Chris’s Summary

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:

The post Social Security Claiming Strategies: EDU #2543 appeared first on The Retirement and IRA Show.

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

The post Spousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542 appeared first on The Retirement and IRA Show.

To skip over Jim and Chris chatting about the government shutdown delaying Social Security and Medicare announcements, and Jim’s upcoming travel plans—including concerns about flight delays and his upcoming elk hunt in Utah you can skip ahead to (8:15).

Chris’s Summary
Jim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth conversions and employer plan transfers. We explain the differences between direct and indirect rollovers, how constructive receipt is determined, and when a spousal rollover might cause unexpected tax penalties. We also outline when 60-day rollovers can still be useful, especially with maturing MYGAs, and share practical tips to avoid triggering unexpected distributions.

Jim’s “Pithy” Summary
Chris and I cover IRA rollover mistakes—especially the ones that crop up with 60‑day rollovers. We’re talking the kind of errors that can cost you taxes, penalties, and your sanity. This all started with some emails about the 60‑day rollover strategy for Roth conversions, but it quickly turned into a full‑blown EDU on how rollovers go sideways—fast.

We explain the difference between a direct and indirect rollover (hint: if you’re frolicking in dollar bills on your living room floor, it’s indirect), why you can’t do more than one IRA‑to‑IRA rollover per 365 days, and how the IRS finally shut down the old rollover shuffle thanks to the poor guy in the Bobrow case—who won one fight and lost the big one in the same ruling.

Then we take it further. Surviving spouses? You’ve got options. But if you’re under 59½ and roll inherited IRA money into your own account too soon, you just triggered the 10% penalty. Only a spouse can do that kind of rollover, by the way. Chris and I get into a whole scenario with a dead husband, a widow, and a girlfriend who didn’t get the memo on common‑law marriage. No joke.

And if you’re sitting on a MYGA in an IRA, you better pay attention when that thing matures. Insurance companies love to auto‑renew on day 31, and we explain how a 60‑day rollover can give you breathing room—if you haven’t already used your one for the year. Our go‑to move with IRA‑based MYGAs? You guessed it: the 60‑day rollover. Just don’t mess it up or you’ll blow your chance at penalty‑free flexibility—and that includes protecting your Minimum Dignity Floor.

The post IRA Rollover Mistakes and Exceptions: EDU #2542 appeared first on The Retirement and IRA Show.

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

The post Social Security, HSA Held Annuities, IRA Annuities: Q&A #2541 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I are joined by Rear Admiral Brian Luther to discuss veterans benefits and military retirement planning. We explore how Navy Mutual supports service members, examine the survivor benefit plan, and talk about the role of annuities in managing longevity risk. Rear Admiral Luther also shares insights on TRICARE, VA health care, and the importance of financial literacy throughout a military career.

Jim’s “Pithy” Summary:
Chris (“Cowboy”) and I (“Bugs”) are thrilled to welcome Rear Admiral Brian Luther—better known on this episode as “Lex”—to discuss veterans benefits, military retirement planning, and the mission of Navy Mutual. Lex brings an incredible background to the conversation: he served as a naval aviator, commanded the George H.W. Bush on its maiden deployment, and ultimately became the budget officer of the entire U.S. Navy. Now, as CEO of Navy Mutual, he’s focused on protecting military families and promoting financial literacy—something that became personal to him after being sold a lousy product early in his career. That bad experience stuck with him, and it shows in how Navy Mutual approaches everything.

This episode covers a lot. We talk about how Navy Mutual came to be, the long-standing military tradition behind it, and how it provides life insurance and annuities without the exclusions and fees often found in commercial products. Lex gives a clear rundown of the Survivor Benefit Plan (SBP), how remarriage impacts SBP eligibility, and why spousal protection is so important. He also introduces their “RETIRE” acronym—risk, education, taxes, investment, retirement, and estate planning—and how those areas guide service members through their financial journey.

We explore how military retirees can use VA health care and how that fits—or doesn’t—with Medicare, TRICARE, and travel needs. Lex explains how Navy Mutual separates education from sales, offers no-commission policy reviews, and discloses actual embedded interest rates in their annuities—something almost no one else does. He also shares how annuities can be used as a risk-transfer tool to manage longevity and support retirement dignity, especially when paired with secure income sources like pensions and Social Security.

The post Military Retirement Planning: EDU #2541 appeared first on The Retirement and IRA Show.

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

The post Social Security, Roth Conversions, RMD Calculations: Q&A #2540 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I return for an EDU dialogue episode focused on a listener’s delay period strategy. His plan includes laddered CDs, equity ETFs, delayed Social Security, and Roth conversions. We use his plan to discuss bracket drift, spending liquidity, and how rising markets can complicate a fixed glidepath. We also cover the tax planning window, crossover risk, and why even strong plans need regular adjustments—especially when they rely on assumptions that may not hold up year to year.

Jim’s “Pithy” Summary
Chris and I are back with an EDU dialogue show, and this one is a deep dive inspired by a listener who shared what he calls a simple delay period strategy. Honestly, I like a lot of it. He’s got a plan. He’s doing Roth conversions, delaying Social Security—all good stuff. He’s even laddered out CDs to fund his Minimum Dignity Floor and his Go-Go fun. That’s great—until you read the line that made me pause: “when the markets rise.” Not “if the markets rise.”

And what if they don’t rise? What if your equity side’s down and your CDs aren’t enough? Now you’re spending from equities when you didn’t want to. Suddenly, the conversion you were planning that year? You can’t do it as planned without jumping to a higher bracket.  So, do you cut back on spending or on your planned conversion? That’s how these things fall apart.

He’s got structure, he’s got glidepaths, he’s even adjusting the ladder year by year. But don’t assume growth will keep bailing you out. If you do and markets stall, your whole glidepath strategy starts to crack. And as Jacob and I just talked about at lunch—Go-Go money is tough. You don’t know if someone’s going to call and ask for money for a dream vacation or a home remodel and we’ve got to build with that in mind. We also explain why I call it spending liquidity. Liquidity isn’t enough. You need cash you can actually spend without penalties, volatility, or surprise taxes. That’s what makes this kind of planning work.

The post Delay Period Strategy: EDU #2540 appeared first on The Retirement and IRA Show.

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

The post Social Security, 60-Day Rollover, Inherited IRA, and Deferred Income Annuity: Q&A #2539 appeared first on The Retirement and IRA Show.

This week, with Jim away at a conference, Chris is joined by Jake for an EDU episode that takes the shape of a Q&A, focusing on tax planning strategies. The guys cover a series of emails that highlight how different tax rules and opportunities intersect with retirement planning, income management, and financial decisions.

(10:30), the first question explores how the new OBBB changes—particularly the $40,000 SALT deduction and $6,000 senior deduction—are affecting Roth conversion strategies. Chris and Jake break down who might benefit from larger conversions, who may want to scale back, and how the extension of lower tax brackets plays into long-term planning.

(26:45), a listener with high health care costs asks what qualifies for deduction, how the 7.5% AGI threshold works, and whether items like chiropractor visits and insurance premiums count. The guys walk through the rules, the limits, and which expenses can make a difference.

(39:00), the third question looks at the backdoor Roth. A “long-lost” 401(k) rolled into an IRA raises concerns about the pro rata rule and whether it threatens the clean execution of annual conversions. The guys explain how to handle the rollover and keep the strategy on track.

(49:45), tax-loss harvesting and the wash sale rule take center stage. The listener wants to know how dividend reinvestments across different accounts might complicate reporting and whether timing strategies can keep things clean. Chris and Jake lay out how the rule works and what to watch for.

(1:02:45), a self-employed listener asks if funding a solo 401(k) before converting to Roth could save self-employment tax. The guys explain the mechanics, the limits on employer contributions, and the modest but real savings this tactic may offer.

The post Tax Planning Strategies: EDU #2539 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions on IRMAA reductions and Roth-conversion effects, widow filing status and IRMAA, in-kind stock Roth conversions and RMD transfers, annuity RMD interactions, and 60-day rollover mail timing.

(7:45) George asks whether an approved SSA Form 44 that reduced 2025 IRMAA will also govern next year, how a large 2026 Roth conversion will be trued up and affect future IRMAA brackets, and whether that conversion will cause higher IRMAA in multiple subsequent years.

(18:45) A listener wonders if a recently widowed spouse’s IRMAA in 2026 will reflect single status or remain based on the 2024 joint tax return.

(24:45) The guys ask whether in-kind stock Roth conversions change the stock’s tax basis inside a Roth and whether an in-kind RMD transfer to a brokerage establishes a stepped-up basis.

(49:45) Jim and Chris consider a hypothetical where an IRA annuity’s annual payout might be less than the RMD and what happens if the RMD exceeds the annuity payment.

(1:02:15) One listener argues that claiming a mailed check took longer than 60 days to arrive is implausible because USPS optical scans and Informed Delivery images could let the IRS verify delivery dates.

The post IRMAA, Widow Status, Roth Conversions, Annuity RMDs, and Rollovers: Q&A #2538 appeared first on The Retirement and IRA Show.