When you realize that your biggest personal and business expense is taxes, it can come as quite a shock. Seeing so much of your money wind up in the government's hands can feel like a shakedown. So, it's crucial to strategize to reduce your taxes. Some people resist enforcing creative tax strategies because they're worried it will get them in trouble with the IRS. However, as long as you do things properly, there's nothing illegal about strategizing to pay the least amount of taxes possible.