If you're in the U.S., navigating health insurance is one of the most difficult aspects of living without a job. While I've tried a lot of approaches, what I find works best is purchasing a high-deductible plan on the health insurance marketplace, then doing whatever you can to limit your health insurance costs. In addition, this opens you up to using a health savings account (HSA), which carries a host of tax benefits. From there, adjust your emergency fund to ensure you can cover your plan's out-of-pocket maximum for the year. Of course, this works best for those without pre-existing conditions that require regular medical care.