Health insurance, which is exceedingly difficult to secure as an individual in New York. Obamacare, while certainly better than nothing, is pretty awful, and if you have a complicated health history, as I do, you need premium insurance, which means private insurance. The challenge, though, is finding a company that will give you the privilege of paying up to $1,400 a month for it. When I didn't have a job, I spent more time thinking about insurance - not just paying for it, but securing it in the first place - than I wanted to.