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Proverbs 1:5-6 Updated American Standard Version (UASV)
5 Let the wise man hear and increase in learning,
and a man of understanding will acquire wise guidance,
6 to understand a proverb and a saying,
the words of the wise and their riddles.
The overly self-confident person speaks arrogantly, who considers himself superior and in no need of learning. Readiness to learn is ever characteristic of the truly wise. That which is worthy of our meditation is not always simply expressed, and so it is true of the book of Proverbs. It is filled with idiomatic, metaphorical, figurative, and poetical language, which is 3,000 years removed from the way we commonly express things. However, the fact that we must take the time to understand what the writer meant by the words that he used is most certainly a blessing. What this does is weed out those who honestly do not want to know God from those that want to know him.
Proverbs 1:4 was concerned with the inexperienced and the young, now we include the wise ones who possess understanding. Only God is beyond the need to learn. Even the wise man needs to continue to grow in knowledge, discernment, and wisdom. The wise man needs to continue to grow in learning. Although he possesses understanding, he needs to continue acquiring wise guidance if he is to understand the wise sayings, the parables, and the riddles. The proverbs contain far more than these short and forcefully expressive sayings. Solomon is here challenging the wise man to continue in his journey of increasing their knowledge, discernment, and wisdom.
In looking at Proverbs 1:5, consider the metaphor of life being like a voyage, reflect on this biblical truth: “Let the wise man hear and increase in learning, and a man of understanding will acquire wise guidance.” The Hebrew term (תַּחְבֻּלוֹת tachbuloth) rendered “wise guidance,” or “skillful direction” can describe the actions of one who commanded an ancient ship. It suggests the experience and knowledge to guide and direct with skill and wisdom. The Hebrew term (שָׁמַע shama) for “hear” means more than simply taking in information through our ears; it also involves listening, wherein we take notice of and act on (ready to obey) the teaching and thoughts of proverbs; responding to the advice and guidance that the proverbs contain. None should ever feel as though they have learned all that there is to learn or is necessary.
Likewise, the Hebrew term (לֶקַח leqach) for “learning” means more than simply taking in isolated facts as it is to gain continued understanding by way of these proverbs, increasing their knowledge, discernment, and wisdom. “A man of understanding” (בִּין bin) is perceptive and possesses insight. This is one who has the ability to see into a situation. One who possesses acts with wisdom, caution, and discretion. The sense of the man who acquires “wise guidance” or “skillful direction” (בֻּלוֹת tachbuloth) can describe the actions of one who commanded an ancient ship. It suggests the experience and knowledge to guide and direct with skill and wisdom. It is one who will be trained in their judgments, decisions, and conduct by the wise sayings that they learned from the proverbs. The wise man should not spurn or reject these proverbs as though they are unworthy of his time.
“Understanding a saying;” (מְלִיצָה melitsah) that is a difficult or perplexing or puzzling saying is to discover a profound truth in very few words. Many biblical proverbs are challenging to understand upon the first reading, as they are perplexing and puzzling at times. Some proverbs are riddles, which are perplexing and complicated statements that require investigating if they are to be solved or explained. Understanding the book of Proverbs will take time and meditation.
A riddle (חִידָה chidah) is a puzzle in the form of a question or rhyme that contains clues to its answer, which is puzzling or confusing. The Hebrew word chidah means “riddle” or “ambiguous saying.”
Framing a riddle, which frequently comprises an ambiguous but accurate analogy, involves a powerful and deep mind. And cracking such a riddle calls for the facility to see how things relate to one another; accordingly, the Bible speaks of riddles as belonging to wise persons, and as something, a man of understanding comprehends. This same Hebrew word, which is rendered “riddles” many times throughout the Hebrew Old Testament, is also rendered “difficult questions” in a different context. – 2 Chronicles 9:1.
God himself inspired writers to use riddles or ambiguous sayings or words when speaking of his will and purposes. These are statements, which at first, seem quite perplexing (because the answer is obscured). Still, after the listener or reader discovers the hidden meaning, they are easily understood, making perfect sense. It is like a complex magic trick that perplexes us until we discover how to do it; then, it does not seem so perplexing.
 Or skillful direction