I'm 51 and even though I have job security (if there is such a thing) I want to teach too but I've always wanted my own business. In July I'm opening a career school. I plan to continue working at my job for two more years, at least part time but I'm not ready to slow down or retire. I just want more freedom to set my schedule to do more stuff I want. It's as an opportunity . The kids are grown. My bills are minimal. The time is right. The only draw back is not losing my health insurance.
Health insurance is overrated and oversold, the three best places in the world to become infected with a disease are a hospital; a doctor's office; and a school.
There are no statistics that show that people who make frequent visits to medical facilities for non-emergency issues live longer or healthier lives than those who shun them.
As politely as I can put this, you are dillusional if you think that is what starting your own business is going to be like. The only part you have right is the part about it being a draw back to lose your health issurance.
One very definate thing you lose when you start your own business is your time. Yes, in a regualar job you might have to be there when they say. But compare that to having to be there when the business needs you - it is ALWAYS tugging on you for time. There is no such thing as a "freedom to set your scheudle" when you have your own business - not when you are first building it.