It’s tax season…do you know where your 1099s are?

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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…]

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A healthcare alternative

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Dr. Freelance, I have a pre-existing health condition, and I am considering taking a part-time position with one of my clients as a way of securing affordable insurance. I haven’t made my final decision, because it feels like I’m “giving up” if I’m no longer freelance-only. What’s your opinion? — 100% 1099

100% 1099, I understand your pride in being full-time freelance. That pride, however, needs to take a back seat to the more practical matters, which are 1) your health and 2) your overall financial well-being. [Read more…]

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