What is tax-loss harvesting and should I do it?

    David TalleyUpdated December 12, 2025

    Quick Answer

    Tax-loss harvesting means selling investments at a loss to offset capital gains or income. You can deduct up to $3,000 in net losses against ordinary income each year, with excess losses carrying forward. The key is replacing the sold investment with something similar (but not "substantially identical") to maintain market exposure.

    Tax-loss harvesting is one of the few free lunches in investing. Let me explain how it works.

    The concept: When investments decline in value, you have an "unrealized" loss. Selling crystallizes that loss, which can offset: 1. Capital gains from other investments 2. Up to $3,000 of ordinary income per year 3. Future gains (losses carry forward indefinitely)
    The process: 1. Identify investments trading below your purchase price 2. Sell to realize the loss 3. Immediately buy a similar (but not identical) investment 4. Maintain your desired market exposure while banking the tax benefit
    The "wash sale" rule: You can't buy a "substantially identical" investment within 30 days before or after the sale. If you do, the loss is disallowed.

    What's substantially identical? - Same stock: Yes (can't sell Apple and buy Apple within 30 days) - Same index fund from different providers: Probably yes - Different index tracking similar markets: Probably no (S&P 500 vs. Total Stock Market is usually fine)

    When to harvest: - Market downturns (more opportunities) - Year-end planning (match gains with losses) - Throughout the year (don't wait for December)
    What to watch: - Transaction costs - Bid-ask spreads - Wash sale violations - Long-term vs. short-term status

    **Is it worth it?** For larger portfolios, yes. A $10,000 harvested loss at a 32% marginal rate saves $3,200 in taxes. Over time, these savings compound. The key is maintaining discipline and not letting tax considerations override good investment decisions.

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