I tell my students, if you ever become comfortable with your role as criminal defense lawyer, it's time to quit. It should be a constant source of discomfort, because you're dealing with incredible moral ambiguity, and you've been cast into a role which is not enviable.
Of the three official objects of our prison system: vengeance, deterrence, and reformation of the criminal, only one is achieved; and that is the one which is nakedly abominable.