Paradoxical Virtues

In this recent conversation between Tyler Cowen and Peter Thiel, Cowen asks the billionaire start-up investor what kind of talent is underrated:

“It’s difficult to reduce [talent] to any single traits, because a lot of what you’re looking for are these Zen-like opposites. You want people who are both really stubborn and really open-minded. You want people who are really idiosyncratic and different, but work well together in teams.”

This is an idea I’ve thought about a lot as well, that many of the qualities you want to cultivate in yourself are seemingly contradictory. I can think of many examples:

• Confidence + Humility
• Consistency + Spontaneity
• Persistence + Flexibility
• Imagination + Skepticism
• Vision + Attention to Detail
• Social Intuition + Nonconformity
• Extroverted Socializing + Introverted Thinking

The list goes on and on. In each case, seemingly opposite, or near-opposite, traits both appear to be valuable.

Is it Possible to Have Both Opposites in One Person?

Thiel, in his assessment on who makes the best employees or entrepreneurs seems to think so. And although it seems to defy logic, I tend to agree. I’ve personally met many people that embody seemingly opposite virtues in a unified personality, without the two simply averaging out to meet in the middle.

One of my heroes, Richard Feynman, embodied many seemingly paradoxical virtues.

He was a man of great focus, winning a Nobel in physics. But he was also intellectually varied, learning as diverse skills as lock picking, Portuguese and the bongo drums.

He had an incredible imagination, allowing him to visualize concepts and teach what he knew. But it was also combined with deep skepticism, aware of both the limitations of his own knowledge, and knowledge in general.

Or consider someone like Steve Jobs, who had incredible vision but also ruthless attention to detail. One story claims when Jobs was presented with one of the first prototypes for the iPhone, he dropped it in a fishbowl. When bubbles came out, he argued that was proof that the engineers had left space inside and could make it even smaller.

I’ve observed these seemingly paradoxical virtues in many of my friends, which suggests to me that they aren’t mythical qualities reserved for famous scientists and entrepreneurs.

Dealing with Paradox

If you think about these virtues, the most common way to deal with the paradox is to deny that one side of the paradox is actually a virtue.

This is a popular strategy in big-idea books. In the book, Smile or Die, Barbara Ehrenreich attacks optimism, arguing it results in taking foolish risks and political apathy. In Never Eat Alone, Keith Ferrazzi argues against the self-made individual, arguing the path to the success must be made through other people. In Good to Great, Jim Collins argues against so-called “foxes” who know a little bit about a lot of things, instead favoring “hedgehogs” who know one thing very well.

But in each of these cases, I can think of counterexamples. Optimists who are prudent and politically minded. Self-made individuals who know how to network. People who have deeply specialized knowledge, but still have intellectual breadth.

I think a better way is to try to dig deeper. Instead of throwing out one half of a paradoxical virtue, just because it seems to contradict with another, see how people who maintain both manage to integrate them. This can lead to interesting discoveries for the nuances of how to get the benefits of two virtues with seemingly opposite tendencies:

Persistence + Flexibility. I suggest here that people who always finish what they start, yet don’t get stuck from stubbornness, maintain an internal distinction between types of projects. If they mentally label a project in one way, they can quit it without guilt. If they mentally label it another, they have to finish it. That distinction allows both qualities to exist in the same person.

Imagination + Skepticism. A possible solution might be that these people practice both, but at different points in time. Generating creative solutions in one phase, and ruthlessly breaking down and fixing those ideas in another.

Social Intuition + Nonconformity. Nonconformists who don’t seem off-puttingly weird might get away with it because they’re actually able to conform to many standard social cues, so when they do flaunt convention they can still be relatable.

Make an effort to look for people who hold seemingly opposite virtues and try to figure out how they maintain the contradiction. Sometimes, as you dig deeper, you might find that the balance is an illusion or it is maintained at a serious price. Other times, however, you may find little rules of thumb that allow the person to enjoy both sides of the paradox.