Aside from the obvious risk of being without health insurance, any lapse in coverage will impose waiting periods on any pre-eisting medical conditions once you do obtain insurance through a new employer. Your length of prior coverage will apply to any of these waiting periods, as long as you have not been uninsured for more than 63 consecutive days. You might consider reducing your current monthly premium by switching to a high deductible plan. In New York, Individuals is guaranteed issue. Meaning that you can always get new coverage. However, the lapse in coverage still applies.