While most people are thinking about turkey this holiday season, savvy investors will have taxes on their mind

Selling stocks at a higher value than what they were bought is ideal, but sometimes investments go sour. In such cases, all hope is not lost – at the end of the year, investors can sell investments that provided losses instead of capital gains.

As the year draws to a close, investors have a unique opportunity to engage in a financial technique known as tax-loss selling, or tax-loss harvesting. Although it may sound complicated, tax-loss selling is a relatively simple strategy that can have significant benefits for investors. In this article, we will explore what tax-loss harvesting is and why investors might want to consider participating in this tax planning.

The tax-loss season typically occurs in the last few weeks of the calendar year when investors evaluate their investment portfolios to identify securities that have experienced losses. The idea behind tax-loss harvesting is to sell these underperforming investments, recognize the losses, and then use these losses to offset any taxable gains realized during the year. By doing so, investors can potentially decrease their overall tax liability, in turn keeping more of their investment profits.

The primary reason investors engage in tax-loss selling is to optimize their tax situation

By strategically selling stocks or other assets that have declined in value, investors can offset capital gains they have realized from successful investments, reducing their taxable income. The losses incurred can be used to offset short-term and long-term capital gains, potentially reducing the investor’s tax burden significantly.

Moreover, tax-loss harvesting allows investors to recalibrate their portfolios. By selling underperforming assets, investors have an opportunity to reallocate their capital to potentially more promising investments. This process can help ensure their investment strategy remains aligned with their financial goals and risk tolerance.

It is essential to note that tax-loss harvesting is subject to certain rules and limitations. For instance, the Canada Revenue Agency (CRA) can provide a means of tax-loss selling, but all investments must come from non-registered accounts and does not apply in tax-advantaged accounts such as TFSAs, RRSPs, RESPs and RDSPs. For U.S. investors, the Internal Revenue Service allows for the offset of capital gains with capital losses, but these losses can only offset gains of the same type. Short-term losses can be used to offset short-term gains, while long-term losses can be used to offset long-term gains.

Tax-loss selling isn’t just something to think about in December. If an investor doesn’t think certain stocks will move for 30 days (as this is the amount of time an investor needs to be out of a stock to claim tax loss), now can be the time to start making plans to get ahead of the curve.

Tax-loss season is a crucial period for investors to carefully assess their portfolios and make strategic decisions. Understanding the key factors that impact an investor’s portfolio during this time is essential for optimizing returns and maintaining a healthy balance. One important aspect to consider is the potential for bounce-back in shares that have become largely oversold.

Tax-loss season is when speculation is at its peak

The month of December can be an ugly time for the speculative investor. The monthly returns of an index such as the TSX Venture exchange come into focus and prove their worth.

This tax-loss season could be particularly painful for some stocks, and this has been a brutal year for junior venture type stocks. Take a look at the year-to-date performance of the small-cap-focused TSX Venture.

TSX Venture exchange chart – Jan. 2023 to Dec. 2023. Source: TMX Group.

So far, the TSX Venture has posted a year-to-date return down 4.57 per cent. While the exchange has seen worse performances in recent years, certain underperforming companies could suffer with further selling.

When market conditions are unfavourable, certain stocks may experience significant drops in value, resulting in an oversold state. This occurs when the market has undervalued a stock, potentially creating an opportunity for investors. Oversold shares might have been beaten down because of factors such as negative news, investor sentiment, or broader market trends. However, it is important to approach these situations with caution and consider the trade-offs involved.

Investors often face a dilemma when deciding whether to hold onto or sell their oversold stocks during tax-loss season

Because capital losses are tax deductible, these losses can be used to offset capital gains and reduce an investor’s tax liability on his or her tax return.

Tax-loss selling generally involves investments related to huge losses, and because of this, these sales generally focus on a relatively small number of securities within the public markets. However, it’s important to be aware that if many sellers were to execute a sell order in tandem, the price of the securities would fall.

While the prospect of a potentially lucrative bounce-back might seem appealing, risks are associated with clinging to underperforming assets. One must weigh the potential for future gains against the possibility of further declines and the opportunity cost of tying up funds in a stagnant investment.

The decision to hold or sell oversold shares should be based on a careful analysis of the individual stock’s fundamentals, market conditions, and the investor’s risk tolerance. It is essential to consider the reasons behind the overselling and evaluate whether the stock’s decline is a temporary setback or a reflection of underlying issues.

For instance, if a fundamentally strong company experiences a temporary setback because of external factors, holding onto the stock might be a wise decision. In such cases, there is a chance that the market will recognize the stock’s true value, leading to a bounce-back and potential profits for long-term investors.

On the other hand, if the share price decline is rooted in fundamental problems within the company or its industry, it might be more prudent to cut losses and sell the stock. While it can be tempting to hold on and hope for a recovery, this strategy may result in further losses and tie up capital that could be better used elsewhere.

Making decisions during the tax-loss season requires careful consideration of tax implications

Selling oversold shares at a loss can provide investors with a tax advantage by offsetting gains from other investments, thereby reducing their overall tax liability. This aspect adds another layer of complexity to the decision-making process, as the potential tax benefits need to be weighed against future growth prospects and the opportunity cost of holding onto underperforming stocks.

While tax-loss selling presents a valuable opportunity for investors, it is crucial to approach it with objectivity and a long-term perspective. Merely searching for losses to minimize taxes without considering the investment’s future potential might not be wise. It is essential to weigh the potential tax benefits against the potential future performance of the asset.

Tax-loss harvesting offers investors an advantageous opportunity to optimize their tax situations and potentially reduce their overall tax liability. By strategically selling underperforming investments, investors can offset capital gains realized throughout the year, potentially saving significant amounts in taxes. However, it is vital for investors to maintain a long-term perspective and consider the investment’s future potential when engaging in tax-loss harvesting. As always, consulting with a qualified tax advisor is recommended to navigate the complex regulations and ensure compliance with regulatory guidelines.

Ultimately, the key to navigating tax-loss season successfully is conducting thorough research, understanding the factors driving the overselling, and carefully evaluating the potential for bounce-back. Investors must strike a balance between risk and reward, considering short-term tax implications and long-term growth prospects.

By approaching tax-loss season with a comprehensive analysis of their portfolios, investors can make informed decisions that align with their financial goals and risk tolerance. While the allure of bounce-back potential might be enticing, it is important to remain objective and consider the challenges and trade-offs involved in holding oversold stocks.

Happy investing!

For further information on how tax-loss harvesting works, click here – Willis Johnson & Associates, “Tax Loss Harvesting: How to Benefit From Your Investment Losses.”

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The material provided in this article is for information only and should not be treated as investment advice. For full disclaimer information, please click here.


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