There is a comment of the Vilna Gaon’s on a line in Mishlei (Proverbs) 4:26 that is included in an introduction to Cheshbon haNefesh. Here’s a translation, any errors are mine:

פַּלֵּס, מַעְגַּל רַגְלֶךָ;    וְכָל-דְּרָכֶיךָ יִכֹּנוּ.

Straighten the path of your feet, and all your paths will be established.

I already wrote that there are two kinds of middos, which are those that are the middos which are born with him by nature, and those that he acclimated himself to. Those that were born with him are called “derakhav” (his paths), for they are his derekh (path) from the beginning of his creation. Those that he habituated himself to are called regel, because he made a habit (hirgil) of them.

To those he made a habit of, he must guard and straighten them a lot. When he guards them, then they which were in his nature, they will of course be guarded. This is “paleis ma’gal raglekha” [straighten the circuits of your feet; the first half of the verse in discussion]. Those which he became used to he needs to straighten and to pass little by little from the bad middos, like a peles, and not to grab right away the other extreme.

Until he habituates himself and it will be to him like nature. (And it says “ma’gal” (circuit) because to those [middos] that he habituated himself to he has to go around and revolve…)

“Vekhol dirachecha yikonu” [and all your paths will be established; the 2nd part of the verse] of course those middos that are his derekh since birth are established (yikonu), from the term of “kan ubasis” (branch and basis, perhaps: branch and trunk). If you don’t guard those [middos that are] from habit, even “derakhav” won’t be established. For middos are like a string of pearls — if you make a knot at the end, then all are guarded, and if not, all are lost. So too are the middos. Therefore [the pasuq] says that if one straightens the circuit of his feet (raglav), then his ways (derakhav) will be set.

The Vilna Gaon refers to “derekh“, a path, and “raglav” which can translate to “his feet” or “his habits”. This being the book of Mishlei, which is literally “Metaphors”, obviously one is meant to stand in (sorry for the pun) the other. Middos are classified as being either an innate propensity or the product of habit — or a combination of the two.

With his metaphor of pearls, the Gaon writes of two sorts of middos, those with which we are born and those that we acquire by habit. If we are trying to modify a middah from what one was born with, the primary tool for doing so is hergeil, habituation.

In Ohr Yisrael, R’ Yisrael Salanter spells out a three-stage process to improving a midah.

1- Hargashah: feeling. Obviously one can not work on a broken middah until one is aware that it exists. As the cliche goes, “Realizing you have a problem is halfway to the cure.” I’m not sure if by “hargashah” (feeling) R’ Yisrael is referring to the awareness of the middah‘s state, or the feeling of a moral imperative to fix it. I could not be aware that I am too timid. Or, I could be aware of my timidity, but think that that it’s proper.

If I may be so bold as to suggest breaking this down into multiple steps:
a- awareness of an ideal,
b- internalization of that ideal until one is motivated to act on it, and
c- developing consciousness of when you are exhibiting the issue.

2- Kibbush hayeitzer: conquering the desire. Don’t start by trying to fix the attitude, rather, start with trying not to act on it. To give a personal example (that I have yet to succeed at): Kibbush of anger doesn’t mean not losing my top when my kid tells me he broke his toy “Because.” It means not acting on that anger.

The route to kibbush hayeitzer can be understood from the mitzvah of the eishes yefas to’ar. A Jewish soldier finds a woman in the enemy camp attractive and wants to take her. He is told that he must shave her head, dress her like a person (rather than booty), and allow her to mourn her family for a month. In short, the Torah allows the relationship but sets limits by requiring that the man take steps to insure treating her like a person. Rashi (Devarim 21:11) quotes Chazal, saying, “The Torah only spoke against the yeitzer hara.” This is usually taken to mean that while the act itself is against Torah values, Hashem realized that banning it altogether would be beyond the soldier’s ability to obey. However, that overlooks Chazal’s use of the word “keneged — against”. We are being given a key tool in fighting against the yeitzer hara.

To conquer a middah one does not try to eliminate it in a single step. Rather, one takes a single step, followed by another and another. It is a process of shteiging, of ever ascending upward. Kibbush HaYeitzer requires deciding to take that small step, to acquire a habit that whittles down the improper middah. Because these practices are accepted upon oneself, they are called qabbalos. Ideally, a qabbalah should meet the following criteria: the content should be (1) small enough that the person has a reasonable chance of following through on it, and yet (2) large enough to be measurable. Third, the length of a qabbalah should be a fixed period of weeks or months, and not an open-ended commitment. At the end of the period, one can assess whether one is ready to progress, or perhaps if the qabbalah was overly ambitious and needs to be rethought.

For example, if someone is working on savlanus (patience), a reasonable qabbalah might be to accept upon oneself not to lose one’s patience for the first five minutes upon returning home, or perhaps not to ever yell at the dinner table. It is not going to conquer the yeitzer all at once, but it is a measurable change that is small enough to actually follow through upon and yet also significant enough to build upon.

The first kind of qabbalah is most direct — picking part of the challenge, and choosing to act appropriately when it arises.

Moshe and the elders of Israel command the Jews, “Observe all the commandments that I will command you today. It will be when you cross the Jordan to the land which Hashem you G-d is giving you, you shall set up for yourselves large stones, and cover them in lime. Write on them all the words of this Torah…” (Devarim 27:1-3)

Crossing the Jordan need not have been a reminder to observe the mitzvos. Moshe commands them, though, to perform a commemorative act, to use the moment. This corresponds to a second kind of kabbalah, an acceptance to use a moment and artificially connect it to the desired goal. This could be because the triggering event is frequent and therefore would serve as a regular reminder to establish a habit. For example, one friend accepted a kabbalah to remember the six basic mitzvos of the mind every time he enters the car, using its ceiling, floor and four sides as a mnemonic for the six beliefs.

A third kind of kabbalah aims to change what used to be a preconscious decision into a conscious one. Dr. Alan Morinis tells of one such, recommended to him by Rabbi Yitzchok Perr, Rosh Yeshiva of Yeshivas Derech Aisan in Far Rockaway. Rabbi Perr recommended that whenever one feels impatient or angry, one should slip a rubber band, one loose enough to be comfortable but yet small enough to be felt, on one’s hand. (Alan Morinis, Climbing Jacob’s Ladder, pp. 47-48) This is also hergel; it is practicing making the process of getting impatient or angry a conscious one, rather than an immediate reaction that short-circuits our free will.

3- Tiqun hamiddah: fixing the desire. This happens as a consequence of prolonged qibbush. The habit changes the middah. As we saw above, from the Vilna Gaon.

This is one reason why giving causes love. It was one of the better-known techniques of the ba’alei mussar; when someone irritates you, or you simply dislike him, give to him more. (See this post on the subject.) Kibbush isn’t just a half-way step to true tikkun, it’s a necessary precondition. It’s through acting as though a feeling exists (or doesn’t) that the change in character occurs. (I found it interesting to compare
this to the approaches of behavior therapy.

A sibling to this notion is a basic part of Jewish observance. Many of the Chinuch’s explanations for each of the various mitzvos begin with the phrase (or a variation of it) “man is affected according to his actions”. It sounds nicer in Hebrew, where the words I translated as “affected” and “actions” have the same root and shares the same letters as “according to”: ha’adam nif’al lefi pe’ulosav.

Four of the above are procedural steps, and the tools developed by the ba’alei mussar can be divided by which of these steps they address.

1a- Learning the ideal:

Mussar Study: This doesn’t only mean opening a Mesilas Yesharim. It’s also how one is listening to what one learns in other subjects. Reviewing parashas Pinechas twice and once in translation isn’t just a means to get through the parashah, it provides lessons in violence by giving an exceptional case where it’s appropriate, it teaches something about leaving a legacy when Moshe ordains Yehushua and appoints him his successor, and when Tzelafchad’s daughters worry about the loss of their father’s legacy, it speaks to us even in the census and the sacrifices of the holidays, although there the language is more obscure.

Of course, it does also mean Mesilas Yesharim, Orchos Tzadiqim, Shaarei Teshuvah, Mishlei…

1b- Internalizing the ideal

Hisbonenus: visualization. People are far more moved by experiences than by ideas. This is why Hashem “speaks” to a prophet in visions, and through the symbols of halakhah. Through the koach hadimyon, one can invent pseudo-experiences. See my earlier entry “I have a Dream“.

Hispa’alus: find some quote (sentence or paragraph length) about the middah in question or about something you feel is one of the causes of it in your own case. Spend time (10 min to start with, working your way up as you get used to it) each morning chanting it in a singsong, until you’ve gleaned some new insight into the problem. For more on hispa’alus, see Mesukim miDevash on parashas Ki-Seitzei (pp 2-4).

For example, if dealing with jealousy (ayin ra), a quote might be “Al tira ki yashir ish, ki yirbeh kevod beiso, ki lo bemoso yiqach hakol, lo yeireid acharav kevodo — Do not be overawed when someone gets wealth; when the honor of his home accumulates; for when he dies he won’t take it all, his honor will not descend after him.” A good line for many in the Orthodox community because it’s pretty well known from songs — but don’t sing it unless the tune helps the line penetrate! Now think about that line. First about the plain meaning, but as you say it REALLY think. For example, why the repetition? How do wealth and honor differ from eachother, and how do they differ from what one really does take with them when one dies, after 120
years?

Tefillah is also far more effective behispa’alus. See this treatment of “Yismach Mosheh” (questions, thoughts) for an example.

Batei Mussar (the Mussar Kloiz): without the proper social setting, doing this work will remain “weird”, and fall into neglect. Peer pressure is a powerful force, too powerful to neglect in our toolset. Also, with continued use of a given space just for Mussar, simply entering a beis mussar places someone in the right mindset.

1c- Consciousness of the real

Cheshbon hanefesh: Keep a diary of all the times you’ve experienced the middah in question and what triggered it. Also keep track of what worked in getting rid of it. Just getting one’s conscious mind involved in the process is a major help.

For more on the centrality of hispa’alus and of keeping a cheshbon see Mesukim miDevash for parashas Shofetim pp2-4.

2- Kibbush haYeitzer

Qabbalos: Slow incremental change is the most sure. So, accept upon yourself one small step away from jealousy. (See Mesukim miDevash for parashas Eikev pp 2-3 for an exploration of how habit can be used to fulfill the mitzvah of loving Hashem.) For jealousy this is difficult, since you don’t want to encourage a habit of “sour grapes” (“what they have ain’t so great anyway…”) Perhaps something that encourages sharing in someone else’s joy in what they have.

A possible qabbalah (perhaps more relevent for a woman) might be that every time you go to shul you’ll find three things to compliment other women about their attire. No back-handed compliments!

Pe’ulos: this is more of a Novhordok thing, so I’m speaking more as an outsider. Basically, this involves role playing. It might even include intentionally going out in a manner that belittles the very thing you’re jealous of. To return to the problem of clothing competition: Not letting yourself go to shul in anything from this year’s (frum) fashion for a period of n months.

Va’ad: a “committee” (literal translation) of friends that can learn the subject and work together on qabalos. Peer pressure and support can be powerful things! See Mesukim miDevash on parashas Nitzavim (pp 2-3) for more on the value of ve’adim and the mussar community.

I’ve often felt that the shemiras halashon (watch your speech) campaign would go further if we organized ve’adim rather than classes. We all know it’s wrong; the problem isn’t a lack of knowledge in the head. It’s getting the heart caught up that takes work.