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Sometimes, opportunity comes buried in jargon that only a tax attorney could love.

The new rules around Roth IRA conversions are an excellent example. I mean, I don't know about you, but terms like "recharacterizations" and "modified adjusted income" work like magic -- to start my eyes glazing over.

For many folks, the rules around IRAs were already arcane enough before the new provisions came along. But these new rules are worth taking a little time to understand, because there is indeed a wealth-making opportunity here.

An opportunity to have much more money when you retire.

I wasn't joking about the "wealth" part
Here's the essence of the new rules, in a plain-English nutshell. As of the beginning of 2010, you can convert your other IRAs to a Roth IRA, regardless of your income. And if you change your mind, you can undo the conversion, and the tax consequences are as if it never happened.

Why is this significant? As you probably know, with a traditional IRA, you contribute pre-tax money, and that money grows without having to pay taxes along the way. But you pay taxes on your withdrawals when you retire.

With the Roth IRA, on the other hand, you contribute after-tax money -- but it (and your capital gains) are tax-free forevermore. A Roth is especially appealing to those who think their income in retirement is going to be high -- but one can only contribute to a Roth now if one's income is below certain limits ($105,000 in 2010, or $167,000 for couples).

Folks who are active, involved investors are often ideal candidates for a Roth -- you'll never pay taxes on your gains! -- except that many have been shut out by those income limits. But with these tax-law changes, you can convert your regular IRA to a Roth.


And that means the big IRA balance you hope to have in retirement will be all yours. See what I mean about making you rich?

Of course, there's a catch -- and a surprise
The "catch" is the obvious one -- you have to turn that pre-tax money in your traditional IRA into after-tax money in your new Roth, and that means sending a big check to the IRS. If you do the conversion in 2010, the IRS will let you split the amount due between your 2011 and 2012 tax returns, to soften the blow -- but in the future, that lump sum will be due with the rest of your taxes on April 15.

The "surprise" is that, if the conversion turns out to have been a bad move, the IRS will let you have a do-over. Called a "recharacterization," this procedure lets you un-convert your IRA, and from the IRS' perspective, it's as if it never happened.

Why would you want to do this? Suppose, back in March, you had chosen to convert your IRA and taken a big position in BP, trading around $55 a share. You'd now be committed to pay taxes on that $55 -- but in the meantime, the Gulf of Mexico disaster happened, and your BP stock is now worth more like $35 a share.

A do-over would look awfully nice in that situation, wouldn't it? It wouldn't restore the value of your stock, of course, but it'll get rid of the tax bill you incurred for converting it.

Putting this to use in the real world
Of course, most people with sizable IRAs have a bunch of different holdings. Some might be higher-risk stocks, some might be bonds or low-drama stocks you're holding for the dividends. Recharacterizing the whole thing after one of your stocks blows up might not be the best plan.

Fortunately, there's a way around that problem. In the new issue of the Fool's Rule Your Retirement newsletter, advisor Robert Brokamp offers a bunch of tips on Roth IRAs, including a simple way to handle that situation: Set up multiple Roth IRAs.

Robert suggests you organize your IRAs around different types of investments. For instance, you might divide your accounts as follows:

  • Put your fixed-income investments in one account. Whether you own bond ETFs iShares Barclays Aggregate Bond Index (NYSE: AGG  ) and Vanguard Total Bond Market ETF  (NYSE: BND  ) , regular bond mutual funds, or individual bonds, keep them all separate from your stock holdings.
  • Put your relatively "boring" long-term stock holdings together in a second account. That could include Kimberly-Clark (NYSE: KMB  ) , Altria (NYSE: MO  ) , or any of a host of other great stocks with rising dividends. It might even make sense to put Apple stock into this category; it's far from boring, and the shares fluctuate, but a huge near-term loss is relatively unlikely.
  • Put your high-octane, speculative investments in a third account. For instance, many are using iShares Silver Trust (NYSE: SLV  ) to speculate on silver catching up to gold's big run. If you think the market is prone to start falling again, ProShares UltraShort S&P 500 (NYSE: SDS  ) is a risky but potentially lucrative way to play it.

See what I mean? Of course, I've barely scratched the surface of the possibilities here. If you're interested in going down this road, you should definitely check out Robert's comprehensive coverage of Roth IRA conversions -- including an interview with IRA guru Ed Slott -- in the new issue of Rule Your Retirement.

Rule Your Retirement is a paid service, but you can check out Robert's article -- and lots of other great content -- for free with a no-obligation 30-day trial.

Want some great stock ideas for your new IRA? Dan Caplinger has six stocks that could save your retirement.

True to its name, The Motley Fool is made up of a motley assortment of writers and analysts, each with a unique perspective; sometimes we agree, sometimes we disagree, but we all believe in the power of learning from each other through our Foolish community.

Fool contributor John Rosevear owns shares of Apple, which is a Motley Fool Stock Advisor recommendation. Kimberly-Clark is a Motley Fool Income Investor recommendation. The Fool owns shares of Altria Group. You can try any of our Foolish newsletter services free for 30 days. The Motley Fool has a disclosure policy.


Read/Post Comments (2) | Recommend This Article (15)

Comments from our Foolish Readers

Help us keep this a respectfully Foolish area! This is a place for our readers to discuss, debate, and learn more about the Foolish investing topic you read about above. Help us keep it clean and safe. If you believe a comment is abusive or otherwise violates our Fool's Rules, please report it via the Report this Comment Report this Comment icon found on every comment.

  • Report this Comment On September 07, 2010, at 4:14 AM, OhNoYouDidnt wrote:

    You have got to be kidding me. You advise holding SDS in an IRA, despite the well-known problems, caused by "reblancing," with holding that 2x Dow-inverse ETF more than one day. Reckless nonsense.

  • Report this Comment On September 09, 2010, at 5:14 PM, SundayRider wrote:

    I have some Roth accounts, but not all. I do worry that if the government needs more money it may become an easy political target to say "Look at all those $100,000 and up Roth accounts and these people don't even pay taxes on that!" Of course that's a lie--already paid taxes on that--but people already paid taxes on at least half their Social Security too, but that didn't stop Congress from taxing all of it (if you have a slightly-more-than-subsistence income).

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John Rosevear
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John Rosevear is the senior auto specialist for Fool.com. John has been writing about the auto business and investing for over 20 years, and for The Motley Fool since 2007.

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