Social Security, Transition Planning, Positioning, Roth Conversions, IRMAA: Q&A #2530

July 26, 2025

Social Security, Transition Planning, Positioning, Roth Conversions, IRMAA: Q&A #2530

Chris is joined by Jake and Jacob to answer listener questions on Social Security, followed by a PSA about unexpected Social Security payment timing, then additional questions on transition planning, asset positioning across account types, weighing Roth conversions against the senior deduction, and planning around IRMAA.
(6:15) George asks what percentage of taxes he should have withheld from his 2025 Social Security income if that is his only source of income.
(22:45) A listener PSA describes how their spouse’s first Social Security payment arrived earlier than expected and shares a 40-day approval timeline.
(29:45) Chris and the Jacobs respond to a question about transition planning focused on protecting principal before retirement and enabling Roth conversions by age 70.
(53:45) A listener seeks guidance on how to position retirement assets across multiple account types when it’s not yet clear which accounts spending will come from.
(1:02:45) The guys consider how a single filer should weigh the value of Roth conversions against maintaining low income to maximize the senior deduction before RMDs begin.
(1:07:00) Georgette outlines her plan to limit Traditional IRA withdrawals to avoid IRMAA and asks whether it’s better to spend from the Roth or take higher withdrawals and accept IRMAA.

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