Shows
The Retirement and IRA ShowSocial Security, IRMAA, Disclaiming Inheritances, Roth Conversions: Q&A #2609Jim and Chris discuss listener emails on Social Security survivor benefits, IRMAA relief and the SSA-44 process, the Social Security earnings test, disclaiming inheritances that are brokerage accounts, and Roth conversion rules for retirees.
(6:00) A listener asks whether his wife’s early Social Security claim at 62 would reduce the survivor benefit she’d receive upon his death.
(14:00) George asks several questions stemming from a successful SSA-44 IRMAA relief request, including whether a retroactive refund is due, whether Step 3 covers the following year, and whether a separate filing is needed for his own income reduction.
(2...
2026-02-2848 minThe Retirement and IRA ShowFisher’s 99 Retirement Tips: EDU # 2608Chris’s SummaryJim and I review Fisher Investments’ 99 Retirement Tips and begin working through the list, covering only a handful in this episode. We discuss estate planning basics such as having a will, the importance of reviewing estate documents, and considering living wills and trusts, with emphasis on incapacity planning. We then examine longevity statistics, why life expectancy at birth is often misapplied, and how that connects to retirement income decisions, including Fisher’s warning on annuities.
Jim’s “Pithy” SummaryChris and I start digging into Fisher Investments’ 99 Retirement Tips and, true to form, we only...
2026-02-251h 39The Retirement and IRA ShowTax Special – Conversions, Contributions, HSAs, Tax Returns, Tax Software PSA: Q&A #2608Jim and Chris are joined by Jake Turner to discuss listener emails in this special tax related episode covering Roth conversions after RMD age, balancing Roth versus Traditional IRA contributions, HSA versus Roth contributions, IRA reporting questions, filing deceased tax returns, and a listener PSA on tax planning software.
(11:30) A listener asks whether converting to a Roth makes sense at age 75 while currently in the 12% bracket and taking RMDs, and whether recent tax law changes create a strategy opportunity.
(20:20) George wonders whether his 30-something children should continue using Roth contributions exclusively or begin balancing with...
2026-02-211h 21The Retirement and IRA ShowUsing Buffered ETFs: EDU #2607If you would rather not listen to the guys’ banter about Jacob’s upcoming move to Iowa, Jim’s garden planning, and a listener correction about the word “imbibe” you can skip ahead to (33:30).
Chris’s SummaryJim and I are joined by Jacob Vonloh as we discuss using Buffered ETFs prompted by a Morningstar article titled “Buffer ETFs Are Not for Everyone.” We explain how defined outcome ETFs use options to provide an explicit amount of loss protection over a given period while limiting potential gains, and we outline why these products are generally suboptimal for long-term in...
2026-02-181h 18The Retirement and IRA ShowMedicare, Social Security, Inherited Roth, Annuities: Q&A #2607Jim and Chris discuss listener emails on Medicare Part B decisions for retirees abroad, Social Security survivor benefit surprises, inherited Roth IRA distribution rules, and balancing Treasuries versus annuities when “safety” is more emotional than mathematical.
(6:45) A listener asks about situations where it might make sense to skip Medicare Part B, including retirees living abroad with strong foreign coverage and people who move to the U.S. later in life and must pay for Parts A and B.
(33:30) George asks why some widows and widowers don’t end up receiving the full benefit their...
2026-02-141h 25The Retirement and IRA ShowCash Balance Plans Part 2: EDU #2606Chris’s SummaryJim and I are joined by Steve Sansone as we revisit Cash Balance Plans and respond to listener follow-up emails.
(8:30) A CPA asks whether cash balance plans could be a fit for farmers with high income near retirement driven by deferred grain and equipment sales.(18:30) A listener with two controlled-group businesses asks how a cash balance plan works with divergent profit cycles, whether it can support succession planning, and whether it makes sense if ownership works until death.(36:45) A financial advisor asks for real-world details on costs, duplication/administration, duration, interest cr...
2026-02-111h 27The Retirement and IRA ShowIRMAA, Early Withdrawal Penalty, 403b Distributions: Q&A #2606Jim and Chris discuss listener emails on IRMAA appeals using Form SSA-44, avoiding the 10% early withdrawal penalty, and whether a 403(b) distribution can be rolled into an IRA. Jim also manages to turn a discussion on Superbowl food to a conversation on retirement planning for the Go-Go phase of life (with a few other stops in between). So, if you typically skip the banter you may want to tune in around (10:10) for that discussion.
(16:30) George shares his experience repeatedly filing Form SSA-44 to correct IRMAA determinations and explains how Social Security processed and applied his updated income...
2026-02-071h 27The Retirement and IRA ShowRetirement Spending Anxiety: EDU #2605Chris’s SummaryJim and I discuss spending anxiety in retirement using a Washington Post article written by a personal finance columnist describing her fear of spending after her husband retires. We look at why the shift from saving to spending can feel destabilizing even when pensions and Social Security are in place, and why fear can persist despite adequate planning. We also address the difference between spending income and spending savings, and how that distinction often affects behavior once retirement begins.
Jim’s “Pithy” SummaryChris and I use a Washington Post article as a jumpin...
2026-02-041h 14The Retirement and IRA ShowSocial Security, SPIAs, SEPP 72(t): Q&A #2605Jim and Chris discuss listener emails on Social Security timing for HSA contributions, investing in a SPIA vs buffered ETFs, and using SEPP 72(t) income to manage ACA credits.(7:00) A listener describes delaying a Social Security filing to avoid Medicare Part A backdating that would have reduced prior-year HSA contributions, while still receiving full retroactive benefits.(28:00) Georgette asks what to do with money originally set aside for a condo purchase, weighing ETFs against buying a single premium immediate annuity (SPIA), given an existing fixed indexed annuity (FIA), and pension income that cover living expenses.(55:45) The guys...
2026-01-311h 36The Retirement and IRA ShowAsset Positioning for Retirees: EDU #2604If you’d like to skip over the guys chatting about cold weather and football you can to (8:15).
Chris’s SummaryJim and I are joined by Jacob as we continue our discussion on asset positioning and explain how we approach managing investment assets within a distribution portfolio. We outline why dollars are assigned based on purpose and timing and how asset positioning functions as a form of asset-liability matching. The episode addresses cash versus cash-like roles, outcome periods, and how specific tools are evaluated within a broader distribution-focused framework.
Jim’s “Pithy” Summary
Chri...
2026-01-281h 10The Retirement and IRA ShowSocial Security, ERISA, LTC: Q&A #2604Jim and Chris discuss listener emails on Social Security survivor benefits and the earnings test, share a listener PSA on Social Security timing and IRMAA, then cover ERISA protections for retirement rollovers and a PSA from Greg on lifetime unlimited long-term care policies.(9:45) Georgette asks whether she must still take her husband’s required minimum distributions if he passes during his RMD year and how Social Security survivor benefits work, including whether she should claim a widow’s benefit or wait to take her own.(50:45) A listener asks how the Social Security earnings test applies when someone reti...
2026-01-241h 21The Retirement and IRA ShowInvesting for Retirees: EDU #2603If you want to miss all the fun banter about Jim’s Singo (song bingo) night and his trip to Kentucky and Amish country you can skip ahead to (16:00).
Chris’s SummaryJim and I are joined by Jacob Vonloh as we discuss investing for retirees, using a listener email as the starting point for a broader conversation about how investment advice and asset management work in practice. We explain why investing changes once people move from accumulation into distribution, including differences in risk tolerance, liquidity needs, and volatility. Jacob outlines how investment tools are evaluated base...
2026-01-211h 36The Retirement and IRA ShowSocial Security, HSA, and Annuities: Q&A #2603Jim and Chris discuss listener questions on Social Security survivor benefits and divorce rules, a listener PSA on spousal benefits, HSA contribution limits, and whether annuities make sense versus Treasury bonds.
(8:45) A listener asks whether someone who is newly widowed can claim survivor Social Security now, keep working part time, and later switch to their own benefit, and also asks whether you still offer a “coffee and second opinion” or an a la carte Social Security review.
(23:00) The guys field a question from someone with two ex-spouses asking if it’s possible to combine their own So...
2026-01-171h 26The Retirement and IRA ShowRoth IRA Mistakes, Part 2: EDU #2602Chris’s SummaryJim and I continue last week’s EDU discussion on Roth IRA mistakes from an Investopedia article. We cover direct versus 60-day rollovers, the one-per-365-day IRA-to-IRA limit, and the 401(k) 20% withholding rule with the RMD and NUA exceptions. We revisit backdoor Roth mechanics and the pro rata rule, then shift to beneficiary designation forms and why naming an estate creates probate and creditor issues. We close with inherited Roth withdrawal timing under SECURE Act rules and the 10-year window.
Jim’s “Pithy” SummaryChris and I pick up where last week’s EDU episod...
2026-01-1459 minThe Retirement and IRA ShowIRMAA, Inherited IRA, LTC, ACA Tax Credits: Q&A #2602Jim and Chris are joined by Jake to discuss listener questions on SSA-44 and IRMAA surcharges, inherited IRA spousal rollover rules, long-term care insurance benefit caps, and ACA tax credits.
(4:45) George asks whether an unexpected W-2 stock option payout in 2025 could support filing SSA-44 to reduce 2027 IRMAA surcharges, especially if he stops consulting income afterward.
(12:00) A listener asks whether SSA-44 can be used retroactively to request a refund of 2025 IRMAA surcharges after a job loss pushed MAGI below the threshold.
(18:15) Georgette asks whether she can take withdrawals from her deceased spouse’s inherited IR...
2026-01-101h 02The Retirement and IRA ShowRoth IRA Mistakes, Part 1: EDU #2601If you want to skip over some weather banter you can go to (14:15).
Chris’s SummaryJim and I review Roth IRA mistakes and walk through key rules on earned income eligibility, income limits, spousal contributions, excess contributions, and qualified distributions. We use an Investopedia article as a framework, clarify how MAGI impacts Roth eligibility, explain the October 15 correction deadline, and break down the two-prong test for tax-free Roth earnings withdrawals, including how the five-year rule is measured across tax years.
Jim’s “Pithy” SummaryChris and I kick off the first EDU show of...
2026-01-071h 11The Retirement and IRA ShowSocial Security, Deemed Military Wages, Estate Planning, QLACs: Q&A #2601Jim and Chris discuss listener emails on Social Security claiming strategies, deemed military wages, and survivor benefits timing, a PSA from Jim and Chris on their New Year’s resolution, and QLAC use for inherited IRAs.
(11:00) A listener asks whether a spouse who will be collecting spousal benefits should ever delay claiming past full retirement age and also asks for retirement drawdown calculator recommendations.
(24:30) George asks how veterans can verify that deemed military wages were credited correctly to their Social Security earnings record.
(36:00) The guys address whether a surviving spouse can keep both So...
2026-01-031h 43The Retirement and IRA ShowNew MYGA Variations: EDU #2553Chris’s SummaryJim and I review new MYGA variations and examine how insurers and product developers are marketing hybrid annuity designs using MYGA language. We walk through four examples from an April 2025 article—“Lockdown,” “Minimum Accumulation Guarantee,” “Extra Extra,” and the “End-of-Term Equity Kicker”—and explain why these products, despite being labeled as MYGAs, rely on index-linked features and do not behave like traditional MYGAs.
Jim’s “Pithy” SummaryChris and I spend this episode talking through an article from earlier this year that highlights where the annuity industry seems to be headed. While not all good or all bad it c...
2025-12-3157 minThe Retirement and IRA ShowSocial Security, IRMAA, ACA Planning, IRA to HSA Transfer, Annuities: Q&A #2552Jim and Chris discuss listener emails on Social Security filing timing and online claiming language, a listener PSA on IRMAA and the online SSA-44, ACA income planning before Medicare, an IRA to HSA transfer, and annuity income needs.
(6:45) The guys address how to word an online Social Security application so the first check is paid for a specific month when claiming at age 70, and whether applying 2–3 months before the 70th birthday is the right approach.
(14:00) A listener shares a PSA on filing SSA-44 online after retirement, including how IRMAA recalculations reflected estimated future-year income and ho...
2025-12-271h 11The Retirement and IRA ShowCash Balance Plans Explained: EDU #2552Chris’s SummaryJim and I are joined by Steve Sansone as we discuss cash balance plans and explain how they function as hybrid defined benefit plans that present as account-based arrangements. We cover who these plans are designed for, including high-income business owners and professional groups, how age and employee demographics affect feasibility, and why allowable contribution levels can far exceed defined contribution limits. We also outline nondiscrimination rules and how they are applied, employer commitment requirements, and other general setup considerations.
Jim’s “Pithy” SummaryChris and I are joined by Steve Sansone as we ta...
2025-12-241h 14The Retirement and IRA ShowSocial Security, RMDs, Money Market Earnings, QLACs: Q&A #2551Jim 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...
2025-12-201h 26The Retirement and IRA ShowMath Act and Automatic IRA ActChris’s SummaryJim and I are joined by Jake Turner as we cover the Math Act and a set of shorter EDU topics Jim has been collecting. We start with an SSA-44 update, including listener and client feedback on submitting the IRMAA redetermination form online through an SSA.gov account. Jake explains how IRS “math error” notices work today, why they’re often vague, and what the new law requires for clearer explanations and response deadlines. Jim then walks through the Automatic IRA Act’s proposals, including an annuity-style “protected lifetime income solution” requirement over certain balances, and we close w...
2025-12-171h 04The Retirement and IRA ShowIRMAA, Social Security, QLACs, Roth Conversions: Q&A #2550Jim 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 retu...
2025-12-131h 31The Retirement and IRA ShowThe Importance of Secure Income for Retirement: EDU #2550Chris’s SummaryJim 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” SummaryChris 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...
2025-12-101h 19The Retirement and IRA ShowSocial Security, IRMAA, Medicare, Roth Contribution Rules, Roth Conversions: Q&A #2549Jim 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...
2025-12-061h 24The Retirement and IRA ShowThe QLAC 1098-Q: EDU #2549Chris’s SummaryJim 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” SummaryChris and I use the QLAC 1098-Q as a way to show how the IRS keeps tabs on your QLA...
2025-12-031h 15The Retirement and IRA ShowIRMAA Brackets and QLACs: Q&A #2548Jim 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...
2025-11-291h 20The Retirement and IRA ShowQLAC Use Cases and Planning: EDU #2548Chris’s SummaryJim 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” SummaryChris and I take a deeper dive into QLACs by taking what we talked about la...
2025-11-261h 12The Retirement and IRA ShowSocial Security, IRMAA, ETFs, Private Investments: Q&A #2547Jim 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 IRM...
2025-11-221h 23The Retirement and IRA ShowQLAC Rules and Uses: EDU #2547If 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 SummaryJim 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” SummaryChris can’t hide his reaction...
2025-11-191h 31The Retirement and IRA ShowSocial Security,Estate Planning PSA, Annuity Payments: Q&A #2546Jim 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...
2025-11-151h 19The Retirement and IRA Show2026 Social Security Changes: EDU #2546Chris’s SummaryWith 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” SummaryWith 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...
2025-11-1250 minThe Retirement and IRA ShowSocial Security and Roth Conversion Strategies: Q&A #2545With 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...
2025-11-081h 09The Retirement and IRA ShowRetirement Preparedness and Planning Lessons: EDU #2545Chris’s SummaryJim 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 sit...
2025-11-051h 02The Retirement and IRA ShowSocial Security, IRMAA Taxation, 529 Rollover, Deferred Annuities: Q&A #2544Jim 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...
2025-11-011h 34The Retirement and IRA ShowSocial Security Claiming Strategies, Part 2: EDU #2544If 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 SummaryJim 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 mathemat...
2025-10-291h 21The Retirement and IRA ShowHSA Contributions, Social Security, Fee Disclosures, TSPs: Q&A #2543Jim 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...
2025-10-251h 14The Retirement and IRA ShowSocial Security Claiming Strategies, Part 1: EDU #2543Chris’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” SummaryChris and I walk through the disagreement between Professor Tharp and Professor Kotlikoff on Social Security claiming strategies. These are incredibly smart guys, and I respec...
2025-10-221h 11The Retirement and IRA ShowSpousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542Jim 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 So...
2025-10-181h 15The Retirement and IRA ShowIRA Rollover Mistakes and Exceptions: EDU #2542To 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 SummaryJim 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 rollov...
2025-10-151h 20The Retirement and IRA ShowSocial Security, HSA Held Annuities, IRA Annuities: Q&A #2541Jim 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...
2025-10-111h 22The Retirement and IRA ShowMilitary Retirement Planning: EDU #2541Chris’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...
2025-10-081h 13The Retirement and IRA ShowSocial Security, Roth Conversions, RMD Calculations: Q&A #2540Jim 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...
2025-10-041h 20The Retirement and IRA ShowDelay Period Strategy: EDU #2540Chris’s SummaryJim 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” SummaryChris and I are back with an EDU dialogue sho...
2025-10-011h 09The Retirement and IRA ShowSocial Security, 60-Day Rollover, Inherited IRA, and Deferred Income Annuity: Q&A #2539Jim 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...
2025-09-271h 47The Retirement and IRA ShowTax Planning Strategies: EDU #2539This 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 lowe...
2025-09-241h 18The Retirement and IRA ShowIRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538Jim 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 re...
2025-09-201h 15The Retirement and IRA ShowDiscussing An Article On Retirement Planning: EDU #2538If 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 ch...
2025-09-171h 11The Retirement and IRA ShowSocial Security, Account Consolidation, and MYGA Selection: Q&A #2537Jim 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 ad...
2025-09-131h 35The Retirement and IRA ShowPlanning for Taxes in Retirement: EDU #2537If 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 SummaryI 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, C...
2025-09-101h 01The Retirement and IRA ShowSocial Security, HSA Reimbursements, and MYGAs: Q&A #2536Jim 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, no...
2025-09-061h 09The Retirement and IRA ShowBehavioral Finance in Retirement Planning: EDU #2536Chris’s SummaryJim 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” SummaryChris and I dive into two listener-sent pieces — a Kiplinger’s article and a research report from Blanchett and Finke —...
2025-09-031h 28The Retirement and IRA ShowSocial Security, Risk Philosophy, Fraternal Benefit Societies, Roth Conversions: Q&A #2535Jim 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...
2025-08-301h 27The Retirement and IRA ShowRoth Catch Ups and the 60-Day Rollover Rule: EDU #2535If 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 SummaryJim and I continue working through Ed Slott’s advisor quiz. After introducing the mandatory Roth catch up rule la...
2025-08-271h 22The Retirement and IRA ShowSocial Security, PSA, Annuities, RMD Rules: Q&A #2534Jim 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...
2025-08-231h 33The Retirement and IRA ShowCatch Up Contributions: EDU #2534Chris’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...
2025-08-201h 19The Retirement and IRA ShowSocial Security, Inherited Roth, and IRMAA: Q&A #2533Jim 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 wh...
2025-08-161h 15The Retirement and IRA ShowFunding Discretionary Spending: EDU #2533Chris’s SummaryJim 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” SummaryChris and I pick up where we left off...
2025-08-131h 03The Retirement and IRA ShowSocial Security, Roth Conversions, Annuities, and Rule of 55: Q&A #2532Jim 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...
2025-08-091h 26The Retirement and IRA ShowRetirement Income Versus Savings: EDU #2532Chris’s SummaryJim 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” SummaryChris 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...
2025-08-061h 20The Retirement and IRA ShowOhio, Medicare, Social Security, Roth 401k, and Annuities: Q&A #2531Jim 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 sw...
2025-08-021h 58The Retirement and IRA ShowBuffered ETFs vs Stocks and Cash: EDU #2531Chris’s SummaryJim 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” SummaryChris and I welcom...
2025-07-3051 minThe Retirement and IRA ShowLiving Benefits on Annuities: EDU #2530Chris’s SummaryJim 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” SummaryChris and I finally deliver the long-promised show on annuity living benef...
2025-07-231h 28The Retirement and IRA ShowSocial Security, Annuities, Roth and Roth TSP 5-Year Rule: Q&A # 2528Jim 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...
2025-07-121h 21The Retirement and IRA ShowOBBBA Tax Changes Explained: EDU #2528Chris’s SummaryI 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 techn...
2025-07-091h 16The Retirement and IRA ShowSocial Security, Pension Buyouts, and Managed Payout Funds: Q&A #2527Jim 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 futu...
2025-07-051h 12The Retirement and IRA ShowBroker vs Advisor Sold RILAs: EDU #2527Chris’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—especi...
2025-07-021h 16The Retirement and IRA ShowPSAs, Spousal Benefits, Annuity Use Cases, and FIAs: Q&A #2526Jim 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...
2025-06-281h 29The Retirement and IRA ShowRILAs vs Buffered ETFs: EDU #2526Chris’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 index...
2025-06-2553 minThe Retirement and IRA ShowSocial Security PSAs, FIAs, SPIAs, and MYGAs: Q&A #2525Jim 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...
2025-06-211h 32The Retirement and IRA ShowFixed Indexed Annuities: EDU #2525Chris’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...
2025-06-181h 32The Retirement and IRA ShowSocial Security, HSA Rules, SPIA Funding, and FIA Details: Q&A #2524Jim 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, Ro...
2025-06-141h 21The Retirement and IRA ShowUnderstanding Annuity Types and Features: EDU #2524Chris’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 bet...
2025-06-111h 21The Retirement and IRA ShowBond ETFs, Social Security, 401k Annuities, and Annuitization: Q&A #2523Jim 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...
2025-06-071h 25The Retirement and IRA ShowAnnuities in Retirement Planning: EDU #2523Chris’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 ar...
2025-06-041h 09The Retirement and IRA ShowSocial Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522Jim 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...
2025-05-311h 16The Retirement and IRA ShowFlexible Retirement Spending: EDU #2522Chris’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 simpli...
2025-05-281h 12The Retirement and IRA ShowSocial Security, IRA Basis, and Roth 5-Year Rule: Q&A #2521Jim 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...
2025-05-241h 35The Retirement and IRA ShowSpending Confidently in Retirement with Kevin Sebesta: EDU #2521Chris’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
2025-05-211h 19The Retirement and IRA ShowSocial Security, HSA Strategy, and Cost Basis: Q&A #2520With 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...
2025-05-171h 17The Retirement and IRA ShowExploring the Retirement Mindset with Kevin Sebesta: EDU #2520Chris’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...
2025-05-1457 minThe Retirement and IRA ShowSocial Security, IRMAA, IRA Beneficiary, and the Roth 5-Year Rule: Q&A #2519
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 Trust as IRA beneficiary, discussing both how to complete a beneficiary designation fo...
2025-05-101h 34The Retirement and IRA ShowRetirement Plans for Aging: EDU #2519Chris’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...
2025-05-071h 31The Retirement and IRA ShowIRA Contributions, Special Needs Trusts, Roth Conversions, and Cost Basis: Q&A #2518Jim 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...
2025-05-031h 30The Retirement and IRA ShowTransition Period Strategy Part 3 – A Case Study: EDU #2518Chris’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 position...
2025-04-301h 27The Retirement and IRA ShowSocial Security Benefits, IRMAA, and QCD Timing: Q&A #2517Jim 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...
2025-04-261h 05The Retirement and IRA ShowTransition Period Strategy Part 2 – Positioning and Repositioning: EDU #2517Chris’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...
2025-04-231h 18The Retirement and IRA ShowTax Planning, Minus-One Method, Inherited Roth RMDs, and Early Social Security: Q&A #2516Jim 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 gu...
2025-04-191h 37The Retirement and IRA ShowTransition Period Strategy Part 1 – Asset Positioning: EDU #2516Chris’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 fi...
2025-04-161h 24The Retirement and IRA ShowSocial Security, RMD age, Tax Planning, and Inherited Roth IRAs: Q&A #2515Jim 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...
2025-04-121h 13The Retirement and IRA ShowDefining Unicorn Status in Retirement: EDU #2515Chris’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 p...
2025-04-091h 12The Retirement and IRA ShowSocial Security, Roth Conversion Tax Strategy, and Identity Theft PSA: Q&A #2514This 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 ab...
2025-04-051h 43The Retirement and IRA ShowWeathering Market Downturns: EDU #2514Chris’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. Meanwhi...
2025-04-021h 05The Retirement and IRA ShowIdentity Theft, Spousal Benefits, RMD Taxes, IRA Withdrawals, and 401(k) Contribution Limits: Q&A #2513Jim 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...
2025-03-291h 16The Retirement and IRA ShowRoth 5-Year Rules and the Tax Planning Window: EDU #2513Chris’s SummaryJim 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 59...
2025-03-261h 16The Retirement and IRA ShowSocial Security Benefits, Roth Conversions, and Annuities: Q&A #2512Jim 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...
2025-03-221h 15The Retirement and IRA ShowThings That Make You Go Hmm – RMD Rules, IRA Mistakes, and Tax Court Surprises: EDU #2512Chris’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...
2025-03-191h 09The Retirement and IRA ShowSocial Security records, GPO, QCD Timing, Annuity Costs, and Excess IRA Contributions: Q&A #2511Jim 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 Co...
2025-03-151h 19
Director's ClubEpisode 228: Jeremy Saulnier (feat. Mitchell Beaupre)It's been six weeks since a new episode of the show but this will be worth the wait, given not only the director we're covering but the guest is one of the best film critics working today. Letterboxd's very own Mitchell Beaupre returns after their debut a couple years ago for a nail-biting discussion on one of our premiere action-thriller directors working today. Jeremy Saulnier has a terrific new movie out on Netflix called Rebel Ridge which we review at length in addition to the rest of his filmography. For the first half hour though after the...
2024-09-302h 18
Director's ClubPop Culture Club: Jeremy Saulnier, John Carney, Shelby Sifers!I have one heck of a lineup in store for you. A format that I hope to do more of as the year continues. For this special edition of Pop Culture Club, I talk with two directors and then one musician -- all inspired in different ways but linked via their love of music. For the first interview, I talk with BLUE RUIN director Jeremy Saulnier about his latest foray into genre filmmaking -- this time, he tackles the world of hardcore punk rock combined with a seige picture in the visceral knockout GREEN ROOM. Secondly, I spoke...
2016-04-211h 24