Our natural instinct is to boast about our wisdom, might, and/or wealth - our accolades, our abilities, and/or our resources - our smarts, our accomplishements, and/or our possessions. "Why is boasting so bad?"
Before I answer that question, we must be able to answer another question... "What is the chief aim of man?" The right answer is "to glorify God and to enjoy Him forever."
Now, let's go back to the former question. It is bad because when we boast (or glory) in anything other than God, we are taking glory away from God... thus sinning against God. At minimum, it is a form of pride. At worst, it is idolatry.
God longs to bless His people, for He is a generous and giving God. However, He warned His people in Deut. to beware not to focus on the 'gift' rather than the 'Giver' (Deut 8:11-20). As God's people, may we not sin against God by boasting in ourselves or others. May we strive to know and understand God and boast in Him for He is worthy of our boast.
Thus says the Lord, "Let not a wise man boast of his wisdom, and let not the mighty man boast of his might, let not a rich man boast of his riches; but let him to boasts boast of this, that the understands and knows me, that I am the Lord who exercises lovingkindness, justice, and righteous on earth; for I delight in these things," declares the Lord. NASU (Jer. 9:23-24)
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