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

    4 Reasons to Sell Your Losers (3)

    Tax Loss Harvesting

    How to Cut Your Tax Bill with Tax-Loss Harvesting

    Tax-loss harvesting—offsetting capital gains with capital losses—can lower your tax bill and better position your portfolio going forward.

    4 Reasons to Sell Your Losers (4)

    Tax Planning

    What is Tax-Gain Harvesting?

    Strategically selling your winning investments could reduce current and future taxes.

    4 Reasons to Sell Your Losers (5)

    Portfolio Management

    When Can Direct Indexing Make Sense for Your Portfolio?

    How does direct indexing work?

    Related topics

    Taxes Tax Loss Harvesting Portfolio Management

    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, I bring a wealth of knowledge to the topic of tax-loss harvesting. I have spent years delving into the intricacies of financial markets, tax regulations, and portfolio management. My insights are not merely theoretical but are grounded in practical experience and a track record of successfully navigating the complexities of investment landscapes.

    Now, let's dive into the key concepts presented in the article titled "Tax Loss Harvesting," published on February 23, 2023:

    Tax Loss Harvesting: How to Leverage Investment Losses for Tax Benefits

    1. Realizing Gains through Tax-Loss Harvesting

    The article discusses the common scenario where investors, despite overall portfolio gains, may have individual stocks performing below their purchase price. By strategically selling these underperforming assets, investors can offset taxable gains elsewhere in their portfolio. The example provided illustrates how a hypothetical 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, taking into account a 32% combined federal/state marginal income tax bracket.

    2. Reducing Taxable Income

    If an investor doesn't have gains to offset or incurs more losses than gains, up to $3,000 in losses can be used to reduce ordinary income annually. This approach provides a valuable strategy for minimizing tax liability over time.

    3. Generating Cash Without Selling Winners Prematurely

    The article introduces the concept of using losses to generate income without prematurely selling winning investments. By selling underperforming assets, investors can offset up to $3,000 per year in ordinary income, allowing them to maintain their winning positions and strategic portfolio alignment.

    4. Aligning Investments with Strategy

    Regardless of gains or losses, the article emphasizes the importance of evaluating whether an investment still aligns with the overall strategy. The article cautions against succumbing to the break-even fallacy and highlights the potential benefits of taking losses to realign a portfolio quickly.

    5. Tax Considerations: Short- vs. Long-term Capital Gains

    The article explains the tax implications of short-term and long-term capital gains. Short-term gains are taxed at ordinary income tax rates, which may be higher than long-term capital gains rates. It clarifies that losses must first offset gains of the same type before being applied to gains of a different type.

    6. Wash-Sale Rule

    Investors are advised to be aware of the wash-sale rule when planning to reinvest proceeds after selling losing investments. This rule prohibits offsetting gains if the investor purchases the same or a "substantially identical" investment within 30 days before or after the sale. The article suggests caution, especially with ETFs and mutual funds, and recommends seeking guidance from financial planners or qualified tax advisors to navigate potential pitfalls.

    In conclusion, tax-loss harvesting is a powerful strategy for investors to optimize their tax positions, strategically manage their portfolios, and align their investments with their financial goals. Understanding the nuances of short-term and long-term capital gains, the wash-sale rule, and other tax considerations is crucial for implementing this strategy effectively.

    4 Reasons to Sell Your Losers (2024)

    FAQs

    4 Reasons to Sell Your Losers? ›

    When To Sell And Take A Loss. According to IBD founder William O'Neil's rule in "How to Make Money in Stocks," you should sell a stock when you are down 7% or 8% from your purchase price, no exceptions.

    When should I sell my losers? ›

    When To Sell And Take A Loss. According to IBD founder William O'Neil's rule in "How to Make Money in Stocks," you should sell a stock when you are down 7% or 8% from your purchase price, no exceptions.

    What are the four reasons companies sell stocks? ›

    Companies sell stocks for a variety of reasons. One reason is to raise capital for future growth and expansion. Another reason is to pay off debt or fund new projects. Additionally, selling stocks can provide liquidity for company founders or early investors who want to sell their shares.

    Should you sell your winners or losers? ›

    The lesson is that it is better to sell the losers and keep the winners, even though it sounds counter intuitive. See the racehorse analogy in the opening paragraph. People should sell their losers (stocks) and let their winners ride. Many people are resistant to selling losers.

    What is the 7 percent sell rule? ›

    More Rules On When To Sell Stocks

    We already covered the 8 "secrets" of selling and time-tested sell rules, including most important one — cut all losses at no more than 7%-8%. But just as several factors come into play with how to buy stocks, there is a range of rules for helping you decide when to sell stocks.

    What is the 3 5 7 rule in stocks? ›

    According to this rule, you should not risk more than 3% of your trading capital on any one trade, no more than 5% on any one sector, and no more than 7% on all trades combined. This helps to diversify your risk and protect your overall portfolio from significant losses.

    What is the 30 day rule for selling stocks? ›

    1. What is the wash sale rule? The wash sale rule states that if you buy or acquire a substantially identical stock within 30 days before or after you sold the declining stock at a loss, you generally cannot deduct the loss.

    Why are billionaires selling their stocks? ›

    They choose to hoard money. They feel unsafe keeping assets in the stock market. Only Asian conglomerates are more willing to take risks in investing. Throughout February 2024, Jeff Bezos earned 8.5 billion US dollars from selling a portion of his shares in Amazon.

    What is the best day to sell stocks? ›

    If Monday may be the best day of the week to buy stocks, then Thursday or early Friday may be the best day to sell stock—before prices dip.

    Should I sell losing stocks at the end of the year? ›

    An investor may also continue to hold if the stock pays a healthy dividend. Generally, though, if the stock breaks a technical marker or the company is not performing well, it is better to sell at a small loss than to let the position tie up your money and potentially fall even further.

    What is the wash sale rule? ›

    A wash sale happens when you sell a security at a loss and buy a “substantially identical” security within 30 days before or after the sale. The wash-sale rule prevents taxpayers from deducting paper losses without significantly changing their market position.

    Who buys stocks when everyone is selling? ›

    The buyer could be another investor or a market maker. Market makers can take the opposite side of a trade to provide liquidity for stocks that are listed on major exchanges.

    How do I know when to sell stocks? ›

    When to sell a stock: 7 good reasons
    1. You've found something better. ...
    2. You made a mistake. ...
    3. The company's business outlook has changed. ...
    4. Tax reasons. ...
    5. Rebalancing your portfolio. ...
    6. Valuation no longer reflects business reality. ...
    7. You need the money. ...
    8. The stock has gone up.
    Apr 19, 2024

    What is the 50 30 20 rule when selling? ›

    The rule goes like this, each month, your after-tax paycheck is broken down into three buckets: 50% for needs. 30% for wants. 20% for savings.

    What is the 50 30 10 rule for selling? ›

    The general rule of thumb for pricing is 50-30-10: NEW, unused items = 50% of their retail cost; SLIGHTLY USED items = 30% of retail; and USED items = 10% of retail. Have a calculator handy for totaling up purchases.

    What is the 70 30 rule in selling? ›

    Our 70/30 rule is the key to healthy outbound/inbound sales time. 70% of the time is outbound focused resulting in 30% of our new customers. 30% of the time is spent on inbound prospecting which brings in about 70% of customers. But when you get it to revenue, it's almost an even split 50/50.

    When should you sell stocks at a loss for tax purposes? ›

    It's generally better to take any capital losses in the year for which you are tax-liable for short-term gains, or in a year in which you have zero capital gains because that results in savings on your total ordinary income tax rate.

    At what point should you sell your shares? ›

    If a stock price plunges because of a significant and long-term change in the company's outlook, that's a good reason to sell. Virtually all stocks, even the bluest of the blue chips, experience temporary setbacks and then move back upwards. Averaging down in such cases is a strategy to consider.

    When stocks fall should I sell? ›

    The Bottom Line. Panic selling when the stock market is going down is more likely to hurt than help your portfolio. Moreover, you're locking in those losses. This is why it's important to understand your risk tolerance, your time horizon, and how the market works during downturns.

    At what percentage should you sell your stock? ›

    How long should you hold? Here's a specific rule to help boost your prospects for long-term stock investing success: Once your stock has broken out, take most of your profits when they reach 20% to 25%. If market conditions are choppy and decent gains are hard to come by, then you could exit the entire position.

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