Dr. Freelance, if I don’t receive a 1099 for each client who paid me $600 or more, can the IRS penalize me?—Infernally Ravenous Scoundrels

Dear IRS: No, as long as you pay the appropriate taxes on your paid freelance gigs, there is no penalty for not having the actual form 1099s. There’s a wide variety of common 1099-MISC issues, such as if they’re too high or low, have incorrect information, or don’t come at all. Because the rules and regulations are too complex to deal with here, I recommend that you consult the IRS.gov site or your CPA for guidance on how to handle those types of situations correctly. [Read more…]