Year End Tax Strategies

It’s that time of year again.  While taxes aren’t technically due until April of next year, most of the techniques to manage this year’s tax bill must be completed by January 1st.  Effective tax avoidance (not to be confused with tax evasion) comes down to two basic strategies:

1. Eliminate as much taxable income as possible
2. Defer the income you can’t shield from the IRS until next year

Your ability to take many of the following deductions depends on your specific tax situation.  Always consult a competent tax accountant before taking any tax advice.

Eliminate Taxable Income

• Sell Taxable Funds At A Loss – Uncle Sam allows you to write off up to $3,000 in capital losses per year against regular income, which is very generous.  If you lost more than $3,000, you can either carry the remaining losses over to next year or use them to offset capital gains.  Be sure to wait at least 31 days before buying back the same investment (be it stock, mutual fund, ETF, bond, etc) to avoid running afoul of the wash sale rule.
• Hold Off On New Mutual Fund Investments Until After Capital Gains Distributions Are Made - You will owe tax on any and all capital gains distributions made by funds you own regardless of whether or not you benefited from the rise in prices that led to the distribution.  That is, if you buy a fund today and it makes a distribution tomorrow, you will owe tax on the amount of the distribution even if the value of the fund goes down.  Wait until after distributions are made to avoid the tax hit.
• Required Minimum Distributions Are Not Required In 2009 – Thanks to the recession, congress saw fit to eliminate the RMD requirement this year.  If you don’t absolutely need the income, you can reduce your tax burden by skipping this year’s RMD.
• Match Winners And Losers – Try to match winning investments with losers to eliminate any tax hit.

Defer Taxable Income Until Later

• Wait Until Next Year To Convert To A Roth – A Roth IRA conversion is a taxable event.  By waiting until next year to initiate the conversion, you can defer paying taxes on it for another year.
• Try To Wait Until You’ve Held An Investment 12 Months Before Selling – While you shouldn’t let tax considerations wag the investment tail, long-term capital gains on assets held longer than 12 months are taxed at a much lower rate than gains on assets held less than one year.
• Sell Securities With The Highest Tax Basis First – If you’ve been investing a while, you probably  have multiple tax lots of the same investment purchased at different prices.  Sell the securities with the highest tax basis first to defer the bulk of your tax liability for later.
• Give A Tax-Free Gift – You can give a gift up to $13,000 per person in 2009 without any tax consequences.  Useful if you want to limit the eventual tax bite the IRS will take out of your estate.
• Avoid Selling Investments With Gains Until After January 1st – If you don’t realize a gain this year, you won’t owe taxes on it come April 15th.