My own opinion is that in the search for wisdom the best way to develop (it) is through experience (mistakes as well), reflection and writing.
I just found on WordPress this book Mindfire: Big Ideas for Curious Minds, written by Scott Berkun. Here is what he explains on his blog:
In the book, you benefit from over a decade of me learning how to be wise, from writing. I write often (…)
In an interesting post How to be a free thinker?, he wrote:
A mind is unique in the world for its infinity of ideas, for it can be used to think about almost anything in a million different ways. Any act that deliberately confines a mind to a singular way of seeing the world can not be acting for good. Most communities, from families, to schools, to gangs, have ideas members are expected to adopt without question. This doesn’t make them evil, but it doesn’t make them bastions of freedom either.
Without questions we can’t discover the chains we’ve hidden. Chains forced upon us as children when we did not have the will to refuse or ask questions. Chains we bound ourselves to in order to fit in to school, or work, or a community. To be a free thinker means forever seeking relief from assumptions, whether it’s those we’ve made or have been given to us, and to work towards beliefs and ideas of our own choosing. Freedom of thought means a perennial willingness to discover better ideas, smarter opinions, more worthy faiths, more honest feelings, a willingness not only to abandon ideas you’ve held dearly, but to actively seek moments of discovery, moments when you learn a closest held belief has been held for the wrong reasons. The first time I ate Ethiopian food I had to ask three times “Are you sure it’s ok to eat with my hands?” (..) Travel makes clear how arbitrary many rules and customs we defend truly are.
The first challenge is the fear of being wrong
(…) how can you know exactly what it is you are right and wrong about in what you believe?
The context (traditions, country, etc.) is key.
It’s ok to be wrong if you learn something and grow from it. In fact often there’s no way to learn without making mistakes.
Instead of allegiance to a specific idea, put your faith in your ability to grow and learn. The former is a chain held in place by your own hand. The latter is a door you can hold open, a door to a better self.
The second challenge is other people
There are no required college courses called “undoing the damage of the last 18 years of your life” or “how to escape the evil tyranny of your corrupted youth”. We are, perhaps as it always has been or always should be, on our own to figure out what freedom means. But there is no starting gun, no wake up call, for when to become free, much less how to go about doing it given how much of our lives function on our being unfree.
Joining a “Free thinking” group can be nothing of the kind, especially if everyone in the group shares the same brand of atheism, deism, or anything-ism. Freedom grows best in diversity. The more ideas you hear, understand and compare, the greater the odds you’ll think freely about all of them. This can’t happen if you mostly spend time “philosophizing” with people who share 97% of your philosophy. Instead you’re likely just sharpening your prejudices.
The third challenge is to be alone
Many of history’s great spiritual leaders chose to step away from their cultures and their worlds for a time. Jesus, Buddha, Moses and Muhammad all took long retreats away from everything they knew, freeing themselves from conventions and commitments of normal life. Only then were the able to discover, to transform, to learn and understand themselves in ways that changed the world. They had to separate from the chains and bonds before they could be free, and only then, with new perspective and priorities, did they choose to return. For anyone who knew them, I doubt this choice was popular. Their children, friends, landlords, and tennis partners were less than thrilled about the prospect of them wandering off the face of the earth for 40 days, or 6 months, or however long they chose. They say the fish is the last to see the water. But what if the fish could step out of the tank now and then? You are not a fish. You can take that step whenever you like.
This begs the question, when was the last time you were free from others? The last day you spent alone and let all the thoughts you bury and hide in everyday life rise in your mind? Travel, meditation, long baths, a run in the woods, are all ways to give ourselves a taste of the solitude needed to think freely. Needed to understand ourselves and feel who we actually are. How can you know how much of what you think you want, and think you need is really coming from you? It may be that our truest, freest voice, the voice we call our heart of hearts, is always talking, but it’s quiet and timid and can’t be heard over the chatter of everyday life. Unless we make quiet time to learn how to hear it. And of course, we’re still free to ignore that voice, but at least we’ve given ourselves a chance to listen. Only then is it possible to sort through our lives to strengthen the connections with others who truly share our feelings and thoughts about life. Being free has never been easy, which explains why so few, despite what they say, truly are themselves.