Singapore’s Straits Times Index (SGX: ^STI) crossed the 4,900 mark for the first time last week.
Buoyed by the bull run, JP Morgan (NYSE: JPM) has raised its target for the index to 6,000 by the end of this year.
Yet, a recent poll we ran revealed that investors are thinking about selling.
Here’s the thing: there are good reasons and bad reasons to sell.
So, let’s talk about them.
Good Reason #1: Your life needs the money more than the market does
Remember: investing is a vehicle to get you where you want to go.
You have heard me say this before: you are successful when you achieve your own goals — not because you beat the market and not because you held on longer than your kopitiam buddy.
But because investing did what it was supposed to do: fund a better life.
So, if taking some money off the table helps you in your life, that’s a good reason.
At the same time, if you’re like my co-founder David Kuo, who is not bothered by stock prices and is happy to receive dividends every month, there’s nothing wrong with holding.
Good Reason #2: Your wealth keeps you up at night
Here’s something few investors talk about openly.
Sometimes a stock does so well that it becomes too large a part of your portfolio.
What started as a modest position is now half your net worth.
You check the stock price first thing in the morning and last thing before bed.
That’s not investing; that’s anxiety with a brokerage account.
Selling a portion to bring a position back to a size you’re comfortable with is not a sign of weakness.
You’re not giving up on the business — you are right-sizing the risk so that you can think clearly.
The best investment decisions are made from a place of calm, not a place of fear.
If trimming lets you sleep soundly, that’s a return no stock can match.
Good Reason #3: The business underneath has permanently changed
Notice I said “business” — not “stock price.”
For instance, DBS Group (SGX: D05) saw its profits dip during COVID.
That was temporary.
The bank’s franchise, its digital capabilities, its deposit base — none of that was damaged.
Selling during a temporary setback would have cost you dearly.
But if a company’s competitive advantage is being eroded, if management is destroying long-term value, if the industry has structurally shifted — those are permanent changes.
Sell for permanent damage.
Hold through temporary discomfort.
The difference between the two will define your returns over a lifetime.
Good Reason #4: You made a mistake you now understand
We all make them, and I’m no exception.
Sometimes you buy a stock based on a thesis that turns out to be flawed.
Not because the market moved against you, but because your original reasoning was wrong.
Selling to correct a mistake isn’t a failure.
It’s a hard-won lesson that helps you make better decisions in the future.
The real failure is holding a mistake because you can’t admit you were wrong.
If Warren Buffett can publicly admit an error with his stocks, so can we.
Get Smart: The one terrible reason everyone uses
“The STI is at an all-time high. Surely it must come down.”
Think about what you’re really saying: the business is doing well, the market recognises it, and therefore you should sell.
Does that make any sense?
Here’s what nobody tells you: the moment you sell, one anxiety is replaced by another.
“Should I sell?” becomes “when do I buy back?”
And that second question has no good answer.
Again, there are good reasons to sell.
If you find yourself in that position, how should you go about selling your stocks?
That’s a topic we will be exploring at The Smart Dividend Portfolio on 12 February 2026.
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Disclosure: Chin Hui Leong owns shares of DBS Group.
