The Art of Selling a Losing Position (2024)

Percentage Loss	Percent Rise To Break Even
10%	11%
15%	18%
20%	25%
25%	33%
30%	43%
35%	54%
40%	67%
45%	82%
50%	100%

A stock that declines 50% must increase 100% to return to its original amount. Think about it in dollar terms: a stock that drops 50% from $10 to $5 ($5 / $10 = 50%) must rise by $5, or 100% ($5 ÷ $5 = 100%), just to return to the original $10 purchase price. Many investors forget about simple mathematics and take in losses that are greater than they realize due to emotional distress. They falsely believe that if a stock drops 20%, it will simply have to rise by that same percentage to break even.

This isn't to say that rebounds never happen. Sometimes a stock has been unfairly pummeled.But the long turnaround waiting period—sometimes years—also means that stock is tying up money that could be put to work in a different stock with possibly better potential.

The Best Offense Is a Good Defense

Championship teams have one thing in common: a good defense. This principle can be applied to the stock market as well. You can't win unless you have a predetermined defense strategy to prevent excessive losses.

Having a defensive strategy, or exit strategy, in place before placing a trade hedges against emotional trading. Once we own something, we tend to let emotions such as greed or fear take over and get in the way of good judgment.

An Adaptable Selling Strategy

The classic axiom of investing in stocks is to look for quality companies at the right price. Following this principle makes it easy to understand why there are no simple rules for selling and buying; it rarely comes down to something as easy as a change in price. Investors must also consider the characteristics of the company itself. There are also many different types of investors, such as value or growth on the fundamental analysis side.

A selling strategy that's successful for one person might not work for somebody else. Think about a short-term trader who sets a stop-loss order for a decline of 3%; this is a good strategy to reduce any big losses. The stop-loss strategy can be used by longer-term traders also, such as investors with a three- to five-year investment time frame.

However, the percentage decline would be much higher, such as 15%, than that used by short-term traders. On the other hand, this stop-loss strategy becomes less and less useful as the investment time frame is extended.

Questions to Ask Before Selling

If you know your investing style and have put some thought into your investment, use this framework to help you think about whether or not you want to sell. Start by asking yourself these questions:

Why did you buy the stock?
What changed?
Does that change affect your reasons for investing in the company?

The first question will be an easy one. Did you buy a company because it had a solid balance sheet? Were they developing a new technology that would one day take the market by storm? Whatever the reason was, it leads to the second question. Has the reason you bought the company changed?

If a stock has gone down in price, there is usually a reason for it. Does the quality you originally liked in the company still exist or has the company changed? It is important to not limit your research to only the original purchase reasons. Review all of the latest headlines related to that firm as well as its Securities and Exchange Commission (SEC) filings for any events which could potentially diminish the reasons behind the investment.

A Value Investor's Approach to Selling

Let's demonstrate how a value investor would use this approach. Simply put, value investing is buying high-quality companies at a discount. The strategy requires extensive research into a company's fundamentals.

1. Why Did You Buy the Stock?

Let's say our value investor only buys companies with a price-to-earnings ratio (P/E ratio) in the bottom 10% of the equity market, with earnings growth of 10% per year.

2. What Changed?

Say the stock declines in price by 20%. Most investors would wince at seeing this much of their investment fall. The value investor, however, doesn't sell simply because of a drop in price, but because of a fundamental change in the characteristics that made the stock attractive.

The value investor knows that it takes research to determine if a low P/E ratio and high earnings still exist. The value investor will also look at other stock metrics to determine if the company is still a worthy investment.

3. Does That Change Affect Your Reasons for Investing in the Company?

After investigating how or if the company has changed, our value investor will find that the company is experiencing one of two possible situations: It either still has a low P/E ratio and high earnings growth, or it no longer meets these criteria. If the company still meets the value-investing criteria, the investor will hang on. In fact, the investor might actually purchase more stock because it is undervalued and selling at a discount.

With any other situation, such as high P/E and low earnings growth, the investor is likely to sell the stock, hopefully minimizing losses. This approach works with any investing style. A growth investor, for example, would have different criteria in evaluating the stock. But the questions to ask would remain the same.

When Should You Sell a Stock At a Loss?

This depends on your trading strategy and overall portfolio composition. You may be able to hold stock at a loss for a longer period if it is a smaller part of your portfolio and doesn't drag your portfolio's value down. 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 Best Time of Day to Sell Stock?

The periods of highest liquidity in the stock markets are always during trading hours, usually right at the open and about ten minutes before the close to the closing bell. Many companies are so liquid that trades are placed near instantaneously throughout the day, but if you are invested in smaller companies, there could be a substantial lag between when you place an order and when it is filled. There may be no one on the other side of the trade, and that is compounded after-hours or pre-market, when liquidity is low.

How Long Should I Hold a Stock?

Your stock placements and how long you should hold them depend on your investing style and goals. Many investors will buy something they intend to hold for years. When harvesting and reinvesting dividends, an investor may hold that position for 25 years or more, as their dividends are used to purchase additional shares. On the flip side, day traders and forex traders may hold a position for less than a minute.

The Bottom Line

Determining when to sell requires thought and work on your part to ensure these guidelines maximize the effectiveness of your investing style. All investors are different, so there is no hard-and-fast selling rule that all investors should follow.

Even with these differences, it is vital that all investors have some sort of exit strategy. This will greatly improve the odds that the investor will not end up holding worthless share certificates at the end of the day. Know what your investing style is and then use that strategy to stay disciplined, keeping your emotions out of the market.

As a seasoned financial expert with a deep understanding of investment strategies and market dynamics, I want to shed light on the concepts discussed in the article and provide additional insights to reinforce the importance of a well-thought-out selling strategy in the stock market.

Firstly, let's delve into the fundamental principles highlighted in the article:

Percentage Loss and Gain:
- The article emphasizes the mathematical reality that a stock that experiences a 50% loss requires a 100% gain to break even. This underscores the significance of avoiding substantial losses, as recovering from them demands disproportionately larger gains.
Defense Strategy:
- Drawing an analogy to championship teams, the article stresses the importance of a good defense in the stock market. This defense strategy involves having a predetermined exit plan to prevent excessive losses, mitigating the impact of emotional trading.
Adaptable Selling Strategy:
- The article acknowledges that there is no one-size-fits-all selling strategy. It discusses the use of stop-loss orders and how the effectiveness of such strategies varies based on the investor's time frame, distinguishing between short-term and longer-term traders.
Questions to Ask Before Selling:
- The article provides a framework for investors to evaluate whether they should sell a stock. By asking questions such as why the stock was purchased, what has changed, and whether the change affects the investment thesis, investors can make more informed and rational selling decisions.
Value Investor's Approach:
- The article demonstrates how a value investor would approach selling. It emphasizes the importance of understanding the fundamental reasons for buying a stock, assessing changes, and determining if those changes affect the initial investment thesis.
When to Sell a Stock at a Loss:
- The timing of selling at a loss depends on the investor's trading strategy and overall portfolio composition. The article suggests that if a stock breaks a technical marker or the company is not performing well, it might be better to sell at a small loss to prevent further decline.
Best Time of Day to Sell Stock:
- Liquidity is highlighted as a crucial factor in determining the best time to sell stock. The periods of highest liquidity are during trading hours, emphasizing the importance of trading during these times, especially for smaller companies with lower liquidity.
How Long to Hold a Stock:
- The duration of holding a stock is contingent on the investor's style and goals. Long-term investors may hold for years, while day traders may hold for minutes. The article underscores the diversity in investment styles and the need for individualized strategies.

In conclusion, the key takeaway is that a well-defined and adaptable selling strategy is essential for investors. This strategy should align with the investor's goals, time frame, and risk tolerance. Understanding the dynamics of percentage loss and gain, having a solid defense strategy, and asking critical questions before selling are crucial elements in navigating the complexities of the stock market.