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Key Concepts of Mishlei 13-19 (Culture)
The culture of a population describes its values and its ways of thinking and acting. We cannot help but be influenced by the social environment in which we live. Therefore it is very important to be aware of the cultural patterns that exist in our working and living communities.
What is the attitude of the local culture toward various aspects of ethics, morality, usage of time, possessions, physical appearance, and social behavior?
Every social grouping, whether it be neignborhood, family, business, social circle, or shul, has a particular set of norms and unwritten rules that affect how its members are expected to behave. People who become part of any such grouping get to know what they need to do to fit in and what will make them outcasts.
Mishlei reminds us here to be aware of all this and he does so using just a few carefully chosen words. In deciding where we live and work, we should make a conscious effort to associate with those people who will attract us to worthy attitudes and behavior. Since the primary focus of Mishlei is upon Torah wisdom, he uses this virtue as the template by which we should evaluate our social environment.
Associating with wise people will have the effect of raising our standards of Torah knowledge and behavior. Howvwever, we are cautioned that associating with fools who denigrate the value of wisdom will have the effect of drawing us into relaxed and undisciplined behavior, which will ultimately lead to tragic results.
Exploring Mishlei
(כ) <הלוך> הוֹלֵךְ אֶת־חֲכָמִים <וחכם> יֶחְכָּם וְרֹעֶה כְסִילִים יֵרוֹעַ:
One who walks with the wise will become wise but the one who seeks the companionship of fools will be crushed.
This proverb compares the one who associates with the wise with the one who associates with fools. Even if one is not yet wise, but walks with them and follows in their footsteps he will gain the benefit of their positive influence and he is likely to become wise himself. Corespondingly, if he chooses the companionship of fools, his quality of behavior will detriorate over time and he will suffer the consequences.
In effect the proverb is comparing two extremes to emphasize the distinction between them. At one end is the person who is not yet wise but seeks to improve himself by quietly following in the footsteps of the wise. At the other extreme is the person who should know better but seeks the companionship of fools, gathering them around him because he thinks he can have a positive influence upon them. He needs to be very careful that he doesn’t get himself in trouble in doing so.
Learning Mishlei
(כ) [הלוך] הוֹלֵךְ אֶת חֲכָמִים 
[וחכם] יֶחְכָּם וְרֹעֶה כְסִילִים יֵרוֹעַ:
One who walks with the wise — הוֹלֵךְ אֶת־חֲכָמִים will become wise — יֶחְכָּם , but the one who seeks the companionship of fools — וְרֹעֶה כְסִילִים will be crushed — יֵרוֹעַ .
 
Additional Insights
A series of insights illuminating this proverb are presented below. The numbers identifying the insights refer to the listing of sources at the end of the segment.
Wisdom in Words
(1) The word הוֹלֵךְ in this context implies walking after someone or following them. It refers to the person who seeks the company of the wise so that he can learn from them. It is analogous to the phrase וְהָלַכְתָּ בִּדְרָכָיו , “if you go in His ways” (Devarim 28:9).
(2) There is a play on words between רֹעֶה and יֵרוֹעַ . The word יֵרוֹעַ can be translated as “broken” or “crushed.” In this case it is the result of being רֹעֶה , “shepherding” or “befriending” fools. But יֵרוֹעַ can also be translated as “being shepherded.” He tries to shepherd the fools, but ends up being shepherded himself.
(3) The word כְּסִילִ , “fool,” refers to someone who has intelligence, but is not motivated by skepticism or an evil character. However, he is foolish because he allows himself to be carried away by momentary desire.
Other Insights
(4). Based on our proverb, the Chazal taught, וֶהֱוֵי זָנָב לַאֲרָיוֹת, וְאַל תְּהִי רֹאשׁ לְשׁוּעָלִים , “Be a tail to lions rather than a head to foxes” (Avos 4, 15) — the tail of a lion is a lion and the head of a fox is a fox.
(5) One who single-handedly attempts to shepherd fools in order to make them become wise, may become foolish like them and will himself need a shepherd.
(6) If he follows the wise, he may not be accepted as a companion at first for wisdom is hard to learn,. He will merely be one who walks humbly in their footsteps. With fools, however, he may call himself a companion right away because foolishness comes easy.
Sources
The primary sources used for the additional insights illuminating this segment are listed below.
(1) – המאירי , רבינו יונה
(2) – רש”י, אבן עזרא, מצודות, מלבי”ם
(3) – מלבי”ם
(4) – המאירי, הגר”א
(5) – אלשיך
(6) – מלבי”ם