I've yet to quit my "other" full time job...the one that pays the bills and provides me with unlimited supplies of post it notes and bottled water. I'd like to quit this job...and God willing, will do so soon, but being a small business owner (along with all of the perks) is a big responsibility and undertaking. Luckily, today there are many more options for those of us who wish to strike out on their own.
Health insurance has always been a huge issue for small business owners. Cobra plans, which allow former employees to continue on their health insurance for a specified period of time after their employment, have been a godsend for some. However, the monthly fees for these plans (which may have just been a few dollars a month after your employer offset the costs) can easily be over $500 a month. Additionally, the coverage only lasts for so long and eventually you'll need a plan B. In New York, where I'm lucky enough to live, there was a program started several years ago to bridge this gap called Healthy NY. They provide fairly comprehensive health coverage for eligible small business owners and their employees including Sole Proprietors and individuals. I'm not sure how far along other states are in this process, but if nothing is in place where you live, do a lot of research. More and more there are independently employed groups of people coming together to form their own unions or coalitions that take on the issue of health insurance for you. Working Today for example, represents the interests of and provides health insurance for freelance workers in New York City. Bottom Line: no one should be without health insurance, so please look around and see what's out there for you.