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

January 29, 2010 by Jake Poinier

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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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Filed Under: Manage Your Freelance Business Tagged With: 1099, freelancing, Taxes

A healthcare alternative

January 16, 2010 by Jake Poinier

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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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Filed Under: Manage Your Freelance Business Tagged With: 1099, full-time freelance, insurance, wage slave

Will layoffs cause a freelance tsunami?

January 2, 2010 by Jake Poinier

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Dr. Freelance, I’ve got quite a few friends in the newspaper business who’ve been laid off in recent months, and many of them are hanging up a shingle as a freelancer. Do you think this is going to lower prices and/or create more competition for freelance gigs? — Freelance Tsunami Watcher

Freelance Tsunami Watcher, I’ve seen the same thing, with tons of friends (in all types of media, not just papers) who’ve lost their jobs in the past year. It’s pretty awful. There are several factors to my answer: [Read more…]

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Filed Under: Manage Your Freelance Business Tagged With: economy, Freelance Forecast, freelance lifestyle, trends

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