Retirement Planning Articles

Long-form, plain-English education on the decisions that move six- and seven-figures of family wealth: Roth conversions, IRMAA cliffs, Social Security claiming, RMDs, the widow's penalty, and the SECURE Act's 10-year rule.

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Roth Conversions · Pillar Guide

The Real Cost of Doing Nothing About Roth Conversions

Most pre-retirees with a meaningful Traditional IRA never seriously evaluate Roth conversions. They assume it's an 'optional' or 'advanced' play. It's not. The cost of inaction is typically the single largest tax decision of their retirement.

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Medicare & IRMAA · Pillar Guide

What the IRMAA Cliff Actually Costs Retirees in 2026

IRMAA is one of the most expensive cliffs in the tax code — and one of the least understood. Most retirees first encounter it via a confusing SSA letter announcing their Medicare premium has tripled. By then it's too late to plan around it.

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Surviving Spouse · Pillar Guide

The Widow's Penalty: The Silent Six-Figure Tax Hit Most Couples Miss

Most retirement plans assume both spouses live the full plan horizon. The math is run jointly because that's how the couple files today. But in reality, one spouse will die first — and the moment that happens, the survivor's tax situation gets dramatically worse.

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Social Security · Pillar Guide

Should You Claim Social Security at 62, 67, or 70? The Real Numbers

The Social Security claiming decision is one of the most consequential financial choices most people make — and one of the least analyzed. Here are the actual numbers, the strategy, and why the answer changes if you're married, divorced, widowed, or in poor health.

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Estate Planning · Pillar Guide

The 10-Year Drain Rule: How the SECURE Act Killed the Stretch IRA

Until 2019, your children could 'stretch' an inherited IRA over their lifetimes — taking small annual distributions and letting most of the balance keep growing tax-deferred for decades. The SECURE Act of 2019 killed that. For most non-spouse heirs, the entire IRA must now be drained within 10 years.

8 minRead →

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