"Sometimes life is like this dark tunnel. You can't always see the light at the end of the tunnel, but if you just keep moving, you will come to a better place."

Iroh, retired General of the Fire Nation, The "Dragon of the West," and proprietor of The Jasmine Dragon tea house in the Avatar: The Last Airbender animated television series

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Most people grow up wanting to be famous, to be wealthy, to be loved, to be powerful.

I've always wanted to be wise.

Of all of the qualities people can develop, wisdom is potentially the most beneficial. If developed and used in a skillful way, wisdom can help you (and the people around you) get most of the benefits of common worldly values like attention, status, money, esteem, and influence while mitigating most of the severe drawbacks and tradeoffs.

It's also one of the most difficult human qualities to define, let alone cultivate.

What is wisdom, really? How do you know if you, or someone you know, is actually wise, not just pretending, bluffing, or trying to signal special insight? Appearing to be wise and actually being wise are very different things, and self-deception and puffery are common, since wisdom is usually considered a valuable status signal.

Philosophers have attempted to define wisdom in many ways over the years, without much luck. Most of the philosophical definitions of wisdom I've found boil down to "acting in a wise way" or an abstract sentiment like "the right application of knowledge," which suffers from hindsight bias. Psychologists and neuroscientists have been studying (and trying to measure) wisdom as well, so they usually define it along the lines of "a demonstrated superior ability to understand the nature and behavior of things, people, or events." ²

Those definitions aren't so useful if you're trying to cultivate wisdom yourself. I'm all about developing "a demonstrated superior ability to understand the nature and behavior of things, people, or events." The question remains: how exactly do you go about doing that?

Media depictions of "wise" characters don't do us any favors, either. In practice, being wise doesn't have anything to do with acting like a Zen master, Yogic guru, or Stoic sage. It's not about spouting aphorisms, acting detached and aloof from the rest of the world, or having supernatural insight above and beyond the reach of mere mortals.

Part of what makes wisdom hard to define is that it isn't just one thing: it's a cluster of several specific qualities that are used together. Here's my current working definition of wisdom, based on many years of research:

1. A set of specific, learnable ways of thinking and acting that…
2. Are used in combination…
3. To make decisions and recommendations that are…
4. Likely to produce positive outcomes…
5. In uncertain, ambiguous, and changing circumstances.

People who decide to learn how to make decisions (or advise others) in ways that are likely to result in positive future outcomes in uncertain conditions are learning to be wise: it's a skill that can be developed, albeit a very complex one.

Here's what I've been able to piece together about the primary qualities of wisdom over the years:

1. Understanding

Accurate knowledge of how the world works in fundamental ways. Why things are the way they are, how they got that way, and how to potentially go about changing them without producing unintended consequences. Acting to change something without understanding it first is the definition of foolishness.

Understanding requires learning as much as you can about the world, cultivating curiosity about how things work, considering novel information, expanding your worldview, updating your mental models whenever you have new information, and noticing when you're wrong, surprised, or confused so you can change your mind and use the information in the future.

2. Prudence

Acting in ways that are likely to produce the best possible outcomes for everyone involved. You don't quite know what the future holds, you don't know what others will do (or not do), and unexpected things always happen, so those uncertainties must be taken into account. It's usually prudent to look out for the best interests of everyone, not just yourself: harming others is myopic, detrimental, and a good way to make enemies.

Prudence requires collecting information, considering the available options, and making considered decisions that use that information to produce the desired result.

3. Discernment

It'd be easy for an omniscient being make the best possible decision, but you're not all-knowing: the future is always uncertain and changing. Making important decisions often feels like trying to walk along a trail in the fog – you can see a step or two in front of you, but beyond that, the path is fuzzy and indistinct. Your desires and goals are often just as fuzzy, other people have their own ideas of what you should do, and people often lie and dissemble to get what they want. If it "sounds too good to be true," it often is, but not always – that's a determination you have to make for yourself.

Discernment requires deciding what you want to do and why, looking for subtle clues to determine what's best and avoid false trails, paying close attention to avoid being mislead or deceived, and being cautious and self-aware when you want very much for something to be true or false.

4. Foresight

What do you want things to look like in the days, weeks, months, decades, and centuries ahead? What do you need to do to make that potential future a reality? Are there challenges, barriers, or potential opponents to that future? How could you work around, avoid, or work with them? Could you develop new skills, find helpful people, prevent unnecessary setbacks, or mitigate the risks?

Foresight requires taking the time to think through likely future events, acting in ways that prevent problems from happening in the first place, and making investments and decisions in the present to make the future better in some specific way.

5. Control

Acting in ways that will lead to more of what you want, less of what you don't want, and avoid major unrecoverable errors. Many a person – even the most "successful" people for various definitions of the term – has been brought low by failing to control their emotions and actions, or failing to act when action was necessary. Inhibiting and tempering hubris, arrogance, anger, and despair is necessary if you want to make good decisions. Even then, you don't want to be too controlled, and overlook the value of flexibility, intuition, and fun.

Control requires fighting akrasia, resisting temptation, and inhibiting unproductive impulse in favor of considered and deliberate action.

6. Flexibility

Avoiding being tied to a single, permanent, static way of thinking and acting. Many things are possible if you're willing to consider all of the possible paths and change your strategy. Rigidity is fragile, and it's easy to over-constrain your options in a way that forces poor decisions. On the other hand, you don't want to be too flexible – compromising on something critical doesn't help anyone.

Flexibility requires active exploration of what's possible, keeping an open mind, and being willing to admit your first impulses or gut instincts might be sub-optimal.

7. Persistence

Moving toward the future you want and overcoming errors and setbacks. Everyone wants to have great results, but few are willing to put in the effort necessary to get them. The most important and valuable things in life require effort, and it's easy to give up too early. Almost everyone who achieves or builds something important or valuable puts in years, often decades, of focused energy and attention.

Persistence requires working through the rough spots, keeping the faith in the hard yards, and being patient enough to keep doing what's important long after most people would give up. As long as Discernment says the goal is still worth pursuing, the wise person keeps going.

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The more you cultivate wisdom, the better your life becomes. You'll produce better results with fewer major issues or unintended consequences. You'll handle challenges in a more skillful way. You'll troubleshoot your own issues, prevent unnecessary mistakes, and give useful advice to people who are struggling with their own unique problems.

The qualities of wisdom aren't innate: they're cultivated, mostly by paying attention in the moment and remembering to use them as the situation requires. Wisdom – real wisdom – changes the way you approach every part of your day-to-day life.

It's also a continuum – wisdom is not a binary thing. Like intelligence, you can go to bed with a little more wisdom than you had when you woke up. All it takes is patient, long-term practice of the right qualities.

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