One of the best ways for companies to foster employee loyalty and tenure i to offer stock options. It’s also a great way for working-class Americans to build significant amounts of wealth, if you’re with the right company.

When it comes time to consider cashing in those shares, I always recommend you seek financial advice. At a minimum, you’ll confirm you’re doing the right thing. And you might avoid severe tax consequences. When exercising stock options, most people never see the warning label …

"The sale of your stock options will likely create a tax situation that will negate your personal exemptions and other deductions. You need to make arrangements in advance so you’ll be prepared for your tax filing."

Normally, the company will withhold the appropriate amount of taxes, but not always. As a result, many people who wait until the last week to prepare their taxes put themselves under significant pressure, which often leads to big mistakes.

And if a lot of money is owed, there’s a mad scramble to come up with the cash needed to pay the IRS. The smart way to handle this is to have your taxes prepared early. But if you owe money, it’s smartest to wait until April 15 to actually send in your return.

Please note my emphasis on preparing taxes early, especially in a year in which there is a major change in income or expenses. The reason is simple: You don’t know what you don’t know. In a perfect world, people should be able to do their own taxes without adverse effects, but our tax system is far from perfect.

This is why tax planning — not tax preparation — is essential. And to plan properly, it’s important to understand the following five guidelines:

Guideline #1) Know the limitations of your financial advisor. The true test of a good advisor lies not in his ability to give answers, but rather in his ability to ask the right questions. It is virtually impossible for any advisor to be up-to-date on every insurance, investment, estate planning and tax law and regulation. But you should expect the advisor to know how each area affects the others, what questions should be asked and which financial professional should be sought for the right answer.

Guideline #2) Get a second opinion from an appropriate professional. We do it with doctors and even with major car repairs, but we rarely do it with money. Go ask a second professional what he or she thinks. It’s a small price to pay for a significant financial decision that could affect you for years to come.

Guideline #3) Engage in tax planning as soon as you realize that your income, expenses or marital status is changing. The nature of taxes is such that any major change will likely affect your taxes. Start early to avoid any unpleasant surprises.

Guideline #4) It costs money to have money. The tax code offers deductions and exemptions to Americans who aren’t rich. But rich people (those who report lots of income in a given year) lose some or all of those deductions. As a result, rich people must pay someone to plan and prepare their taxes in order to preserve as many tax breaks as possible.

Guideline #5) Paying the IRS later is a lot better than paying the IRS sooner. The best tax planning confirms that you are withholding enough to meet the "safe harbor" rules (to avoid penalties), while allowing you to invest money you owe that isn’t due until the filing deadline.

When it comes to big financial decisions and the tax consequences that go with them, keep in mind that having to pay taxes is not a crime. (The amount you must pay is the crime!) After all, owing taxes is something all Americans aspire to do (though they rarely say it quite that way).

Discovering that you owe the IRS a huge sum is a terrible feeling. One of the most important ways to avoid this problem is to seek the advice of a professional early on. That way those terrible unexpected surprises will never arise.