In the practical application of seeing our position in devotional service there seem to be paradoxes or contradictions. One such pair is 'Humility and Self-Confidence'. A good place to begin is to define what humility isn't? A good definition is both inclusive and exclusive...So what humility isn't? It is not thinking, "I am bad. I better jump off the cliff. I am terrible. Etc". Notice who is in the center when we think like this. It's "Me-Me". That is not humility. That is the mode of ignorance. Real humility is thinking, "Search within me and you will not find any good qualifications. If you find anything worthy of praise or some value, it is only because of the mercy of guru & Krishna." Humility is based upon a spiritual conception. A very simple example of humility is when we look at Krishna and then look at ourselves; we feel that we are tiny. Srila Prabhupada would often say, "Krishna consciousness is very simple. God is very great. I am very small. So I should serve God." That is humility. The more we understand how great Krishna is, there will be more feelings of humility.
Srila Prabhupada would often combine the two terms - 'Humility and Pridelessness'. It's a couplet and goes together like we say 'Knowledge and Detachment'. Humility is how we see ourselves, and pridelessness is how we see those things in relationship to ourselves. This is similar to the conception of 'I and Mine'. The conception of ‘mine’ is based on the ‘I’ conception. Whoever we think we are determines what we think is ours. So, pridelessness accompanies one who is humble. When we lose the spiritual conception, pride will be there immediately.
Krishna likes when the devotees are prideless. Conversely, Krishna does not like when His devotees are proud. Even the gopis, when they felt that they were special to Krishna, Krishna immediately disappeared to destroy their pride, and also to increase their hankering and love for Him through feelings of separation. Especially for those who are sincere devotees, who wish to become pure, if pride enters the heart, Krishna will correct through instructions. We can hear and learn voluntarily, or, we can choose to not hear and to learn the hard way. Better to learn by hearing.
-- From a lecture by HH Romapada Swami on 'Humility and Self-Confidence Part One' during the Christmas Weekend Seminar on 'Seeming Paradox or Contradictions' delivered on December 2009, in Chicago, US.