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The worst year in modern American history to retire wasn't 1929. It was 1966 and understanding why explains almost every mistake on this list. Thirteen years into retirement, the 1966 retiree still had $769,000. The 1929 retiree was down to $394,000. And the 1929 retiree was in better shape. Here's why, plus the ten decisions that quietly destroy otherwise excellent retirement portfolios. Nine of these ten mistakes are made by careful people. That's what makes them worth talking about. 📬 GET MY FREE WEEKLY NEWSLETTER: socialcapconnect.substack.com/subscribe 📕 Pre-Order my book, REAL WEALTH: tylergardner.com/book 🎧 THE PODCAST - Your Money Guide on the Side: https://podcasts.apple.com/us/podcast/your-money-guide-on-the-side/id1799219049 DISCLAIMER: I'm not a financial advisor, attorney, or licensed specialist of any kind. I'm an educator sharing publicly available information. Nothing in this video is individualized financial, legal, or medical advice. Always consult an expert and not some ding-dong walking through the woods of Vermont. SOURCES 2026 IRMAA brackets and Part B premium: CMS fact sheet, November 14, 2025 2026 standard deduction and senior bonus deduction: IRS inflation adjustments for tax year 2026; OBBBA §70103, P.L. 119-21 Retiree asset decumulation: EBRI, "Asset Decumulation Over Retirement and the Role of Guaranteed Income Streams" (Health and Retirement Study, 1992–2022) Alternative assets in 401(k)s: Executive Order, August 2025; DOL/EBSA proposed rule, March 30, 2026 1966 and 1929 retiree cohort data: Shiller dataset, 60/40 portfolio

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