Skip to navigationSkip to main contentSkip to right columnADVERTISEMENTCaroline LubinskyTue, June 30, 2026 at 3:46 PM GMT+2 8 min readBenzinga and Yahoo Finance LLC may earn commission or revenue on some items through the links below.Bluntly, yes, and he would also say this is fixable starting today. Being self-employed does not mean being uninsured. It means the responsibility for finding coverage falls entirely on you instead of a payroll department, and that is a responsibility too many freelancers, contractors, and small business owners quietly ignore until a hospital bill arrives and resets their entire financial life. A $14,000 ER visit is not bad luck. It is what happens when you self-insure without the balance sheet to back it up.Why Ramsey Takes Health Insurance SeriouslyDave Ramsey is not someone who loves paying for insurance. He has spent decades teaching people to self-insure over time as wealth grows. But health insurance is one area where he draws a hard line. The potential downside of being uninsured, a serious illness, a surgery, a multi-day hospital stay, is so financially catastrophic that no emergency fund provides adequate protection. The average cost of a three-day hospital stay runs around $30,000, and a major diagnosis like cancer or a cardiac event can generate hundreds of thousands in bills.Don't Miss:The Baby Steps framework assumes you have basic insurance in place before you start building wealth. That includes health coverage. Without it, every dollar you save and every debt you pay off is exposed to a single bad medical event that can wipe it all out.The Self-Employed Coverage ProblemThe challenge for self-employed people is real. When you leave a W-2 job, you lose access to group rates, and individual plans purchased on your own can feel eye-wateringly expensive. But expensive compared to what? Compared to a $14,000 ER visit, a $400-a-month premium looks like a bargain. Compared to a $200,000 cancer treatment, it looks like one of the best financial decisions you ever made.The Health Insurance Marketplace at healthcare.gov is the starting point for most self-employed individuals. Depending on your net income, you may qualify for premium tax credits that significantly reduce your monthly cost. The IRS outlines the self-employed health insurance deduction at Publication 535, which allows you to deduct 100% of your premiums from your gross income, making the after-tax cost considerably lower than the sticker price suggests.Terms and Privacy PolicyEU DSA contactPrivacy & Cookie SettingsMore Info