"It's a mistake to only consider expected value." Agreed, to be precise, one has to look at the entire value range, associated probabilities, and their effect

"It's a mistake to only consider expected value." Agreed, to be precise, one has to look at the entire value range, associated probabilities, and their effect on one's personal "happiness function". That's what I was trying to do with my variance "estimates", since most of these things are pretty gaussian anyway. "Risk is something that should be intelligently assessed and balanced, not blindly embraced." Also agreed, and that is precisely what I am trying to do with regards to the real value of health insurance (admittedly without much quantitative data). So far, all I see in this thread is anecdotal evidence of some catastrophic events. "I'd rather work at a string of unsuccessful but fun startups than some soul-crushing big company.": Me too, but that depends on a whole lot of personal factors, and there is no one right answer for everyone. Likewise for health insurance.