Why short selling is not the opposite of going long

Short selling and going long are two fundamental investment strategies with distinct risk profiles and market expectations. While going long involves buying assets with the expectation that their value will rise over time, short selling is the practice of borrowing assets to sell them at current prices, hoping to buy them back later at a lower price, profiting from the difference. The key differences, particularly the asymmetric risk profile and market tendencies, can be better understood through the lens of financial experts and the insights of Nassim Nicholas Taleb.

Asymmetric Risk Profile

  1. Going Long: Limited Loss, Unlimited Gain – When you buy (go long on) a stock, the maximum you can lose is what you have invested, as a stock’s price cannot go below zero. However, the potential for gain is theoretically unlimited, as there is no cap on how high a stock’s price can rise.
  2. Short Selling: Unlimited Loss, Limited Gain – In contrast, short selling exposes you to potentially unlimited losses because there’s no upper limit to how high a stock’s price can go. However, the maximum gain is limited to the initial value from which the stock is shorted, minus the cost to buy it back, as a stock’s price cannot fall below zero.

This asymmetric risk profile is crucial because it reflects the fundamental difference in risk exposure. Nassim Nicholas Taleb, in his discussions on risk, probability, and unpredictability in markets, often emphasizes the importance of managing tail risks – rare and extreme events that can have disproportionately large impacts. Short sellers are particularly exposed to these tail risks, as unforeseen positive news or market shifts can lead to significant losses.

Markets’ Tendency to Rise Over Time

Historical data shows that over the long term, markets tend to go up. This upward bias is attributed to economic growth, inflation, and reinvestment of dividends, among other factors. This tendency means that going long generally aligns with the overall direction of market movement, offering a tailwind to investors.

On the other hand, short sellers bet against this general trend, which can make short selling a more challenging and risky strategy over the long term. This is not to say that short selling cannot be profitable, but it requires accurate timing and often a contrarian view that a particular stock or the market will decline. Financial experts and economists often point out that while short selling can be a useful hedge against market downturns or for arbitrage, it is a strategy fraught with risks, especially considering market efficiency and the difficulty of timing market movements accurately.


In essence, while going long and short selling are both strategies used to seek profit in the markets, their risk profiles are fundamentally different due to the asymmetric nature of potential gains and losses and the general upward trend of markets over time. Short selling, while potentially profitable, requires careful management of risks, especially those associated with rare but extreme market movements that various financial experts warn against. Investors must carefully consider these dynamics and their own risk tolerance when choosing between these strategies.

For further detailed analysis and insights, consulting specific sections of Nassim Nicholas Taleb’s writings on risk and unpredictability, as well as financial literature on investment strategies, would provide deeper understanding and context.