5 Rules for Selling Short in the Stock Market - Cabot Wealth Network

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.

Market Sell Off - 5 Rules for Selling Short in the Stock Market

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 have bounced back remarkably well in the almost two years since, it has struggled through the first three months of 2022, with the S&P 500 correcting and growth stocks entering full-on bear market territory again in mid-March.

Now, though, the bull market has returned, with stocks reclaiming about half their winter losses. And that means you should not start selling your 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.

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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.

So what stocks might be good for selling short in the future? Off the top of my head, I’d keep an eye on these current favorites:

Canon (CAJ) is an old-school photography company facing competition from digital upstarts; in fact it’s easy to draw a parallel with Kodak. Revenues peaked at $45 billion in 2011; last year they were $32 billion. The stock peaked above 40 in January 2018 and, other than participating in the broad post-pandemic rally, has been mostly trending down since, currently trading at 24.

Triumph Group (TGI) is not as well known as the other companies here—it’s a supplier of aerospace services, structures and systems to aircraft manufacturers (like Boeing and Airbus). But revenues peaked in 2015 at $3.9 billion—and the stock’s long-term trend has been down since 2013.

Xerox (XRX) is well known as the inventor of the pioneer copy machine, but its glory days are long over. The stock sold off with everything else in early 2020 and has just recouped its pre-pandemic lows. The stock peaked at 39 in 2014.

But don’t forget Commandments #1 and #2.

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. 

Timothy Lutts

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


  • Victor H.

    Also, keep in mind you have to pay the stock’s dividend to the person you borrowed it from. And one wonders after having covered the stock at a lower price, what is the income tax classification? thanks for being brave enough to publish an article about shorting. Best, V.

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