"There are a few tactics to avoid this predicament… (a) Sometimes, one spouse will continue to work a corporate job while the other pursues entrepreneurship. The employed spouse can then cover the whole family on her corporate health insurance. (b) Some employers, such as Apple, offer excellent, affordable health insurance, even for part-time employees. (c) A clever entrepreneur may be able to tailor her taxable income so as to be, “not too poor, but not too rich” to qualify for discounted healthcare. (d) Depending on where you live and your comfort with international travel, you may be able to get excellent care at much better prices by flying abroad. For example, a top-quality dental procedure that costs $10,000 in South Florida, may cost less than $1,500 in Colombia, which is an easy three-hour flight away. The healthcare situation for the self-employed is not pretty in the United States, but with proper planning and a proactive attitude, you can get by."