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Being humble is a two edge swords. On the one hand, it is a positive state where the person concerned knows all is equal, everyone divine and life is wondrous, thus treating themselves and everyone and everything they meet with respect and acceptance.
This person doesn't need to be right, or wrong. He or she doesn't need to make you right or wrong, nor do they think you are right or wrong. A true ascended master is humble and non judgmental, simply because judgment, rightness and wrongness, do not exist in his or her reality.
On the other hand, there is the socially imposed righteousness of humbleness. Living a humble life, then becomes living a poor life. Being humble, then becomes being inferior to others or to God, and forcing humbleness becomes superiority over others. Religious zealots are usually found in this category of humbleness. And it is a road to ascension too.
I, while living my moments of ego inflation and judging from my extremely large soap box, cringe at the second type of humble person, while value the first greatly. This viewpoint, of course, is the antonym of humbleness and I laugh at my simple attitude, my personal mind chatter and realize, from a wider standpoint, that it is in reality an unimportant aspect of reality. It is, after all, the viewpoint of judgment, which is as necessary in every day life as is breathing.
Therefore, I feel comfortable striving for the first type of humbleness, I believe that, while there, life is delicious.