With so much physical and emotional capital invested in buying shares, it would be easy to think the hard work of investing is over once you’ve hit the buy button. In reality, the strain of stock selection is more than matched by the big question that comes some time later: when to sell?

Deciding why and when to sell shares is one of the biggest uncertainties in the minds of many investors. And to an extent, that’s no surprise. After so much effort upfront, it’s understandable that decisions about when to sell a holding often lie in a hazy place somewhere on the horizon.

But over time, the risk of not having an exit plan is that you become a hostage to some destructive cognitive and emotional pressures. These unseen and sometimes instinctive influences can be a drag on your portfolio and may even make your best investments turn sour.

Why is selling so hard?

Buying and selling are both highly personal decisions. In turn, they depend on very personal components like your strategy, risk appetite, personality and short- and longer-term objectives. As such, a carefully crafted investment approach should ideally cover what to buy as well as when to sell. Yet many seem focused on the former but much vaguer on the latter.

In the stock market, some of the clearest thinking on selling actually comes from technical traders like Charles Kirkpatrick, William O’Neil and Mark Minervini (and others in the same mould). Successful trading demands a cast iron approach to risk management. So traders preserve their capital by being very strict about selling trades that haven’t performed as expected, as well as those that have.

In his book Think and Trade Like a Champion, Minervini devotes an entire chapter to selling, and focuses on the challenges of how to exit both winning and losing trades. As he explains: “As with everything in trading, selling brings its own emotional pressures. Selling at a profit is not as easy as it looks - and it’s fraught with emotions.

“The best - in fact, the only - way to control these emotions and keep them from undermining your success is with sound trading rules. Otherwise, you’re always going to get caught in the crossfire of your own excitement and doubt.”

In the construction of your own trading rules, here are a few of the more treacherous behavioural pitfalls that…

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