Turn investment losses into tax savings without changing your portfolio strategy
Tax-loss harvesting is a strategy where you sell investments that have lost value to realize a capital loss, then use that loss to offset capital gains taxes on your winners. You then immediately buy a similar (but not identical) investment to maintain your market exposure.
In short: you capture a tax benefit from an investment that went down, without actually changing your portfolio strategy. It's like getting a tax refund from bad luck.
Here's a simplified example: You bought $10,000 of Fund A, and it dropped to $8,000. You sell Fund A, realizing a $2,000 loss. You immediately buy $8,000 of Fund B (a similar but not "substantially identical" fund). You now have the same market exposure, but you can use that $2,000 loss to offset gains elsewhere.
If you have $2,000 in capital gains from other investments, this loss cancels them out — saving you up to $600+ in taxes. If you have no gains, you can deduct up to $3,000 of losses against ordinary income and carry forward the rest.
Offset capital gains dollar-for-dollar with harvested losses
Deduct up to $3,000/year of excess losses against ordinary income
Unused losses carry forward indefinitely
Must avoid "wash sale" rule: don't buy the same or substantially identical fund within 30 days
Research suggests tax-loss harvesting can add 0.5–1.5% in after-tax returns per year, particularly in volatile markets where there are frequent opportunities to harvest losses.
Many robo-advisors (like Betterment and Wealthfront) have popularized automated tax-loss harvesting, making it accessible to everyday investors. Before these tools, the strategy was mostly used by wealthy investors with tax advisors.
The wash sale rule is crucial: if you buy a "substantially identical" security within 30 days before or after selling at a loss, the IRS disallows the loss. Use a different (but similar) fund as your replacement.
Reduces your tax bill without changing your investment strategy
Losses can offset gains or reduce ordinary income
Unused losses carry forward to future years
Can be automated with robo-advisors
Most valuable in taxable brokerage accounts
Wash sale rule requires careful planning
Only applies to taxable accounts (not IRAs or 401ks)
Doesn't eliminate taxes — it defers them
Requires tracking cost basis carefully
Can generate complexity at tax time
Tax-loss harvesting is most valuable for investors with significant holdings in taxable brokerage accounts.
Taxable account holders: If you invest outside of retirement accounts, this strategy can save you real money.
Higher-income earners: The higher your tax bracket, the more valuable each dollar of harvested losses becomes.
Robo-advisor users: Many robo-advisors do this automatically — it may be happening in your account already.
Review your taxable accounts: Look for positions that are currently at a loss. These are your harvesting candidates.
Identify replacement funds: Find similar but not identical funds. Example: sell VOO (S&P 500) and buy IVV (also S&P 500, different provider) — but check with a tax advisor first.
Execute the swap: Sell the losing position and buy the replacement on the same day to maintain market exposure.
Track the 30-day window: Don't buy back the original fund within 30 days. Set a calendar reminder.