By SARA HOROWITZ APR 18, 2017 

For the 55 million Americans who make their living as freelance workers, tax day is more than just a headache. It's an annual fleecing. Freelancers now constitute a third of the American workforce, and over the past decade, 94% of new jobs added to the U.S. economy were created in the so-called gig economy. Yet freelancers must retrofit themselves into an archaic system designed for the industrial era, one that taxes independent workers disproportionately even as they benefit less from the social safety net.

A quaint 400 pages, the original tax code was adopted in 1913, when industrial-era workers might have had one or two jobs for life. It has since evolved into a 74,608-page behemoth that few self-employed individuals can navigate on their own.

Hiring an accountant to serve as one's guide through the Byzantine process is only the first step — and only the first expense. Freelancers must collect 1099s from each of their multiple clients, organize countless bills and small receipts into deductible expenses, and plan out a confusing payment schedule for making separate, estimated outlays toward federal, state and even local tax collectors.