No one wants a big payday to morph into a beastly tax burden. So while the best tax strategies are usually those crafted long before you actually collect any income, there are some last-minute moves that can help shelter at least a few of those zeros—even for those with poor planning skills.

1. We're In the Money

Options that are suddenly worth more than their strike price can create a sizeable tax bill when they're exercised and sold. Executives often will work with financial advisers to craft a series of puts and calls—selling points for the stock so it's not liquidated all at once, generating a monstrous tax bite.

However, Steve Parrish of Principal Financial Group notes that spreading the sale of corporate stock can bring other concerns. "You run the risk of something like Enron's stock," he says. "It could plummet."

So while selling that heap of options all at once creates little opportunity for protecting the gain from tax, Parrish is sanguine on the situation.

"With capital-gains tax at just 15 percent, there's an argument that it will never be this low again," he says. "In the 1990s there was almost no difference between ordinary income tax and capital-gains tax rates. Now there is more than a 50 percent difference. This is the lowest I've ever seen."

2. Web 2.0 Venture Pays Off

Ever wonder why angel investors are usually former entrepreneurs who struck gold on an I.P.O.? Thank Section 1045 of the Internal Revenue Code.

That provision allows them to sell stock in their original venture and plow all of that capital into a new launch—without paying tax on the gain. The only restrictions: The new investment must occur within 60 days of the stock sale and it cannot exceed $10 million.

This one's a favorite of venture capitalists, says Alan Olsen, of Greenstein, Rogoff, Olsen & Co., a leading Silicon Valley C.P.A. firm. "And if you keep starting new companies, that capital can stay protected," he says.

The rest of the money? That's subject to capital-gains tax of 15 percent.

3. The Wall Street Bonus

Signs don't look promising for big bonuses on Wall Street this year, but it's not uncommon for traders to walk away with cash that is several times as big as a base salary—almost guaranteeing a fairly substantial check to the I.R.S.

But Tad Borek, a lawyer and investment adviser in San Francisco, suggests that traders uncork some losses to offset that gain. And losses are sadly likely to be in abundance this year.

"If you already have ordinary income from regular bonds, for example, or a money market fund that's generating interest, get rid of those and put the capital into municipal bonds or a tax-exempt money market," Borek says. "These may pay less but you need to bring down your income—and cut the tax bite for this year."

Borek also suggests selling investment property if you have a high income, and have a loss from the property that is being carried forward, rather than being used. "If you sell the property, and terminate that activity, you can unlock that loss," he says.

Fire sale in the Hamptons, anyone?

4. Going Public

For a founder working toward an I.P.O., exercising some strategy before shares blossom into millions can make a big difference in tax payments.

"Two years out is the opportune time to plan before going public," says Greg Horning, director of SC&H Financial Advisors Inc., in Sparks, Maryland. Shares sold on the day the company goes public—commonly done—generate hefty (but avoidable) capital gains, he says.

Horning's solution? Trusts.

Taking a small percentage of the company's prepublic shares, and placing them in a tax shelter can protect that capital from an immediate tax bite.

How does this work? Say an early startup is valued at $1 million. A founder gives 1 percent of the company to each of his children in the form of a trust. While these shares are technically worth $10,000, they're likely valued less than that because as nonpublicly traded stock, they're harder to sell.

That means the founder could transfer even more shares as long as the value stays south of $12,000 and not spark gift taxes.

Two years later, the startup goes public and is suddenly worth $100 million. That 1 percent is now worth $1 million. And when the trust sells the shares, it pays capital-gains tax too—but only on the profit.

For a founder who's too late to the trust-planning stage, and sells off shares, Horning suggests at least prepaying state income taxes so these can be deducted on the federal tax return. "It's not a big dent on the taxes, but it's something," he says.

5. Walking With Vested Stock

That C.E.O. leaving with millions in vested stock needs a good financial expert on hand. The first thing to assess, says Ernst & Young's Elda Di Re, is which stocks have the highest cost basis—and the least profit—and which have the lowest.

"Sell the ones with the highest, which will generate a lower tax," she says. "And think about putting those with the most profit in a charitable remainder trust, or give them away outright."

A big advantage to this kind of trust is that it generates an immediate tax deduction from the value of the stocks used to fund it, plus it creates an annual annuity for the C.E.O., who then pays capital-gains tax only when he draws this income—and not on the full amount.

Ultimately, each scenario brings its own unique tax footprint. So, in the end, what is the best strategy for high earners?

"They need to pick the best preparer they can afford," says Alvin S. Bailey, a tax attorney specializing in I.R.S. issues, who spent 27 years working with the agency's chief counsel. "This can prevent problems in the long run."

Enough said.