Just playing with some numbers, if you work in "Information" in California and make $100k, you're looking at just over $100/month in payments according to their calculator. Say you get laid off two years from now, you would have paid $2,400 for the insurance. Payments don't kick in for two weeks, and only add $511/week over what normal unemployment would give you, so you would have to remain out of work for 7ish weeks to break even.