The Retirement and IRA Show

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

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

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

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

Listeners dive into the intricacies of spousal Roth IRA contributions even after retirement. They explore the benefits of switching from a SEP IRA to a solo 401k for backdoor Roth opportunities. Timing for claiming Social Security at 62 comes under scrutiny, especially for those with sufficient pensions. The discussion covers post-tax contributions to IRAs and 401ks, and how HSA withdrawals can be strategically used to maximize Roth conversions. Essential strategies for smarter tax planning are revealed throughout the dialogue.

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 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 rollovers can still be useful, especially with maturing MYGAs, and share practical tips to avoid triggering unexpected distributions. Jim’s “Pithy” SummaryChris 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.

Dive into a listener's intriguing delay period strategy, blending laddered CDs, equity ETFs, and delayed Social Security. Discover the importance of spending liquidity and how market conditions could impact planned withdrawals. The hosts discuss the dangers of reliance on market growth and why continuous adjustments are crucial. They also highlight the crossover risk with Social Security and advocate for regular monitoring of Roth conversions. A solid plan can falter without flexibility, especially in unpredictable markets!