Maybe some of this will make more sense if we talk about what real humility is. As C.S. Lewis said, true humility is “not thinking less of ourselves, but thinking of ourselves less.” We can spend a lot of time thinking less of ourselves but we only end up thinking a lot about ourselves. The problem of pride does not boil down to whether we think high thoughts or low thoughts about ourselves but that we think lots of thoughts about ourselves.
Humility is fundamentally a form of self-forgetfulness as opposed to pride’s self-fixation. Humility can set you free because when you think about yourself less you are free to think about Christ more. Humility puts us on the path of grace; pride puts us on the path of opposition. God opposes the proud, but gives grace to the humble (James 4:6; 1 Peter 5:5).