JILLIAN KAY MELCHIOR: The unemployment rules discouraged me from working.

But unemployment makes freelancing complicated. According to the rules, “each day or part of a day of work will result in a payment of [only] a partial benefit.” If I worked one day, my unemployment payment would be only $303; two days meant only $202.50. If I earned more than $405 in a week, I got nothing.

That made freelancing costly for me, regardless of how much I wanted to spend my time productively. Say I earned $75 in one day of freelance work. I would then receive $303 in unemployment that week, and my total weekly haul would be $378 — less than the $405 in standard unemployment. In other words, if I couldn’t earn more than $100 in a day, I’d actually be losing money by working.

The unemployment rules also subjected me to a bizarre work schedule, because they stipulate that “you are considered employed on any day when you perform any services — even an hour or less — in self-employment, on a freelance basis, or for someone else.” In other words, taking two days instead of one to do an assignment meant I’d lose an extra hundred bucks. As a result, I tried to pack all my freelance writing and pitching into a single weekday, pulling the sort of late nights I’d once hoped I had left behind in college.