As a small business owner, you have good odds of someday facing a penalty for late filing and/or late payment of your or your corporation’s taxes. It’s likely you will think that you have to pay the penalties. But as you’ll learn here, when you know the rules of the road, you can travel the IRS mercy path and have those penalties forgiven.

Do you have significant insurance needs? If so, the captive insurance company might save you money on your insurance, create a nice tax shelter, and produce a pile of cash. To achieve this agreeable result, you have to follow the rules and consider the tax code safe harbors.

You can make your tax life easier with a business credit card—but only if you use that business credit card correctly for tax purposes. For example, charging an expense to a credit card does not make it tax deductible. You need more proof. And you could create a type of double jeopardy if you operate your business as a corporation.

Here’s a handy-dandy strategy for getting some money to your college student to help him or her pay for school. Have your child engage in an activity that’s not subject to self-employment taxes. If you operate your business as a corporation or your child is age 18 or older, this is a great college funding tool that you need to consider.

Do you rent property to your business? Under the self-rental rule, you could forfeit your expected tax breaks and end up on the hook for unexpected taxes. This is true even if you create a separate entity to rent the property to your business.

If you want to rent one, two, or twenty bedrooms in your home, you need to avoid one big trap and navigate two sets of rules to obtain the tax benefits you likely were hoping for when you thought of this rental activity. This is an area where tax knowledge is power. Without the knowledge, you could create a very unsatisfactory tax result.

You might want to tap your IRA penalty-free for medical expenses. If so, avoid the three traps that we explain in this article. Don’t be a victim. You suffer first because you incurred medical expenses, then you have to pay income taxes on the withdrawal of money from your traditional IRA, so the last thing you want is to pay a 10 percent penalty on top of all that.