Techniques for preparing for teshuva?

Question

I'm attempting to prepare for Yom Kippur, and among the preparations is the issue of determining what, exactly, I should be focusing on during viduy this year. I'm curious whether there are any particular techniques espoused by either chazal, modern Roshei Yeshiva, or other notable Torah personalities regarding this topic. Currently, I'm simply attempting to compile a list of aveiros or la'avim that I find myself struggling with; if there are any better ways of going about this, I'm curious.

Note: I'm not sure whether this question is appropriate for this more halachic-oriented forum, so feel free to close it if necessary.

Answer 1

This may not exactly answer your question, but Sharei Teshuva (as well as Rambam) brings 24 categories that impede teshuva:

1. One who frequently spreads Rechilus (slanderer)
2. One who regularly speaks Lashon Hara (Gossiper)
3. One who gets angry quickly
4. One whose bad (impure) thoughts control him
5. Being connected to a rasha (evildoer)
6. Taking from food that isn't sufficient for its owner
7. Gazing at Arayos with sinful intent
8. Partnering with a thief
9. One who says "I will sin and repent afterwards" or " I will sin and Yom Kippur will atone for the sin"
10. One who derives honor [and pleasure] from his fellow man's humiliation.
11. One who separates him/herself from the Tzibbur (congregation).
12. One who ridicules his forefathers and/or teachers
13. One who curses the public
14. One who prevents a group of people from doing a Mitzvah
15. One who causes another Jew to leave the good path and take a bad path [of living not according to the Torah]
16. One who uses the pillow of a poor person [i.e. causes a poor person to lose the use of any of his meager possessions]
17. One who accepts bribes in order to skew and distort justice from prevailing.
18. One who finds a lost object and doesn't [try and] return it to its proper owner.
19. One who sees their child going off the [Torah] path, and doesn't admonish them.
20. One who eats [i.e. usurps] the food [i.e. livelihood] of poor people, orphans or widows.
21. One who argues [and does an action] against the will of the sages.
22. One who accuses good people of doing wrong [without proper proof or reason]
23. One who hates [and cannot accept constructive] criticism.
24. One who ridicules all or some of the Mitzvos of the Torah [or those instituted by the sages]

(Translation copied from halachafortoday.com)

Answer 2

http://diaspora.org.il/ethics/acc03.htm
http://jewishmag.co.il/58mag/chesbon/chesbon.htm

Above are two links to the cheshbon hanefesh method. The following is extracted from the second link, “Doing an "accounting of the soul" is actually very simple. As a first step, you compose a list of thirteen qualities that you undertake to observe in yourself. The traits that belong on your list are those aspects of your inner life that tend to trip you up, in one way or another. Maybe you're already aware that you aren't too accurate in your speech, (which is something I've had trouble with in the past). Or maybe it's greed that sends you off in ways that don't yield up anything except a bad taste in your mouth. Is it arrogance that has you puffing up your ego like a peacock, or do you have the opposite tendency, allowing yourself too readily to be walked all over?”

This does not tell you how to choose these 13 qualities. There are some sample trait lists at http://diaspora.org.il/ethics/acc07.htm which may help. Don’t worry about getting a perfect set of traits, just get started and see what you learn about yourself. You can always refine the list as you go on as long as you do it honestly. Hatzlocho!

Answer 3

try reading shaar hateshuva from chovos halevavos. this is the climax of the entire book

it's not too long and very, very, very powerful

english translation online http://dafyomireview.com/article.php?docid=388