A. Depends what you are ashamed about. Being bashful is “a trait of the descendants of Abraham” (Avot 5:19) and “the shame-faced go to Paradise” (Avot 5:20) stemming from humility. It is a sign of sensitivity to be bashful when honored or the like. But “the bashful student can not learn” (Avot 2:5) and Pride in who we are (as Jews, as people, as professionals etc..) is very important. While self-centeredness and arrogance are out, a healthy self-esteem, confidence and meaningful pride are necessary for growth and are perfectly consistent with humility. We did a Torah-Tues class on “Torah and Self-Esteem”.
