Is 'sell' really a dirty word? How to know when to let go of your ASX shares

With tax time looming and the S&P/ASX 200 Index (ASX: XJO) up around 35% since its March lows, there's no better time to review the ASX shares in your portfolio.

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Share investor with chess pieces deciding to buy or sell ASX shares

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With ASX shares now getting a grip on their earnings following the recent crash that left most of them oversold, it's time to take stock of what the current 'recalibration' means for the overall market. The end of the financial year is looming large, and with the S&P/ASX 200 Index (ASX: XJO) up around 35% since falling to 4,546 points on 23 March, there's no better time to review the ASX shares in your portfolio.

Cutting your losses on non-performing shares is never easy. What makes it doubly hard is broker aversion to the S-word, with their recommendations typically gyrating between 'buy', 'hold', and 'accumulate'.

But sometimes it simply pays to bite the bullet and take a loss. This, incidentally, can have some favourable tax considerations: notably the ability to offset losses against future gains. On the flipside, an attempt to avoid paying tax on a capital gain is insufficient reason not to sell a stock when you should.

Take gains off the table while you can

But it's not only the rotten apples that you should consider selling down. Sometimes it's equally important to know when to lock in some profit. That doesn't necessarily mean existing a quality stock completely.

For example, many shares have seen major gains recently. One strategy for shareholders could have been to reduce their stake, and potentially buy back in following a share market correction, or via corporate activity. Due to a slew of recent capital raisings, some shareholders have been able to offload shares only to top up their holding at attractive discounts to the current price.

Admittedly, there's nothing wrong with letting your profits run, especially if future upside is yet to be factored into the price. However, savvy investors know when to take profits before prices potentially fall.

The art of selling shares is also considerably less predictable than buying, so it pays to have a solid strategy.

Do your reasons for selling stack up?

Shares that have enjoyed a strong run up may start to look decidedly overheated. This often triggers smart investors to sell out at a price they perceive to be close to the top. While calling the top (or bottom) is something even most professional investors struggle with, one tell-tale sign that the price is looking decidedly 'toppy' is how far it rallies above any reasonable estimate of value.

One of the investment truisms coined by Warren Buffett is that the share price cannot continue to outperform the underlying business forever. At some point, something has to give. Unless there are future upsides to current valuations, the closer a company's share price gets to its intrinsic value, the greater the potential risk of holding onto the stock.

So when the share price runs way ahead of value and for no justifiable reason, don't get too greedy and don't simply rely on raw exuberance or momentum. Equally important, remember that it's over the short-term that the gap between the share price and the underlying performance of the business will be at its widest.

If you're unsure of where a share price is heading, ask yourself this: If a stock trades at $10 today, while the intrinsic value is $20, do you expect the price to rise to $25 next year, and maybe $35 three years later? Can you afford to wait? If the answer's yes – consider holding. If not – consider selling.

While it's not rocket science, the conclusion you come to should be based on research into future valuations, rather than an educated hunch.

Take the money and run

You may also think about selling-down stocks that are starting to slip into what's known as value-trap territory. Typical candidates include former share market darlings. While their best days might be behind them, these ASX shares can still attract investors due to their sheer size, dividend history or an instantly recognisable household brand.

Remember, shares that appear to be under-priced have typically become that way for good reason. For example, bad management, declining business performance, declining competitive edge (due to regulatory or technological change), excessive debt, an over-priced acquisition, or an unaffordable dividend payout ratio.

These factors will result in declining intrinsic valuations and future growth that's less promising. This will eventually find its way to the share price. Unless you sell these stocks, they will continue to drag down the value of your overall portfolio.

The trick is to take these suppurating time-bombs – which, I'm sorry to tell you, are destined to be liquidated, enter receivership or administration – out of your portfolio before they do greater damage. Before they do, why not deploy what value is left in these lame shares into the market's next best opportunities.

Motley Fool contributor Mark Story has no position in any of the stocks mentioned. The Motley Fool Australia has no position in any of the stocks mentioned. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy. This article contains general investment advice only (under AFSL 400691). Authorised by Scott Phillips.

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