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

Investing Articles

Is this the best time to invest in a Stocks and Shares ISA – or the worst?

Investors looking to use this year's Stocks and Shares ISA may be deterred by current market volatility but this could…

Read more »

Fireworks display in the shape of willow at Newcastle, Co. Down , Northern Ireland at Halloween.
Investing Articles

I asked ChatGPT if the FTSE 100 would hit 12,000 before 2027

Is the 12,000 mark possible for the FTSE 100 in 2026? Let's take a quick look at what ChatGPT has…

Read more »

DIVIDEND YIELD text written on a notebook with chart
Investing Articles

With an 8.8% yield are Legal & General shares a once-in-a-decade opportunity?

Legal & General shares are back to where they were a whole 10 years ago. Harvey Jones is tempted by…

Read more »

Young female hand showing five fingers.
Investing Articles

5 shares close to 52-week lows. Could they rise in value by 44% over the next year?

Identifying value shares is the key to investment success. These five UK stocks are trading close to their 52-week lows.…

Read more »

Black woman using smartphone at home, watching stock charts.
Growth Shares

Up 25% in a month, this growth share is flying despite the market falling!

Jon Smith points out a growth share that's bucking the broader market trend in recent weeks, with momentum potentially continuing…

Read more »

British flag, Big Ben, Houses of Parliament and British flag composition
Investing Articles

£20,000 invested in a Stocks and Shares ISA on 7 April is now worth…

The Stocks and Shares ISA is a proven wealth-building machine. But was one year ago a great time to be…

Read more »

Man hanging in the balance over a log at seaside in Scotland
Investing Articles

The stock market hasn’t crashed yet. Make these 3 moves before it does

If an investor is prepared for a stock market crash they can soften the blow, and more importantly, capitalise on…

Read more »

Investing Articles

£1,000 buys 300 shares in this red-hot UK gold stock with a P/E ratio of 3

This UK-listed gold stock is on fire at the moment amid the historic rally in precious metals. But it still…

Read more »