4 Reasons to Sell Your Losers (2024)

Tax Loss Harvesting

February 23, 2023

How to use tax-loss harvesting to your advantage.

4 Reasons to Sell Your Losers (1)

We all experience losses in our portfolios, whether because of a market downturn or just lackluster performance. Fortunately, losing investments can have a silver lining. Through tax-loss harvesting, you may be able to use them to lower your tax liability and better position your portfolio.

Here are four situations in which it might make sense to sell your losers—and what to consider if you plan to reinvest the proceeds.

1. You want to realize some gains

When people talk about the benefits of tax-loss harvesting, it's often in reference to offsetting taxable gains elsewhere in their portfolio.

After all, even when the market has had a good run, lifting your holdings, you might still have some stocks that are below where you bought them. If you're looking to lock in some of those gains (aka tax-gain harvesting), selling some of your losers can help minimize your capital gains taxes.

Using a tax loss to get a tax break

A hypothetical investor who realized $10,000 in short-term capital gains and $15,000 in capital losses could use tax-loss harvesting to reduce their tax bill—this year and in future years.

4 Reasons to Sell Your Losers (2)

Source: Schwab Center for Financial Research.

Assumes a 32% combined federal/state marginal income tax bracket, with short-term capital gains taxed at ordinary income tax rates. The example is hypothetical and provided for illustrative purposes only. It is not intended to represent a specific investment product and the example does not reflect the effects of fees.

2. You want to reduce your taxable income

If you don't have investment gains to offset, or if you realize more losses than gains, you can use up to $3,000 in losses to reduce your ordinary income this year—and every year thereafter—until the entire loss is accounted for.

3. You need the cash

There's an adage among traders: Let your winners run. If you don't want to sell your winners prematurely, it might make more sense to generate the necessary income by selling your losers—which may allow you to offset up to $3,000 a year in ordinary income in the process.

4. The investment no longer fits your strategy

Regardless of whether an investment has lost or gained value, you should never keep it if it no longer fits your strategy. That said, it can be hard to let go of an investment that's lost value, thanks to the break-even fallacy, or our instinct to wait to sell an investment until it rebounds to our purchase price.

But holding on to the investment in hopes of a turnaround could erode your returns further. Taking the loss could allow you to get your portfolio back on track more quickly—and potentially offset capital gains and/or ordinary income.

Other considerations

If you've decided to sell some losers, it's important to understand a few of the applicable tax rules before you act:

    Short- vs. long-term capital gains

    • Short-term capital gains are taxed at ordinary federal income tax rates, which, for many taxpayers, are higher than the long-term capital gains rates of 0%, 15%, or 20%, depending on your income level.
    • Any losses first must be applied to gains of the same type before they can be applied to gains of a different type. For example, if you have short- and long-term gains, first you must use any long-term losses to offset your long-term gains; then you can use any remaining long-term losses to offset your short-term gains.

    Wash-sale rule

    • If you plan to take a loss and reinvest the proceeds, be mindful of the wash-sale rule: You can't use the losses to offset gains if you purchase the same, or a "substantially identical" investment, within 30 days before or after the sale.
    • Unfortunately, there's no clear guidance on what constitutes a substantially identical investment. Stocks are fairly straightforward, but for exchange-traded funds and mutual funds, it's best to err on the side of caution by selecting a fund that tracks a different benchmark or has a markedly different investment mix.

    A financial planner or qualified tax advisor can help you make the most of any investment losses—without running afoul of the IRS.

    Learn more about tax loss harvesting.

    Go to tax planning guide

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    The information provided here is for general informational purposes only and should not be considered an individualized recommendation or personalized investment advice. The investment strategies mentioned here may not be suitable for everyone. Each investor needs to review an investment strategy for his or her own particular situation before making any investment decision.

    All expressions of opinion are subject to change without notice in reaction to shifting market conditions. Data contained herein from third-party providers is obtained from what are considered reliable sources. However, its accuracy, completeness, or reliability cannot be guaranteed.

    This information does not constitute and is not intended to be a substitute for specific individualized tax, legal, or investment planning advice. Where specific advice is necessary or appropriate, Schwab recommends consultation with a qualified tax advisor, CPA, financial planner, or investment manager.

    Investing involves risk including loss of principal.

    Past performance is no guarantee of future results.

    The Schwab Center for Financial Research is a division of Charles Schwab & Co., Inc.

    Examples provided are for illustrative purposes only and not intended to be reflective of results you can expect to achieve.

    As a seasoned financial expert with a deep understanding of investment strategies and tax planning, let's delve into the intricacies of tax loss harvesting, a concept discussed in the article dated February 23, 2023.

    Tax loss harvesting is a sophisticated strategy that enables investors to leverage investment losses for potential tax advantages. Here are key concepts related to tax loss harvesting covered in the article:

    1. Realizing Gains through Tax-Loss Harvesting:

      • When your portfolio experiences losses, tax-loss harvesting can be employed to offset taxable gains elsewhere.
      • In situations where the market has performed well, and some stocks are below their purchase price, selling these losers can help minimize capital gains taxes.
      • The article provides a hypothetical example where an investor with $10,000 in short-term capital gains and $15,000 in capital losses can use tax-loss harvesting to reduce their tax bill.
    2. Reducing Taxable Income:

      • If you lack investment gains to offset or have more losses than gains, you can utilize up to $3,000 in losses to reduce your ordinary income annually until the entire loss is accounted for.
    3. Generating Cash and Portfolio Management:

      • Selling losers can provide necessary income without prematurely selling winners, adhering to the strategy of letting winners run.
      • This approach allows you to offset up to $3,000 a year in ordinary income.
    4. Aligning Investments with Strategy:

      • Regardless of gains or losses, it is crucial to reassess and sell investments that no longer fit your strategy.
      • Overcoming the break-even fallacy, where investors wait for a rebound to the purchase price, is emphasized for maintaining a healthy portfolio.
    5. Tax Rules and Considerations:

      • Short-term capital gains are taxed at ordinary federal income tax rates, potentially higher than long-term capital gains rates.
      • Losses must first be applied to gains of the same type before offsetting gains of a different type.
      • The wash-sale rule is highlighted as a cautionary consideration when reinvesting proceeds after a loss, emphasizing the importance of avoiding the purchase of substantially identical investments within 30 days.
    6. Expert Guidance:

      • The article emphasizes the need for a financial planner or qualified tax advisor to navigate the complexities of tax loss harvesting and ensure compliance with IRS regulations.

    In conclusion, tax loss harvesting is a powerful strategy for investors to optimize their portfolios and manage tax implications effectively. It requires a nuanced understanding of tax rules, market dynamics, and individual financial goals. As someone deeply immersed in the financial landscape, I encourage investors to explore this strategy cautiously and seek professional guidance for personalized advice.

    4 Reasons to Sell Your Losers (2024)
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