How much risk have you taken?

A bachelor friend of mine, who comes from affluent background left his job at Microsoft and joined another established start-up(which was about to get acquired) and his facebook wall reads "It was a very tough decision".

I thought "Really"?

Entrepreneurs take much bigger risks when they leave their full time corporate job to chase start-up dream and plunges into unknown with the hope that he would be able to raise money in next 3 months and everyone would be fine, including wife and kids (who would no longer have best medical coverage) and are not going for vaccation this year..and not sure when they would next. Maybe they would have to leave the country if nothing works out...

Whats your story? Want to share how much risk have you taken and what was the lowest point from which you came back?