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When is the right time to pull the plug on an investment?

When I said recently that it can be better for an investor to travel than to arrive, I was referring to the Japanese market’s surge to within a whisker of the peak level it reached back in 1989. But the Nikkei 225 is not the only investment begging the question of whether or when to sell. Recently both the US and India hit new all-time highs.

Of all the questions facing an investor, when to sell is perhaps the hardest. Not least because, unlike with the decision to make an investment, selling it requires you to undo something in which you have already invested intellectual, emotional and financial capital. That is psychologically hard to do.

There are plenty of reasons to sell an investment. Some of them are good, some bad. It’s important to understand why you are deciding to pull the plug.

One of the reasons people struggle to decide whether or not to sell is that they don’t know why they bought in the first place. It is impossible to judge whether your investment thesis has changed if you don’t know what it was at the outset. So, write it down. Keeping an investment diary can give you something tangible against which to measure your decision. It’s good to remind yourself why you got together all those years ago!

Good reasons to sell

Changing circumstances are a good reason to change your mind. The danger here is that you’re not the first to notice that things are different. Markets are pretty good at pricing in change. But what they are less good at is assessing the scale or durability of that change. This is why selling after bad news can still make sense. Humankind cannot bear very much reality. It can take quite some time for the penny to drop, and a share that has fallen by 50% can still lose another 100%.

Another good reason to sell is because you made a mistake. We all do it. Indeed, a successful investor can be one who simply makes more good decisions than bad. If you run your profits and cut your losses, a hit rate of only 50% might be good enough.

One underrated reason to sell is to reduce the risk of holding onto a winning trade. I once advised a friend who had made a fantastic investment to sell enough shares to reduce his purchase cost to zero. It’s much easier when it’s other people’s money. At the time he could have done this by selling as little as a third of his holding. Doing so would have ensured that the worst possible outcome would be just getting his money back. He didn’t and it wasn’t.

Most of the other good reasons for selling are personal. Your risk appetite may have changed, and you can no longer tolerate the potential downside of an investment. You might simply need the cash. That, after all, is the reason we invest in the first place. To be able to spend our money one day in the future. Eventually, that day arrives. Meanwhile, you might be lucky and find that one or two good investments have shifted your portfolio away from your desired weightings. Rebalancing is a good reason to sell.

Bad reasons to sell

What about the bad reasons to sell? Again, there are many. The worst reason to sell is because you have made a profit. Ironically this is also the easiest circumstance in which to bail out. Securing a profit provides temporary validation. And if the investment fails to notice that you have sold it and continues to rise, it’s easy to look the other way. Having a target price sounds sensible but it rarely makes sense to exit a winning trade. The trend is usually your friend.

Almost as bad is to sell because you have made a loss. At times, it can make sense to draw a line under a failed trade, but never simply because the price has gone down. This tells you nothing except what other investors are doing and how deeply ingrained is your loss aversion. It says nothing about the investment itself or whether you should stay or go.

The only thing worse than acting on the basis of what other investors are doing is responding to what they are saying. By definition, the commentary and news flow around a share that has fallen will be negative. Being a contrarian is a hard trick to pull off consistently, but it is essential. Going against the herd stimulates the same part of the brain as physical pain. It really hurts to be outside the group. But it is madness to do what everyone else is and to expect a different outcome.

One final, really bad reason to sell is because you are scared. If the news headlines are so grim that you want to hide in a corner until things look better, you can be sure every other investor feels the same way. That can be a recipe for abandoning an oversold investment that’s ripe for a rebound. The only worse emotion than fear as a trigger for selling is boredom. Very often we just feel we need to do something. Invariably we shouldn’t.

Sticking with it

Given the propensity for markets to go up over time, the safest default is to do nothing. Time is a great healer. But there are times when the odds are stacked against you making an acceptable return in a reasonable timescale. Signs that the risks outweigh the potential rewards include significantly higher valuations than the long-term averages, very narrow market leadership, and a widely shared consensus. Nothing should get your antennae twitching more than everyone agreeing about something.


Tom Stevenson is an Investment Director at Fidelity International, a sponsor of Firstlinks. The views are his own. This document is issued by FIL Responsible Entity (Australia) Limited ABN 33 148 059 009, AFSL 409340 (‘Fidelity Australia’), a member of the FIL Limited group of companies commonly known as Fidelity International. This document is intended as general information only. You should consider the relevant Product Disclosure Statement available on our website

For more articles and papers from Fidelity, please click here.

© 2021 FIL Responsible Entity (Australia) Limited. Fidelity, Fidelity International and the Fidelity International logo and F symbol are trademarks of FIL Limited.


John Wilson
February 11, 2024

Another reason to sell hasn't been mentioned: the delays and complexities in dealing with investments that have delayed tax documents that delay receipt of tax rebates and multiple "independent" companies.
Most REITs and managed funds take until August or September to provide tax documents, which delay my receipt of tax rebates resulting from franking on other investments. While they do provide diversification benefits, there is a cost - interest payments, time value of money and opportunity cost. The organisations can easily be overcome that moving away from a July-June year, as some REITs do.
A feature of REITs is their tax deferred income, which is not immediately taxable, but does reduce cost base - which requires record keeping by the investor. For heaven's sake, companies have depreciation until an asset is fully depreciated, immediatly reducing their taxable income, and the record keeping is only by the company, not the investor.
What also drives me nuts is the propensity to restructure and the complexity that brings to cost bases. I have held Abacus since the late 1990's as an interest in a particular building, then they added an additional asset with an associated organition, then another and another. In August 2023, they demerged into Abacus Storage King (ASK) and Abacus Group (ABG). To my knowledge, there has not yet been a ruling by the ATO on what the cost base allocation in the demerger should be - 6 months after the event!
While I would like to continue to hold ASK but not ABG, I've had enough and will sell both. That will eliminate delay and complexity that I don't want.

February 09, 2024

I'm firmly in the camp of doing nothing,less than nothing if I can.Summed up in 2 companies, CBA and NAB. $7K each to buy 1,000 shares in each of them when super started.Retire on 30/6/24 and you'll have somewhere between $750 and $850K probably,if there isn't a crash.

The second prize looks like a complete loser compared to the gold medal winner.The second prize winner looks great if you broaden the outlook a little bit and compare it to other things.

I'm now at the stage where I am questioning if the time to do the tax form at the end of the year is worth it. Should I just outsource that and have an extra couple of hours a year for the sheer joy of retirement.

February 09, 2024

I sell the instant management proves incompetent, win or lose. ASX losing millions on the CHESS replacement was one example.

Peter Thornhill
February 08, 2024

As I have neither the time nor the timing skill I prefer to leave this to a specialist team.Thus I use Listed Investment Companies so that I can get on with all the things I love in life.

February 09, 2024

Many LICs don't follow the market, so now you have to figure out if and when to sell each LIC. From personal experience, I suggest this no easier!

Peter Thornhill
February 09, 2024

Graeme, it is quite simple. I have chosen the LIC, Whitefield as it has been around for 100 years and is solely invested in Industrial shares. It will remain in our family for generations to come. If I might add, an apprenticeship in the UK introduced me to this concept. City of London Investment Trust has been around for over 160 years.
Its recent dividend history shows the last 56 years dividends with an increase every year. I''l take that thanks.

Jethro L
February 08, 2024

The George Soros quote comes to mind: it's not how often you have a winning versus a losing trade, but how much you earn when you win compared to when you lose. It would seem to lend itself to letting your winners run, and cutting your losers.


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