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NOTE: For a PDF copy of this segment, please click here. This will enable you to print out the entire text of the article. [Rev 0]
Key Concepts of Mishlei 16-20 (Success)
What does it take to succeed in any endeavor? The answer is to carefully think through what you want to do, what you want to achieve and what it will take to get it done. Why do projects fail? Because people haven’t given the matter enough thought. They embark on an activity without considering what effect it will have on other people and whether the desired result will be pleasing to Hashem. Even if they are optimistic about the means and the result they allow themselves to be carried away by wishful thinking and by their illusions.
If a person has given the matter sufficient thought and taken into account all of the factors, there is a good likelihood that he will succeed. But there is a real possibility that whatever he hopes to achieve was not meant to be because Hashem has a different plan. Ultimately, it is a person’s challenge to trust in the will of Hashem and to accept the outcome graciously.
Exploring Mishlei
(כ) מַשְׂכִּיל עַל דָּבָר יִמְצָא טוֹב וּבוֹטֵחַ בַּה’ אַשְׁרָיו:
One who thinks through a planned action will be likely to find a good result. Fortunate is he who trusts in Hashem to provide the right outcome..
This proverb advises a person planning a course of action to carefully consider the implications. If he does so, he is likely to meet with success. However, despite the best intentions, the definition of success may not be what he thought it would be. That is up to Hashem. If his trust in Hashem is sufficiently great, he will be satisfied with the result.
The concepts of this proverb are also explored in Segment 16-01 (Control) and 16-09 (Accomplishment).
 
 
Learning Mishlei
(כ) מַשְׂכִּיל עַל דָּבָר יִמְצָא טוֹב 
וּבוֹטֵחַ בַּה’ אַשְׁרָיו:
One who thinks through a planned action — מַשְׂכִּיל עַל דָּבָר is likely to find a satisfactory result — יִמְצָא טוֹב . Fortunate is he who trusts in Hashem — וּבוֹטֵחַ בַּה’ אַשְׁרָיו to provide the right outcome.
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.
(1) The better a person is able to visualize the outcome and the impact of his proposed initiative, the more likely he is to succeed.
(2) The better a person is able to visualize the conditions and resources that are needed for his proposed initiative, the more likely he is to succeed.
(3) The better a person is able to visualize the consequence of what he sets out to do, the more satisfactory will be the outcome.
(4) The better a person is able to visualize the sequence of steps that will need to be performed in what he sets out to do, the more likely will he be to succeed.
(5) The first part of the proverb may be understood as referring to learning Torah. If a person puts in the necessary thought and effort he can be assured of success. The second part of the proverb refers to the efforts a person undertakes to pursue his livelihood. There can be no guarantees or assurances here. Ultimately the person needs to trust in the will of Hashem.
Sources
The primary sources used for the additional insights illuminating this segment are listed below.
(1) – מצודות
(2) – מלבי”ם
(3) – רבינו יונה
(4) – המאירי, רלב”ג
(5) -הגר”א