Although one big problem with COBRA is that if you go work for a start up and it fails you're ineligible, there's no one left for you to buy insurance from. That happened to me a few years ago and if the timing had been slightly different it would have left us uninsured during the birth of my son. Another point is that the difference between your employer "subsidising" your health coverage and you paying for it yourself is that under the current system you get a tax break for your employer paying for your insurance that you don't get if you pay it yourself. So not only do companies pay less in general for insurance, the tax benefits represent a huge jump in out of pocket expenses for people looking to leave their employer and strike it out on their own.