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Imagine making a smart move: selling a stock at a loss to lower your tax bill through "tax-loss harvesting". This video explains why trying to repurchase that stock too soon can be problematic due to the "wash-sale rule" and other critical "tax rules". Understanding these nuances is essential for effective "tax planning" in your "investing" journey and improving your financial education. 💡💰 You think you're being smart by harvesting a tax loss, but a hidden clock is ticking. ⏰ If you buy that stock back too soon, the IRS will disallow your deduction, and you might not even realize it until it's too late. The Wash Sale Rule is one of the most common traps for investors trying to lower their tax bill. In this video, we break down the infamous 61-day window that determines whether you keep your money or hand it over to the Treasury. 💸 We cover the definition of "substantially identical" assets, the specific danger of triggering a wash sale inside an IRA (where the loss is gone forever), and how automatic dividend reinvestment can accidentally ruin your strategy. 📉 Learn the protocols to safely swap funds and protect your portfolio. Timestamps: 00:00 – The Cold Open 00:59 – The Setup and Early CTA 02:02 – The Myth of the 30 Days 06:15 – Retention Reset: The Identity Trap 06:53 – The Definition of Substantially Identical 10:54 – Retention Reset: The Spouse Rule 11:34 – The Married Filing Separate Myth 14:56 – Retention Reset: The IRA Death Trap 15:28 – The Mechanics of the Permanent Loss 18:50 – Retention Reset: The Robot Uprising 19:21 – The DRIP Problem 22:28 – Summary of the Battle Plan 23:28 – Final Thoughts Sources: ✅ IRS Publication 550 ✅ Investor.gov: Wash Sales ✅ Fidelity: Wash Sale Rules ✅ Schwab: Primer on Wash Sales #personalfinance #investingforbeginners #howtomakemoney #financialeducation #moneymanagement #compoundinterest #passiveincome #howtoinvest #savemoney #budgeting #financialindependence #wealthbuilding #investingstrategies #retireearly #washsalerule #taxlossharvesting #taxplanning #irs #stockmarkettaxes ⚖️ Disclaimer: I am not a financial advisor. Content is for entertainment & educational purposes only. Investing involves risk. Always do your own research. 🤖 Production Note: This channel utilizes AI tools for voiceover & visual rendering, but every single video is originally researched, scripted, storyboarded, and manually edited by me, Tom. The sketch-style visuals are designed to simplify complex topics. This is a human-led project dedicated to high-quality financial education.