"What is the best way to increase wisdom? Rote reading? To be able to apply wisdom, we must first know it, see it works, then we can own it, though repetition is the only way I know for that 3rd step. The goal being a fearless, tranquility, and freedom."
There are a number of interesting leads in this. I also like the last sentence, proposing an ends to increasing wisdom. Is this the purpose of wisdom; to allow us to be fearless, tranquil, and free?
The question about rote reading and talk about learning something, applying it, and 'owning it' seem to imply that wisdom is knowledge - more specifically, that wisdom is knowledge of a large set of algorithms or procedures which we can first memorize, then apply for specific effects.
This doesn't seem right to me. Knowledge, or perhaps life experience, is certainly helpful in living a happy life. But in reality, knowledge itself is a commodity, and to assume that we increase wisdom by our accumulation of knowledge, seems to me dangerously similar to thinking that we can increase wisdom by our accumulation of material goods, friends, or status.
Are educated people more wise than people lacking formal educations? Can I become more wise by reading Plato, Socrates, Epictetus, Kant, and Hume - or by reading the various self help books of our age? Maybe these things, if learned and applied, might improve our skill of 'life practice', but that still doesn't seem like wisdom to me.
I saw a bit of a recent television program where a young girl, 18, wanted to get married and she was arguing with her mother, who was trying to tell her it was foolish at her age. The mother brought up some points and the girl answered with responses that seemed to miss the point. What often happens with young people is they believe they can figure out all of their actions and their future effects logically. When told something is a bad idea, they want specific reasons that will show how things will turn out badly, and if they don't find them convincing they will plow ahead. I remember when I was that age and older people would say, 'you'll learn when you get older'. I would ask them to just tell me now! When they couldn't I assumed they were simply ignorant or trying to use their age as justification for a position that had no merit.
What less experienced people don't yet understand is that some realizations can't be communicated simply with words or simple 'this leads to that' formulation. If they could, then all you'd have to do to make a young man as wise as an older man would be to sit him down and explain to him what he's going to learn over the next 40 years that is so damned important. But this isn't possible.
Perhaps wisdom includes a very subtle and complex 'weighing of the facts' that is the accumulated perspective one gets after millions of observations which, individually don't mean much and may even be forgotten in an ocean of fine-tuned neurons over a lifetime. Thus, explaining why an 18 year old shouldn't get married to a 40 year old is easy, but almost impossible to an 18 year old. When she gets to 26 she starts to say, 'oh! I get it now', but alas, when she tries to tell her little sister, regardless of the detail of her arguments and her eloquence of speech, the little sister simply doesn't have a sufficient reserve of experience to fully grasp or appreciate (grock) what is being told to her.
The image pictured with this post is a sort of wisdom labyrinth which represents walking the path to wisdom. There is a church my wife and I visited when we were in California which has this pattern in a large courtyard. It was designed for people to start at the outside and meditatively walk slowly the entire path to the center. This ritual is designed to instill in our minds that we can look at the path, we can know the path, and even memorize it - but we can't have wisdom until we actually walk it ourselves. I think some of what I've been writing about above must relate to this notion.
There are also important discoveries being made about changes in body chemistry and brain structure that happen as we enter different periods of our lives. These may indicate that certain realizations, perspectives, dispositions, and responses in various situations may be incredibly difficult for some people to achieve at certain times - regardless of what they have read or memorized.
Therefore, I would advise to the seeker: yes, keep reading, learning, and applying. But have patience with yourself and others. What may be difficult or unclear now may become easier with age and experience. You may find yourself returning many times to material you thought you understood years ago, but then suddenly grasp it on a deeper level - as if looking at one of those optical illusions that look like one subject until you stare at it long enough and see another. I would also therefore advise (especially for those in their early 20s or younger) that it is equally important to have some degree of trust in your elders and understand that they may know things which you simply cannot grasp at the moment, regardless of explanation. This trust includes some degree of obedience to proper authorities without always having full understanding. For adults, it means not assuming that older people may not have many things to teach us, even if they haven't read as much as we.
Several years ago, when I began actively looking for ways to increase my wisdom, I began first with the question: what exactly is wisdom? What I thought would be the first step turned out to be the journey. Above all I would recommend: ask the question. As I have explored what wisdom is and what it means to be wise, I have found this very exploration helpful in increasing it. I'm still no wiser than many people, but I can't help but think that careful and detailed pursuit of this question has helped me.
Thanks for the question Matt!
Incidentally, over at my philosophy site, one section of my 'Noble Conspectus' is titled 'Wisdom' [link HERE]. It may contain some more thoughts on Matt's question. More than myself however, I'd recommend any number of wiser people, perhaps starting with some on my recommended reading list.