In the last post, I spoke about two types of obstacles: the ones that say "turn around" and the ones that say "keep going." To recognize those obstacles that tell us to turn around, we need humility, the recognition that we are quite obtuse by nature because of our inherent human limitations. By acknowledging those very real limits on our knowledge, intuition, and natural discernment, we are open to turning around when that is necessary. (Notice how pride so often leads to a refusal to turn around--we plow forward because we refuse to admit error, often because admitting error would require wrenching personal change, change that is also known as conversion.) In addition, because of humility, we can turn around without first needing to fully and thoroughly understand or identify the reasons why we need to turn around (compare this last point to my most recent post on Fr. Philippe's book).
This insight is one potential way to understand the biblical aphorism that the beginning of wisdom is the fear of the Lord. The "fear of the Lord" contains an aspect of realizing that we are woefully limited in our capacity to understand when compared to that of the Creator. We recognize the gigantic difference between our comprehension and His. In this sense, we seriously respect the Lord as being profoundly wiser than we are; and so we are ready to turn around even if we do not comprehend all the reasons for such a course of action.
In addition, recognizing our limits enables us to see and be grateful for the mercy and kindness of the Lord--he rescues us from many terrible mistakes even if "we don't get it" at the time, just as a parent will rescue a small, oblivious child from crossing a busy and dangerous city street. In these ways, humility is a key to wisdom, to docility ("teachability"), to "fear of the Lord," and to thankfulness for his kindness. In the end, humility leads to great freedom because we are not enslaved or manipulated by what can harm us or possess us, just as the sheep who follow the shepherd are "free" to flourish when compared to the sheep that run off into predatory danger. Moreover, with humility, we are free to take risks that often our pride stubbornly refuses to take simply because of the paralyzing fear of public failure or embarrassment. The humble person is truly free from those constraints.
Ask yourself in how many ways pride constrains us. Then imagine living free of those constraints, in humility.