The difference between the Wicked and Wise thief who shared Golgotha with Christ is the exercise of judgement, as the Wise Thief revealed in admonishing the other for lacking the ability to discern that while all were under same condemnation, but this man is innocent. judgement belongs to God alone, and to no person ever, for being judged we are judged. 

The wise thief, the last, is the first to enter into Paradise and finds peace, because he asks for a blessing from Christ on the Cross, rather than judge as he himself is being judged.

As the root of judgement is the idolatry of pride elevating the self above the short-comings of others, in the monastic life non-judgement is fundamental. Not only is a person's past rarely discussed, and then only if that person brings it up in order to edify others, and new names given as one proceeds toward tonsure so that others might not even know the name of someone as given them by their natural parents, but in through the most fundamental aspects of daily life. Regardless of rank or seniority, self-will is surrendered to a life of obedience and asking of blessings. 

In strict hierarchy of authority, the Doctrines and Traditions of the Church, the monastery's rule, or typica, charismatic authority of the abbot, the discernment of confessors and priests operating with the permission of the abbot, govern daily life.

Daily obediences ensure that the mundane requirements of daily life are accomplished and good order is maintained in the monastery.  All special tasks and the exercise of responsibilities are assigned according to the discernment. No initiative or activity may be under taken without a blessing from the abbot or someone he as designated. At first, this is very relaxing, all one has to do is what one is told: simply follow the directions, but, with attention and fidelity. As attentiveness increases and the demands of fidelity become clear, there is great spiritual warfare as thoughts of pride and self-will assert themselves. By considering that Adam had only one commandment and even that was too great, one can begin to appreciate what might be required.

The outcome of work of being obedient in seeking blessings while surrendering self-will to one with authority is the acquisition of the virtue of discernment, the ability to look into a situation and see what temptations and provocations for oneself and others are hidden beneath the surface, and to prepare a strategy to overcome it.

The abilities to make wise choices and to discern the challenges are genuine freedoms that come from having liberated the soul from the prison of pride in which we die to the grace of God. 

In discussing the fourth step in the practice of Christian philosophy, St John Climacus writes of the practice of "blessed and ever-memorable obedience":

Obedience is absolute renunciation of our own life, clearly expressed in bodily actions. Conversely, obedience is the mortification of the limbs while the mind remains alive. Obedience is unquestioning movement, voluntary death, a life free of curiosity, carefree danger, unprepared defense before God, fearlessness of death, a safe voyage, a sleeper's progress. Obedience is the tomb of the will and the resurrection of humility. A corpse does not argue or reason as to what is good or what seems to be bad.  He who has devoutly put the soul of the novice to death will answer for everything. Obedience is an abandonment of discernment in a wealth of discernment.

 So it is. Turning from judgement to obedience in the quest for blessing furthers the search for peace by living according to the natural liberty of humanity to love all creation.