Paul was 'proud' of others. He even boasted of others as a way to encourage them. I see a lot of that 'fatherly pride' exhibited by him when people under his ministry did well. Surely the Father commended the Son very highly. Is the Father 'proud' of the Son? I don't know why He wouldn't be.
One thing I have loved about growing belief in the Gospel is the chance to re-define myself and my life thus far in honesty and knowledge. I am a beast, as He says. But I am not a worm. I am a beast of the species 'mankind'--a creature, not the Creator. I don't rate next to God, but though He created me weak, He did not create me inperfectable. We all need encouragement (just as we all need correction) and
sometimes that encouragement has to come from within our own selves in the light of the sum of God's word about us.
When I think of the pride of life, I think of the book of Ecclesiastes. This guy did it all, had every accomplishment under the sun. What all his experience and knowledge brought him was humility, in the end. We're not to be puffed up, high-minded, boastful. But it is 'dishonest' to rate ourselves too lowly also, as we are bought with a great price. We're even warned not to be 'falsely humble'.
I think we tend to admire people who have succeeded in some way, yet retain that sense of 'humility'. That's a good quality--maybe one we don't see often, but when we do, it shines. That's something to emulate, and I can usually sense in myself when I'm 'doing' that. And when I'm not? Pride also goes before a fall.
If it was easy, everybody would be doing it. His rod of correction nudges us both to the left and to the right whichever we need to get our basic path/life straight.
Just some thoughts--not very 'theological', but I think I could find support in examples of Scripture.