Readjusting Your Stocks to Save on Taxes

Nov. 25, 2008 — -- As 2008 nears an end, it's time for ravaged investors to make the best of a bad situation.

There are a number of tax-planning moves investors can make to help mitigate some of the losses they've suffered this year. They include selling losing investments to offset gains and deducting losses and converting a traditional IRA into a Roth IRA at a depressed value to realize future tax savings.

One other move that some investors should be considering in the coming weeks is the opposite of a Roth IRA conversion; it's a Roth IRA recharacterization. That's a mouthful for sure, but a recharacterization essentially is a do-over in the tax world. It's a chance to go back and undo what you did.

Those who will want to consider a do-over are retirement savers who earlier this year converted their traditional IRA to a Roth IRA and then watched stock prices enter a free fall.

If the $20,000 you converted into a Roth IRA at the beginning of this year now stands at $12,000, you should consider a recharacterization. Why pay taxes on that $8,000 in lost value when you can go back and redo the conversion at a lower cost?

To understand how a recharacterization works, first you need to know a little bit about why you'd want to have a Roth IRA in the first place. The primary benefit is that money held in a Roth can be withdrawn in retirement with no income taxes due. A secondary benefit is that there is no requirement for mandatory withdrawals after age 70½ as with traditional IRAs and other retirement savings accounts.

The downside of a Roth is there are no tax savings on the front end when contributions are made as with other retirement plans. However, the tax-free withdrawals in retirement can more than make up for that disadvantage if you believe your tax rate is likely to be higher in retirement than it is now.

You can establish a Roth IRA by making annual contributions provided you meet the income guidelines, but you're limited to contributing $5,000 a year (or $6,000 a year if you're 50 or over).