Getting self employed medical insurance is not impossible, but will be a little harder to achieve than working for a company that supplies your health benefits. If you are leaving a pre-existing job, The Consolidated Omnibus Budget Reconciliation Act of 1985, otherwise known as COBRA, allows workers to extend those benefits for up to 18 months after leaving a job. The down side: employers no longer pay their portion of the plan’s premium, which can be anywhere from 75 to 80 percent of a plan’s cost. By keeping the coverage and paying the employer portion, you’ll likely see a huge difference in what you pay for the coverage.