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How to Retire Without Being Taxed to Death

PORTLAND, Ore. (TheStreet) — Know that tax-deferred retirement account you've been feeding during your working years? Yeah, you can't defer that pain forever.

You need a strategy if you're going to keep that tax bite from sinking too deeply into your savings. Figuring out how and when to withdraw money from taxable, tax-deferred and tax-free accounts can save retirees a lot in taxes, says Anthony D. Criscuolo, a senior financial planner with Palisades Hudson Financial Group. That's especially true for wealthier clients, who started paying a new 3.8% Medicare surtax aimed at taxpayers who have net investment income (NII) and whose modified adjusted gross income (MAGI) exceeds $250,000 for married taxpayers and $200,000 for singles.

“A large part of their income often comes from investments, so this new tax may significantly impact them,” Crisculo says.

The first and easiest step is to withdraw funds from taxable accounts. Stocks and mutual funds that have appreciated longer than a year incur a long-term capital gains tax, which is relatively low for most taxpayers.

The second step is where it starts to get painful. Here you'll have to dip into tax-deferred accounts such as IRAs, 401(k) plans and Keogh plans that are taxed at your ordinary income tax rate. Once you reach 70.5 years of age, you have to take the annual required minimum distribution anyway to avoid a crushing excise tax, so just grit your teeth and get on with it.

The last to go should be tax-free accounts: basically, the Roth IRA.

“The longer you can keep your money in them, the better,” Criscuolo says. “If you withdraw a lot of money from a tax-deferred account, it might push you into a higher tax bracket. But pulling a large amount from a Roth IRA will not impact your overall tax rate.”

If you're among the wealthier retirees, you're going to want to switch up that strategy a bit to avoid the full brunt of the Medicare surtax. That requires reducing your NII and/or MAGI, which could mean investing more heavily in municipal bonds and/or tax-deferred annuities, buying cash-value life insurance, carefully planning the timing of estate or trust distributions, converting a traditional IRA to a Roth IRA, or creating a charitable trust.

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