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.

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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.

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.

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.

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

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.

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.

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