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5 Rules for Selling Short in the Stock Market

With so much uncertainty in the market, today I want to discuss my five commandments for selling short - before you need to use them.

Stock Selling Short Selling

The market is a two-way street. Sometimes traffic flows up, and investors who own stocks (who are “long”) make money. And sometimes traffic flows down, and those investors lose money. But there are some investors who make money when stocks fall—investors who are “short” the market—and if you’re nimble enough, you can successfully join them. But selling short is not an enterprise to be undertaken lightly; it’s an easy way for amateurs to lose money!

So before you enter into this arena, consider my rules for selling short in the stock market.

5 Commandments for Selling Short

1. Thou shalt sell short only in bear markets.
“The trend is your friend” is one of the most valuable of the scores of market truisms that I’ve internalized over the years.

For more than 10 years, the market’s trend was up, and anyone who bet against it (hedge funds, for example) suffered.

But a bear market suddenly, historically arrived along with the coronavirus pandemic in March 2020, and while stocks bounced back remarkably well in the ensuing 20 months, they struggled in 2022, with the S&P 500 and growth stocks entering full-on bear market territory again.

So, 2022 was a good time to sell, particularly if you owned a lot of growth stocks. The biggest reason for shorting only in confirmed bear markets—and most people forget this—is that the real long-term trend of the market has been up for centuries, and will continue to be up as long as investors perceive that the U.S. economy is growing. Usually, this long upward trend helps investors, which is why holding index funds for decades is one decent investing strategy.


2. Thou shalt sell short only stocks that are trending down.
This rule, like the first, ensures that the odds are on your side when you short. Trends, once in place, tend to continue, so you want to be sure that the stock you’re shorting is already in a downtrend. Sure, it’s nice to dream about shorting a ridiculously overvalued stock at the top and riding it down, but picking tops (and bottoms) is a fool’s game. Put the odds in your favor and only sell stocks short that are in confirmed downtrends.

3. Thou shalt sell short only when public opinion of the company behind the stock has a long way to fall.
Stocks decline because investors as a whole lower their expectations about the stocks’ future—and when they do, some stop buying and others start selling. For little-known stocks, expectations can’t fall much because there aren’t many expectations. If anything, expectations are likely to rise as people discover the company and the stock.

It’s far better to short stocks that are over-owned, and stocks that are or were well-loved, and which are thus ripe for lowered expectations. Chipotle (CMG) was a classic example of that. When everyone loved the stock back in 2015, it was “priced to perfection.” And once the bad news about contaminated food got out, the stock had nowhere to go but down—and once the downtrend got rolling (with selling intensified by repeat incidents), it was hard to stop! In fact, at the stock’s low, it was off 67% from its 2015 high, even though revenues were down only 9% from the peak. (Trouble is, earnings were down 71% from the peak.) Chipotle stock has since completely recovered.

Blockbuster Entertainment is another great example. At its peak in 2004, it dominated the video rental business. But then Netflix (NFLX) came up with the revolutionary idea of mailing DVDs, and that marked the start of Blockbuster’s big decline.

Kodak is another classic example; once king of the photography industry, it was killed by the digital revolution.

4. Thou shalt, at all times, beware of the mathematical realities of short selling.
When you buy a stock, hoping it will go up, the most you can lose is what you invested—while there’s no limit to what you can win. That’s a pretty good trade-off.

However, when you sell a stock short, the very best result—if the stock falls to zero—is that you double your money. But if the stock goes up instead, there’s no limit to the amount you can lose! That’s not a great trade-off.

5. Thou shalt not get greedy.
When you put it all together, it becomes clear that selling short is a high-risk proposition that can only work during certain periods, and even then, it’s unlikely to work for long. So when you find yourself with a profit from selling short, take some off the table. Let some ride, if you like, but remember that eventually, the market’s long-term upward trend will return, and it will be hard to swim against that tide.

What are your personal rules for selling short in the stock market? Share them in the comments below.


*This article has been updated from an original version that was published in 2014.

A growth stock and market timing expert, Michael Cintolo is Chief Investment Strategist of Cabot Wealth Network and Chief Analyst of Cabot Growth Investor and Cabot Top Ten Trader. Since joining Cabot in 1999, Mike has uncovered exceptional growth stocks and helped to create new tools and rules for buying and selling stocks. Perhaps most notable was his development of the proprietary trend-following market timing system, Cabot Tides, which has helped Cabot place among the top handful of market-timing newsletters numerous times.