Social Security and Roth Conversion Strategies: Q&A #2545
November 8, 2025
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 he and his wife need to do Roth conversions, and, if so, how much....
Listen NowRetirement Preparedness and Planning Lessons: EDU #2545
November 5, 2025
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...
Listen NowSocial Security, IRMAA Taxation, 529 Rollover, Deferred Annuities: Q&A #2544
November 1, 2025
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...
Listen NowSocial Security Claiming Strategies, Part 2: EDU #2544
October 29, 2025
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...
Listen NowHSA Contributions, Social Security, Fee Disclosures, TSPs: Q&A #2543
October 25, 2025
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...
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