Key things to consider before selling an investment

Selling an investment is the one aspect of investing that often goes undiscussed. But it is an integral part of the whole long-term process. Here are some key reasons to consider selling an investment.

Selling an investment might be on your mind when markets are down. In recent weeks, financial markets have been anything but calm. 

With headlines screaming about inflation fears, geopolitical tensions, and unpredictable shifts in major indices such as the S&P 500, it’s no surprise investors are feeling jittery. 

For many, the instinct might be to sell off investments and retreat to the safety of cash. But selling in a panic rarely pays off. Deciding to offload your investments is a big move, one that deserves careful thought, not a knee-jerk reaction to the latest market wobble. 

Whether you’re a seasoned investor or someone managing a modest portfolio, there are critical factors to weigh up before hitting the sell button. 

The most important considerations for when you should sell an investment should reflect your own life, long-term financial plans and the fundamentals of your portfolio. 

We’re going to look at the five big reasons why you might be considering selling investments, including: market turmoil, chronic underperformance, cashing in on success, portfolio rebalancing, and planning for retirement.

1. Market turmoil

Let’s start with the elephant in the room – market turmoil. Right now, it’s hard to escape the sense of unease particularly as the President of the US plays fast and loose with economic warfare. 

It’s tempting to see red numbers on your investment app and think: ‘time to get out!’ But selling during a downturn often means locking in losses rather than escaping bigger losses.

History tells us markets tend to respond sharply and build slowly. This makes the immediate sense of loss more painful than the gratification of gains over time. 

Investment markets across the world and spanning a wide range of sectors have weathered storms such as the 2008 Great Financial Crisis (GFC) and Covid, only to recover and climb again. 

That said, turmoil isn’t always just noise. If the current volatility is tied to deeper structural issues – such as a prolonged economic shift, or a sector-specific collapse – it might signal a need to reassess. 

The key here is to put into perspective whether movements are down to short-term panic or long-term trends. 

Samantha Rosenberg, co-founder and chief operating officer at investing app Belong comments: “When markets drop, it’s crucial to slow down and step back from the noise.

“Sensational headlines and spicy soundbites from politicians may grab attention, but they rarely support sober decision-making. Quite the opposite, in fact. The market-wide flurry tends to fuel fear, triggering our inherent loss aversion. 

“With this, a little bit of perspective goes a long way. At the time of writing, the market is approximately 9% off its all-time high, which is about where it was in September 2024. Therefore, if you invest today, you are getting the same price you would have got if you invested six months ago.

“Market fluctuations are normal, and reacting impulsively often does more harm than good. After all, you don’t make a loss when the stock price falls; you make a loss when you take an active decision to sell your portfolio while the price is down.”

Ask yourself: Is this a temporary blip, or a sign of something more systemic? Look at your investment’s fundamentals – company earnings, sector outlook, or fund performance – and compare them to broader market conditions. 

If the foundations still hold, holding tight might be wiser than selling into a dip. Timing the market is notoriously foolhardy, even for the pros.

2. Chronic underperformance

Beyond the daily ups and downs, there’s another reason to consider selling: chronic underperformance. Maybe you’ve held onto a stock or fund that’s been lagging behind its peers for years. 

Take the UK retail sector as an example – some high-street names have struggled to adapt to online competition, leaving investors with lacklustre returns. If an asset consistently fails to deliver, it’s worth asking whether it’s still pulling its weight in your portfolio.

Underperformance isn’t just about comparing numbers to a benchmark such as the FTSE All-Share Index. It’s also about opportunity cost.

Could that money be better invested elsewhere? Before you sell, dig into why it’s underperforming. Is it a temporary hiccup – like a company navigating a tough quarter – or a sign of irreversible decline? 

Check analyst reports, earnings calls, or even news about leadership changes. If the outlook remains grim with no turnaround in sight, selling might free up capital for more promising opportunities. 

Caution is however warranted – sometimes investments that have underperformed for years are forgotten by the market and due a turnaround. This could be an indication it is worth adding more to that position as its potential for a rebound increases. But it is essential to understand the fundamentals behind the underperformance and whether they are cyclical or systemic issues.

And be sure to factor in any tax implications, like Capital Gains Tax (CGT), which could nibble away at your proceeds.

3. Cashing in on success

On the flip side, sometimes selling isn’t about dodging losses – it’s about pocketing wins. Imagine you invested in a tech firm a few years back and its share price has soared thanks to a breakthrough product. 

Your initial stake is now worth considerably more. Well done! But here’s the dilemma: do you hold on for more growth, or cash in before the tide turns?

This is where greed and realism collide. Selling a winner can feel counterintuitive – why ditch something that’s doing so well? If your investment has hit a personal target (say, a 200% return), or if valuations look overstretched compared to earnings, it might be time to take profits. 

You don’t have to sell everything – trimming your position can lock in gains while keeping some skin in the game (more on rebalancing below).

For UK investors, remember the CGT allowance (£3,000 as of April 2024) – selling strategically can help you stay within it depending on your holdings. 

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4. Portfolio rebalancing

Investing isn’t always  a set-it-and-forget-it game. Over time, your portfolio can drift out of shape. 

Maybe your equity holdings have ballooned during a bull market, leaving you overexposed to stocks, while your bonds or cash sit neglected.

 Or perhaps a single sector now dominates your mixture. This is where portfolio rebalancing comes in, and selling might be part of the fix. Rebalancing is an important step to ensure your portfolio – either through success or not – has developed too much exposure to one particular market or asset class.

Hal Cook, senior investment analyst at investment platform Hargreaves Lansdown explains: “It’s important to check if your portfolio needs more diversification and understand where you are invested.

“The problem is that determining exactly how diversified your portfolio is not always as easy as you might think. For example, an investor could buy a global fund, a US fund and a technology fund where there could be more overlap in these funds than it seems.

“The MSCI World index currently has 74% exposure to the US. The MSCI technology index has 90% exposure to the US. The MSCI World and MSCI USA indices have 25% and 31% exposure to technology respectively, which is likely a bigger overlap with the pure technology fund than you may have thought. 

“To top it off, all these indices have the same top three investments: Apple, Nvidia and Microsoft. So, although you are buying three seemingly quite distinct funds, in reality there is a big overlap in the underlying holdings.

“Conversely, an investor may have a portfolio with one provider which only has one or two holdings in it. On the face of it, this would appear to be the very definition of a concentrated portfolio. However, it’s quite possible that they might have other portfolios with other providers, meaning that overall their investments are quite diversified.”

Rebalancing is about risk management. A portfolio that’s too stock-heavy could take a bigger hit in a crash, while one skewed towards low-yield bonds might not grow enough to beat inflation. 

The classic 60/40 split (60% stocks, 40% bonds) might not suit everyone, but whatever your target allocation, check it annually. Selling overweight assets – like a tech stock that’s tripled – can bring things back in line. 

“The important thing for all investors is to understand exactly what they own, whether they have a concentrated portfolio or not, and if they do, that they are happy with the risks that poses,” Cook adds.

It’s not about abandoning winners though. It’s about ensuring your portfolio reflects your goals and risk tolerance. And if markets are turbulent, rebalancing can double as a chance to buy undervalued assets with the proceeds.

5. Retirement

Finally, retirement looms large for many investors. If you’re nearing that milestone, selling investments might be less about market conditions and more about life planning. 

The closer you get to drawing down your pension or living off your portfolio, the less risk you might want to stomach. A 30-year-old can afford to weather a multi-year bear market. A 65-year-old, not so much.

This doesn’t mean selling everything at once. It’s about shifting gears. Moving from growth-focused assets (such as small-cap stocks) to income-generating ones (such as dividend-paying blue-chips or gilts). 

Selling growth assets to fund a more stable income stream can make sense, but timing matters. 

Offloading during a downturn could shrink your nest egg, so consider a phased approach, selling gradually as retirement nears. And don’t forget tax wrappers such as ISAs or SIPPs, which can shield your gains from HMRC’s grasp.

For those near to these kinds of decisions it is important to consider whether financial advice would be a beneficial and affordable option. 

This is especially the case with products such as pensions which can have significant tax rules to navigate. Plus, important considerations such as inheritance tax (IHT) start to come into play (although it is important to have in mind at any age depending on your net worth). 

Think, don’t panic

Market turmoil might be the spark that gets you thinking about selling, but it shouldn’t be the driver. Whether it’s cutting losses on a dud, cashing in a winner, rebalancing your mix, or preparing for retirement, every decision needs a clear rationale. 

Start by revisiting your goals. Why did you invest in the first place? Then crunch the numbers: fees, taxes, and potential returns all play a part. And if you’re unsure, a chat with a financial adviser can cut through the noise.

Selling investments isn’t a sign of defeat, it’s a strategic choice. But in a world of 24/7 news and market swings, the biggest risk isn’t always the market itself, it’s acting rashly. So, take a breath, weigh your options, and make your move when the time’s right. Your future self will thank you.

This article is provided for informational purposes only. All investing carries risk and you could lose money. If in doubt, seek professional advice.

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