In Chapter 4 of Hilkhot Teshuba Maimonides enumerates twenty-four actions, personality patterns or attitudes which prevent or make very difficult for a person to begin or undergo the process of repentance.
Three illustrations.
DOMINO EFFECT (4:1)
Those who because of their teachings or their bad example…. induce or influence other people to sin. Sometimes, if we have taught or inspire other people to act in the wrong way, we have triggered a negative domino effect which eventually gets out of our hand. In this case repentance is virtually impossible. Why? Because part of the process of repentance consists in repairing what I have done wrong. So, even if I personally repent from my wrong actions, how could I be able to repair the damage other people have caused because of my wrong teachings or bad example? In this scenario, I’m virtually beyond redemption. Because despite my own personal repentance my example is still exerting a negative influence in other people to an unknown extent.
CALCULATED TESHUBA (4:1) Sinning with the intention of repenting later. Maimonides refers here to a situation in which I’m about to commit a sin and before I do it I say to myself : “I will sin now and repent for this sin later on.” Or I say to myself: “Since Yom Kippur is the day of forgiveness, I will sin now and God will forgive me for this sin in Yom Kippur”. In these conditions Teshuba is unacceptable. Because Teshuba is welcomed by the Creator when it comes from a sincere remorse, not when it is part of a calculated game-plan.
DEFENSIVE PERSONALITY (4:2) Someone who refuses to be corrected or criticized. Imagine a person incapable of accepting a minimal dose of positive criticism, even when coming from those who care for his or her well being. Many times, this type of personality-disfunction is a consequence of a low self esteem or other psychological issues which prevent a person to cope with any criticism. This person, Maimonides concludes, will likely continue with his or her bad habits because is incapable of seeing himself as other people perceive him.
