Retirement Spending Phases: EDU #2617
April 29, 2026
Chris’s SummaryJim and I continue our discussion of the New York Times article titled “You Saved and Saved for Retirement. Now You Need a Plan to Cash Out,” focusing on Retirement Spending Phases as the article moves into go-go, slow-go, and no-go years. We walk through how the article is using that framework and how it compares with how we approach retirement planning,...
Listen NowSocial Security, Wash Sales, Taxes: Q&A #2617
April 25, 2026
Chris is joined by Jake Turner, while Jim is traveling, to discuss listener emails on Social Security spousal benefits, wash sales across brokerage and IRA accounts, estimated tax payments for Roth conversions, and tax withholding strategies in retirement. (6:45) A listener asks when an ex-spouse can claim a spousal Social Security benefit and if retroactive benefits are available. (19:20) The...
Listen NowRetirement Spending Plans: EDU #2616
April 22, 2026
Chris’s Summary Jim and I discuss retirement spending plans through the lens of a New York Times article titled “You Saved and Saved for Retirement. Now You Need a Plan to Cash Out,” reviewing its key arguments about decumulation and where we agree, question, or hold no opinion. We cover why the Minimum Dignity Floor™ rarely fails in projections, why the 4% rule may be...
Listen NowSocial Security, ERISA, Trusts: Q&A #2616
April 18, 2026
Jim and Chris discuss listener emails on Social Security benefits for a family with a disabled adult child, survivor benefits, ERISA vs. non-ERISA 403(b) protections, a listener PSA on Monte Carlo simulations, special needs trusts, and how a revocable living trust handles a primary home transfer. (5:00) A listener asks whether her husband’s early Social Security filing while still working...
Listen NowTax Rules and Mistakes: EDU #2615
April 15, 2026
Chris’s SummaryJim and I are joined by Jake as we discuss tax rules and mistakes through two tax-focused PSAs before moving into listener emails. Jake covers a denied non-cash charitable deduction due to an incomplete Form 8283 and missing contemporaneous documentation, then walks through how estimated tax payments and safe harbor rules are calculated from prior-year tax liability. We then...
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