The Bold and the Shy
The Medzibozer Rabbi quoted Ethics of the Fathers (5:23): "The bold-faced are for Gehinnom (purgatory), the shame-faced for the Garden of Eden." He explained it as follows: "We see oftentimes that one is impudent and bold-faced when he is about to commit a transgression, which leads him to Gehinnom. But one who is about to perform a good deed which leads him to the Garden of Eden, is quite shy and shame-faced about it. The reverse would be more natural."
Source: Or Yesharim
