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The Mesilat Yesharim brings down zehirut (watchfulness) as one of the first steps to master.

Zehirut in essence means working on cleaning oneself up from all bad behavior through analyzing one's daily actions.

How much time per day is one supposed to devote to this practice, and how much detail should he look into his actions?

(If anyone also has tips/experience in how to work on this please comment. biggest problem i have with it is getting stuck in some area.)

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    Wouldn't this be different per person? – Double AA♦ Nov 19 '13 at 14:44
  • @DoubleAA so let's say for an average person – ray Nov 19 '13 at 18:57
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The Zohar recommends examining one's deeds and repenting every night before going to sleep (Korach 178a):

הא אוקמו דבכל לילא ולילא, עד לא ישכב ועד לא נאים בעי בר נש למיעבד חושבנא מעובדוי דעבד כל ההוא יומא ויתב מנייהי ויבעי עלייהו רחמי

This is cited approvingly by poskim such as the Mateh Moshe (Amud Ha'avoda §829):

יעשה כדעת הזוהר וישב קודם שישכב ויתאונן גבר חי על חטאיו ויפשפש במעשיו ואם ימצא ישוב בתשובה שלימה

As mentioned in DoubleAA's comment, the amount of time spent should depend on the individual, although a person should probably not spend so much time that it would disrupt his ability to live a balanced life (see Rambam, Hil. Dei'os 1:7, הדרך הבינונית שאנו חייבין ללכת בה נקראת דרך זו דרך ה; regarding going to extremes as a temporary measure, see ibid. 2:2).

The Vilna Gaon encouraged the contemplation of fear of Heaven before and after Torah study (see Even Sh'leima 1:1):

צריך לפנות לבו בכל יום קודם הלימוד ואחריו מעיפוש הדיעות והמדות ביראת חטא ומע״ט

The gemara (Shabbos 31a), discussing the need for Torah study (and other laudable pursuits) to be accompanied by fear of Heaven, draws a comparison to mixing one part of preservative into 180 parts of grain. According to R' Chaim Volozhiner (Ru'ach Chayim 1:1), one may infer that a person should preface his Torah study with a proportionate rather than excessive amount of time devoted to introspection and contemplation:

עכ"פ התורה היא העיקר ובכור תורה די קב יראה, והוא ערך חלק ק"פ. ולערך בט"ו שעות תורה די בה' מינוטין יראה, רק שתקדם היראה לתורה שקודם לתורה יהרהר ביראת ה' כדי שתהא יראת חטאו קודם לחכמתו ותתקיים חכמתו, כענין שא' ערבת קב חומטין כו' מוטב שלא העלית, אף כי ירצה עתה ליתן קביים חומטין מ"מ מוטב שלא העלית

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    If you're up 16 hours a day, that's 5 minutes and 6 chalakim or introspection. – Double AA♦ Nov 20 '13 at 5:29
  • @DoubleAA Yup. Torah study itself is imbued with properties conducive to yir'as HaShem, so I sort of think of those couple of minutes as a jump start to properly orient one's mind while learning (and from there the learning itself continues to sustain the yiras HaShem). – Fred Nov 20 '13 at 5:41
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    I heard that a non-Chossid (IIRC it was R' Chaim Volozhiner or one of his talmidim) came to the Alter Rebbe and asked him why Chassidim learn Chassidus for such a long time? The Alter Rebbe quoted the Gemara, to which the misnaged answered like DoubleAA. The Alter Rebbe answered that it's the mixing that takes a long time – Shmuel Nov 20 '13 at 6:30
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    @ShmuelBrin Cute. So they had different ideas as to which element of the mashal provides guidance on the appropriate amount time to spend. – Fred Nov 20 '13 at 7:08
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    @Fred He only learned 15 hours a day?! Feh! – Double AA♦ Nov 26 '13 at 4:02

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