For the reasonably healthy who know what they are looking for, ehealthinsurance.com got fairly good reviews. The site, which has the feel of an Expedia or Orbitz for purchasing health insurance, allows you to compare a variety of policies offered through about 70 insurance providers. One caveat, pointed out by several readers, is that ehealthinsurance.com does not serve consumers in all states. Rhode Island, Vermont, Massachusetts, Maine and North Dakota are excluded. The company also covers only individuals. So if your company has employees, you will need to explore other options, like starting a group if your state permits that.

Another possibility for consultants and independent workers is the Freelancers Union, which won consistently good reviews in the reader comments. But the union also has some limitations. It operates in only 30 states, and you have to work in one of the industries or occupations it serves.

While healthy business owners have to incur high costs and navigate a maze of choices, the truly unhealthy face the biggest challenges.

To learn more about options for those whose health is getting in the way of their self-employment, I spoke with Ms. Jaff, the woman who directed me to healthinsuranceinfo.net. Ms. Jaff, a lawyer who has worked on legal issues surrounding health care in both the public and private sector, now runs Advocacy for Patients With Chronic Illness (advocacyforpatients.org), a nonprofit organization in Farmington, Conn., that advises and advocates on behalf of the chronically ill. She says she works with about 1,000 patients a year, handling everything from battles to get insurance companies to pay for treatments prescribed by patients’ doctors to helping people figure out the best coverage.

Ms. Jaff speaks from experience. She suffers from Crohn’s disease, a condition so severe that she does not leave her house during flare-ups except to get to a doctor’s appointment or to the hospital. She wanted to find something she could do out of her home and as she went through the challenge of finding her own health insurance, she discovered what she calls “a community of patients in desperate need of help.”

Ms. Jaff qualified for the Municipal Employees Health Insurance Program, offered by Connecticut to cover small-business owners as part of a plan for state employees. She knew about the plan, which she recommends to all small- business owners in Connecticut, from her days as a lawyer in the attorney general’s office. Even with her extensive experience, Ms. Jaff has not been able to find the holy grail  good coverage at a great price. When she started on this insurance, her premium was $400 a month. Last year, the monthly payment went up to $800.

“I don’t know if people who don’t have chronic illnesses can really understand this,” she said. “But I have worked full time my entire adult life  generally 15 to 18 hours a day. I have paid into the system for all those years. And there is only one thing that could bankrupt me, and it is my health. I could lose every penny I own from one serious hospitalization without insurance. So I chose the plan that would give me the most possible coverage because the year I don’t is going to be the year I get really sick.”