Tax Strategies:
If You Plan to Sell,
Do It Now!

by Adam Martin, Editor
Market Logic

Most people think of April as "Tax time." They struggle through the first half of the month worrying whether they'll finish their returns by April 15. Foremost in their minds is how much they detest lining the IRS' pockets, or how big a refund they have coming. But smart investors avoid last-minute struggles and emotionally taxing ruminations by embracing "Tax time" right now. Yes, now. It's Novemberthe time to take steps designed to minimize your tax bill. To wit:
Make a concerted effort to balance gains against losses. Any realized gains on stocks and funds (including taxable capital gains distributions received from funds) can be offset by realized losses, and you should have some losses because many stocks and funds are well below their highs. Also, sell poor performers this month. Don't wait until December, when a flood of tax selling depresses already depressed issues. That's the time to buy back any attractive stocks or funds you've sold, as long as you satisfy the 30-day waiting period. follow this strategy and you'll reap the biggest gains from the so-called January Effect in which smaller stocks typically score their best gains of the year.
Calculating gains or losses from the sale of stocks and funds can be tricky. Generally, the most favorable method involves "specific identification." Pick the specific shares that you want to sell now. By selling those with the highest cost basis, you minimize your taxable gains. To address potential IRS questions, written confirmation of such sales is typically required. Try faxing, e-mailing, or writing a sell-instruction letter to your broker or fund, and request a confirmation.
If you are self-employed and want to defer taxes on a portion of your 1999 earnings by making a deductible contribution to a Keogh plan, you must open the plan by December 31. But you have until as late as April 15, the tax return filing date, to contribute to it.
Planning to make charitable contributions to cut your tax bill? Try donating shares of stock or mutual funds that have made money and that you've owned for at least 12 months. You can deduct those shares' entire market value and avoid paying any capital gains taxes on their accrued value. That's a double bonus.
Editor's Note: Adam Martin is editor of Market Logic, 2200 SW 10th St., Deerfield Beach, FL 33442. 1 year, 24 issues, $200.

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