Health insurance should not depend on your employment status. What kind of health insurance you can get should not depend on who you work for. (I have a friend who can’t even insure his young son unless he works for a company that offers health insurance!) This New York Times article argues that separating health insurance from employers would enable more people to work more flexible hours and in flexible locations:
But if workers’ benefits weren’t tied to employers, then they could
transition into independent status without fear of losing their health
care or pensions, and more employers would gladly oblige, since they
could move costly benefits packages off their books.
Many jobs, especially those that are computer based, don’t require people to be in an office or even to work fixed hours. It would be easier to work on an "as needed" basis if those people didn’t depend on one fixed employer for health insurance.