Recognize Capital Gains Now

Here's the first and easiest idea to consider: Book any long-term capital gains right now, before 2008 ends.

Here's why: While the IRS taxes long-term capital gains at a relatively low 15% rate, Obama proposes raising this rate to 20% for individual taxpayers making more than $200,000 a year and for families making more than $250,000.

While a 5% rate increase may seem modest, long-term capital gains are often substantial. Long-term capital gains regularly break into seven figures if the gains stem from decades of appreciation in a real estate investment or from decades spent building up a successful business.

Note: The fifteen-percent preferential capital gain rates were originally set to expire in 2010, so capital gains rates were always at risk of sneaking back up.

Delay Capital Losses Until Later

A quick related point: Because capital gains and losses offset each other, you might decide to delay recognizing any capital losses until the point capital gains tax rates rise.

The savings calculations related to this technique are tricky. But delaying a capital loss a few weeks could in many cases save you several thousand dollars because the loss will be applied, or netted against, either capital gains or ordinary income that would otherwise be taxed on a higher rate.

Extract Earnings and Profits Now

If you own a C corporation or former C corporation, you should be aware of a potential tax time bomb that may exist inside your corporation: previously taxed profits retained inside the corporation.

Here's the problem: Right now, if the corporation pays out these earnings and profits to shareholders as dividends, the shareholders pay a modest 15% qualified dividends tax on the dividends. And that's pretty good.

However, this qualified dividends tax rate expires at the end of 2010. And after that, dividends paid from C corporation earnings and profits will get taxed at the shareholder's top marginal rate. That top rate may be close to or even exceed 40%.

You see the savings, right? Paying, say, a 40% tax rate instead of a 15% tax rate will have a huge effect.

Accordingly, as much as is possible, withdraw previously taxed C corporation profits now, before the low dividend tax rate expires or before tax law changes close this corporate tax loophole.

And a special note for any S corporations that used to operate as C corporations. If you retained some of your C corporation profits during the years you operated as a C corporation, talk with your CPA about this issue, too. You've got the same tax time bond ticking inside your books.

Reconsider the Roth Option

One powerful long-term tax planning technique is worth mentioning for high net worth business owners. If you're someone with more than adequate retirement savings, you may want to setup and use a 401(k) plan to make Roth contributions.

Here's the logic. Typically, high income tax payers can't contribute money to a Roth-IRA account because the Roth-IRA cutoff point is $160,000. Rise above that income level and you lose your Roth eligibility.

However, no income cutoff exists for Roth-401(k) plans. And this opportunity creates a long-term tax saving opportunity for business people who've accumulated substantial assets.

Say you've a fifty-year-old who's got a sizable taxable investment account. In this case, almost without effort, you could transfer $40,000 a year from your taxable investment account to a couple of Roth-401(k) nontaxable accounts for you and your spouse.

In this case, you end up with a million dollars in your Roth-401(k) at the point you retire. You won't have saved any tax (yet) with the 401(k). But the money you've accumulated and the investment earnings on the money won't be taxed. Not ever.

This is big. During your retirement years, having this $1,000,000 of Roth wealth could save you $30,000 to $40,000 a year in income taxes.

And if you've got kids or grandchildren, this tax planning trick gets even better: Your kids can (with a little bit of clever upfront planning) continue to save the $30,000 to $40,000 a year over their lifetimes.