What if you have a chronic illness that will never allow you to be "healthy" regardless of what lifestyle choices you make? Additionally COBRA allows you to pay the full unsubsidized cost of your insurance, not your normal subsidized premiums. As far as employer culture, that is something you really do not understand fully until you've been on the job for awhile. You could very well end up in a worse position than the one you left. You can't just say "I don't like it here, so I am going to go over there for awhile, if it doesn't work out then I'll come back'. No. It's a risk & the risk is your livelihood & possibly your health. All are reasons people don't just bail when the job starts going downhill.