With tax season finally over, now seems like a good time to talk about how to make next year’s taxes go as smoothly as possible. I especially want to focus on the self-employed and contractors. While there are all kinds of variables that complicate tax-filing (owning a home, dependents, interest income, divorce, marriage, death), many of us still work for corporations where we file a W-2 and our withholdings become automatic. For entrepreneurs, or people in more less formal income situations, it can be a bit trickier.