Your other option is to exercise the free market strategy and try to find a private insurer. Unfortunately, these are also often very expensive. There are some plans that might fit into your budget, but you typically don't get what you're paying for in terms of coverage. However, there are situations where you're going to need coverage—any coverage—in order to make it through until you find another job. For example, if you currently have a condition that forces you to purchase a lot of medication, prescriptions, or medical hardware, you'll have to think about COBRA. If what you need in order to survive or stay healthy is, on a monthly basis, more expensive than COBRA, you'll be saving money by continuing your plan. Additionally, it might be difficult for you to find different coverage because you'll have a “preexisting condition.”

Preexisting conditions are something you need to be incredibly careful of. If you have a chronic or long term illness, other insurance companies will be hesitant to pick you up, and they won't cover any of the costs of your chronic illness, because you were diagnosed before you were insured. If you are diagnosed with cancer while you are unemployed and you do not have insurance, even when you regain some coverage, you will have to pay for the cancer treatments out of pocket because it would then be a “preexisting condition.” If you happen to get sick while you're uninsured, it could make future health care very difficult. That said, your health is more important than anything, and you should never postpone going to a doctor because of insurance problems. You have to take care of yourself, first and foremost.

Finding health insurance while you're unemployed is, unfortunately, very difficult. It seems to be filled with more hazards than benefits, but that's why you need to take some time and make the decision that's right for you. If you can afford it, you definitely do not want your coverage to lapse, because if anything does happen, it will hurt you far more in the long run. That said, sometimes you just can't afford it, and you've got to do the best you can. Health insurance is tricky, and sometimes, even if you do have it, your plan won't cover all of your costs. In the end, you've got to do what's best for you and your family.

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