Heybro - while it is true that for those who worked for a company, their health insurance was often provided as a benefit of their employment, I secured my and my family's health insurance for the decades I worked before stepping away from work last year. Finding health insurance that fits your situation is not a mystery, but rather is like handling your money in general -- it's unlikely anyone else will do it better than you can do it yourself, assuming you do your homework. Study up on what you need, on what's available, ask questions when you're uncertain, and then make your best choice. This is a rational process, and you need not be ruled by fear of the unknown -- even employer provided health insurance was analyzed by mere human beings set out to determine the best overall options. If you are otherwise ready to RE, don't let fear of health insurance keep you working. If you expect your income to exceed such as would qualify you for subsidy, or you want to hedge your bets, make sure you have enough cushion in your savings to cover a reasonable amount for health insurance. (What's reasonable depends on your age, location, health needs, # and age of dependents, etc... all mostly quantifiable.) Best of luck.