Most business people hate this time of year and hate dealing with doing their taxes. Most “average” people with a J.O.B. love this time of year because they think of it as time for getting their “free” play money. They don’t realize that it was their money in the first place that the government took from them and is only giving back a small portion of it.

I wish withholding tax didn’t exist and everyone would have to actually write a check this time of the year to the government. It would give a big wake up call to a majority of Americans in realizing how much of their paycheck goes to the government. The truth is, most people wouldn’t have the money to pay it and there would be a large outcry about how high taxes are and there would by scrutiny of where every tax dollar is spent. It would be a very good thing to happen to the country. However, the IRS knows this too and that is why the system is the way it is and most people don’t know any better.

Entrepreneurs and business people of all kinds understand the way the tax system works since we must pay estimated taxes and all kinds of employment taxes (if we have employees) as well as setting up employee social security, withholding, and other taxes. It can be a big headache. But that is a just part of doing business and another reason why the other 98% of people don’t get into business for themselves.

Having said all of that, one of my goals every year is to pay more taxes. I hate paying taxes and don’t want to increase paying taxes for any reason other than it means my income is increasing. Of course, it could also mean the tax system or rates changed for the worse even with my income staying the same. But in general, if I am paying more taxes, my income increased. So, I hope my taxes go up every year based on my income going up every year.

Do you want to pay more taxes because you are generating a lot more income? I wouldn’t mind paying an additional $100,000 per year in taxes if it means my income increased by $250,000. I would still be ahead by $150,000.

- Hill Robertson