Why it’s so hard to run winners

Introducing the biggest foe in your investing career… yourself.

The content of this article was relevant at the time of publishing. Circumstances change continuously and caution should therefore be exercised when relying upon any content contained within this article.

You’re reading a free article with opinions that may differ from The Motley Fool’s Premium Investing Services. Become a Motley Fool member today to get instant access to our top analyst recommendations, in-depth research, investing resources, and more. Learn More.

Ever taken profits on an investment at the slightest whiff of volatility only to see its share price soar higher a few days/weeks/months later? Don’t despair, most of us struggle to keep our fingers away from the ‘sell’ button, even when things seem to be going swimmingly. Here’s why.  

Know your enemy

The tendency of investors to sell their winners (and retain their losers) is what behavioural finance boffins call the disposition effect. It happens because we’re primed to do what makes us feel good and avoid things that cause regret.

The disposition effect has its roots in the work of psychologists Kahneman and Tversky. They believed most people looked on losses and gains differently. When faced with two options, we’re more likely pick the one presented in terms of potential gains over the one presented in terms of possible losses. 

Here’s an example. If I were to give you the choice of a) winning £20 or b) winning £40 and then losing £20, what would you do? Research shows that people would pick the option a), simply because we’re hardwired to avoid the greater emotional impact caused by option b). By choosing the latter, we’d inadvertently make £40 our reference point. To then walk away with anything less would feel like a loss, even though the actual choice doesn’t matter — you get a crisp £20 note whichever option you go for.

It works the same way in investing. We’re far more likely to realise a small gain rather than hold on for a potentially far larger one because the pain we’d feel if the latter were to then reduce would be too great. Besides, a profit is a profit. It feels good to be right.

To make matters worse, we cling to losing stocks. After all, in addition to hurting financially, it would involve us acknowledging we’d made a mistake at some point in our selection process. 

The real kicker in all of this is that research has shown that the stocks sold by investors (the winners) tend to continue outperforming the losers they hang on to. 

To be clear: over a long enough time period, the disposition effect could seriously reduce your chances of achieving financial independence. So, knowing that we have a habit of behaving like this, what can we do to reduce our susceptibility to it?

Resist temptation

Start by ignoring your gains. Instead, focus on re-evaluating your winner. Was the company undervalued to begin with? While it now trades at fair value, that’s still no reason to sell if the story hasn’t changed. Even companies with seemingly inflated valuations can be worth sticking with if the future looks rosy. That’s why I remain invested — for now — in companies like Blue Prism and boohoo.com, despite both registering incredible share price gains over the last year.

Also consider the consequences of selling. Is it worth taking profit on a seemingly great company to reinvest in what might turn out to be a very average alternative? If it’s true that great investors hang out with great companies, why leave the party so soon?

Remember that successful investing is not about how many winners you own but how profitable they are. A few great stocks held for the long term can be far more rewarding than a portfolio full of average ones.

Paul Summers owns shares in boohoo.com and Blue Prism. The Motley Fool UK has recommended boohoo.com. Views expressed on the companies mentioned in this article are those of the writer and therefore may differ from the official recommendations we make in our subscription services such as Share Advisor, Hidden Winners and Pro. Here at The Motley Fool we believe that considering a diverse range of insights makes us better investors.

More on Investing Articles

Young mixed-race couple sat on the beach looking out over the sea
Investing Articles

Looking for a £750 monthly passive income? Here’s how much it takes

The idea of buying dividend shares for their passive income potential can sound promising. How might the nuts and bolts…

Read more »

Calendar showing the date of 5th April on desk in a house
Investing Articles

£20,000 in this ISA portfolio would generate £1,400 in passive income

Ben McPoland presents a ready-made Stocks and Shares ISA portfolio containing five UK names that as a group currently yield…

Read more »

Person holding magnifying glass over important document, reading the small print
Investing Articles

The most underrated stock in the FTSE 100?

Nobody seems to like the FTSE 100’s water utilities. But could Severn Trent be the biggest opportunity that investors aren’t…

Read more »

a couple embrace in front of their new home
Investing Articles

£1,000 now buys 1,075 Taylor Wimpey shares. Worth it for the 8% dividend yield?

There’s a massive dividend yield on offer from his well-known UK housebuilder right now. But what are the risks for…

Read more »

Night Takeoff Of The American Space Shuttle
Investing Articles

Want to invest in SpaceX, Revolut, and TikTok? Consider buying this FTSE 100 stock

Ben McPoland thinks this FTSE 100 investment trust is a top stock to consider buying to gain exposure to the…

Read more »

Calendar showing the date of 5th April on desk in a house
Investing Articles

Here’s my Stocks and Shares ISA plan for 2026/27

Stephen Wright has a clear plan when it comes to investing in his Stocks and Shares ISA. But do the…

Read more »

Two elderly people relaxing in the summer sunshine Box Hill near Dorking Surrey England
Investing Articles

Where to look for safety in today’s stock market?

Stephen Wright has been looking for safety in a specific place in today’s stock market. And Warren Buffett’s firm has…

Read more »

Young black colleagues high-fiving each other at work
Investing Articles

This 5-share ISA could deliver an amazing second income of £762 a month

As the world’s stock markets plunge, many yields are rising. James Beard looks at five shares that could generate an…

Read more »