Social Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522
May 31, 2025
Jim and Chris answer listener questions on Social Security filing, a PSA on SSA’s online application process, the Roth 5-Year Rule, HSA strategy, and bond principal risk. (8:00) A listener asks whether Social Security’s claim that delayed retirement credits aren’t applied until the end of the following year is accurate, and whether anyone receives them without persistent follow-up. (29:15) The...
Listen NowFlexible Retirement Spending: EDU #2522
May 28, 2025
Chris’s Summary:Jim, Jake, and I use this Dialogue EDU episode to explore how we approach flexible retirement spending. We respond to listener emails about DIY simplicity, budgeting for irregular expenses, and how we assign assets to spending needs. The conversation highlights why we prioritize adaptability over rigid withdrawal rules. Jim’s “Pithy” Summary:Chris, Jake, and I use this Dialogue...
Listen NowSocial Security, IRA Basis, and Roth 5-Year Rule: Q&A #2521
May 24, 2025
Jim and Chris answer listener questions on Social Security timing, the Earnings Test, nondeductible IRA basis, and the Roth 5-Year Rule. (16:15) Georgette asks whether filing retroactively in December, with Social Security payments issued in January, ensures that all income—including the retroactive amount—will be reported on the following year’s tax return. (28:00) A listener working in a State...
Listen NowSpending Confidently in Retirement with Kevin Sebesta: EDU #2521
May 21, 2025
Chris’s Summary:Jim and I are joined again this week by Kevin Sebesta from the Rock Retirement Club in this EDU episode. We explore what helps retirees start spending confidently—especially when markets are volatile or the saver mindset is hard to shake. Kevin shares how structure, support, and community all play a role, and why building confidence takes more than just having a solid financial...
Listen NowSocial Security, HSA Strategy, and Cost Basis: Q&A #2520
May 17, 2025
With Jim away at a conference, Chris is joined by Jake and Jacob to answer listener questions on child-in-care spousal benefits, the Earnings Test, HSA strategy, reconstructing cost basis, and Social Security timing concerns. (6:00) A listener asks whether reaching full retirement age makes him ineligible for child-in-care spousal benefits, and what steps he can take to appeal the denial....
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