If you own your own business: You may have fallen into the trap of thinking that the money you get from selling your business will fund your retirement. Big mistake, notes Barbara Weltman, author of "JK Lasser's 1001 Deductions and Tax Breaks 2008." "That business may be all about you. You may be so critical that there is no business without you. Plus, you are missing a huge opportunity to shelter income in one of several retirement accounts." There are several types of plans to look at: A defined benefit plan (a self-funded pension that is set up to pay you an income in retirement) can allow you to sock away up to several hundred thousand dollars in deductible contributions per year. A solo 401(k) is another good option. It's not too late to contribute a deductible $15,500 for the tax year 2008 (if you're 50 or over, you can kick in another $5,000), but your company can match it and reduce its taxable income as well. Keogh plans (if you have employees) and SEPs (if you don't) are also on the menu, but at the very least you should put $5,000 into an IRA or a Roth. Then automate your contributions for 2009 so you're funding the account throughout the year rather than writing one painfully large check.
Business owners -- even part-time, moonlighting-style business owners -- know that much of their business life can be deductible. Yet, says Weltman, many people don't take the deductions and other breaks they're entitled to. Why? Fear of the audit police. "They lack documentation," she says. "They don't have the paperwork and receipts so they don't take what they're entitled to." It's most likely too late to fix this problem for 2008. Your credit card statements won't cut it --when you take a client out for drinks or dinner, you not only need to record who it was, but why you were there and what business was discussed. Going forward, however, start documenting these work ventures. "It's absolutely worth the trouble," Weltman says.
If you're heading back to school: Education tax breaks are among the most missed. That's in part because there's such an extensive list of them, but you can only take one in a given year. The two to consider are the Lifetime Learning Credit, which is worth up to $2,000 off your tax bill (it phases out if your adjusted gross income is more than $57,000 for singles, $114,000 for couples filing jointly), and the Tuition and Fees deduction, which reduces your taxable income by up to $4,000 (it phases out if your AGI is more than $80,000 singles, $160,000 couples). If you're improving your skills in your current line of work or hunting for a job in the same field, you may also find yourself eligible for the miscellaneous itemized deduction. These miscellaneous expenses -- like traveling to job interviews or taking classes related to your field -- have to top two percent of your AGI.
If you want to pass assets to your children: The down stock market makes it a very good time to give money away. If you are financially independent and want to move assets out of your potential estate, you can give up to $12,000 a year to any person you like (a couple can give $24,000) without running into lifetime gifting restrictions or a gift tax. Giving shares of stock that have sunk (particularly ones you believe will come back) is a way to move any future appreciation out of your estate and into that of your kids or other beneficiaries. (Note: This is precisely the opposite of the strategy tax experts use for giving to charities. Because charities are allowed to sell shares without paying taxes and you are not, you're better off giving shares that have had a great run. That allows you to give more to your causes than if you sold the stocks yourself and bequeathed the money.)
One final point. Congress is notorious for making tax changes close to the deadlines so that they don't make it onto the pre-printed forms. And some of those breaks can be very valuable. Your best bet is to keep your eye on the news and if you have any remaining questions, check out the IRS's Web site, www.irs.gov.