and Chris discuss listener questions relating to Survivor Benefits, Social Security Disability Insurance, and Donor Advised Funds. Before diving into listener questions, Jim shares insights from his recent trip to an industry conference, where he investigated financial planning software options that might align with their Secure Retirement Income Process and Fun Number . The guys also discuss the challenges of retirement projections and why existing tools often fall short. (29:00) The guys address a question about whether someone can claim six months of retroactive Social Security benefits before switching to a survivor benefit if their spouse passes away. (42:30) A listener wonders if their mother-in-law may have permanently reduced her Social Security benefit after being advised to file while waiting for SSDI approval. (53:30) George asks if his children can establish their own Donor Advised Fund (DAF) to receive Qualified Charitable Donations (QCDs) from his IRA after his death, avoiding federal income tax. The post Survivor Benefits, Social Security Disability, and Donor Advised Funds: Q&A #2506 appeared first on The Retirement and IRA Show .

Feb 5

While Jim is at a conference, Jake joins Chris to discuss a listener’s simplified retirement planning approach. They examine their straightforward strategy, focusing on key points like living within your means, how finances often simplify in the mid-70s after covering the Minimum Dignity Floor , and the impact of passing the delay period for larger withdrawals. They also consider potential risks, such as inflation and interest rates, in this type of allocation. The post A Discussion on Simplified Retirement Planning: EDU #2506 appeared first on The Retirement and IRA Show .

Feb 1

Jim and Chris discuss listener questions relating to Social Security, QLACs, TIPS ETFs, and buffered ETFs. (9:00) A listener who worked in Australia in the late 1980s asks how the U.S.-Australia Totalization Agreement might affect their Social Security benefits. Jim and Chris discuss whether their earnings record can be adjusted and what steps to take. (16:00) The guys respond to a listener with a sizable public pension who is considering claiming Social Security at 62 and investing the funds. They analyze the strategy and explain why delaying benefits is often the better choice for protecting the Minimum Dignity Floor . (47:30) Jim and Chris address a question about QLACs and IRA valuations: Should the end-of-year fair market value of a QLAC inside an IRA be included when calculating the total IRA balance for pro-rata basis conversion purposes? (58:15) George asks about TIPS ETFs—if phantom income from inflation adjustments isn’t reinvested, does that diminish or eliminate inflation protection? (1:07:30) A listener nearing retirement lays out their funding strategy for a 5.5-year delay period and beyond. Jim and Chris share their thoughts on the approach and the role of buffered ETFs. Show Notes: Article discussed in Question 2 The post Social Security, QLACs, and ETFs: Q&A #2505 appeared first on The Retirement and IRA Show .

Jan 29

Jim, Chris, and Jake share their thoughts on a recent Morningstar study that lowers the industry-standard safe withdrawal rate to 3.7%. They review a MarketWatch article discussing the study, highlighting points of agreement and disagreement. Throughout the conversation, they explore their approach to retirement planning, including the Minimum Dignity Floor , See-Through Portfolio , and Fun Number concepts, comparing these to the safe withdrawal rate and Monte Carlo methods for determining retirement spending. Show Notes: Read in MarketWatch Watch the video from Morningstar The post Safe Withdrawal Rate: EDU #2505 appeared first on The Retirement and IRA Show .

Jan 25

Jim and Chris discuss listener questions relating to Medicare enrollment, Social Security benefits, and estate taxes. (6:00) George asks about Medicare’s special enrollment period and the impact of large Roth conversions on IRMAA thresholds after retirement. (18:30) A listener wonders about the impact of the Social Security (Un)Fairness Act on spousal and survivor benefits eligibility. (23:00) The guys weigh in on a question about eligibility for survivor benefits after delaying Social Security to age 70. (28:30) Jim and Chris address concerns about strategies to mitigate estate taxes, including the use of Qualified Charitable Distributions (QCDs) and trusts. The post Medicare Enrollment, Social Security, and Estate Taxes: Q&A #2504 appeared first on The Retirement and IRA Show .

Jan 22

Jim, Chris, and guest Paul Neiffer, CPA, continue their discussion on Charitable Remainder Trusts. They also answer listener questions related to CRTs, CRATs and CRUTs. The post Charitable Remainder Trusts Part 2: EDU #2504 appeared first on The Retirement and IRA Show .

Jan 18

Jim, Chris, and Jake sit down to discuss listener questions relating to contributions, Social Security, 415 limits, and beneficiaries. PSA: Chris and Jake review several questions from this weeks EDU show relating to 415 limits, new age 60-63 “super” catch-up contributions effective under SECURE 2.0. (10:30) A listener looks for clarification on his wife’s spousal Social Security benefit. (13:30) George provides some additional thoughts surrounding 415 limits and maxing out 401k contributions. (23:00) PSA to clarify the question from last week’s Q&A Show regarding a person who inherited an IRA directly from his mom as a primary beneficiary, and a different IRA from his mother as a successor beneficiary. They dive deeper into the difference between a primary and successor beneficiary when inheriting an IRA. (51:45) Georgette looks for some additional information on Social Security issues surrounding widowhood. (1:01:00) A listener wonders what happens when the market is closed on a day that someone passes away and how to value the security on that given day when it’s inherited. The post Contributions, Social Security, 415 Limits, and Beneficiaries: Q&A #2503 appeared first on The Retirement and IRA Show .

Jan 15

Chris and Jake discuss the new “Super-Catchup” retirement plan contributions , explaining who qualifies and how they work. The post “Super-Catchup” Retirement Plan Contributions: EDU #2503 appeared first on The Retirement and IRA Show .

Jan 11

Jim and Chris sit down to discuss Social Security, inherited Roth IRAs, an inherited IRA RMD case, and reporting Roth withdrawals. (12:45) The guys answer a question about earning enough Social Security credits while working overseas and how this impacts Medicare eligibility and spousal benefits. (22:45) Georgette asks whether taking a Child-in-Care benefit now will allow her to switch to a higher survivor benefit later. (33:00) A listener wonders if a trust can preserve the tax-free growth of an inherited Roth IRA beyond the 10-year withdrawal rule. (46:15) Jim and Chris talk about a very confusing inherited IRA RMD case they are working on. (1:12:00) George seeks advice on reporting Roth IRA withdrawals after a Roth conversion and dealing with AGI changes when filing taxes. The post Social Security, Inherited Roth IRAs, Inherited IRA RMDs, and Roth Withdrawals: Q&A #2502 appeared first on The Retirement and IRA Show .

Jan 8

In this EDU dialogue show, Jim and Chris are joined by Jake to explore listener questions about Social Security, income annuities, strategies for deploying dollars in retirement, and other Retirement Planning related topics. Mentioned JP Morgan Article The post Retirement Planning Dialogue: EDU #2502 appeared first on The Retirement and IRA Show .

Jan 4

Jim and Chris discuss listener questions relating to Social Security spousal benefits, IRMAA planning, step-up in basis rules, family maximums, IRA beneficiaries, and factoring inheritances into retirement planning. (12:00) George asks how his wife’s spousal Social Security benefit will be calculated, specifically regarding COLA increases to his PIA and his delayed filing at age 70. (20:30) A listener inquires about minimizing IRMAA surcharges following Roth conversions by using form SSA-44 to waive the surcharge for consecutive years. (31:15) In a PSA, Jim and Chris clarify a mistake from a previous episode regarding the IRS definition of fair market value (FMV) for determining the stepped-up basis of inherited stocks. (38:15) A listener seeks clarification on Social Security family maximum benefits and how spousal and child benefits are calculated when the family’s total benefits change over time. (43:00) George asks for advice on naming IRA beneficiaries, including per stirpes designations, contingent options, and considerations for blended families and remarriages. (1:08:30) The guys discuss how to factor potential inheritances into retirement planning, particularly when the timeline and asset usage remain uncertain. The post Spousal Benefits, IRMAA, Step-Up Basis, Family Maximums, Beneficiaries, and Inheritances: Q&A #2501 appeared first on The Retirement and IRA Show .