My 2022 Tax Season Freelance Tax Hacks

Photo by StellrWeb on Unsplash

If literally any of your income is derived from self-employment, the expense sorting lead-up to your yearly CPA tête-à-tête* likely falls somewhere between “lost afternoon” and “waterboarding.” And, if you’re like me and tend to leave that sorting to the last minute, there’s a good chance you’re missing the boat on some perfectly claimable expenses that would spare you from parting with some of your hard-earned cash.

I’m not an accounting expert in any way, but I am someone who’s been around the freelance tax-filing block and learned a thing or two. So, here’s some advice from me, a high-functioning procrastinator:

1. Take advantage of spending summaries. I’m lousy at saving receipts. This is bad. The good news is that my bank tracks my credit card spending by category of purchase: groceries, shopping, entertainment, and so forth. Yours probably does, too. This online banking feature makes it really easy to keep tabs on exactly how much you can claim towards professional expenses by allowing you to go through your spending records, month by month and for the whole calendar year, and single out anything that would defensibly qualify as a professional expense.

To further simplify things, I basically use the same credit card to pay for 99% of my day-to-day expenses, and then pay off the whole balance at the end of each month. Once I do that, I’ll also go through my spending for that month and apply the “professional services” label onto all work-adjacent purchases or recurring charges. As a freelance news and culture writer, this includes: all of my gazillion magazine, newspaper, Substack, and streaming subscriptions; tickets to movies, museums, concerts; books; records; airfare and lodging for vacations I either wound up writing about or am absolutely certain that I will; software subscriptions; transcription services; web hosting; union dues and other professional membership fees; transportation to meetings or interviews; any drinks or meals consumed in a setting with a current, former, or potential colleague where work was discussed in any way (it’s called networking, bay-bee!).

I’m ultimately probably still missing out on some expenses that fall through the cracks of a more receipt-focused approach but, by and large, the system works.