You are humble or you are not. Normal people are not humble. We are infected with vanity, small or big. Call it dignity, ambition, honour, self-worth or other names much less honourable, the flaw of pride is a prime mover for us.
Genuine modesty is a rare virtue that cannot be suddenly willed. It grows in time, if ever, by means of intelligence and understanding, through suffering and loss. But you can practice honest humility right now, and it gives amazing power. In time it may become a habit or even the real thing.
Imagine humility as the daily hunting of your pride. If you learn to catch yourself when you are about to be driven by pride you will harness frustration, stupid expense, imprudent risk-taking, unintentional offending of people, rousing envy, bragging ridiculously, making hollow promises,... a long list of foolish loss that diminishes our choices and so, our freedom.
All you have to do is to observe that your pride is at work; once observed, you can decide whether you stop being plaid or, why not, that you allow your pride to be tickled in this harmless occasion – for sheer cheap pleasure, as a treat of indulgence. However, be careful not to fool yourself into addiction.
Detect the many who exploit your pride and flatterers will lick you with no profit. Blackmailers of the loss of face, racketeers of self-admiration will lose a fat client.
Imagine humility as seeing yourself and everybody else as the tiny, fleeting, vulnerable, forever ignorant being which we are in this infinite universe. Mere intelligence proves the truth of this. You will suddenly be wiser than most around you, a Socrates qualified to understand people because you use the same measure to judge yourself.
Humility is to declare yourself agnostic of absolute truth and religion, because if God exists, we are nothing and nobody indeed to pretend that we understand Divinity and fools indeed to pretend that we are entitled to represent Divinity on earth or speak on its behalf. By this awareness you will be entitled to judge how grotesque are the morons and fanatics who pretend to revenge their God or impose to other people their own faith.
Learn to say: “I do not know”, “It is the first time I hear about this.”, “No, I never read that book.”, “Sorry, I was wrong.”, “Please help me”, “Yes, you were right.” and “I will do my best.” People will respect you.
Though, to practice humility you need a certain well being. You behave humble because you chose so, not because you were thrown down on your knees and humiliated. To behave humble you must have a choice. There must be someone inside. You need reserves o self-esteem and dignity and courage built up inside you, some experience with pride satisfied. Insecure nobodies anxious to pretend that they know when they don’t or than they can when they are useless, cannot conceive humility; it is for them like losing their trousers in public.
The supple can overcome the stiff.
Under heaven everyone knows this,
Yet no one puts it into practice.
Therefore the sage says:
He who takes upon himself the
humiliation of the people is fit to rule
True words seem paradoxical
The Tao Te Ching, #78, Translation by Gia Fu Feng & Jane English Vintage Books, 1989