The season of repentance began with the first of Elul. We are now in the heightened time of awareness between Rosh HaShanah and Yom Kippur called the Days of Awe.
Repentance is not just turning away from bad and turning toward good, but it is also about coming to grips with our sins and learning not only the things we should be doing but also the things we shouldn’t be doing.
Jewish ethical teaching prescribes a study of both good and bad character traits to discern proper behavior. We find in the sixteenth-century Jewish ethical work Orchot Tzaddikim:
The righteous man must recognize good and evil and be an expert in the value of each trait. He must properly observe and reflect upon them and exert himself physically and intellectually to rid himself of folly and to embrace understanding and remove admixture of dross. 
Mesillat Yesharim (eighteenth century) echoes this sentiment:
Now if someone wants to oversee himself, there are two things which he needs to consider. First: what true good is that one should choose, and the true evil that one should eschew. Second: He should consider the things he is wont to do day after day. (Mesillat Yesharim 5) 
Only through the study and contemplation of evil traits can we completely rid these qualities from our lives. If we don’t know how to recognize wrongdoing, we will not be able to purge it.
Messianic luminary Paul Philip Levertoff comments on the order of the prayers in the Amidah where the prayer for knowledge is before the prayer for repentance:
First it says, “You grant knowledge to mankind.” After the petition for knowledge, we ask for repentance. Without knowledge of sins, one cannot differentiate between good and evil. Without knowledge, a person would not come to repentance. 
It is this knowledge of sin and then recognizing where it is in our own lives that brings us to complete repentance.
Additionally, if we do not continually eradicate evil traits from our lives, thereby allowing these qualities to gain the upper hand in our nature, we will eventually come to despise good character traits. Orchot Tzaddikim continues:
Know and understand that one who by nature inclines to an evil trait or has become habituated to such a trait and does not take it upon himself to forsake it, but constantly strengthens himself in it—such a one will come to despise and abhor the corresponding positive traits. 
This is why the Didache dedicates an entire chapter to the Way of Death. This instills in new disciples to be wary of its traps and exercise healthy introspection, examining the evil traits that could ensnare them and removing them from their lives. It begins with a list of twenty-two evil traits that should be avoided at all costs:
But this is the Way of Death, which is first of all evil and full of curses: murder, adultery, lust, sexual immorality, theft, idolatry, magic, use of potions, robbery, false witness, hypocrisy, duplicity, deceit, arrogance, malice, egocentrism, greed, foul speech, jealousy, overconfidence, loftiness, and pretension. (Didache 5.1)
Scholars have noted that there is the same number of vices found in Romans 1:29-32 and the Vidui (“confession,” ודוי) prayer of Yom Kippur.  Why twenty-two? Most likely, as is made explicit in the Vidui prayer, there is a sin listed for each of the twenty-two letters of the Hebrew alphabet. Here’s what that looks like in the Vidui:
א We have incurred guilt, ב we have betrayed, ג we have robbed, ד we have slandered, ה we have acted perversely, ו and we have caused wickedness, ז we have been insolent, ח we have been violent, ט we have libeled. י We have given evil counsel, כ we have lied, ל we have mocked, מ we have rebelled, נ we have despised, ס we have disobeyed, ע we have committed iniquity, פ we have transgressed, צ we have shown hostility, ק we have been stiff-necked, ר we have been wicked, ש we have acted corruptly, ת we have been abominable, we have gone astray, You have allowed us to go astray. (Vine of David Translation)
This similarity has caused some scholars even to speculate that the Didache represents an early version of the Vidui prayer that is now in the Yom Kippur liturgy. 
In this season of repentance it would behoove us to examine the Way of Evil and see where we have fallen short and what paths we should avoid. Didache chapter 5 is a great place to start, and it seems it might have even had its roots in Yom Kippur itself.
For more on the Didache, see Vine of David’s Messianic Jewish translation and commentary on the Didache entitled The Way of Life: The Rediscovered Teachings of the Twelve Jewish Apostles to the Gentiles.
- Rabbi Gavriel Zaloshinsky, The Ways of the Tzaddikim (trans. Rabbi Shraga Silverstein; 2 vols.; New York, NY: Feldheim, 1996), 1:15.
- Rabbi Moshe Hayyim Luzzatto, The Complete Mesillat Yesharim in Two Versions Dialogue and Thematic (Cleveland, OH: Ofeq Institute, 2010), 71. Cf. “Ultimately, they were counted and concluded: It would have been preferable had man not been created than to have been created. However, now that he has been created, he should examine his actions that he has performed and seek to correct them. And some say: He should scrutinize his planned actions and evaluate whether or not and in what manner those actions should be performed so that he will not sin” (b.Eruvin 20b).
- Paul Philip Levertoff, The Religious Thought of the Chasidim (Marshfield, MO: Vine of David, 2017).
- Rabbi Zaloshinsky, The Ways of the Tzaddikim, 1:13.
- J. Rendel Harris, The Teaching of the Apostles (London, England: C.J. Clay and Sons, 1887), 82-86.
- For example, building off the connection between the Vidui prayer and Didache 5.1, E. Bruce Brooks feels that similar lists of sins found in Mark 7:21-22, Galatians 5:13-6:10, and Barnabas 18:1-20:2 along with Didache 5.1 all go back to a proto-form of this Vidui prayer, which is best preserved in the Didache (“The Two Ways,” Alpha: Studies in Early Christianity vol. 1 : 39-47).