Would it be easier to make that transition if you could buy health insurance at the same price as your current employer?
The reason I ask, I bumped into my old financial planner a few days ago. He was working at Starbucks because he couldn't get health insurance any other way.
The man is a tax attorney with a masters in finance and can easily pull 75k a year. But he has Parkinson's. As a lawyer or financial planner in most firms he'd be responsible for his own insurance. He ran his own firm for 20 some years. For the last 2 he's been pulling lattes at $9/hr because he would otherwise have lost everything he owned to the medical bills.
Now, I don't like anecdotal evidence. On its own it doesn't prove anything. But it does illustrate a principle. There are people out there right now who would be entrepreneurs but are punching a clock instead; because it's the only way they can get health insurance.