With Jim is away at a conference, Chris is joined by Jake to discuss listener questions on Social Security survivor benefits, and Roth conversion strategies. (6:30) A listener asks how a widow can maximize her Social Security benefit when her late husband had not yet claimed his. (14:15) George seeks guidance on figuring out if […]

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Chris’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 […]

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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 […]

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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 […]

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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 […]

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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™, […]

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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 […]

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

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 […]

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