Developing Wisdom Part 2: Experience

Part 2 in a series about how to develop wisdom

In the opening part of this series on the development of wisdom, I argued that humility is the foundational attitude a person needs both to make specific wise decisions in the present and to open himself to life’s experiences which builds up his general wisdom for the future. Now I focus on what follows from the second part: how we use life’s experiences to grow wiser in that general sense.

A caveat here is that I have only been at this wisdom project part time for a couple of years. At this point, even though I’ve developed a definition of “wisdom” in which I am reasonably confident, I can’t commit to it absolutely yet, as I recognize that it could still change as I learn. What I mean by wisdom as I write this is the ability to make good decisions that relies, not on conventional knowledge, but on an advanced sense about knowledge itself, an internal familiarity with what knowledge means rather than what it says. It is an adeptness or facility with knowledge rather than the possession of raw knowledge in greater quantities, and it includes the capacity to deal correctly with a lack of knowledge. And perhaps that last bit is the real crux of wisdom.

But having said all that, this is only what I am using as my working understanding of wisdom. It could change as I learn more, and Part 1 of this series, on humility, should explain why I see it that way. But also in line with Part 1, I can’t let my healthy acknowledgment about my own limitations prevent me from acting on it to develop these ideas further. It is a seeming paradox that you need to reach a definition of the thing you are studying before you can study it enough to be confident in your definition of it. In this context, this means I am willing to publish this series outlining my current state of thought on wisdom, even though I admit I am likely wrong about some things. I strongly expect that anything I will learn going forward will not be drastically different from what I believe now. I may need to revise some things, but I expect the bulk of new revelations to expand on what I have already said rather than contradict it. As I have said, the point of humility is to be prepared to change your answers, not to be paralyzed from ever taking action.

The other caveat is that this definition is meant to describe just one of several meanings of the word “wisdom.” For example, one meaning of wisdom is the literal content of wisdom, and an exploration of this would involve perusing proverbs and fables and extracting specific lessons from them. I am instead seeking general wisdom, which might be thought of as the faculty of the mind that enables men to think up specific wise lessons in the first place.

With these caveats in mind, I ask the reader to bear with me. This series should be treated as a progress report on a yet incomplete exploration and a guide for further exploring. I haven’t yet reached the summit, so I can only give my impressions so far, but I think they are important enough impressions about the route to the summit that they warrant being put into a more systematic form as a jumping off point for more focused study going forward.

Unassuming nature

Something I’ve noticed about older people who I thought were wise is that they don’t tend to expect anyone to listen to them. They offer their advice when asked, but are often reserved about offering it unsolicited (with the exception of telling kids it would be wise to get off their lawn). It only tends to be the young who figure themselves as wise who seem to impose themselves into every conversation, spouting know-it-all-isms to anyone in earshot whether they asked or not (I should know because I was one of them). This may be a modern affect caused by our culture that celebrates youth and seems to hate the old. We celebrate “questioning authority,” and treat with suspicion anything someone believes because “their parents told them to believe it.” It wouldn’t be surprising to learn that older wise people recognize that modern society is infertile soil in which to plant their wisdom. But, it could still also be true that there is something about “aged” wisdom that is naturally reserved about being shared regardless of the culture.

This would be consistent with my sense about how general wisdom is acquired in the first place. Wisdom is not the gathering of more facts than everyone else, and so wise advice does not consist of regurgitating those facts back at people. True wisdom lies in knowing what to do with those facts we do have, and what to do about those facts we don’t have. And, if I am correct, real wisdom is the result of personal experience that must be lived out and thus cannot be conveyed in the general sense with words alone. For example, you can’t just tell someone how to sense that a leader is being disastrously overoptimistic, you only really get this sense from having seen it happen a few times.

Also, what counts as wisdom is not an isolated lesson disconnected from present circumstances, but the ability to reliably answer a real pending problem. There must be some circumstance actually at work in the world before this type of wisdom even has a problem to solve and give someone holding this kind of wisdom an opportunity to share it. To reuse the same example, you can’t really tell people how to be on the lookout for overoptimistic leaders, you can only only point them out when they appear. This kind of wisdom would seem unlikely to interject at times when it is not asked for, which I think explains at least part of the reason why older wise people tend to be more reserved about the advice they give.

Neither does this kind of wisdom ever seem to be the product of pure reason. Reliable use of reason is necessary in almost any decision, but examples of wisdom that reach beyond what could be derived just from thinking hard about a problem tend to involve a kind of instinct. Often, wise advice comes with a story about how something similar did or didn’t work, and the exercise of wisdom may lie in recognizing the applicability of past examples rather than thinking through all the possible permutations of the present dilemma. To reuse our example one last time, no one could explain exactly why invading Iran today would probably be a disaster, but we can remember the time “Mission Accomplished” banners were unfurled on the USS Abraham Lincoln.

As mentioned above, I am not seeking the content of wisdom, not directly at least. I am not looking for parables, proverbs, and fables; I am looking for the characteristics of the people who wrote them in the first place. How did they reach those insights that were so universal that they made their way into pithy lessons we remember centuries later? I propose that this quality is ultimately the product of experience.

Insufficiency of knowledge

There is nothing wrong with acquiring knowledge, per se. The more you know, the more relevant information you will have to make decisions with. On average, this should help you make your decisions better. The limitation lies in overreliance on knowledge, not on the knowledge itself. It is when a decision-maker approaches problems under the increasing belief that his powers of knowledge and reason are what fueled his past successful decision-making that he begins to commit the error of dismissing the role of wisdom.

I’ve mentioned in the past that even the simple recognition that there are things you don’t know is a basic use of wisdom. Most everyone over the age of twelve has at least this much wisdom to some degree or another. Through our experiences we learn to navigate decision making, and whether we realize it consciously or not, almost every decision we make involves dealing with at least some unknowns. Whether I should wear a coat today depends on how likely it is to be unexpectedly cool. Whether I should watch a movie depends on whether it will turn out to be entertaining or a waste of time. The trick to all of this is that we make those decisions subconsciously, so quickly we don’t really recognize the thought process. And when we do recognize what we are doing, it appears from our own perspective that we are actually using our knowledge rather than dealing in the unknown. Consider the first example: a typical thought process might look like this:

1. Should I wear a coat?

2. It’s been warm lately, so I probably won’t need it.

3. But, I remember a few days this time last year that were unexpectedly cold.

4. I will be outside for a couple of hours today, I’d better be safe and take it.

We don’t expressly consider that we are dealing with unknown facts. It isn’t that we don’t know what the weather will be, it’s that we do know that it can change unexpectedly. But, we think in terms of what we do know. Really, what else could we think about besides things known to our minds? The fact that we solved our own problem appears to be the product of knowledge and reason, as demonstrated by the step-by-step process, above. But it is easy to miss that the entire thought process depended on recognizing gaps in knowledge. Step 1 tacitly recognizes this by raising the question in the first place. Steps 2 and 3 mask that we are weighing how unknowns fit into the problem by phrasing it as a known probability of what might happen. Step 4 involves yet another form of wisdom, which is appropriately valuing something like the security of having a coat under complex circumstances. Yet, it is all framed in our minds as if we were applying reason to knowledge.

This is a simple example, but simple examples are the most common and therefore most prominent in forming our habits of thought. As we go through life, some of us become convinced that we have answered these questions reliant on our reason. (Others act on feeling alone, never considering reason, and are perhaps wise in certain ways, but their wisdom is futile if not paired with reason—a subject for another time.) We see all of our decisions through the illusion of our thoughts adding knowledge and reason to the problem, rather than fully grasping that beneath all of this we are overcoming the gaps in our reason by making judgments based on what values seem best to us and overcoming gaps in our knowledge by making estimates based on our past experiences.

These values and estimates that are needed to fill the gaps are two examples of what I think goes into true wisdom. While I don’t go in for mysticism, or anything like that, I think many of the mental characteristics that go into wisdom are beyond easy explanation (which is a subject perhaps fitting for yet another installment essay). Values and estimates are more easily grasped concepts, and so they serve as useful examples to help explain the general category of experiential wisdom.

Values serve as the connection we make between two ends that give us a sense of relative preference between them. In any material sense, there is no value difference between eggshell white paint and electric purple paint to cover a wall. But we humans have the unexplainable capacity to instantly say that one is better than the other. And we may even disagree on which is better, but almost every one of us will prefer one to the other. Yet there is no argument purely from knowledge or reason that could answer it. You could only point to the “knowledge” that I will hate the purple paint and the “reason” that determines I shouldn’t surround myself with something I will hate, but the hating of the thing in the first place relies on that value. Without the value, none of the reasoning that follows makes any sense.

But there are harder questions of value. Which in the following pairs do we value more: a free society where mobility is a given or one in which we can prevent foreigners from taking advantage of us? A foreign policy divested of Middle East affairs or one invested in ensuring that governments we don’t trust aren’t harboring destructive weapons? Seizing a moment of conservative control of the government regardless of a few policy disagreements with the President, or opposing that President’s legislative bills because parts of them recklessly increase spending?

While we probably all know where we stand on these, they are a bit more difficult. But it is still a question of values, and values are innate to us as the decisions makers, so the task should be easy, right? Well, the problem is that establishing our values correctly is not easy. It is precisely the kind of thing for which there is no knowledge to guide us. If you are deciding whether to ask a woman out, you can’t appeal to a guidebook to tell you if she is attractive enough. And asking your friends what they think doesn’t work because they’ll just think it’s funny to convince you to ask an ugly woman out.

And, it turns out, values can be wrong. That will be shocking to liberals (and anarcho-capitalists like I once was). The whole idea of the liberal project was that everyone’s values were equally valid and democracy was the way to permit them to live together in harmony. You are free to make your choices in line with your values and I’m free to make them in line with mine. Well, that only worked when everyone happened to have basically the same values.

It is a little different with estimates, but similar principles apply. You can locate charts and tables to give you an idea of some estimable parameters, but not in cases where real wisdom is needed. You can measure questions like how long it takes to drive to a certain place or how much it will cost to do some project. But other questions do not lend themselves to anything like a simple numerical measurement. How will this person react to bad news? Will anyone find out if I do something dishonest? Will I enjoy a certain career? Does that mountain lion want to eat me? Where an important parameter in question is one that is not subject to easy measurement may be what makes certain questions more reliant on wisdom than others.

My contention is that the answers to correct values and reliable estimates (and the other more mysterious factors I hope to discuss in a later installment) can only come from experience.

So then, what is wisdom?

What separates wisdom from knowledge and reason is that wisdom is a kind of instinct or innate sense about what is right or best as opposed to what is certain or provable. Anyone can, in theory, get to what is certain and provable with enough observation and study. The lesson for obtaining knowledge and reason is thus already well known: make observations and study them.

But the lesson for obtaining wisdom is by its nature obfuscated. It is the difference between knowing how to throw a curveball, and actually being able to do it. You can sit in a classroom with a Major League pitcher for weeks, taking assiduous notes about putting your finger on a seam here and flicking your wrist there, but until you actually hold a ball in your hand, feel it leaving your grip at speed, and watch as it does or does not behave as expected can you begin to comprehend what all of those lessons really meant. You grip one part of the ball in a certain way in order to impart a certain spin on it. You can know this, but until you know the parts of that lesson that can’t be put into words, how the grip feels, how the ball reacts as you release it, when in your delivery you apply or release pressure, you won’t actually know very much about throwing a curveball. The familiarity with a movement that comes with practice is a close relative to the wisdom in life that comes with experience.

Or talk to a musician about “laying back in the beat.” Whatever this means, I can’t explain it, but after a few exhortations from high school jazz band directors, I must’ve figured it out because I stopped getting yelled at for not doing it. To this day, I couldn’t tell you where in relation to a musical beat the “laying back” portion refers to. If I had to describe it, it is more like an emphasis on certain notes in a phrase or the way you attack the notes, but somehow “laying back in the beat” seems to communicate the essence of it. You just have to do it and hear it enough times, and fail at it enough times, to have a sense about what it means in any given context.

Our examples of values and estimates are useful to discuss this indirect nature of wisdom. While it is common to say that there are no correct or incorrect values because they are subjective, the truth is that some valuations are foolish. But this is part of what is so elusive about wisdom: any given person’s valuation of something is in fact subjective, yet we can still call it incorrect in the grand scheme of things. If a person’s subjective valuation causes him to make decisions that ultimately lead to error, then his valuation has been incorrect in some way. Not false, but incorrect. How many times have we heard someone say, regretfully, “I thought I wanted that” after they finally received the reward for their efforts but ended up dissatisfied?

So it is that a wise valuation must somehow be able to see through the haze of our subjective sense of preference. How much we want it seems to be an independent psychological formation within us. We have no yardstick against which to measure it, so we have no rational way of calling our valuation wrong.

Except, that is, for something everyone over a certain age knows all too well. I think most people past their 20s can think back to times they were overwhelmed with desire for a thing. Anyone who has ever been inflicted with youthful romance can remember telling their parents “you don’t know what it’s like to be in love,” and having earnestly believed it to be true. It is true that we felt the way we felt, so our valuation was not incorrect in the sense that we didn’t subjectively feel the values we thought we did. But that valuation did cause us to do things we ultimately regretted even though they were totally rational given the valuation we held. We did unwise things because of those valuations, and we usually held such unwise valuations because in our youth we hadn’t experienced enough disappointment to realize some deeper truths about the things we think we want.

An example of this is the desire for revenge or payback, even when it seems just. An abandoned spouse or a betrayed friend is seeped in feelings of hurt and anger. In their weaker moments, the only outlet that they can see for their frustration may be to bury the one who hurt them in guilt. But what seems right to them comes from the pain and anger they feel so strongly in the moment and not from a calm reckoning of their situation. Humility is needed for the “in the moment” decision to keep in mind all the relevant facts and see through the pride that seeks to justify revenge. But to properly attune their valuation, humility is not enough. It cannot come from intelligence or reasoning ability, but from the experience of having felt the same feelings before. It is found in having lived a life of lessons, gradually building a sense about how to navigate hard decisions from experience to experience. Where a lack of experience tells a child (and a lack of listening to experience tells too many adults) that the thing desired above all else is revenge, years of contemplation of the terrible things the desire for revenge does to you yield wisdom in the form of a correct valuation of of it, reducing its perceived value in order to make a true wise decision.

Conclusion

Thus the broad conclusion of this piece is that the means of developing general wisdom is through experience. There is simply no shortcut to having experiences in life, and there is no substitute for making mistakes along the way.

But, while this means true wisdom only comes with age, it doesn’t mean we take no part in developing our wisdom. Consider that not all older people are wise. Some remain foolish far further into adulthood than others, and some remain so their entire lives. Thus, while experience is necessary, it isn’t sufficient alone for wisdom, meaning we can and should take active steps to avoid remaining foolish into old age.

So, it is not simply a matter of waiting for experiences to happen to a person. There are a few things I have so far considered that one can do actively.

First, as mentioned previously, developing a humble disposition enables a person to recognize more readily when he has made an error and to internalize the lessons of such experiences. Life can either force its lessons on you after repeated failures, or you can learn them the first time or two that you experience them.

Second, an open curiosity about what others have done or what might have been had different choices been made may also yield a mild substitute for direct experiences. One may also reflect on fiction or literature, which can provide hypothetical problems he hasn’t already experienced in real life. If he maintains a humble attitude, and the literature or fiction is somewhat realistic to the actual human condition, he can learn from the life experiences of fictional characters without going through the same mistakes of his own. Biographies may in fact be an even better source of this kind of access to the life experiences of others, as long as it is an honest look into the subject’s life.

Lastly, I propose that a person can improve how effective life’s experiences are at teaching wisdom by actively engaging in reflection and consideration of his own daily experiences. Even in the small details of life, active thought about how people reacted to things said, what people expected you to do, how long things took to complete, and so on, with a focus on what lessons were buried in these events and how they might go into use in the future, will likely result in a more ready mind for similar situations when they arise again. In other words, even if you are young, put as much as possible of the limited experience you do have to good use.

Parenthetically, a corollary of all of this is that simple a substitute for wisdom is to ask the opinion of a someone who is wise. If you are young, and therefore have not had sufficient life experience to develop that facility with knowledge that only real wisdom provides, the next best thing is to seek the mind of someone who has. In any given problem or project, ask a trusted older person what unexpected pitfalls they see, what miscalculations or overzealous valuations are likely. What assumptions that you are relying upon are likely to be unreliable? Will you really find the help you need? Will the end product really be as worthwhile as you think it will? Even if you ignore their advice and venture forward on your own hubris, when you see how some of their warnings nearly come about, you may be able to glean some real experience of your own from the process.

As I have continually mentioned, this is an ongoing project for me, and as I go through the parts of this series, I find myself in increasingly speculative territory. Part 3 will continue this trend when we consider the wisdom of taking action.