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How to sell your losing stocks to reduce taxes

Defining tax loss selling

Tax loss selling, also known as tax-loss harvesting, is a strategy employed by investors to offset capital gains and reduce their taxable income. This approach involves selling stocks or other securities that have experienced losses to counterbalance capital gains realized throughout the year. By doing so, investors aim to mitigate their tax liability and potentially improve their after-tax returns.

Mechanics of tax loss selling

Identifying losses. Investors begin by reviewing their investment portfolio to identify stocks or securities that have declined in value since their purchase. These are considered paper losses, representing the difference between the purchase price and the current market value.

Selling securities at a loss. Once losses are identified, investors decide to sell the underperforming securities. The sale generates a capital loss, which can be used to offset capital gains.

Offsetting capital gains. Capital losses can be used to offset capital gains realized during the same tax year. If an investor has capital gains from the sale of profitable securities, the losses from tax loss selling can be applied to reduce or eliminate the tax liability associated with those gains.

Limitations on deductible losses. Tax regulations limit the amount of capital losses that can be deducted against other income. In the U.S., for example, individuals can deduct up to $3,000 of net capital losses against ordinary income. Any remaining losses can be carried forward to future years.

Benefits of tax loss selling

Tax efficiency. Tax loss selling is a tax-efficient strategy, allowing investors to use capital losses to offset capital gains. This can result in a lower overall tax liability, leaving more money in the investor’s pocket.

Portfolio optimization. Selling underperforming securities as part of tax loss selling provides an opportunity to reassess and optimize one’s investment portfolio. Investors can reallocate funds to more promising investments without incurring a tax penalty.

Creating tax loss carryforwards. If an investor’s capital losses exceed their capital gains, the excess losses can be carried forward to future years. This can be particularly beneficial if the investor anticipates capital gains in subsequent years.

Considerations for investors

Wash-sale rule. Investors must be aware of the wash-sale rule, which prevents them from claiming a tax loss if they repurchase substantially identical securities within 30 days before or after the sale. To avoid this, investors may need to adjust their portfolio carefully.

Balancing act. While tax loss selling can be advantageous for tax planning, it’s essential for investors to strike a balance and not let tax considerations drive investment decisions exclusively. The fundamental soundness of an investment should remain a primary consideration.

Long-term vs. short-term gains. Tax loss selling is often more impactful when used to offset short-term capital gains, which are taxed at higher rates than long-term gains. Investors should assess their overall tax situation and the type of gains they have realized.


Tax loss selling in stocks is a valuable strategy that allows investors to leverage market downturns to their advantage for tax planning purposes. By thoughtfully managing their portfolios, investors can optimize their tax outcomes while maintaining a focus on their long-term investment goals. As with any financial strategy, consulting with a tax professional or financial advisor is recommended to ensure compliance with tax regulations and to tailor the approach to individual circumstances.

Amarish Dave is a board-certified neurologist with over 20 years of experience in both neurology and active stock investing. In addition to his medical career, he holds a background in business from the University of Michigan and has successfully passed the SIE exam administered by FINRA. Dr. Dave is founder,, a website dedicated to educating doctors at all stages of their careers, ranging from residents to retirement, about financial planning.

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