Having finished offering the 20 principles of teshuva (returning to G-d), Rabbeinu Yonah now completes the first gate of “The Gates of Repentance” by presenting us with a list of things that hinder teshuva.

It’s important to note that we’re told that G-d “never closes the door to teshuva to us” no matter how unrighteous we’ve been; and that G-d will always sympathize with us and be merciful. Nonetheless the stark truth of the matter is that there are instances and situations in which teshuva will be difficult– though never impossible.

Rabbeinu Yonah advises us to be strong in those instances, though; to speak to G-d and to others about the things we’ve done wrong, pray and plead for forgiveness, and engage in the 20 principles of teshuva. You’ll then be shown mercy both in Heaven and on earth.

We’ll now list the 24 instances Rabbeinu Yonah cites and offer comment on just a few, for lack of space. You’ll find it difficult to come to teshuva if you engage in the following actions repeatedly and stubbornly:

1. rumor-mongering,
2. slander,
3. fury ,
4. thinking untoward thoughts,
5. associating with wrongdoers,
6. regularly accepting food from those who don’t have enough,
7. staring at instances of nudity,
8. sharing in stolen property,
9. saying, “I will sin (now) and then do tshuvah (later)”,
10. achieving honor at another’s expense,
11. separating yourself from the congregation,
12. belittling your ancestors or teachers,
13. cursing the masses,
14. preventing the masses from doing a mitzvah,
15. causing another to deviate from the path of good and to follow a bad one instead,
16. using a pauper’s pledge for personal gain,
17. taking a bribe to pervert justice,
18. finding a lost object and not returning it to its owner,
19. seeing your child going bad and not objecting,
20. eating from the sustenance of paupers, orphans and widows,
21. arguing against the words of sages,
22. suspecting the innocent,
23. hating criticism, and 24) maligning mitzvot.

“Rumor-mongering” and “slander”… because of all the complications and people involved. After all, you’d have spoken ill of people unnecessarily, word of that would have gotten out and their reputation would have been besmirched, and their careers and lives might be unalterably affected. It would indeed be very hard to undo that.

“Associating with wrongdoers”… because you’d grow used to hearing them say bad things and boasting of their untoward acts, and you’d find it hard to withstand the social pressures to be accepting of them.

“Sharing in stolen property”… because you’d never know whom the goods were stolen from, since you didn’t steal them yourself. So it would be very hard to return them and make amends.

“Saying, ‘I will sin (now) and then do tshuvah (later)'”… because while teshuva will indeed undo sins, sinning with that expectation in mind from the get-go and thus taking teshuva lightly will make it hard for you to truly return to G-d, since you’d arrogantly assumed you could always get Him to forgive you.

“Hating criticism”… because you’d hardly be likely to acknowledge your errors and own up to your flaws if you couldn’t take criticism.

“Maligning mitzvot”… because mitzvot are G-d’s guideposts in the world– they indicate where He’d prefer you go and what you’d be best to do under all circumstances. If you malign such things you’re hardly likely to take anything of import seriously, including your own lapses.

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