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Key Concepts of Mishlei 15-23 (Timing)
One of the pleasures of life is talking. For many people the experience of expressing their thoughts through the spoken word is so enjoyable that they engage in it at every opportunity. Of course they can only do this as long as there ïs somebopdy willing to listen to them. The chances of finding a willing listener naturally goes up if they limit their talking activity to those occasions when they have something meaningful to say.
To determine whether something will be thought of as meaningful, the speaker should consider the time and place. He also needs to consider what thoughts have just been expressed. Somebody can say something that is intelligent and useful, but if it is out of context with the flow of conversation or other social interaction, the speaker will be met with blank stares.
If the speaker is sharing Torah thoughts, they will be especially appreciated if they are in response to a question that the listener has raised or if they are expressed at a time or circumstance when the knowledge provides helpful halachic or inspirational guidance.
One of the benefits of having Torah wisdom at one’s fingertips is the ability to readily respond to questions and to changing circumstances. This arouses the gratitude of the listeners and increases the satisfaction that the speaker has in his achievement.
All of these ideas are alluded to by Mishlei in a single proverb.
Exploring Mishlei
(כג) שִׂמְחָה לָאִישׁ בְּמַעֲנֵה פִיו וְדָבָר בְּעִתּוֹ מַה טּוֹב:
(23) A man rejoices in the words of his mouth, but how good is a word at its proper time!
This proverb compares the general pleasure of unrestrained talking with the enhanced pleasure of saying something at the right time within the context of what has gone before. To limit oneself to talking at the right time requires a degree of self-control, a concept which was treated in Mishlei Segment 15-21.
Learning Mishlei
(כג) שִׂמְחָה לָאִישׁ בְּמַעֲנֵה פִיו 
וְדָבָר בְּעִתּוֹ מַה טּוֹב:
A man rejoices  שִׂמְחָה לָאִישׁ in the words of his mouth  בְּמַעֲנֵה פִיו , but how good is a word at its proper time  וְדָבָר בְּעִתּוֹ מַה טּוֹב !
Additional Insights
A series of additional insights illuminating this proverb are presented below. The numbers identifying the insights refer to the listing of sources at the end of the segment.
(1)The joy of speech is enhanced when the speaker expresses himself calmly in a soft-spoken manner. This results in the goodwill of the listeners and that in turn increases the pleasure that the speaker gains from his experience.
(2) The word מַעֲנֵה may be translated as “reply.” In that case it refers to a person who gets pleasure from intelligently answering a question. A person who is learned and is able to respond quickly gains pleasure from that experience. The pleasure of the listener derives from the fact that the answer comes at a time that it is needed.
(3) Alternately, word מַעֲנֵה may simply be translated as “expression.” Every act of speech is pleasurable. However, a person is advised to avoid saying whatever happens to come into his mind, even if it gives him pleasure. Instead he should restrain himself and speak only that which is timely to the circumstance.
(4) The pleasure that one gets from speaking is especially great if he is talking to someone of importance. Then the pleasure is enhanced by the knowledge that he has captured the attention of an important person. However, in such a case the value of waiting until the time is right becomes even greater.
(5) The pleasure that one gets from speaking is especially great if he is giving advice or guidance that affects another person’s behavior. The acceptance of his guidance becomes all the more important and that requires the advice to be timely.
(6) Choosing the right time to speak is more important for the student who asks a question than for the talmid chacham who responds. The talmid chacham must be prepared to answer at any time, no matter what the question. However, the student should show repect by asking only within the context of the subject matter currently being discussed. Thus, the first part of the proverb is referring to the answer being given by the talmid chacham and the second part is referring to the time when the question is asked.
(7) Even for the talmid chacham who is not answering a question, there are circumstances when timing is important, such as giving a shiur on the halachos of Pesach during the month before Pesach. However, there are circumstances when the situation is urgent because of an immediate danger and in such cases the talmid chacham should disregard the constraints of time and interrupt whatever is happening.
The primary sources used for the additional insights illuminating this segment are listed below.
(1) – רש”י
(2) – מלבי”ם
(3) – מצודות, רבינו יונה
(4) -רלב”ג
(5) – חנוך לנער
(6) – שבט מיהודה
(7) – הגר”א