I get this, especially given that things are getting more expensive and so the cost (not just money) of doing something that turns out to be wack hurts more. However, I think life is much less interesting when you try to manage out all the risk. Seeing a couple crappy movies makes the great ones more special; a bad restaurant puts the good ones into perspective.
Of course, the way to make this more palatable for people who Are Not Rich is a better distribution of income, but, alas, solving income inequality is outside the bounds of this message board.