Dear Liz: After accepting a layoff in exchange for a separation package earlier this year, I have started writing articles for a subscription website. My stories have become popular enough that I’m starting to earn some money and expect a 1099-K this year. I have enjoyed the work and want to cultivate a dedicated audience. I need a few things to improve my output (dedicated laptop, improved writing software, etc.). These will cost more than I plan to earn this year from my new gig but I have cash from my severance. What are my best options? Should I wait until I’ve earned enough from writing before purchasing upgrades?
Answer: The IRS doesn’t want people writing off losses if they’re not making a serious effort to make money. This is known as the hobby loss rule.
The agency understands, however, that not every business turns a profit every year and many businesses have significant start-up costs that may exceed their income for a time. Generally, if you make a profit in at least three out of five years, the IRS presumes you’re engaging in a real business rather than pursuing a hobby.
If you’re planning to spend more than you make this year and write off the loss on your taxes, you’ll want to make sure you’re running this new business in a business-like way. Consider hiring a tax pro who can advise you about how to structure your company, keep good records and file estimated tax payments when necessary.
Your tax pro also can make sure you don’t inadvertently over-report your income.
Forms 1099-K are issued by third-party payment networks including Venmo or PayPal to report payments over $600, but those transactions can include personal as well as business payments. A client may have used Venmo to pay you for a story, for example, but you also may have received payments from friends for their portion of a lunch tab. Plus, if that client pays you more than $600 in a year, you’ll also be issued a Form 1099-NEC. You’d be double reporting your income if you used both the Form 1099-NEC and the Form 1099-K.