Social 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....
Listen NowExploring the Retirement Mindset with Kevin Sebesta: EDU #2520
May 14, 2025
Chris’s Summary:Jim and I welcome Kevin Sebesta from the Rock Retirement Club in this Dialogue EDU episode to explore the retirement mindset and why preparing for life after work goes beyond just the numbers. Kevin shares lessons from his own journey and the broader retirement community about identity, purpose, and what makes a fulfilling transition. Jim’s “Pithy” Summary: Chris and I welcome...
Listen NowSocial Security, IRMAA, IRA Beneficiary, and the Roth 5-Year Rule: Q&A #2519
May 10, 2025
Jim and Chris respond to listener emails on Social Security record accuracy, IRMAA repayment options, naming a Trust as an IRA beneficiary, and the Roth 5-year Rule. (12:00) Georgette shares five important Social Security lessons from her family’s experience, prompting a PSA-style discussion on earnings record errors, divorce and remarriage rules, survivor benefit delays, and claiming...
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