While I wouldn’t trade working for myself for almost any other type of job, dealing with self-insured healthcare has been painful. Trying to get a policy can take hours of time, effort, and research. The application process can take hours (even when done online). A typical section requires you to list all of the doctor’s you’ve seen in the last 10 years. If you leave something out (and just about everyone will), you leave yourself open to having the insurance company claiming you falsified your application. Add in too much detail, and you’ll enjoy overly broad waivers that will prevent you from getting any reasonable amount of coverage (my
“crime” was having allergies). Based on that, Blue Cross/Blue Shield (with whom I had my COBRA-based health plan) refused to offer me any coverage for any price.
You have to apply to a policy to figure out how much you’ll pay and what waivers you’ll have. Generally, you’ll want to apply to multiple policies, each of which will bill you in advance. Should you decide to cancel a policy, you’ll have to wait several months to get a refund. That was exactly my experience.
MSN Money has an interesting article entitled How early retirees insure their health. These people are generally in the same boat as the self-employed an anyone that doesn’t have employer-sponsored health insurance (a rapidly growing segment of our population). Unfortunately, there just aren’t many good options (short of leaving the country). Perhaps we can all be considered members of the “high-risk” pool, simply for choosing to live in the United States.