I find this to be one of the biggest indicators. I have friends whose parents are extremely wealthy and they tried all sorts of random careers before finally settling on something. For them there was zero real risk since they always had their parents to fall back on. One's dad even told him to come up with a business idea and he would fund it and help him make it happen. Instead he goofed around for awhile, before simply going back to school.
Personally, I'm more irked at potential wasted than jealous. I have no one to fall back on, and that has made me fiercely independent, but also very risk conscious. The good thing is that it is easier than every to bootstrap ideas with minimal time.