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How to Save Taxes by Selling Your Losing Investments


As the year-end approaches, many investors are looking for ways to reduce their tax bills. One strategy that can help is tax-loss selling, which involves deliberately selling an investment at a loss to offset your other investment gains.

Tax-loss selling can be used for any investments subject to capital gains tax, such as stocks, bonds, ETFs, mutual funds, and even rental properties or cottages. However, it does not apply to investments held within registered accounts like RRSPs or TFSAs, as those gains are already sheltered from taxes.

To benefit from tax-loss selling, you need to realize your capital losses before the end of the year. This means you have to sell your losing investments by December 27, as trades generally settle two business days after the transaction date.

Once you trigger your capital losses, you can use them to offset any capital gains from the same year. But if you have more losses than gains, you can also carry them back to offset gains from the previous three years, or carry them forward indefinitely to offset future gains.

This way, you can reduce or eliminate the taxes you owe on your investment returns, which means more money in your pocket.

However, tax-loss selling is not a one-size-fits-all solution. There are some factors you need to consider before implementing this strategy, such as:

  • The impact of transaction costs and timing on your net returns
  • The risk of triggering the superficial loss rule, which denies the capital loss if you buy back the same or identical property within 30 days of selling it
  • The potential opportunity cost of missing out on a rebound in the price of the sold investment
  • The alignment of the strategy with your overall investment goals and risk tolerance

Therefore, it is advisable to consult with a financial advisor before taking any action. A financial advisor can help you evaluate your unique financial situation and determine if tax-loss selling is suitable for you.

Tax-loss selling can be a powerful tool to boost your investment returns by saving taxes. But it is not a magic bullet. You need to weigh the pros and cons carefully and make sure you are not letting the tax tail wag the investment dog.

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