Wise investing strategy calls for buying low and selling high, or buying good-quality securities and holding them for the long term.

Sometimes, however, it makes sense to go against these market maxims and sell a security at a low point. Tax-loss selling — as the strategy is called — is effective for clients who have money-losing investments outside their RRSPs and are looking for ways to reduce their tax liabilities.

Tax-loss selling involves the client selling the investment at a loss, then applying the losses from the sale of that security against capital gains earned on the sale of another investment — thereby reducing income taxes. Normally, 50% of net capital gains are fully taxable as income each year.

The strategy can be applied to a variety of capital holdings, including stocks, bonds, exchange-traded funds, mutual funds and real estate investments other than the person’s principal residence. The strategy makes sense only for investments held outside of tax-sheltered registered plans, such as RRSPs or RRIFs.

With the hot markets of the past several years, your clients may be sitting on large gains on profitable securities, rental properties or family cottages. Long-time shareholders of BCE Inc., for example, are sitting on huge gains — assuming the deal goes through — and may be looking to minimize their tax hit. Meanwhile, this year’s turbulent markets have certainly created some losses.

“With securities trading at depressed prices due to the market activity in recent months, it could be smart planning to utilize the tax-loss strategy,” says Carol Bezaire, vice president of tax and estate planning with Toronto-based Mackenzie Financial Services Inc. “It’s a good time to take a look at the portfolio, look at the losses and gains, and do what’s most beneficial for the overall portfolio. It’s important to think about two things: first, the wisdom of selling the holding; and, second, the tax impact.”

The S&P/TSX composite index is in negative territory so far this year, indicating that it may be a down year in the market after five consecutive years of gains.

With many securities, both in Canada and around the globe, dropping in price, this is likely to be a busy year for tax-loss selling, market observers say. As professional managers and individuals cull their holdings, that downward pressure on some losers could increase toward yearend.

So, says Abby Kassar, financial advisory consultant with RBC Wealth Management Services Inc. in Toronto, if the decision to sell has been made, it might be advisable for clients to sell sooner rather than later.

What makes the tax-loss selling strategy particularly attractive is that once losses have been applied against this year’s realized gains, any unused losses can by carried back and applied against any net realized gains incurred during the past three years. The losses can also be carried forward indefinitely, and applied against future gains to reduce taxable income.

Likewise, unused capital losses from previous years may be brought forward to apply against this year’s gains.

Keep in mind that it takes at least three business days for a trade to settle, so any tax-loss selling for this year must be done by Dec. 24.

John Waters, manager of tax planning with BMO Nesbitt Burns Inc. in Toronto, says it’s important to assess the reasons why a security was purchased in the first place — before hastily heaving it overboard. If the security has long-term potential, it may be worthwhile to hold until it recovers: “If clients have doubts, they can sit on the security for a while and see how it performs. If they decide next year that it’s a bad investment and won’t improve, they can always sell the security at that time, then apply the loss to offset next year’s gains or carry it back for three years.”

Another consideration is the tax bracket of the client, Waters says. If the client expects to be in a lower tax bracket next year, perhaps because of retirement, it could make sense to trigger a loss this year when the client is facing a higher tax bite, and reduce this year’s capital gains by as much as possible.

Selling a security that is a bona fide loser is a relatively easy decision. But many clients are holding some attractive holdings in their portfolios that have been beaten up by the prevailing downward drift in the marketplace. Even if a client wants to hold a security for the long term, he or she might benefit from the strategy of selling to crystallize the loss this year, then subsequently repurchasing that security.

@page_break@However, tax rules say the security cannot be repurchased for 30 days, or the losses will be considered “superficial” and denied by the Canada Revenue Agency.

With this strategy, then, clients are taking the risk that such securities could increase in value in 30 days and thus be so expensive to buy back that any tax advantages would be wiped out.

On the other hand, if a client waits to sell an investment in a future year, it may have rebounded in price and the opportunity will have been lost to trigger a loss that can be used to offset gains on other investments, now or in the future.

“If the client likes the security for the long term, and decides to sell it in a downturn,” says Waters, “he or she is exposed to any market fluctuations in the 30-day period. A lot can happen in 30 days, and there’s no guarantee the price will be the same or lower. It’s a bit of a gamble.”

Note that neither the client, his or her spouse nor a corporation or trust controlled by either the client or the spouse can purchase the same security or an identical one within 30 days, either before or after the sale of the loser stock. The rules extend to any RRSP in the name of the client or spouse.

However, there are a variety of ways to minimize the potential damage of the 30-day rule. One way would be to find another investment that is similar but not identical to the one being sold. Various mutual funds have similar portfolios but are not exactly the same.

Alternatively, the client could sell one bank stock or energy company, and immediately purchase a competitor or an ETF that represents the sector. That way, the client is not left sitting in cash if the market goes up. After 30 days, if the client still wants the original stock back, a switch can be made. Whether or not the client pays commission costs on every trade will have a bearing on whether this strategy makes sense.

“If clients are concerned about being shut out of a stock for 30 days, they can buy something highly correlated,” says Keith Greenard, an investment advisor with the Greenard Group, which operates under ScotiaMcLeod Inc. ’s umbrella in Victoria.

Such a client can also switch from one mutual fund to another that has an identical portfolio but is registered differently. For example, many fund manufacturers offer funds that are classified as trusts; also, many funds are part of a corporate-class structure, which allows investors to defer taxes when switching among funds held within the same corporate structure.

If a client sold Toronto-based Mackenzie Financial Corp.’ s Mackenzie Cundill Value Fund, for example, and immediately purchased Mackenzie Cundill Value Class, the 30-day rule would not apply because the two funds are not considered identical, Bezaire says. Selling one index fund for another fund tracking the same index would probably be seen by the CRA as the purchase of an identical security for the purposes of the superficial loss rules, however.

Tax losses may also be transferred to a spouse who has significant capital gains to offset or who is in a higher tax bracket, but the 30-day rule must still be observed. The client must sell the security to the spouse at fair market value, and the spouse must pay for the stock. The original owner loses the ability to claim the tax loss, but the loss is applied to the cost base of the security now held by the spouse. After 30 days, the spouse may sell the security and realize the loss. The client’s tax return must state that an interspousal transfer took place at fair market value.

Another alternative for clients is to gift a losing fund or stock to a child, says Kassar. The security is considered sold at fair market value, and the client may claim the loss. If the investment later increases in value, the child is responsible for paying taxes on the capital gain. But as long as he or she has income under the basic personal exemption of $9,600, the gain would be tax-free.

Attribution rules would require the original owner to pay taxes on any dividends or interest income paid by the security. IE