The individual health insurance market actually worked quite well before Obamacare.
Unless you are a young, healthy male, nothing could be farther from the truth.
If you think working well means that the insurance you've had for years suddenly drops you when you get cancer, then maybe.
If you think working well means that women paying upwards of 50% more than men, then maybe.
If you think working well means that maternity coverage is nearly impossible to find, then maybe.
If you think working well means that people take jobs specifically for the employer's health insurance and to avoid the individual market, then maybe.
Fifteen years ago I had an accident (not a car accident) where I fractured two vertebrae. My insurance covered my care and rehab, but since then I have had several "life events" that involved changing insurance, and I've always had a rider in my insurance that anything related to those fractured vertebrae would not be covered. Fortunately, I've never had any issues, but maybe someday I might, right? Then what? If you call that an insurance market that is working well, I don't want to know what you think would be a bad one.
Face it, the free market has failed in the health insurance arena. It just doesn't work. You can't "shop around" while you are having a heart attack or after you've broken your leg. And most importantly, you can't just decide, "oh, I don't need my leg fixed today."
Market forces don't work, so the work-around right now, at least, is to force every one into the market.
It would be like not getting house insurance, having your house burn down, and then claiming that the insurance company shouldn't deny you due to this pre-existing condition.
A better analogy would be this: you have house insurance. Your house burns down. Your insurance company starts paying for rebuilding the house, and then after putting up walls, but no roof or windows, they say, "Oops, you've reached your lifetime benefit max. Sorry, and good luck with that coming storm." Then you get a new insurance policy, and they say, "you have a house-fire pre-existing condition, so we will not insure you against fire."