Tax-Loss Harvesting
Mechanics of harvesting losses, the wash sale rule, pairing gains with losses, and when it backfires
In December 2022, an investor held $40,000 in unrealized losses across several tech positions after the market downturn. She sold those positions, immediately bought similar (but not substantially identical) ETFs to maintain market exposure, and used the $40,000 in realized losses to offset $40,000 in gains she had taken earlier that year. At a 15% long-term rate, this saved her $6,000 in federal tax — money she reinvested.
She stayed fully invested in the same sector the entire time. The tax code effectively paid her $6,000 for doing paperwork. Tax-loss harvesting is the deliberate realization of paper losses to create a tax deduction — while staying invested in the market.
You sell the losing position, book the loss on your tax return, and buy a replacement that gives you similar exposure. The loss offsets gains dollar-for-dollar. If your losses exceed your gains, you can deduct up to $3,000 per year against ordinary income, carrying the rest forward indefinitely.
That is the opening. Finishing a lesson is where it stops being interesting and starts being useful: the full lesson runs to 5 sections and ends with 5 practice questions. A free account is what opens the rest, and the other 255 lessons in the Academy with it. No card.
What this lesson covers
- 1Tax-loss harvesting, defined
- 2Worked example: harvesting a loss in your portfolio
- 3Wash sale timeline — the 61-day danger zone
- 4Pairing gains and losses strategically
- 5Tax-Loss Harvesting Calculator