If wisdom is the sum of all of our experiences and permits us to make decisions based on what we already know, it's tempting to think that wisdom would make us confident, perhaps even arrogant. And it does (and it can), but real wisdom also comes with humility.
Because wisdom recognizes a couple of things about itself. First, it recognizes that it may not have all of the information it needs. It knows that it only knows what it knows, that it is limited by its own experience and that some of what wisdom decides is, basically, an educated guess. It knows this because wisdom has made these educated guesses before - sometimes rightly and sometimes wrongly. Wisdom has discovered first-hand what it has not known, but only by choosing without knowing and then finding out what that missing information would have contributed.
I keep saying that wisdom chooses without knowing, and that is true, but I don't want to create the impression that wisdom always chooses to act without knowing. Sometimes, wisdom chooses not to act because of not knowing, and that is a choice, as well. Sorry - just a small interjection, but I don't want you to get the wrong idea.
What wisdom also recognizes is that it's never going to make the same decision twice. That's because as soon as wisdom chooses (to act or not to act), it adds another piece of data to itself. It has another point of experience to draw upon for the next time. So when the next decision rolls around, it is a different consideration, a different set of wisdom that makes it - a wisdom that has been added to by what it did the last time.
That's why wisdom requires such humility, on both of these counts. It recognizes its own limitations and thus, has to confess that it knows that it does not know everything. It also recognizes its own developing nature and thus, has to be mindful of what it may learn from acting on itself. It knows that it is never complete, that it never will be complete, but that it will always be adding one more thing, one more thing, one more thing to its understanding to the point that a wise decision today might not be a wise decision tomorrow.
But that doesn't mean we shouldn't make it today.
That is why when asked whether, knowing then what I know now, I would do something differently, the answer is no. The answer is no for a couple of reasons: first, I didn't know then what I know now, which means I could not have used today's information to make yesterday's decision. Today's information comes from having made yesterday's decision, so the fact that I can even ask the question is a reflection of the nature of wisdom itself.
More than that, however, to have made any other decision along the course of this journey would have required, every time, deciding that what was true this time could have been true at any other time and always living deciding based on the unknown and not the known. It would have required me to always choose what I didn't know as the basis for my movement in this world, and that's not wisdom. Wisdom confesses what it does not know, but it moves based on what it does know. Otherwise, we're all living some kind of paralyzed life where we're afraid to move at all because we don't know everything. (We know persons like this; it's not pretty.) Life is meant to be lived. Wisdom tells us how to live it. Fear keeps us from living it. That's why we always choose wisdom.
It's tough. I get it. It's not easy. We get a little better at it as time goes on (hopefully) by learning from our mistakes and our successes, from our failures and our victories. We add to our pool of wisdom every time we choose (even when we think we choose not to choose, which is a choice in itself). And in the meantime, there are very real consequences (good and bad) for us and for others in our community when we move according to wisdom. That's why we need humility.
Humility and wisdom go hand-in-hand. Both are necessary for navigating our world, no matter what it throws at us. Both are necessary for living together, which is what we are called to do.