The Bible speaks of both positive and negative pride. In one sense, pride in ones country, land, children, accomplishments, (etc) seems to be a natural (in a good sense) trait. In another sense, though, the Bible is clear that God hates prideful arrogance. Pride blocks grace and breeds quarrels. Pride goes before a fall.
Our cultures, also, both loves and hates pride. Arrogance is considered an anti-quality, but at the same time a high sense of self-worth, self-esteem & self-confidence is valued. According to the culture, most people's emotional problems would be solved if they thought more highly of themselves. Willimon states that "pride has been rehabilitated from being a vice to be avoided and has become a great virtue to be cultivated."
In apparently stark contrast, however, the Scriptures say that the road to happiness is paved in humility, meekness, and brokenness. It's not that Scripture calls us to think nasty thoughts about ourselves. God calls us to think highly of Him and this, in turn, will allow us to think of ourselves accurately. Our problem is not a lack of self-esteem, but that we too highly esteem ourselves.
Willimon concludes, somewhat surprisingly, that the sin of pride is unavoidable. I would only say that the temptation toward pride is the strongest of the Seven and the struggle with pride the most lifelong. Pride is the shrewdest sin insofar that it can attack you from any angle. One moment you can have pride in your accomplishments. The next moment you can repent of your pride and then become prideful of your new found humility.
Surely victory over pride is only possible in a life committed to repentance and brokenness before God.