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When Should You Actually Sell Your Stocks

When Should You Actually Sell Your Stocks?

profileSudhan P


There’s a famous maxim in the investing world that goes like this:

“Buying is easy, selling is hard.”

We can spend weeks and months analysing a company.

But when the company’s shares crash for temporary reasons, we might panic-sell in an instant due to fear, erasing all our efforts spent on doing our due diligence on a stock.

That emotionally-driven action would be detrimental to our long-term investment returns.

So, here are some guidelines to help us determine rationally when to sell a particular stock.

(Hint: Selling due to a stock market crash is not one of them.) 

Source: Giphy

TL;DR: When Should You Actually Sell Your Stocks?

  • When the business fundamentals have changed
  • When you’re rebalancing your portfolio to reduce risks
  • When there’s a change in your lifestyle/life stage
  • When you want to invest in better opportunities
  • When the initial investment decision was a mistake

Disclaimer: The information provided by Seedly serves as an educational piece and is not intended to be personalised investment advice. ​Readers should always do their own due diligence and consider their financial goals before investing in any stock. 

Business Fundamentals Have Turned for the Worst 

When investing in stocks, it is imperative that you outline exactly why you’re buying the stock in the first place and how it fits into your portfolio.

Some of the factors are whether the company has:

  1. A wide economic moat;
  2. A track record of growth (growing revenue, net profit and cash flow);
  3. High gross and net profit margins;
  4. A strong balance sheet (more cash than debt);
  5. High return on equity;
  6. Honest and competent management; and
  7. Favourable long-term prospects.

If something has fundamentally changed within the company or its industry that no longer aligns with the reasons you’ve set out since you bought the stock, it could be a good reason to sell.

A great example is that of the telecommunications industry.

Telcos were popular among investors back in those days as they were seen as defensive.

They provided essential services that no one else could. No matter what the economy went through, people would still need a telco subscription service to communicate with their loved ones.

And that gave the telcos predictable recurring revenue and cash flow.

However, the grip by the incumbent telcos on the consumers was loosened when competitors and services such as new telcos, WhatsApp, and Netflix started to enter the market.

Keen competition has caused telco stocks like Singtel and StarHub Ltd (SGX: CC3) to perform poorly over the past couple of years.

Source: Yahoo! Finance

From the chart above, we can see that Singapore’s stock market benchmark, the Straits Times Index (as represented by the purple line), has clearly outperformed Singtel (dark blue line) and StarHub (light blue line) over the last five years.

Rebalancing Your Portfolio

With a diversified portfolio, there may be times when a certain asset rises beyond or falls below your allocated percentage.

For example, an aggressive investor with a growth-focused portfolio may have a stock, stock A, that has seen substantial gains, causing it to go above his/her allocated weightage of 30%.

In order to mitigate risks, he/she may sell a portion of the stock A and reallocate the funds into stock B that has gone below the allocated weightage, essentially rebalancing the portfolio and bringing back the weightage of stock A to 30%.

This helps you better manage your investments during uncertainty as you’re aware of your risk exposure.

When There’s a Lifestyle Change

Selling a stock when you’re in a different life stage or when there’s a change in your lifestyle is also a valid reason.

For younger investors with a typically larger risk appetite, one may consider selling a stock to make a down payment for a house or a car.

If you’re a successful investor who is ready for retirement or the FIRE life, you may also consider selling your stocks for income or reallocating funds to dividend paying stocks.

Better Investment Opportunities

The next reason to sell is to raise funds to buy into a better company with better prospects than the current invested one.

This is harder to determine than the first two as it’s never easy to know for sure if the other company is indeed a better buy than the one we are vested in.

A clear-cut example of this would be when we are vested in a local public transport company, but we feel a tech business listed in the US with worldwide operations has better growth opportunities, allowing us to grow our money faster.

In that case, it could be worthwhile to sell the former’s shares and buy the latter’s stock.

When a Mistake Has Been Made 

The last point is one that is pretty obvious.

This happens when we make a mistake in the original purchase of the stock, and the company is not as favourable as originally thought to be.

Source: Giphy

To handle this situation, we must have self-control and the ability to be honest with ourselves.

Oftentimes, ego gets in the way, and we may not want to admit that we have made a wrong decision.

But there are opportunity costs involved by holding on to a losing stock as the money could be put into far better companies.

When we realise we have made a mistake with our investment and we thoroughly learn from it, we won’t make the same error again in the future, helping us grow as an investor.

I have made many mistakes myself in my investing journey, and one of them was buying into Sembcorp Industries Limited (SGX: U96) after the 2014 oil price crash.

From that episode, I learnt to avoid commodity-related business as it’s hard to predict the price trajectory of a commodity like oil.


Many investors approach the buying of shares methodologically but don’t have a similar stringent framework when it comes to selling shares.

Selling a company’s shares due to fear of a market crash is a major no-no.

Or pressing the “Sell” button because the stock has gone way up in price (without any regard to growth prospects) is also not encouraged.

Hopefully, by internalising these reasons to sell a stock, we can become better investors over the long run.

Further reading: If you want to learn more about when to sell stocks, you can also check out Chapter 6 of Philip Fisher’s well-known book Common Stocks and Uncommon Profits and Other Writings.

About Sudhan P
It isn't fair competition when only one company in the world makes Monopoly. But I love investing in monopolies. Before joining the Seedly hood, I had the chance to co-author a Singapore-themed investment book – "Invest Lah! The Average Joe's Guide To Investing" – and work at The Motley Fool Singapore as an analyst.
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