Nobody enjoys seeing an investment decline in value. Tax-loss harvesting is a technique that attempts to find a silver lining: selling an investment at a loss in a taxable account to realize that loss for tax purposes, while keeping your overall portfolio positioned the way you intend.
How it works
Realized capital losses can generally be used to offset realized capital gains. If your losses exceed your gains in a given year, you can typically deduct up to $3,000 of the excess against ordinary income, and carry remaining losses forward to future years. By harvesting a loss and reinvesting the proceeds in a different, non-substantially-identical investment, you may maintain market exposure while capturing a tax benefit.
The wash-sale rule
The main constraint is the wash-sale rule: if you buy the same or a “substantially identical” security within 30 days before or after the sale, the loss is generally disallowed for current use. This includes purchases in other accounts you own, and in some cases accounts belonging to your spouse. Automated dividend reinvestment is a frequent, accidental culprit.
What tax-loss harvesting cannot do
It is worth being clear-eyed about the limits of the strategy:
- It applies only to taxable accounts, not IRAs or 401(k)s.
- It defers taxes more often than it eliminates them, since reinvesting at a lower cost basis can mean larger gains later.
- The value depends on your tax bracket now versus in the future.
- Selling solely for tax reasons should never override your investment strategy.
The bottom line
Tax-loss harvesting is a useful tool in the right circumstances, particularly for investors in higher brackets with meaningful taxable accounts. Like most tax strategies, the details matter, and mistakes such as wash-sale violations can undo the benefit. Coordinate with your advisor and tax professional before acting, and remember that tax considerations are one input to an investment decision, not the whole decision.
Important disclosures
This article is provided for educational and informational purposes only and should not be construed as personalized investment, tax, or legal advice. The information presented is general in nature and may not be appropriate for your individual circumstances. Litchfield Financial, LLC does not provide tax or legal advice; please consult a qualified tax professional or attorney regarding your specific situation. Investing involves risk, including the possible loss of principal. Past performance is not indicative of future results. No strategy, including diversification or asset allocation, assures a profit or protects against loss in declining markets.
Litchfield Financial, LLC provides investment advisory services through Claro Advisors Inc. (“Claro”), a registered investment advisor. Claro Advisors Inc. is a Registered Investment Advisor with the U.S. Securities and Exchange Commission (“SEC”) based in the Commonwealth of Massachusetts. Registration of an Investment Advisor does not imply any specific level of skill or training. Information contained herein is for educational purposes only and is not to be considered investment advice.



