I admit it: I’m bad at selling shares

If you wouldn’t buy the business today, why hold it now?

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.

As investors, all of us have our own individual weaknesses. Mine is simply stated: I’m very bad at selling.
 
Over the years, I’ve done well out of shares such as Greggs, Reckitt Benckiser, Compass, GKN and Weir, for instance. In each case, the shares soared in value, and then slid back.
 
I’m still well up, of course.
 
But in theory, I could have sold, and banked decent profits – profits rather higher than I’d be looking at, were I to sell now.

Sticking to a strategy

This aversion to selling isn’t necessarily a mistake.
 
As a strategy, I pursue ‘long term buy and hold’, for one thing. So jumping in and out of shares is clearly inconsistent with that objective. And as objectives go, I’m in good company: remember Warren Buffett’s oft-repeated remark about his ideal holding period being forever.
 
For another thing, these days I’m primarily an income investor – and certainly so as individual shares go, rather than index tracker funds and ETFs.
 
So to that extent, hefty capital gains are irrelevant. At best, all they provide is an assurance that the stock market thinks that my shares are decent picks, worth bidding up the price to acquire.
 
And at worst – were I to use a broker that charges portfolio fees based on portfolio value – all a rising share prices does is add to my costs.

Run winners, sell losers

Some investors take a very different approach. In particular – like me – they tend to ‘run winners’, namely hold on to shares that have done well, rather than take profits.
 
But they’re also keen to cut their losses and dump shares that have performed poorly, or announced profit warnings or similar bad news.

Here again, I’m very bad at selling. I still hold a large stake in Tesco, for instance. I held on to Lloyds as it plunged during the banking crisis.
 
And in neither case could I take refuge in the fact that, as an income investor, it’s the dividends that count: in both cases, the companies cut their dividends completely – Lloyds for six years.

Hanging on for recovery

To behavioural psychologists, this kind of behaviour is classed as ‘loss aversion’.
 
Investors don’t like to lose money, goes that argument, so they hang on to shares in order to avoid recording a loss.
 
Well, yes. But I’m also acutely aware that shares (and the companies behind them) can recover, and sometimes quite quickly.
 
Businesses can ‘self heal’ as managements take remedial action, for instance, and the stock market can re-rate a share as it takes a different view of its prospects.
 
Indeed, one of the consequences of a strategy of opportunistically buying beaten-down shares and sectors is that it’s difficult to call the bottom: the fact that a share has fallen in value doesn’t mean that it won’t continue to head lower.

So when do I sell?

Well, part of the answer is that I rarely need to. That’s not arrogance: it’s just a reflection of the fact that, like our analysts on the Motley Fool Share Advisor service, I tend not to buy without giving careful consideration to the company in question.
 
Typically, I’ll have identified it months in advance, and will simply have been waiting for an attractive entry level before buying.
 
Again, it’s a strategy that has consequences. As I’ve remarked before, international drinks giant Diageo has never quite got cheap enough for me to push the buy button. Ditto specialist engineering firm Renishaw, and a number of other sound businesses.
 
Instead – again like my colleagues at Share Advisor – I’m most tempted to sell when the original investment thesis has materially altered.

All change

There’s nothing particularly complex or abstruse about this. It’s simply a way of saying that the company in question no longer ticks the boxes that it did when the shares were bought.
 
And I suspect that I’m – unusually – about to reach that conclusion in respect of a share that I hold, namely publishing firm Pearson.
 
I think of it as the “Woolworths test” – a nodding reference to the criticism often levied at the troubled high-street retailer before it finally collapsed.

Namely, if it didn’t exist, would you invent it?

A different focus

Or, in the case of shares, would you buy this same business today?
 
Back when I bought into Pearson, it owned publishers Penguin Group, the Financial Times, and a 50% stake in The Economist. It’s since sold the Financial Times, disposed of the stake in The Economist, and merged its Penguin consumer books divisions with German giant Bertelsmann.
 
In addition, it’s declared itself to be 100% focused on education, and on the American education market in particular – which happens to be struggling.
 
It’s not, in short, the same business that I bought into. And I wouldn’t buy into it today. So I suspect that I’ll soon be selling Pearson – despite the loss that I’ve made.

Malcolm owns shares in Greggs, Reckitt Benckiser, Compass, GKN, Weir, Tesco, Lloyds Banking Group, and Pearson. The Motley Fool owns shares in GKN, and has recommended shares in Reckitt Benckiser, Weir, Diageo and Renishaw.

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 »