The Smartest Money Move You'll Ever Make

Smart investors know that delayed gratification can lead to some amazing results. With one new opportunity that nearly everyone can take advantage of right now, swallowing a bitter pill right now could help make you a millionaire in the long run.

As I wrote about yesterday, Roth IRAs have the capacity to save you thousands in taxes throughout your lifetime. Yet many people with relatively high incomes haven't been able to use Roth IRAs in their financial planning. Now, though, the doors are open for those who want to convert existing retirement accounts to Roth IRAs. And never before have so many people been interested in making the move.

What's all the hubbub?
The big benefit that Roth IRAs give to investors is the ability to enjoy tax-free growth from their investments. As long as your assets stay within your Roth, you can buy and sell without incurring capital gains. Moreover, when you withdraw money from your account after you reach retirement age, then you can do so without paying taxes or penalties. That's an advantage you won't find with traditional IRAs and 401(k) plan accounts.

That's why converting to a Roth is appealing to many. Since regular Roth contributions still have income limits, many can't make them. But if you have a traditional IRA, you can now convert no matter how much money you make. Now, anyone who's ever saved for retirement can enjoy the benefits of a Roth.

Sounds great, right? Hold on a minute, though. Converting isn't free. You have to include the amount you convert on your tax return as taxable income, increasing your current tax bill. If you convert all of your retirement accounts, that could easily create a five- or six-figure tax bill just from the conversion -- tax that you'd have to pay a lot sooner than you would if you just kept your money in a traditional retirement account.

Why convert?
So given the possibility of a huge tax bill, why would anybody ever want to convert to a Roth? Again, it comes back to delayed gratification.

One way or the other, once you have money in a traditional retirement account, you'll have to pay tax on it. The question is whether to pay those taxes now or later. For a couple of reasons, it may make sense to pay them now:

• Taxes on the rise? From all indications, it appears that the current tax rates still in effect for 2010 may be headed higher in the near future. When tax breaks enacted back in 2001 expire next year, there's a high likelihood they won't come back -- and that will increase taxes greatly on the very high-income taxpayers who now have access to Roth conversions.
• Boost your retirement account's power. If you can pay the tax from assets outside your IRA, conversion effectively boosts the after-tax value of your retirement assets.

Let's take a closer look at that last point. Say two investors owned the same portfolio of stocks in an IRA 10 years ago, with $10,000 invested in each. One of them converted, while the other didn't. Now, they're both retired and looking to withdraw their money.

Source: Yahoo! Finance. Assumes traditional IRA investor is in 35% tax bracket.

After 10 years, both investors have the same amount in their retirement accounts, but the traditional IRA investor faces a huge tax liability. By paying taxes back in 2000, the Roth investor was essentially able to boost the after-tax value of the Roth portfolio by nearly $70,000 -- the value of the original portfolio. And while the traditional IRA investor could have invested the extra money that the Roth investor paid in taxes, that money would have been subject to ongoing taxation that the Roth investor could ignore.

Weigh your options
There are reasons not to convert as well. If you expect lower tax rates after you retire -- perhaps because your income will be lower, or you'll move to a state with a lower income tax -- then it may pay to wait. In addition, higher taxable income from a Roth conversion can cause you to lose some other tax benefits. Finally, if you can't afford the taxes without tapping the IRA itself, conversion loses much of its power.

Converting isn't an all-or-nothing decision, though. Even if you don't convert all of your traditional retirement accounts, moving a portion into a Roth may make sense.

Whatever you decide, you'll want to take a close look sooner than later. Tomorrow, we'll take a look at why making your conversion decision as soon as possible gives you some added flexibility that could save you even more.

Stay tuned the rest of this week as Dan looks into the benefits of the new Roth conversion. Up tomorrow: Why acting now gives you an opportunity you won't want to miss out on.