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 […]

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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 […]

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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 […]

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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 […]

The post Social Security, HSA Strategy, and Cost Basis: Q&A #2520 appeared first on The Retirement and IRA Show.

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 […]

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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 […]

The post Social Security, IRMAA, IRA Beneficiary, and the Roth 5-Year Rule: Q&A #2519 appeared first on The Retirement and IRA Show.

Chris’s Summary:Jim and I take a step back in this Dialogue EDU episode to explore how we design retirement plans for again. We talk through common misunderstandings around projections, explain how our See Through Portfolio™ helps people navigate retirement with more confidence, and clarify how simplicity is built into the process. Jim’s “Pithy” Summary: Chris […]

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Jim and Chris are joined by Jake and Paul to discuss tax-related listener questions on IRA contributions from self-employment income, special needs trusts, year-of-death Roth conversions, Cost Basis, and IRMAA. (9:00) George asks how QBI and self-employed health insurance deductions affect how much he can contribute to a traditional IRA.(20:00) Jim, Chris, Jake, and Paul […]

The post IRA Contributions, Special Needs Trusts, Roth Conversions, and Cost Basis: Q&A #2518 appeared first on The Retirement and IRA Show.