Here is a brief synopsis of the 52 points in the first chapter of Rabeinu Yona’s classic work Shaare’ Teshuva.
1 The opportunity for repentance is a kindliness of HASHEM. Teshuvah is acceptable even from duress.
2 Know that the more one delays teshuvah the greater the punishment.
3 Only ignorant people delay teshuvah.
4 Delaying teshuvah causes a repetition of sin which is disgraceful.
5 Repeated sins become like permissible and then thoughts are counted as deeds.
6 One mistake repeated many times can be considered a great blemish.
7 Each repetition is a separate accounting.
8 Many are strict in numerous ways but fail repeatedly in a single area.
9 There are many levels of teshuvah. Some merely erase sins and others clean them completely.
10 Regret: Feel the pain of loss and saying” what have I done?!”
11 Letting go of the sin: Changing one’s ways from now on.
12 Sorrow: Magnify the feeling of loss and sigh bitterly.
13 The degree of teshuvah corresponds to the intensity of the sorrow.
14 Sighing and worry stem from recognition that one has not approached HASHEM properly.
15 Active suffering: The eye that saw needs to cry and the haughty heart needs to break.
16 Worry: “To what extent, if any, will I be hit due to inadequate teshuvah?!”
17 “Maybe this desire will overcome me again” -I am never safe till the end.
18 Undo publicly that which was done publicly.
19 Although there are many levels of teshuvah mercy is achieved by admitting and letting go of the sinful activity.
20 “Happy is the man who was always afraid!” Constantly capitalize on teshuvah.
21 Shame: the awareness of Heaven should be as real as the awareness of people.
22 The higher-level is to feel embarrassed to have acted so before HASHEM.
23 Humbling one’s self with a broken spirit before HASHEM.
24 Appreciate the privilege to serve. Take no credit for yourself. Work secretly.
25 Take no pride in wealth, strength, wisdom etc.
26 Humility is obligated because it counters the attitude of pride.
27 Pride itself is a sin and is the father of all other failures.
28 Humility yields forgiveness from others and causes HASHEM to forgive him too.
29 Humility in deed: A soft answer, lowered eyes, and modest dress.
30 Breaking physical desire: Even in relation to things that are permissible.
31Desire is the root of all action. Let your intellect dictate your actions or your desires will dictate your intellect.
32 If the desire is broken, how can one become tempted by forbidden things?!
33 Breaking one’s desire is a demonstration of sincerity in teshuvah.
34 Follow the Way of Abraham by adopting a lowly soul, namely self-control of physical desires.
35 Reversing one’s deeds: One who ran to sin now runs to Mitzvos etc.
36 Searching one’s ways: To become aware, to become humble, and to protect against future failures.
37 Realize the grand consequence, penalty, and the value of each wrong.
38 Small violations lead to larger ones and are also considered rebellious.
39 Fearing small transgressions are counted like keeping away from big ones.
40 Admit to HASHEM the nature and details of your sins and the sins of ancestors that linger.
41 Pray- plead for forgiveness.
42 Petition to HASHEM that the sins should be erased as if they never occurred.
43 One should constantly ask and plead for divine assistance to do teshuvah.
44 Undoing the harm: as much as possible one should repay and appease and repair as part of the teshuvah process.
45 When one repays and appeases before confessing is more pleasing and acceptable to HASHEM.
46 Consider that the righteousness of HASHEM is demonstrated in teshuvah.
47 Doing kindly acts and passionately pursuing truth alleviates the need to suffer.
48 The memory of the sin should forever remain before the eyes of the baal teshuvah.
49 HASHEM should be able to testify about us that we would never do it again.
50 Help as many as possible to return to HASHEM. Teach others the ways of teshuvah.
51 Know that if one has fallen into one of the 24 deterrents to teshuvah the labor must be intense.
52 Know well the 24 deterrents to teshuvah to avoid the rough road. DvarTorah, Copyright © 2007 by Rabbi Label Lam and Torah.org.