Health insurance! With the astronomical cost of healthcare in the U.S, I've heard from a lot of Americans that losing company-sponsored health insurance is one of the main concerns they have when it comes to quitting their job before theyβre of retirement age β and that was once one of my main concerns, too. If you're a self-employed or unemployed nomad... you have some options when it comes to insurance coverage. Here's my experience over the years.