Many of us are sitting on stocks and funds whose losses are so big that it's depressing. Take heart. The loss may be worth more than the stock. If so, here's how to benefit from your misfortune.

 
After another lousy year on Wall Street, investors are tallying up some depressing negative returns. But before you weep into your year-end statements, take heart: With some careful planning, you may be able to use your losses to your benefit.

Losses that you incur when you sell your investments -- whether stocks, bonds or other securities -- can be used to offset gains, dollar for dollar.

“What gains?” you might ask. Indeed, many people who started investing in recent years are sitting on piles of losses but have no gains to offset this year.



“But it still can make sense to realize some losses,” says Lisa Osofsky, a tax specialist at M.R. Weiser in New York.

For one thing, you can deduct up to $3,000 of losses against your adjusted gross income if you have no gains or if your losses exceed your gains. And any unused losses can be carried forward indefinitely to offset gains or deduct against income in future years.

Say you realized $5,000 in long-term gains this year and $12,000 of losses. Without the losses, the $5,000 gain would be subject to the 20% long-term capital gains tax. But the losses wipe out the gain -- and your capital gains tax bill. Of the excess $7,000 loss, $3,000 of it could be deducted against this year’s income on your tax return. The balance, $4,000, could be carried forward to another year.

In some cases, it’s more beneficial if you have no gains and you deduct losses from your income. “You can get more mileage out of your losses that way,” Osofsky says. That’s because marginal income tax rates can be much higher than long-term capital gains tax rates -- up to 38.6% vs. 20%.

For example, if you’re in the 27% tax bracket and you deduct $3,000 of your losses from your income, that would mean an $810 in savings you can use now. If you used the $3,000 to offset long-term gains, you would save yourself just $600.

How to turn a tax loss into cash
In future years, to turn that $3,000 deduction into cash that you can use for more promising investments, you can adjust your withholding on your W-2 so that less of your paycheck goes to the government and you can pocket more. For this year, if you take the deduction, you will either owe less when you file your tax return or get a refund.

What should you do with your extra cash? Steven Enright, an investment adviser in River Vale, N.J., suggests staying away from individual stocks and choosing a steady all-weather mutual fund performer. Enright likes Oakmark Equity Income, a fund with about 60% in stocks that has not had a down year since it was launched in 1995, Enright says. In 2000, when the S&P 500 was down 9.53%, Oakmark was up 20%. And in 2001, it was up 18% vs. the S&P’s 13.63% loss. Through November this year, the fund was down 1.6%, but the S&P was down 18.45%. During bull market years, the fund is likely to lag the S&P, “but the bottom line is it will never get killed,” Enright says.

To sell or not to sell
The big question, of course, is whether it makes sense or not to sell shares to realize losses. “If you sell, it has to make sense from an overall economic standpoint, not just from a tax point of view,” says Bernie Becker, tax manager at Bederson & Co., a Butler, N.J., accounting firm.

If you’re holding a true dog that shows few signs of recovering, it may make sense to stop the bleeding.

But if there are good prospects for a company despite a recent drubbing of its share price, it can be a tricky call. "A lot depends on your time frame. Companies like WorldCom and UAL Corp., the parent of United Airlines, may end up being OK in the long run, but you may decide you don't have time to wait. Then you should dump your shares," Osofsky says. "Other companies, like Wal-Mart Stores and others in the retail sector, have gotten hit, but they're probably going to have steady solid growth so they may be worth holding on to."

If you’re approaching retirement or need your money in less than five years, you may want to dump a loser even if it promises eventually to rebound. What you’re doing is engaging in preservation, and that’s an honorable move to make, Osofsky says

“But if you’re 30 or 40, and the stock is in your retirement account, leave it alone.” Let time do its magic.

A final test before selling: “If you paid $5,000 for an investment now worth $1,000, ask yourself this question: If you had the $1,000 to invest today, would you buy that investment? If not, then it might be time to sell it,” Osofsky says.”

Limit your cost basis
If you do decide to sell shares at a loss, and you are sitting on gains, this might be a good opportunity to realize some of the gains even on stocks you would like to hold for the long term. “It’s an opportunity establish a higher cost basis on stocks you have been holding for years that were purchased at very low prices,” Becker says.

Say you inherited some Johnson & Johnson stock while you were in college 20 years ago, and you want to hold a position in the company for the long term. The stock has appreciated significantly since then -- roughly 15% a year BEFORE dividends and DESPITE a recent plunge in its price. You can sell some shares, offset the gains from your losers, so there are no tax consequences.

Then, you can buy back shares and establish a higher cost basis. “When the stock does go back up and you eventually sell it, you will have less of a gain to report,” Becker says.

The tricky part is that you cannot buy the stock back immediately. Under so-called wash-sale rules, you can’t buy a security back within 30 days after dumping it. If you do, you lose the chance to claim the loss until you unload the shares you repurchased.

So if you use the strategy to establish a higher cost basis, you run the risk that the stock's price will rise significantly during the 30 days before you can buy back shares.

If it’s a sector or industry you’re interested in more than a specific company, you have more flexibility under wash-sale rules. With individual stocks, you can buy back a similar stock in the same industry --for example, if you dump Pfizer you can buy Eli Lilly. If you unload a fund, you can buy back a similar fund as long as it is managed by a different fund family.

You also have to consider the distinction between short- and long-term losses before you take advantage of your losses. Short-term losses, which are those realized on investments held for less than 12 months, can be used to offset either short- or long-term gains. The same goes for long-term losses, which are realized on investments held 12 months or longer.

But there are some restrictions: If you have short-term losses, you must first use them to offset any short-term gains. Any leftover short-term gains can be used against long-term gains. Similarly, long-term losses must first be matched with long-term gains.  

 

 

2003 small business aide