Humility and pride are connected, though not necessarily as opposites, as one might suppose. Humility is about putting others before yourself. According to the Christian worldview, this is one of the highest virtues. However, for many in today's competitive world of work, humility is seen as a weakness. Instead, pride (or even arrogance) is seen as one of the highest virtues.
In essence, pride is nothing more than the confidence which comes from a satisfaction in one's own accomplishments. Arrogance, by contrast, lacks the genuine accomplishment that is behind this good sort of pride. When pride is warranted, but is allowed to speak for itself, this demonstrates humility. So it is possible to be both proud and humble in this sense.
Furthermore, when the development of humility is treated as a goal in itself, it is possible to be proud of your humility. This is a potential stumbling block. It is one thing to be proud of your humility with the understanding that your humble nature will make a difference, and quite another to be proud of such an accomplishment for its own sake.
To know it will make a difference, is to use it as a stepping stone to the real work. To treat it as an end with no further goal, is solely to bolster one's own ego. To be perfect for perfect's sake is to have an excuse for never daring to fail. It is easy to be humble when one has no accomplishments.
Unfortunately for the soul which tries to live life to this purpose, "no accomplishments" becomes an accomplishment. It is an accomplishment that benefits no one on Earth. It is neither applauded nor recognized—even condemnation would be a recognition. The inevitable pride that comes from this accomplishment is therefore bittersweet, leaving the soul restless and frustrated.
To what purpose are you humble? Of what are you proud? What mark do you hope to leave on the universe?